World’s Best Boss: Jascha Kaykas Wolff

Meet Jascha

Jascha’s coaching philosophy drives high‐performing teams with an emphasis toward valuing team success above individual achievement, developing inclusive work practices, and building ‘T’ shaped professional skills.

World’s Best Boss with Ruckus is a series of conversations with business leaders, entrepreneurs, and thought leaders that explore how the best bosses attract fantastic people, build up their teams, and keep their employees happy.

In this first clip, Jascha dives into his thought process when finding his next career opportunities. By viewing his work through the lens of ‘being a tourist,’ he aligns himself with those roles that leave him feeling excited about his work and continue to point him towards his greater goals.

In the next clip, shares a method he uses with his teams to help them navigate what they enjoy doing, what they are great at doing to be doing, and aligning that towards the ultimate goals they have for their careers.

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Jascha Kaykas-Wolff, is an executive business leader with a creative flair, who has built teams that transformed the customer and user experience.

A champion for supporting company values and mission; his coaching philosophy drives high‐performing teams with an emphasis toward valuing team success above individual achievement, developing inclusive work practices, building ‘T’ shaped professional skills and constantly reinforcing the importance of business acumen in addition to functional expertise.

In his current role as President of Lytics, Jascha is responsible for Go-To-Market, Customer Success and operations. Previously, at Mozilla, BitTorrent, Webtrends, Microsoft and more. Jascha has a strong track record of building robust brands with hockey-stick growth trajectories for new products.

Host: Anish Shah is the CEO & Founder of executive search agency Ruckus. Anish has worked in-house in Growth roles at Snapfish and Getable. He started Bring Ruckus as a Growth consultancy 11 years ago working with 40+ clients, then re-focused his firm on executive recruiting for Growth leaders.


  • 6:45 – Jascha explains how he became CMO of various popular companies and the mindsets that helped him get there
  • 9:56 – Jascha compares his current role to past one at Mozilla as CMO
  • 13:31 – Anish shares advice for interview process that lights CEOs’ eyes up
  • 15:05 – Jascha comments on the biggest risks he’s taken along his career
  • 18:40 – Jascha shares why understanding what your team defines as success is so important
  • 20:20 – Jascha speaks about the true role of a manager in any organization
  • 25:07- Jascha shares how you can create a system to create an opportunity for your employees to be successful
  • 26:26 – Jascha advises on how to onboard new team members and how to get them up to speed in the company’s culture
  • 28:20 – Jasha’s former Microsoft manager questioned him and shared the heart, tree, and star system – system used for career development
  • 38:28 – Jascha’s anecdote about how he didn’t get a role he wanted and how it had nothing to do with his qualifications
  • 49:19 – Jascha encourages leaders to create scenario planning into their cultures moving forward
  • 52:33 – Jascha focuses on online mentorship and how to approach this new virtual reality
  • 56:00 – Jascha replies on “What makes a good marketing leader and which attributes you appreciate in leaders around you?”
  • 1:07- Jascha dives into his current role as Lytics president

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Grace Portillo (00:00:01):
Hello, and thanks everyone for joining World’s Best Boss with Jascha Kaykas-Wolff.

Anish Shah (00:00:09):
The earliest point that I was able to cross paths with him, he was working at a company which was run by people in their mid twenties. Everyone who worked there was in their mid twenties. Everyone who worked there also would just show up in ratty, torn up t-shirts and sandals, and, you know, not really trying very hard in their appearance on, on a day to day basis. And then through, through some of the people who worked there, who were my friends, I meet Jascha, who was their CMO at the time. And Jascha is wearing a sport coat with a a pocket square. And, and so just, you see these sea of people just like unshaven, like messed up hair, just broken down clothing. And then you see Jascha coming like straight out of like a Brooks brother catalog. And it was just like, who is this guy? This, this guy is completely different. And it was great. So today I wear a sport coat and a pocket square in his honor.

Jascha Kaykas-Wolff (00:01:17):
I’m wearing shirt button all the way up and a cowl neck in your honor. So I appreciate that.

Anish Shah (00:01:20):
I’m loving it. Jascha is bringing out Jascha keeping the Brooks brothers at home and breaking out the breaking out the Brooklyn hipsters. So I’m, I’m really into it. and I, and if anyone knows me, reg knows me or talks to me regularly, I’m very critical of CMOs. I’ve met a lot of them throughout my career. I’ve walked away from those conversations 90% plus of the time thinking, wow, I’m not impressed whatsoever by this person. I don’t know how they got to where they are. I don’t know who hired them, but somehow they got there. And I’ve maybe had four to five conversations with Jascha throughout my entire career. And each one of them, probably each one of them actually changed the trajectory of my career at those exact times. And this is why I can very definitively say, Jascha is the smartest CMO I’ve ever met in my life.

Anish Shah (00:02:12):
The first time I met him, I was deciding whether to join a small company or a larger company at the time. In turn, you know, I, I was sick of consulting. I was tired of being a, I was tired of chasing people down for bills. I was just like a little burnt out. So I just wanted a nine to five. And so I, I asked Jascha do I go big company or small company? And he said, look, you’re asking the dumbest questions that, that like big company versus small company does not matter at all. There’s literally only one thing that matters in terms of the next company you choose. And that is just the team. Like, it doesn’t matter if you’re at the biggest rocket ship on earth or a, a startup that maybe won’t make it for the next year.

Anish Shah (00:02:56):
If you can’t get along with your team, if you don’t even them, if you don’t see you being cohesively, capable of performing well with them, you’re just not going to be successful and you’re not going to enjoy it. And then he walked me through some, some times within his career where he’s both been successful with teams and less successful with teams. And I was like done, I’m going to choose the team that I enjoy being next to the most. And so, yeah, I did that. I joined a startup that, that ended up not working out and, but Jascha completely right. I enjoyed, you know, I was there for roughly eight months and I enjoyed my time there and it was a company that ended up failing, but I, it didn’t really bother me at all. And then as I was sort of exploring recruiting Jascha actually introduced me to someone who runs a recruiting shop in in, in San Francisco.

Anish Shah (00:03:48):
And also said like, that’s actually a really good career that not, not very many people do and can be lucrative and it can be something you build upon. And I just didn’t take it very seriously. And sure enough, after Jascha kind of gave that push of like, this could be actually something that, that you could do that, that has some legs. I started diving a little bit further. And then off of the introduction that Jascha made, I was like, oh yeah, this is actually not the worst. And I actually dove a lot more deeply into recruiting after, after that conversation. So at two points, you’ve you’ve definitely influenced me heavily in my career. So I appreciate you taking the time time for that. Of course, of course. That’s

Jascha Kaykas-Wolff (00:04:27):
Really nice. I really appreciate that.

Anish Shah (00:04:29):
Yeah. Yeah. And absolutely. And within one of these worlds where like, you know, people who hit a certain echelon, it’s pretty hard to get a response from any sort of like email or text or anything like that. I mean, it’s great to, to see like someone like you who’s out there. Who’s like, oh no, let me give you some real, some real advice. Some no bullshit, real advice when you need it. And it’s, it was awesome. So thank you for that. Cool. And this is our series where we kind of interview the world’s best bosses. Obviously our firm is focused on talent. So we want to know how different companies and people think about and approach the subjects of hiring the best people, retaining the best people, motivating the absolute best people, and can, can officially get the responses that they need from, from all of these different, different levels. So thanks everyone for kind of listening in on this. And so we had asked all the registrants to throw up your questions and we sort of ranked the, the most interesting questions. So the first one, you know, how did you get to becoming the CMO of so many popular tech companies across so many industries? What, how, yeah. What, what, how how’d you end up there?

Jascha Kaykas-Wolff (00:05:41):
Yeah, well, I’m first and foremost, like very fortunate that I’ve had enough of a body of experience to where I can be an interesting candidate at lots of different kinds of organizations. So for, for me, you know, how you kind of maintain and a excitement about the potential roles that you have comes from kind a, a personal philosophy that I have. Let me kind of share a little bit more information about it in some context around it, cause it maybe it’s useful for, for others. I think it’s really important to find a, a space where you get to spend your time during the day when you’re working, where you get to be a tourist. And, and I don’t mean tourist in a pejorative way at all. I think about being a tourist a little bit, like going to an amazing city somewhere in the world for the first time.

