Succession planning for Founder-CEO’s - Evgeny Shadchnev

11 Jun 2024 · 1 h 13 min

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Podcast Summary: Secret Leaders - Succession Planning for Founder-CEOs with Evgeny Shadchnev

Episode Overview In this episode of Secret Leaders, hosts Dan Murray-Serter and Chris Donnelly speak with Evgeny Shadchnev, the co-founder of Makers, a coding bootcamp. Evgeny shares his personal journey of stepping down as CEO after nearly a decade, highlighting the emotional and strategic challenges involved in succession planning.

Key Themes

  • The Emotional Journey of Succession: Evgeny discusses the difficult decision to step down, driven by personal challenges and the realisation that the company required a different leadership style for its next growth phase.
  • Importance of Planning Ahead: The episode emphasizes the need for founders to plan their succession well in advance, as transitions can take a substantial amount of time (often 12-18 months).
  • Commonality of Founder Transitions: Evgeny argues that founder CEO transitions should not be viewed as failures, but rather as marks of success when the company is ready for a new leadership approach.

Highlights

Recognizing the Right Time to Transition

  • Moment of Clarity: Evgeny felt the need to step down after a particularly taxing funding round and personal struggles, leading to a conversation with his chair about succession.
  • Reflection on Leadership: It’s crucial for founders to reflect on whether they are the right fit for their company as it grows.

Strategic Planning for Successor Onboarding

  • Hiring the Right Candidate: Evgeny describes the importance of finding a successor who aligns with the company's culture and has the skills needed to lead in the next phase.
  • Trust and Communication: Building a strong trust between outgoing and incoming leaders is vital for ensuring a smooth transition.

The Role of Money

  • Financial Considerations: Discussing the financial security of founders during transitions is crucial. Evgeny highlights the importance of settlement agreements and share buybacks to alleviate financial stress when stepping down.

Common Pitfalls

  • Sitting on the Fence: Delaying the decision to step down can create uncertainty and distraction within the business.
  • Lack of Due Diligence: Emphasizing the need for proper due diligence during the transition to prevent unforeseen issues from arising post-succession.

Emotional Intelligence in Leadership

  • Navigating Communication: How to communicate the transition to the team is crucial, ensuring clarity and reducing chaos.
  • The Need for Reflection: Evgeny advises taking time for personal reflection after stepping down to determine future career paths.

Key Takeaways

  • A Mark of Success: Recognizing that stepping down as CEO can be a sign of success rather than failure is essential for the entrepreneurial community.
  • Understanding Your Role: Founders must differentiate between their roles as creators versus the operational needs of a scaled company.
  • Proactive Planning: Engage with the board and establish a clear plan for succession early in the process to set the company up for future success.

Conclusion Evgeny’s experiences illustrate the complexities and nuances involved in transitioning away from the CEO role. The episode encourages founders to embrace these transitions as a natural progression in their entrepreneurial journey and underscores the importance of careful planning, communication, and emotional intelligence in leadership.

For further insights and resources, listeners are encouraged to subscribe and engage with the Secret Leaders community.

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Transcript

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0:00The truth is, not every founder makes for a good CEO. This almost feels forbidden to say, because the popular image of a founder is of this one person who has a brilliant idea, turns it into a successful business, and leads it until it is a global empire. Either that, or they exit by selling to Google for a billion dollars. But that's not how things usually go. Sometimes, the company just enters its next phase, and the best thing to do for both the company and the founder is for the founder to step down. As necessary as this might be, it certainly won't be easy. Imagine building a company from the ground up, pouring your heart and soul into it for years only to reach a point where you realise it's time to step aside as CEO.

0:53How do you know when it's the right time? How do you navigate that transition while setting the company up for continued success? And what comes next for