Jascha Kaykas-Wolff (00:06:28):
And for somebody who’s lived there for a long time, you start to forget about all of what’s beautiful and amazing and exciting about that city. But for you as a tourist, the first time you show up in that city, your eyes are wide and you’re excited about exploring if you can kind of hold onto that idea of being a tourist in any kind of a role that you’re in. When you find a path with the skills that you have into an organization, as a brand that you’re excited about, excited about, it can become a really strong, really true for you professionally and personally. So in, in my case, what I’ve tried to do is be very purposeful about the kinds of brands and they are ultimately are all tech companies that I want to work for. So what I look for kind of with this idea of being a tourist first is ideologically, what the organization is trying to accomplish, right?

Jascha Kaykas-Wolff (00:07:15):
Are they building products that are about helping people be more efficient and effective in the workplace? That happens to be something I’m excited about. Are they technology companies that are focused on and care about empowering more people to be in control of their lives online? That’s something that I also happen to be excited about. It, it is a framework for me that helps me find brands that I’m excited about. And from there, it becomes an exercise in trying to find who the people are that are in that organization. And if you have a connection with them and in turn, they have a connection with you. My experience finding Mozilla was a really, I think, interesting one where the brand was an organization that, or the brand was built by an organization whom I’d had lots of respect for over time, but I really didn’t know a lot of details about I was trying to explore at that point in my career, how a mission driven organization, one that was actually governed by a not-for-profit could exist and be competitive with companies like Google and, and Microsoft and others that are out there.

Jascha Kaykas-Wolff (00:08:16):
And so I, I spent my time trying to learn more about why people had chosen to work there and what they felt like their biggest challenges were as a person who sat inside that organization and that kind of exploration for me, being excited about it kind of as a tourist, created a space where the senior management and the CEO at the time actually was excited about the potential to invite me in. So long story short is that if, if anyone is able to say that I’ve become a CMO or in my current role the, the President of Analytics in an organization, that’s interested in them please know that it’s incredibly purposeful. Like I want to be a part of teams that have a chance to be successful and are excited to work with each other and good people, good human beings, and organizations that are trying to accomplish something that I’m excited about. And, and when you’re purposeful about finding those connections and you put in the work to try and kinda meet the right people in, in those organizations, I think it opens up the possibility to have roles there. So, so don’t, don’t let it happen by accident, be purposeful about it.

Anish Shah (00:09:20):
That’s amazing. Thanks a lot for that. And before you actually took the full time job at Mozilla, you actually were very intimately knowledgeable about the organization. And you went, I wouldn’t say necessarily went, you, you, you, you took a unique path there, but you, you definitely took a path that some people wouldn’t have done, which might have just put extra work on your plate unnecessarily. I’d love to, I’d love to explore that a little bit and what you learned in terms of like the pros and cons and, and, and if you mind kind of explaining how you, how you got to know the organization before even joining.

Jascha Kaykas-Wolff (00:09:56):
Sure. Well, I, I actually think that the current organization and the current role that I’m in is a very similar scenario. And in both cases I’ve never felt like the existence of a role and my potential fit is the right way to make the equation. So I really do believe that it’s important to put in the work. Putting in the work to me means getting to know kind of how the organization’s performing and you do that by learning from people that are in the organization, which means that you need to spend time with them. In Mozilla’s case, I spent over the course of a four months, I believe time meeting with about 30 different people inside of the organization that was both in front of, and then inside of the interview process. Right? And part of the reason that that was an important investment for me, right,

Jascha Kaykas-Wolff (00:10:43):
Like compare that to a typical interview process where maybe you meet with five to seven people right before you make a decision and then make a decision about you. Putting that extra time in to make sure that they knew me, and I knew them made it very clear both to them and to me at the time that it was the right fit, right? The end result was that I ended up in a role where as an organization we were able to have a good amount of impact and grow the business and meaningful ways. And I was in a place where over the course of the last half of a decade I was very happy and satisfied and able to grow personally, and professionally. Lytics has been very similar. I’ve known the founder of Lytics for the last decade. The two of us have had a strong kind of friendship and even a good working relationship in the past.

Jascha Kaykas-Wolff (00:11:25):
And over the course of several months, I had the opportunity because they give it to me, to meet with different members of their team to learn more about the way that the organization was working and in turn them to learn more about me. And it was because of that kind of elongated, which maybe doesn’t feel great for everyone, but that elongated process of getting to know each other, that we can all be comfortable, that we’re making the right decision. Right. And you never remove risk in any situation, in any decision that you may make entirely. However, when you’ve got a much stronger knowledge about the way that an organization works, how teams have interacted with each other and what the product is trying to accomplish. I think it’s much the, the likelihood of success is much greater. And I think that’s an, that’s been an important lesson. And takeaway for me that I would expect will be a part of my professional journey, well, well, well, into the future.

Anish Shah (00:12:15):
Amazing. Thanks for that. And yeah, very, very much within our kind of interview processes with clients and candidates, a majority of the candidates are just looking to get to the final stage as quickly as possible with as few conversation as possible and, and, you know, push that, that push that timeframe as tight as possible. But, you know, there’s also a counterpoint where if you do lengthen it, if you do kind of take the extra time, you’ll really get to be able to hedge your bet a little bit more and understand what you’re getting into. So there’s also, there’s a lesson to be learned from, from having a little bit of patience there.

Jascha Kaykas-Wolff (00:12:49):
Yeah. I think, I mean, you and I have talked a bit about this in the past too. Like interview processes are oftentimes pretty dumb, right. And they’re very one sided . And, and I think it’s our responsibility as somebody who is a part of the process. If we’re on the side where we’re trying to hire someone, we need to be respectful of this, but if we’re on the flip side, we’re thinking about a role we need to force the space for the process to be about both parties, about you as the candidate and about the organization. And only when you create kind of that level of, you know, kind of a shared understanding that it’s a mutual process and not a one way process I think can, can you find a path through, to a successful role?

Anish Shah (00:13:28):
Amazing, that’s really great advice. And, and what I can say from, from, from helping lead a lot of these interview processes for different, for different companies, almost never does a candidate ever come in and say, Hey, can I talk to more people at the company? Can I do a little bit more research? Do you have some more numbers for me to dig through? Can I do a little bit extra? And when someone does do that in an interview process, you just see a CEO’s eyes light up, like, but they want to take more time with us. They want to sit in on some of our, our meetings without even being asked. So it’s, it’s not only just hedge your own bets and learn more about the company, but it makes you look really impressive that, that you’re genuinely curious about what’s happening within the company and not just looking for, you know, quote unquote J-O-B.

Jascha Kaykas-Wolff (00:14:14):
I certainly appreciate when someone who I’m excited about the potential to work with shows that curiosity, right? Like that’s an attribute that I think is super important in a person that you’re friends with, but it’s also a really important attribute in somebody who you might be able to work with. Like that, that kind of curiosity that want to be a lifelong learner is a really critical attribute in being a successful teammate. So, I love to see that.

Anish Shah (00:14:40):
Awesome. So our next question what’s the biggest risk you’ve ever taken in your career?

Jascha Kaykas-Wolff (00:14:49):
Well I think it’s probably unfair for me to call it my risk that I’ve taken in my career. Like many of us are in relationships and fortunate in some cases to have families that are built around those relationships. And in my case, the risks that we have taken as a family have oftentimes included not just a role that I might have an opportunity to, but and ask for our family to think about changing their lifestyle, like potentially moving, like over the course of the last 15 years. I think the biggest single risk that we took as a family was for us to leave the Northwest, which is the place where my wife was born and lived and spent most of her life and where I had spent quite a few years and had a, a kind of comfortable career and, and a nice career trajectory to move into the bay area.

Jascha Kaykas-Wolff (00:15:39):
And it, wasn’t just the kind of change of moving outta the Northwest into Northern California that is potentially scary and risky for a family. It’s also for me, moving out of large organizations where I had spent the previous several years of my career at Microsoft, Yahoo and, and a company called Webtrends into a startup, which is incidentally where you and I met for the first time. I was the first hire in marketing technically in this organization. It was the first executive hire outside of the founding team. And it was a 19 person team and company at the time. So the kind of the, the risk really was about us as a family, moving into an environment where there were a lot of unknowns and, and then individually kind of the risks were around identifying if what I felt I was capable of and excited about actually showed up on a day to day basis, moving into an organization where I’d be responsible for doing everything, not just looking for and building team support around some of the ideas that we had.

Jascha Kaykas-Wolff (00:16:35):
So it was a, a real kind of test of our family and a real test of how I thought I could show up in an organization and ultimately ended up being a risk that has paid dividends for us as a family. And I think for me, helped uncover some of what really gets me excited about what I get to do on a day to day basis, which is not be a thought leader, but be a “do leader” whenever I have the opportunity to, to kind of be in supporting and, and participating in the things that we’re trying to accomplish, not just talking about them and asking other people to do them.

Anish Shah (00:17:07):
Yeah, that’s great. You had to go from being a peer manager or someone who oversaw a lot of things to like, oh, wait, I have no one to do this. I’m just going to have to figure out how to do it myself? Was that, was that exciting for you or was it kind of stressful? Like, oh man, I have to learn how to launch an email or, or little things like that.

Jascha Kaykas-Wolff (00:17:24):
It it’s exciting for me, but I, I, I feel that kind of excitement on a day to day basis. I, I fundamentally don’t believe that I’m ever the smartest person in any room or any conversation that I’m in. So my, my kind of mindset is, well, I need to learn more. I need to spend more time and I need to put in more work than anybody else. And so the, kind of the ability to turn that part of me on, in any scenario that I’m in gets me excited. And and I, I, I hope to never lose that.

Anish Shah (00:17:51):
Nice. Yeah. That childlike wonder. Right. That’s awesome. Let’s jump into the next one here. What is your approach for rapid team assessment when you come into a new organization? How do you make the most out of a team you’ve inherited where some people might be significantly underperforming are performing?

Jascha Kaykas-Wolff (00:18:10):
There. There’s two things I think everyone should look to when they’re joining a new team to understand kind of who’s doing what and maybe who’s performing well and, and who has opportunities to improve. This is not necessarily from a manager’s perspective. This would be from a teammate’s perspective as well. And then I’ll that I’ll share a point of view as a manager of people on a way that you can kind of help teams normalize performance and, and then improve performance over time. So, so the, the, the number one thing that everyone should look for as a teammate, as a manager, as an individual contributor to the joint the team, is how well your teammates understand what success looks like and how it’s measured. So the, the very first thing that I would recommend doing that I do when I join a new team or start up a new project, is to spend time with each individual person in that organization, in that team, on that project to have them help me understand exactly what they believe success to be and how they’re going to measure that success.

Jascha Kaykas-Wolff (00:19:09):
It sounds really simple. And it sounds like maybe in no duh, you would probably do that. However when you start to have discussions with individuals on a team, in a project, in an organization, what you will find in a healthy team where there are lots of high performers is a very clear understanding of what success looks like. And you can see almost immediately when you start to interview people across an organization, a project, or a team that if they’re not able to articulate that, well, you’re going to have to move into a next level of assessment to understand where you’re going, need to spend more time or help the team be more performant. So that’s kind of piece number one for me. First thing, absolute first thing for rapid assessment is just getting an understanding of who knows what success looks like, how they describe it and how they measure, what impact looks like behind that success.

Jascha Kaykas-Wolff (00:19:54):
Step number two, from a manager’s perspective, when you join an organization to kind of make the most out of a team. That sounds not as human as I suppose, I, I would like it to be the way that the question is framed, right. I don’t think it’s our role to make the most out of a team. I think it’s our role as manager is to create an environment where everyone’s able to be their best selves. And the way that I like to think about that is by deploying systems, that teams are able to reinforce what we were just talking about. So if you are new to a team and you’re in a managerial position, one of the first things you can start to do is bring the team together against the critical areas that you understand as a manager to drive the most impact into the business.

Jascha Kaykas-Wolff (00:20:37):
When you bring people together, that’s not an obtuse term or even a, a strange concept. It’s quite literally think about your meeting structure and how you use meeting structure to reinforce an understanding of what priorities are being worked on and how those priorities are progressing and what impact those priorities are going to have. So, a very generic example, if you join a team as a manager, and let’s say it’s a marketing team, and the marketing team believes that their theory for impact in the organization includes growing awareness for the brand, for the product within a specific group of people. In some part of the world, one of the first things you can consider is bringing together all of the people at a higher frequency, let’s call it on a weekly basis. The team members who are responsible for driving awareness in the organization. You spend the first week going through an analysis of which projects, which programs, which individual tasks are on flight.

Jascha Kaykas-Wolff (00:21:33):
And then you take the burden as the manager of organizing all the work that’s happening in a way that is human readable for that group of people. And then you create a cadence with that list of priorities, so that you’re able to come together as a team and start to focus on communications each week when you come together, if that’s the cadence that you choose, that team of people from across the organization, who all believe that they’re impacting the awareness of the brand, that you’re part of, you’re going to help them communicate about what expectations they’re setting to their teammates that they’re going to execute against, and you can match that with progress. And then you can have a discussion around relative prioritization within the team. So I believe that it’s important and critical and a requirement of managers to make sure the team has a system that helps them all understand what success looks like. And when you do that, I think you can help a team be as effective as possible by helping each individual know how that they can show up and be their best selves.

Anish Shah (00:22:36):
Okay. That makes a lot of sense. So sounds like you’re, you’re, you’re, you’re essentially creating frameworks to, to help every person know where they should be and to help them let you know sort of what their priorities are, what their goals are and so forth, and just kind of consist, be level of consistency around that within your regular meetings.

Jascha Kaykas-Wolff (00:22:55):
Yeah. I, I think that, like one of the kind of fatal flaws of humans is that we oftentimes make an assumption that someone that we know, that we work with, understands what we’re thinking. And while it emotionally may be tough, it is our responsibility to not just believe that somebody understands what we’re thinking, but to actually express it in a way that is meaningful for them. And that may be in written communications. It may be in meetings where you’re live. It may be in some other way that is easier for you to communicate, but it is all about creating a framework where you can set expectations well, and you can help meet those expectations. And if you do that across an organization, across projects that you’re working on with individuals and teams, you create an environment where trust is the norm, and it’s not an anomaly and trust helps us, I think, be our best selves professionally or personally.

Anish Shah (00:23:48):
Absolutely. That makes a ton of sense. And then the second part of that question, maybe, maybe rephrase a little bit differently as you’re coming into your organization and assessing that team, and, you know, notice there might be some folks who maybe are underperforming versus what you sort of expect. I think the, the decision kind of tree for a lot of people who are coming in the situation is okay, do I invest a lot of time in coaching this person to help bring them up to, to where I’d like them to be? Or, you know, at what point do I say, you know, this person just isn’t going to work out within this organization. And there’s probably a better opportunity out there for them than this organization. Is there any sort of litmus or sort of like point where, you know, you kind of have to go one direction or the other?

Jascha Kaykas-Wolff (00:24:31):
Yeah. it, it is really specifically around setting and meeting expectations. So if, if you, through the process of meeting team members, identify that they’re a handful of people who can’t explain how the things that they’re focused on are impacting the business and they can’t explain how they measure success. It is important to create an environment where you can temporally, like in a short period of time, set up simple tasks where the two of you can agree on once they’ve completed them, right. Or once they’re finished working on them, that you’re both on the same page that could be developing like a plan that could be developing their KR’s, that could be a, a multitude different things. But when, when you have a question mark around the capability of a person, you, it is your responsibility, especially as a manager to create an environment where they’ve got an opportunity to be successful.

Jascha Kaykas-Wolff (00:25:19):
And you do that by creating really clear expectations with each other, and then following through to expect that those things are delivered on, like, in my mind, once you have identified that there is a gap, because there isn’t a, an awareness of how the work that, that they’re doing, that’s contributing to the business and you’ve set an expectation that you both agree is something you can deliver against, if something extraneous happens and it’s not possible for that person to do what they have said that they’ve committed to. Right? That’s an exception, but for the most part, because… If, if, and when you and I have set up what we agree on and you don’t do it, or I don’t do it, like we are not right for each other. And, and you need to make a move at that point.

Anish Shah (00:26:01):
Okay. That’s great. And again, pretty good framework to, it sounds like you’re not just going with your gut and saying, this person stays this person doesn’t, but it’s great that you’re creating a system and process for all of that. Cool. we’ll just jump into the next one. What’s the secret to onboarding new team members? How do you get them up to speed and incorporate it into the culture of your company?

Jascha Kaykas-Wolff (00:26:25):
But the, the, the responsibility of somebody onboarding into the organization successfully lies squarely on the shoulders of the person who is hiring them and the team that they’re going to be on. So there isn’t a secret there that’s just a an accountable kind of requirement that you should have if you’re a manager at the hiring. The, the kind of responsibility of you is the manager, the person who’s hiring somebody in has to be, to develop a plan for that person to be onboarded into the team, to understand what the business is trying to accomplish, what your theories of impact are, and how they’re going to fit into that puzzle. It doesn’t mean you have to do it all yourself. It just means that you have to be very specifically responsible for making sure every new person in the organization has that person who’s going to be their advocate to help them onboard.

Jascha Kaykas-Wolff (00:27:09):
When an organization is let’s call a more sophisticated and has thought about onboarding as one of the key success measures for their longtime health, what you will oftentimes find is that the people team becomes one of the best partners for departmental managers and managers of people, because the people team is thinking about what additional context can we help every new person in the organization have. So that, that additional context is a shared set of understandings that provide even more clarity around how and why someone is here and how and why that someone is going to have an impact into the organization. And it makes the job of the individual manager that much easier. So it is all about taking responsibility. That’s the secret, which is not really a secret as a manager for an individual that comes into the organization.

Anish Shah (00:28:06):
That’s great. Thanks a lot for that right there. How do you help your employees with their career development? Any, any best practices here?

Jascha Kaykas-Wolff (00:28:20):
I had a, a manager when I was at Microsoft named Meng, it was a, a very long time ago and, and Meng was very professorial. And so we, he would oftentimes ask me like, almost brutal type questions when we would sit down for our one on ones. And sometimes it used to frustrate me, especially early in my career. Cause I didn’t really understand what he was trying to do. And at one point in time, I tell this a story often, I went into a 1-1 with him and he asked me what I wanted to do. And I kinda looked at him like, I, I think you’re teasing me. I don’t quite know what this kind of professor riddle thing is that you’re asking me here and I immediately responded with, okay, well, I think you’re just trying to goad me and you already know what I’m going to do and what I want to do, because we’ve set our goals together.

Jascha Kaykas-Wolff (00:29:03):
I’m going to beat those goals. You’re going to give me a promotion and a bonus. And, and, and and, he is like, that’s not really the question that I’m asking. What do you want to do? I was like, I don’t understand what you mean. So he said, that’s fine. Just come back tomorrow and let’s have the conversation. So I come back the next day and I’m like, maybe I understand what you’re asking, but I’m not totally sure. He’s like, listen, you’re in a role right now. And you’re probably going to be successful in this role, but what do you want to accomplish over time? I’m like, okay, now you’re just really trying to get under my skin. I think that’s what you’re trying to do with me, Meng. And he is like, listen, let me tell you about my favorite business book of all time. It’s written by an author maybe that you wouldn’t have thought of as a business book, author Louis Carol.

Jascha Kaykas-Wolff (00:29:42):
So I went to a liberal arts school. I read a lot. I know that Louis Carol wrote handled books, maybe the one that we all know most is, do you know, Alice in Wonderland? I don’t no. Alice in Wonderland I don’t. No, I just easy. So Alice in Wonderland. So he tells me Alice in Wonderland. I’m like I don’t like where this is going, man. He’s like, no, no, just wait and paraphrase this. And I’ll paraphrase here too. He’s like, there’s, there’s this one part of Alice in Wonderland where Alice is lost. And she meets the Cheshire cat for the first time. She’s at this fork in the road. And Alice asked the Cheshire cat I’m lost, which way should I go? And he says, where are you trying to get to? And she says, I don’t know, I’m lost. Just tell me which way to go.

Jascha Kaykas-Wolff (00:30:23):
And he said, well, pick any path you want. That’ll all get you there. And, and then he said, okay, we’re done with this meeting, come back tomorrow and we’ll have another conversation. So I came back the next day and I’d been thinking about this. And I’m like, okay, I think I kind of understand what you’re asking me is where I want to go to, what I want to do professionally. And you’re asking me so that when I’m making decisions with you, that I know that I’m on the path that I should go to make sure that it’s not just contributing to what I need to do right now. But also to my future, he’s like, right. How do you do that? He’s like, well, I have a system for you. He was like, okay, great. So 15 years ago I got introduced to the system called Heart, Tree, and Star.

Jascha Kaykas-Wolff (00:31:02):
And this is still something that I think is incredibly important. I use it myself and I share it with the people that I work with as well. So Heart, Tree, and Star is somewhat simple and that the metaphors are kind of are what they are, but it starts with the idea that in order for you to be able to be confident that whatever decision you’re making, whatever path you’re taking, you’re moving in a direction that is important for you. You have to understand what your north star is. Your north star is simple. It’s the industry that you think you want to work in, the kind of role that you want to have combined with the amount of time that you think is reasonable for you to achieve that position, that role, that opportunity an example would be if I told you, well, I want to be the CEO of general electric.

Jascha Kaykas-Wolff (00:31:44):
And I want that to happen in three years. If I were to tell that to you, you might look at me and say, let’s might not be practical, right? Ambitious, but not practical. Cause three years probably isn’t the amount of time that is necessary for you to have the right kind of skills and experiences to get that role. So you start with your north star, it’s about the period of time that you want to invest in and the path that you want to take or where, where you want the paths that you choose to take you, you then match it with what I consider to be a very cathartic process of identifying the things that you’re amazing at. So there, we all have rough days, right? Like we roll outta bed and we’ve got sleep in our eye. Maybe we roll off the couch and we gotta pop into our next zoom meeting.

Jascha Kaykas-Wolff (00:32:20):
I mean, it’s just like some days just don’t work well for us. And there are still things on those days that are tough days, that we’re awesome at. You probably haven’t taken stock in what those things are. Maybe there’re as simple as you’re really amazing at writing emails. You can put together project plans, you can build a great presentation. You can do a great 10 minute extemporaneous speech. There are things that you are amazing at that just you are amazing at even on your worst days. So you write down that list, it’s called your anchor list and you match that anchor list with a similar kind of a process called your heart list. These are the things that you love doing. If I told you I have a job for you, a role for you, a part of your career path that I could sponsor.

Jascha Kaykas-Wolff (00:33:00):
And it included all of these things that existed in this heart list. This is only context of work. And the only catch was, I didn’t have anything to pay you. You might have to think about it. It’s not practical that you’d ever take a role that doesn’t pay anything, but you’d have to think about it because you you’re so excited about where these things are that you could spend your time on. So you’ve now got three tools to work with. You’ve got this north star, that’s helping you make decisions about which paths you want to take. You’ve got a list of what you’re great at, a list of what you love. You can start to make very purposeful bets on yourself. You can do that independent of, but oftentimes is a lot more powerful when you’re having this conversation with your manager, but you can make bets on yourself.

Jascha Kaykas-Wolff (00:33:39):
Those bets are the trees and the heart tree and the star. Trees a great metaphor because trees come in all different shapes and sizes, right. Sometimes to get to that north star, what you really need is great, vertical expertise. You need more and more strength and confidence in the areas that you’re currently working in. That’s your Redwood tree, right? It’s all about strong roots and vertical, vertical scale. Or maybe that north star that you’re planting for yourself includes more capabilities and skills that are closely related to what you love doing. So you have to extend your capabilities out to maybe it’s more like planting the banyan tree where you kind of reach out branch, you know, and, and kind of regrow other roots. So this system for me has been something that I have used for more than a decade now. And it’s something that I talk to most of my team members and teammates about, because I think it’s a great system that helps you be in control of your career path. Being in control of your career path is not just about your quarterly goals, your half-yearly goals, your yearly goals. It’s about being very conscientious about what you’re doing right now and how it has a relationship and the decisions that you should be making that are going to help you achieve that north star.

Jascha Kaykas-Wolff (00:34:51):
So that’s my system.

Anish Shah (00:34:53):
Can everybody listen in and see how any conversation anyone can get with Jascha gets the craziest knowledge bombs? That, that right there is just so useful. Thank you for that. Yeah. Thank you. I, I really have no follow up there.

Jascha Kaykas-Wolff (00:35:13):
Well, we’ve written about this it’s this is not a, a unique system by the way, Meng taught it to me while I was at Microsoft that has a relationship to some Microsoft systems. And if you just search for heart tree and star, there’s actually quite a bit, that’s written about it all over the internet now. Including some stuff that I’ve put up there and teams that have worked at that as well.

Anish Shah (00:35:33):
That’s amazing. Thanks for that. I, I guess what I’ve learned when I’ve, when I’ve asked…so, you know, given, given what our firm does, I do get friends or friends or friends coming to me, sort of asking for career advice, what to do next, whatever it might be. And then my first question back to people is what do you want to do? And more often than not what I get from people is, well, my last job was doing this. Therefore I’m qualified for X, Y, Z, and, and then I have to go back to them and say, that’s not what I asked you. I didn’t ask what your, I didn’t ask, what your resume qualifies you for. I asked, what do you want to do? What is your ideal job? What is your ideal way to spend, you know, five days a week, roughly 40 hours, 40, I’m sorry, five days a week, 40 hours a week, whatever.

Anish Shah (00:36:23):
And I have to repeat that three, four times because they will still go back and be like, well, my degree is like, I, again, I did not ask you that. Yeah. It’s fascinating how people get stuck in that cycle, because of course, when you’re applying to jobs, you’re just thinking, what am I qualified? What am I qualified for? Because you’re thinking of what can I get immediately? What can I land in the next month, two months, three months. Yeah. Not what can I land in the next two years, three years, four years. And it’s fascinating once you get people thinking, okay, in three years, I’d love to whatever it might be. You can then work backwards with them. Like you were just saying another tip I’ve noticed to help people get out of that, that rut of just like, what am I qualified for next?

Anish Shah (00:37:04):
What am I qualified for next is go on, go, go find person who has the career you want on LinkedIn, go look at the companies, go look at the roles. Maybe think of someone who you listen to on a podcast, whatever it might be, go look at how they got to where they are and then go find their LinkedIn, whatever it might be, find five of those types of people who you really like their, their, their trajectory, or like where they’re at currently, and then work backwards. Are you noticing a pattern at that point? All five of those people did this and then this, and then this and you know, some people might say, well, oh, I don’t have, I don’t have this particular thing on my resume. Therefore, you know, I can’t get to where they are, but Jascha, both you and I, you know, one of the things I hear frequently is like, well, I didn’t go to the right school, but both of us did not go to Ivy league schools. I went to a school where literally anybody gets into and you know, that hasn’t stopped being able to move forward in my career. I’ve noticed a lot of people say that, well, I didn’t get into a top 10 school. Therefore, no one would ever consider me for this would do it neither.

Jascha Kaykas-Wolff (00:38:09):
I went to a tittle liberal arts private school in Southern California. And I loved the experience and I carried a chip on my shoulder for years and years and years that I wasn’t an Ivy league kid. And it doesn’t matter as long as you can help tell the story about why you can be impactful inside of an organization. I’ll tell you one quick, maybe funny story about a maybe a kick in the pants that I got in my career where I didn’t get a role that I was excited about. So I interviewed with a company called Invidia. If anybody was familiar with Invidia, it was several quite a few years ago, maybe in a decade plus ago. And I interviewed with Jensen, it was for a VP of corporate marketing role. And we sat down together and about 10 minutes of the conversation, he’s like, tell me your story.

Jascha Kaykas-Wolff (00:38:50):
Like how, how do we fit into kind of your story over time? And so I immediately launched into like, well, let me tell you about what I did at this job. And here’s the impact that I had and let tell you about what I did at this job. And here’s the impact that I had. And about seven minutes to 10 minutes into me getting about three quarters of the way through my career to get up to this particular role, he was like, listen, that’s not the question that I asked. I just wanted to understand your story and why we make sense for you right now. And I would expect that somebody in the kind of role that you’re in ought to be able to do that. And so I was like, heartbroken. I was like, this is like, I just got like in, like in person turned down because I couldn’t tell a story.

Jascha Kaykas-Wolff (00:39:29):
And that’s what I thought my role was. So I kind of internalized that and I been thinking about it a lot. And I ask that question, oftentimes when I meet people that are new, like tell me the story, your story, and how we fit into your story and the organization I’m part of, and it, it goes to everything that you’re saying, like part, part of what we have to be very conscientious of is how we tell the story that we are in control of our career with. And, and it’s something that’s looked over because we were a little bit like cobbler’s children. Like we just don’t spend the time on ourselves and the way that we do and the things that we work on. So taking a little bit of time to focus on yourself, to do that heart, tree, star exercise, to think about the career path that you’re on and to practice and think about, and practice and think about, and practice and think about your story is really important.

Anish Shah (00:40:19):
Absolutely. That makes a ton of sense. And also just that the opportunities that, that don’t come to you weren’t right for you in the first place, right. I’ve absolutely been rejected from certain opportunities strictly on university. And those looking back on it, you know, those particular companies, you know, many of them ended up being successful when you look at their LinkedIn, literally every person went to Stanford. It wasn’t right for me. I wasn’t going to be the right fit anyways. So it doesn’t matter.

Jascha Kaykas-Wolff (00:40:47):
It has to be mutual. It, it really does. And, and if someone or some organization doesn’t think that you’re the right fit but you really do, like, that’s not an equation that would’ve worked for you anyway. So it it’s really important to find that kind of mutual connection.

Anish Shah (00:41:02):
Absolutely. Thanks for that. So jumping into the next one here what is your favorite team building practice?

Jascha Kaykas-Wolff (00:41:09):
Well I’ll just cue on, on one thing, which is my favorite. I think there are a lot of really wonderful tools that you can use professionally to help your team kind of grow closer and closer together. But probably the, the kind of most important for me, my most favorite has a lot to do with how I grew up and where I grew up. So I grew up on a, a little hippie commune outside of Eugene, Oregon, like suffice it to say we were very, very poor growing up. My mom took care of myself. My two younger brothers did everything she possibly could for us. And I remember so distinctly growing up you know, like one day on a Sunday we would make a bunch of black beans. And then we would, that’s what we would eat for the week. Right? Like every day it would be some different thing.

Jascha Kaykas-Wolff (00:41:49):
Maybe that was a tortilla and the next day is something else and something else. So for, for me, I’ve always had this kind of deep, want to be in environments where I can create a connection around food because it was something for me as a kid that it just, it didn’t work out the way that I wanted to all the time. It’s not that I grew up in a and I had a, a horrible childhood just, but because I didn’t, but, but this context for me makes it super important when I am a part of a team to bring food and the experience around food together as one of the most important and my favorite team building practice. So I think it’s incredibly important to spend time with the people that you work with and eat with them right. To experience different kinds of food with them.

Jascha Kaykas-Wolff (00:42:32):
And I think it’s equally important to not just do that with the team that you spend your time with, but also to be very purposeful about bringing the people who support your team together as well. So one of, one of the things that I like to do when we’re in environments, where we’re not locked down is make sure that a couple of times a year we’re bringing together our significant others, our partners, and our spouses on our key teams and sharing meals together. And that could be at people’s homes. It could be at restaurants, but that kind of communal offering and that communal experience I think is critical in building really strong teams.

Anish Shah (00:43:07):
Amazing. Thanks for that. And I guess in times like this where it’s a little bit more difficult to do any, any other tips or, or advice on, on how you can get that, that same feeling of, of bringing everyone together around a dinner table?

Jascha Kaykas-Wolff (00:43:24):
To, to be determined. And I actually don’t think that it’s easily replaceable, right. I, I don’t, I think right now we have to focus very much on how we create communication flows that allow for us to feel connected and practically be connected around things that are important for the business. But I, I, I don’t quite have the answer. In fact, I don’t have really good theories yet around how we can be in this kind of environment and and really try and recreate those kind of in-person experiences around a dinner table. So if we’ve got suggestions, I’m all ears, but it’s something that I care deeply about. And, and I’d like to find kind of new ways to explore new tools. I’m just not convinced that it’s sitting around and eating together on zoom yet.

Anish Shah (00:44:07):
Our, our team actually did a zoom happy hour a week ago, just, just, just trying to recreate the whole thing. So hopefully something great that does pop up with that, I mean, just being a, just being an avid follower of your Instagram feed when you were at Mozilla, you were on a plane very regularly because you managed large global team teams. And I was always sort of curious, like, is it, is it necessary to be on a plane so regularly, if you do manage global teams, do you need that in person? Do you need that in person interaction? Now that we have Zoom now that we have Slack, now that we have all these communication channels, can that slow down? You know, now that we have all these communication channels?

Jascha Kaykas-Wolff (00:44:52):
Yeah. It, it can and should slow down. Like we, we don’t need to be out and traveling in the same way that we did. There’s some notable exceptions. And part of the reason that I traveled as much as I did with Mozilla is that we operated marketing programs in, I think our focus countries were five different countries around the world. We had teams in 17 different countries around the world, and it’s important when you’re making decisions, in my opinion, that are directing investments in marketing programs to have a better understanding of cultural differences in the places that you work in. So I thought it was important and I made investments in spending time in Germany and in Taiwan and in China and in different parts of Europe like France and, and, and the UK as well, not because I wanted to just be there with the teams that we were with, but because I thought it was really important for me to understand the implications, the decisions that I were making and the impact to local teams and see the performance of local program. So it was a cultural empathy that was particularly important. But I, I don’t think you have to be there all of the time. And I don’t think you need to travel in the capacity that we thought that we did historically.

Anish Shah (00:46:10):
Okay. Makes sense. So maybe you can slow down a little bit, but there’s still, there’s still a ton of value from you going out there. And, and I always hear this when I, I ask people this a lot. Right. Because I, I, I don’t travel very much for work and I avoid traveling very much work. But I do run a company where we have people in roughly three different locations. Right. And, and when I ask people, is it necessary to travel? Is it necessary to, to, to go see those teams in person? The answer I get from people who do advocate for, for needing to travel regularly is you know, one word it’s it’s generally face time. Do you, do you, do you agree with that or do you feel like your answer for why it is necessary? Goes, goes a little bit more, more deep than face time?

Jascha Kaykas-Wolff (00:46:53):
I, I don’t think face time is a, is the, the right response to why we need to travel. I don’t. Okay. I think we have to work a lot harder when we’re in environment, like the one that you and I are in. Right. Like, I, I can’t let myself be distracted while we’re talking, because I, I want to pay attention to your body language. I want to pay attention to what you’re looking at. I want to pay attention to what’s happening around you, because I, I want to interpret the context so that I can be better for you. And for me in this conversation. When we are together physically, I think we can be a little bit lazier because we can fall back onto a lot of our other senses. And I’m not saying that’s wrong. I’m just saying that as long as we’re willing to work a little bit harder to be intentional about the communications, we can have a lot of the same face time and the same benefits of face time, just like we’re doing right now, that we can, if we happen to be together in real life.

Anish Shah (00:47:47):
Okay. Makes a lot of sense. So it’s sort of the it’s sort of the dedication to that, to the time that you’re spending with someone, the, the presence that, that really matters. And maybe the actual in person face to face can, can slow down a little bit from, from where you, I guess you, you previously were with Mozilla.

Jascha Kaykas-Wolff (00:48:05):
Yeah. I mean, I, I think we’ve all read a lot about like Zoom fatigue and it’s a super popular thing to kind of write about right now. It, when, when you’re really paying attention to the people that you’re working with and spending time with, and you’re doing it in an environment like this, you are going to be emotionally drained at the end of the day and probably physically drained as well, because you do have to work harder because you really only have your eyes and your ears to read the context around that person and how they’re interacting with you with, and, and I think that’s the byproduct of right now. So finding a balance would be good. Like I said before, I don’t think that in real life goes away, but I don’t think that it’s necessary in the capacity that it was, because I think a lot of it was us taking advantage of all of the other senses that we have and being a little bit lazy and we don’t need to do that. Right.

Anish Shah (00:48:57):
That makes a ton of sense. I want to be mindful of your time. It is 3:26. I don’t know if you have a couple more minutes once we hit that 3:30 end mark, or how are you doing over there?

Jascha Kaykas-Wolff (00:49:09):
Yeah, we’re okay.

Anish Shah (00:49:12):
All right, perfect. We won’t go too much longer but we got a couple questions here. Given the uncertainty brought on by COVID 19, how do you encourage leaders to build or create co-create scenario planning into their cultures moving forward?

Jascha Kaykas-Wolff (00:49:28):
Yeah shared understanding is the absolute, most critical encouragement that I can give to any leader right now. I’d probably give you the same kind of kinda recommendation or encouragement three months ago. And I would probably give you similar types of recommendations eight months from now, but right now it is even more critical. So how do you create shared understanding? And I think this is what’s most critical being very purposeful about how you communicate within an organization and laying out strategies, creating a space for feedback on strategies, taking that kind feedback from strategies and actually changing or augmenting what’s appropriate sharing how feedback was collected and what’s been changed. And then getting actual acknowledgement that someone’s bought into that strategy. Like being super purposeful about that shared understanding is what we all have to do right now. So if you are in a process right now where your organization has to change what it’s doing, your responsibility as a manager, and as a leader, there is to understand how you can best clearly describe the strategy that you’re trying to deploy, create spaces for your team to provide feedback against it, and then empower your team to create plans, to execute against that strategy.

Jascha Kaykas-Wolff (00:50:49):
And you can’t do that in closed board rooms, right? You have to do that in a much different venue right now. Because so it’s even more important for us to create that context that shared understanding around the path that we’re on than it ever has been. And that’s the big encouragement here. You’re kind of doing the same work. You just need to be a lot more open about it. I need to be even more purposeful about how you create feedback loops within your teams within the org.

Anish Shah (00:51:16):
Okay. Makes a lot of sense.

Jascha Kaykas-Wolff (00:51:20):
One of these times you can be like that doesn’t make any sense.

Anish Shah (00:51:23):
With a new work from home reality, how do you recommend leaders to actively practice coaching slash mentoring when remote from their teams?

Jascha Kaykas-Wolff (00:51:36):
Yeah. I, I was turned onto the idea that mentoring and coaching could be in a remote environment about three years ago and, and worked with a handful of really great coaches personally in only remote environments when I wasn’t forced to, and I’ve gotten a tremendous amount of value around it. You you’ll definitely hear some repeated themes from me, I think right now, if you are a leader who is taking on an active mentor ship responsibility with a team member, or if you’re a mentee that is currently engaged with a coach, that could be somebody who’s in your org or somebody who’s a support for you outside of the org on both sides, your responsibility is to be very purposeful about what you’re trying to accomplish. And I think we have a tendency and we can be on occasion a little bit lazy if I’ve got a mentor mentee relationship.

Jascha Kaykas-Wolff (00:52:26):
And I see that person in real life, we may grab a coffee and like just chit chat and chit chat and chit chat as we’re walking around somewhere. Because when we sit down in a zoom meeting or whatever, and we’re talking about an and, and we’re talking about something that’s personal to me, that’s related to what I need as a mentee or what I’m searching for as a mentee, or if I’m trying to discuss things that I think are important for you to take away as a coach or as a mentor, like we can’t let that happen by accident. The kinda serendipitous connections have a much less likelihood of happening. So this new reality that we’re going to be in for the next bit of while, if you are a leader who is a mentor, if you’re a leader who is a mentee, you need to be very purposeful about what you’re showing up to discuss. Don’t leave it up chance, have your agenda, spend time beforehand to write it out, think it through right. Set expectations. When you sit down and each here’s what I want to talk to you about today. These are the things that I’d love to get your feedback on. Is that okay with you? And if you say yes, great. Now we can start in that conversation, right. Be intentional, be super purposeful. Hopefully that will continue kind of post this environment being purposeful. But right now it’s more important than ever.

Anish Shah (00:53:42):
That’s amazing. I’ve noticed a lot of people when you give them the advice to just speak up and say what, say what you’d like. It, it, it creates a certain level of anxiety for them just to even, and it doesn’t even matter necessarily where they are in their career or, or how smart they are or how, how much their boss loves them or the organization loves them. I’ve just noticed that people really have trouble speaking up and, and saying, this is what’s working for me. This is kind of not what’s working for me. And this is where I’d like to go. So hopefully having like a little bit more of the framework that you lay out can help people understand can help people even just jot down those things on paper that they’d really like. And then, you know, hopefully eventually get the nerve to, to speak up to their boss or whoever they think and can have a real impact to them, whether it’s even just a mentor that they don’t even work directly with whatever that is. I don’t know if there’s any advice for, for someone who does have a little bit of that anxiety of speaking up. Yeah. But is, is a really high contributor.

Jascha Kaykas-Wolff (00:54:44):
Look, I, I sit into that category. I’m an introvert. I don’t get my energy from being around big groups of people. And, and so I, I really want to be in a scenario where I feel safe to be able to share how I get through that anxiety, if it’s with my boss or board members or whomever, is that I’ll be really clear about what I’m asking for. So I’m going to, I will ask for permission. I would like to do the following kinds of things in our time together, but I want to check in and make sure that that’s okay with you, if that meets your expectations. And that sounds kind of strangely formal, and it is the, it’s the tool that I use to kind of break through the things that I thought might be uncomfortable for me. So make the expectations clear up front. And if you do that, that’s a big part of getting through whatever anxiety, at least for me, that I may be dealing with, or they may be, you may be dealing with at the time.

Anish Shah (00:55:32):
That’s great. And it probably gives you a little bit of confidence when you’ve, you’ve started off with that sort of like that sentence that allows someone to bat it away and you get some of that approval, then you’re like, okay, well, this approval cycle is, is going to continue and continue. So building confidence is just so huge. Let’s see here, let me see what makes a good marketing leader, which attributes do most appreciate and the leaders around you.

Jascha Kaykas-Wolff (00:55:58):
Yeah. There, there are two that I think are critical. There’s more than that obviously, but two that I get excited about one like somebody who is curious, that is a kinda lifelong learner. So curiosity would be the attribute. Lifelong learner is kinda what that person shows up as I think is incredibly important. Doesn’t matter what stage in your career you’re in. Like I get excited about marketing leaders and leaders in general, who I know are excited to try and learn new things. The second thing that I think is incredibly important, and this is really specific to marketing leaders. Like I want to see a, a strong business acumen. I don’t know how to break that down as an attribute of a person, but when, when you find a person who has had experience in marketing and had leadership roles in marketing and is growing their career, and they are a great business leader first and a very capable marketer, second, and a super curious person, who’s going to kind of learn and want to learn new things over time. Like the probability of that person being an awesome teammate and an awesome partner, an awesome team member, right. Or a boss is a lot higher in my mind

Anish Shah (00:57:02):
That makes a lot of sense. And a lot of lifelong marketers I’ve interviewed sort of feel like they’ve already achieved the answer to everything through, through growing through the ranks from a previous organization or whatever that might be. And that curiosity is just gone. And then it’s just, when they jump into their next role, it’s just, oh, when I was at this other company, we did this. So that, that’s why we’re doing it here. And, and it worked, don’t worry. It worked. So we’ll just, we’ll just do it here. And, and it does not always work across the board, so, yeah. Yeah, I love that. Kind of what you mentioned in terms of business first marketing next.

Jascha Kaykas-Wolff (00:57:35):
Yeah. I, I think that we all should aspire in every role that we have, especially as we going to move up in the hierarchy inside of the business, we should expect that we are becoming better and better, better business leaders. We come from a specific discipline expertise often. And, and that’s what makes us unique in our approach as a business leader, but we all ought to aspire to be the best business leader we possibly can be. I think you, you’ve got an opportunity to learn. We all have opportunity to learn so much from the people that we spend our time with professionally, as long as we’re open and willing to be great learners. Like I, I work with so many amazing people. Nalytics now from our head of HR, to our CFO, to, we have a brand new head of product marketing, and I had of services that we’ve been together now for a month and a half. And I feel like I am getting to learn so much because of their expertise and their different approaches. And you know, I like I’m, I, I feel really privileged that, that part of my brain isn’t shut off where I’m still really excited about learning from different people and learning kind of new tools and, and new skills. And, and I want to be around people that do that as well.

Anish Shah (00:58:36):
Amazing. so we have one more question from the audience and then we will get all of your different properties to plug Jascha the podcast, the book, the company, all of that, because, because you’ve got a few thanks for all this wisdom. Jascha, if you are pitching yourself for a role that align with your north star, but doesn’t make perfect sense based on resume, what can you do to tell an impactful story and really stand out any more tips?

Jascha Kaykas-Wolff (00:59:00):
Yeah, well resumes, don’t tell a story and, and that’s going to tip them for one. So every role that you’re thinking about, if resumes are a part of it if a written resume is a part of it, you should be adjusting your resume for that particular role, so that it matches the story that you think is important for, for you to, to kind of help make them see you and in their organization and help see is their organization as a part of your story over time. So one resume is don’t tell the story, like you gotta make the resume, make the story with you. That’s not to say make the stuff up. Yeah, obviously .

Anish Shah (00:59:41):
Yeah. And, and what I, what I would add to that is, is, is just from, from our experience, obviously interviewing a ton of candidates and having, watching them go through the interview processes and different companies, I would say that unless being pushed to do extra work by the actual hiring company, it’s very rare that we seek any candidates doing extra work. Yes. So let’s say you are more of a product marketer, but you are about to interview for a role that has some product marketing and also some growth marketing step into that interview process by outworking all the other candidates. Yeah. Go and, you know, go and dive into that. Website’s the company’s website and find all the things you would fix, go and figure out what their SEO rankings are, go and find their ads and see what you would change. And, you know, don’t live the interview process.

Anish Shah (01:00:30):
Don’t pretend to be a expert in growth marketing when you know, you’re not, but show up with actual materials and say, Hey, look, this is me trying, this is me using my business. And I think it goes to what Jascha was saying also about being a great marketing leader. Number one, business sense. Number two, curiosity, if you have, if you have good business sense, you can do some level of analytics. You don’t have to know each of the platforms inside and outward outside. You can show your thinking within some of the first initial chats. And we’ve seen that work really well with certain candidates getting, getting hired into roles where other candidates were significantly better on paper. For example, one of the companies that we we hired for the person who ended up getting hired did not have all the marks on the resume that the, the hiring manager wanted.

Anish Shah (01:01:21):
Also culturally, this company was Ivy league from top to bottom. This person went to a state school. What this person started doing was putting together presentations without being asked. He started sitting in on meetings without being asked. He started interviewing some of the agencies that the company was interviewing. So if you, and look, some people get burned by this and they feel well, Hey, I, I took that approach this one time I put in all this extra work and I didn’t get hired. So screw that I’ve so you just have to know going into it, there’s that risk that you’re going to put in a lot of work and, you know, you may not get hired, but you also want to go into this process knowing that you put it all out there, you didn’t leave anything on the table. And so that if you don’t get hired, you can’t necessarily say, well, you know, I didn’t do everything.

Anish Shah (01:02:08):
I hedged my bets a little bit. You know, I only had a few hours to put into researching the company. And I think that’s the best advice I can, I can give outwork, every other candidate do as much free work as possible if you really, really, really want to role. And at the very least, and, and at the very least you’re that CEO or hiring manager is going to notice you. And then six months later when they have something that you’re more qualified for or even if that person who they hired doesn’t work out, you’re going to be one of the first phone calls.

Jascha Kaykas-Wolff (01:02:41):
I, I think it’s awesome advice. It’s number two on my list. The first is your resume. Doesn’t tell your story for every role. So make it, make it, do that. And the second is like, do your homework, right? When, when I got the role at Mozilla, part of what I did when I was meeting all these different people across the org is actually went out and did my own research. So I hired Google. I spent a couple hundred dollars at the time, which seemed like an acceptable amount for me to spend so that I could go understand what I thought the key audience of this organization were and what they thought about the company at the time. And that informed the point of view that I came to the table with and said, listen, I think I know how that organization works because I spent the time here.

Jascha Kaykas-Wolff (01:03:18):
I have a point of view into the way that I think we need to be positioned based on this research that I did, right. This may not all be correct, but what I’m trying to share with you is a part of the, what you’re going to get with me, which is the system thinking and the processes that I’d like to make sure that our teams are using. And even if I didn’t get the role, like it, would’ve been fine. It’s an okay investment for me to make, because it gave me confidence in my processes, as much as it in this case gave confidence to the team that I was joining.

Anish Shah (01:03:44):
Absolutely. and there’s a, there’s a trade off. There’s a lot, there’s a big debate that a lot of people kind of throw out there in terms of free work versus not, you know, and they, they, they feel like it just hurts them on inside doing free work. But what I can tell you is the more senior you get in any industry the closer you get to the sun, the more free work you’re doing. And, and that’s what I’ve seen across the board. Ceos of major companies are doing free work all the time to get the next thing that they need. Investment banks are doing free work all the time to close that client down the road. When I was consulting for, for, for companies, I would just go in and rip apart all of their, all of their marketing strategies for free.

Anish Shah (01:04:27):
And that was part of the pitch. If you’re running any kind of agency, you’re putting a ton of hours into pitching every particular client, that’s all free work. It’s just, there’s higher stakes involved, maybe higher dollar amounts involved, but the higher you get, you’re just doing more and more free work. Yeah. So really get out of this mentality of not putting in that extra work, just because it’s, it’s unpaid because it’s not going to go away. if you want to, if you want to always never do free work well then you should not grow your career because it’s just a natural, it’s just a natural thing that’s going to happen.

Jascha Kaykas-Wolff (01:05:00):
I think that the, even the framing around it being free work free work is a challenge, right? It’s like if, if part of your goal is you want to be a fit and healthy person and you choose to not go to the gym, right. Or, or to exercise, like you’re probably never going to be the fit and healthy person that you want to be. If you have an objective professionally and you want to get to somewhere, like you take all the opportunities you can to practice and, and to work out. And every time you have an engagement with a new organization where you’re thinking about a new role or a new project, if you’re practicing, if you’re going and doing that workout in advance, you’re not doing that workout for somebody else. It may happen that those things make a connection together because you have a shared approach and a shared understanding, but you’re doing that workout for yourself. And, and I think that’s a good framing, at least in my mind for why you would do the work, why you would spend the extra time you’re doing it for yourself. You’re not doing it for the organization.

Anish Shah (01:05:46):
That’s amazing. And this is why ya is the best CMO in the world. I call it free work. He’s calling it, working out and, and practicing. So it’s, it’s a nice, it’s a nice rebrand right there, which I I’m really into. You have a lot of things that, that you’ve done. You have an amazing company, which we haven’t heard much about just yet. And you also have a podcast. You have a book would love for you to plug that before we before we head out.

Jascha Kaykas-Wolff (01:06:10):
Awesome. Well, I’ll, I’ll, I’ll tell you a little bit about the organization that, that I was fortunate to be able to join a couple months back and, and maybe end on the podcast, which is kind of a labor of love. So I I’ve spent the last 20 years, as I mentioned, working in go to market executive roles in different kinds of organizations. And there’s like one real big challenge that I’ve always had. And I think all of us, especially for in go to market position to have, is that we, we’re always trying to understand who our customers are a little bit better because when we do that, we can give them a better experience. And when we give them a better experience, we can help our business be more successful. We’ve been investing in like marketing technology over the course of the last 15 years.

Jascha Kaykas-Wolff (01:06:46):
Now, 12, 15 years, everything from, you know, like log file analytics and the web trends and amateurs to CRM, to marketing automation, to DPS, and like pick your, your acronym, like fundamentally everything we’ve been doing, all these investments we’ve been making have been all about. How do I understand my customer a little bit better so that I can give them something that gives more value to them so that I can help my business be more successful. Lytics was started about six years ago by a person who happened to be very good friends with James McDermot and his as a friend, Aaron Raden and, and their belief was that. And is that as an organization, you have enough information about your customers so that you can know them a little bit better. You just don’t quite know how to put that to bear into practice.

Jascha Kaykas-Wolff (01:07:30):
And so they, they kind of created this category that we now talk about quite a bit called CDPs customer data platforms. They kind of coined the term a few years back and their approach has been quite different. So if you’re a business who has access to information because your customers have given it to you, so let’s say behavioral information on your website, maybe they’ve given you some information through purchases or CRM or, or, or what have you, what they do. And what we do, they, we do is we help take all that information. Not some gigantic big project to connect together all of the different data sources in your data lakes, but just the right information to be able to help you as a business, make better decisions about what to do with your customers right now. And, and the team has built up a platform that is kind of fundamentally CDP.

Jascha Kaykas-Wolff (01:08:16):
So it connects together data sources from lots of different locations, but very distinct and unique in that it uses machine learning to make recommendations for decisions that marketers can make everybody from the marketing executive down to the email marketing manager. So we, we built a CDP that helps businesses make better decisions so that their marketing teams can be more impactful. And it’s kind of, for me, this kind of culmination of this professional journey that I’ve had looking at spending and building teams that are focused on technology and process. So to be a person who’s responsible for a big part of this business is really exciting to me. And, and if making better decisions so that your business can be more impactful within your marketing organization is interesting. Like this is the kind of technology investment that you absolutely have to be making right now, as most businesses are transitioned fully or in the processes transitioning almost fully online.

Jascha Kaykas-Wolff (01:09:05):
So, so I’m, I’m excited about what Lytics does and, and where I think as a business we’re going to go and where the industry is going to go overall. That’s what to do all during the day and the night and the weekends. And in addition to that my friends, Cindy Raman and I for the last few years have been recording a podcast called this is your life in Silicon valley. He was the kind of owner of an and manager of the Bal, which is a local San Francisco online magazine. For, for several years, it’s now owned by medium. And while he was with the Bullit, he and I started talking about there being a lack of kind of cultural insights into San Francisco that were available to us, accessible to us in a podcast form. And so we, we decided we would try a podcast together and started with interviewing people like Kara Swisher and Mike Isaac, New York times, and, and VCs like James courier at Amex.

Jascha Kaykas-Wolff (01:09:56):
And, and then over the course of the last few years, we’ve gotten everybody from governor J Insley to, you know, many of the biggest dating sites in the world CEOs to the CEO of Instagram. And yesterday we just released a new episode with Austin Allred. Who’s the CEO and founder of Lambda school. So it’s a kind of this interesting hodgepodge of amazing guests who all have a point of view on the bay area. And we don’t break news. It’s talking about kind of, what’s interesting and going on in culture in San Francisco, how it relates into the businesses that we work and, and kind of the fetishization of the bay area that has grown out into all different parts of the world. So it’s a really, just a personal passion and a lot of fun, but if you get a chance, highly recommend checking it out, this is your life in Silicon valley. This we’re on our almost fourth season now with close to 60 different interviews.

Anish Shah (01:10:43):
Awesome. And two more plugs if you’d like you have a book, and then maybe if you’re hiring for your team, someone on here might want to be dying to work for you. So what, what, if anything, are you hiring for

Jascha Kaykas-Wolff (01:10:56):
Cool. We’re taking a look at our services team in particular. So we’re looking for a great solution architects at technical account managers project managers, program managers, those kinds of roles are, are generally ones that we’re always excited about if you’re into ML. And, and you’re into graph databases and the application of graph databases into marketing work. Also a very cool place to, to take a look at. I, I, I wrote a book a few years back with a, a, a buddy of mine in, in Portland it’s called growing up fast. It’s kind of more of a, a business philosophy book than it is a kind of a practical business book. It’s about the kind of need for businesses to recognize that there are two sometimes in conflict, but absolutely two different systems that we need to work within kind of mom and dad.

Jascha Kaykas-Wolff (01:11:42):
So to speak on one side, it’s all about kind of functional pragmatism. Like how do you set up an organization that knows how to hire people? Set goals grow have individuals with career paths. And the other side, the mom, so to speak is all about thinking through how do we be more effective and successful. And that isn’t necessarily about the kind RO structure of the organization. It’s about the way that we work. And so this book kind of growing up fast, talks about how we need to find a balance between kind of the patriarchal and matriarchal functions or systems within an organization to truly be healthy, quick read too, an audiobook.

Anish Shah (01:12:17):
Amazing. Amazing. well, thanks a lot. Jascha thanks for, thanks for dropping knowledge bombs for for about 75 minutes here. And anyone who’s interested in working for Alytics L Y I T I C S check out their jobs page. You get to work for an amazing boss like Jascha. And yeah, again, thanks

Jascha Kaykas-Wolff (01:12:40):
So much, man. Thanks for having me. And I’m going to go take this calx sweater off now and, and get back to my suit jacket with the Bo square.

Speaker 4 (01:12:47):
This is wonderful. Thank you.

Jascha Kaykas-Wolff (01:12:49):
thanks for having me. I appreciate the time. It’s fun conversation.

Anish Shah (01:12:54):
Have a good one. Thank you.

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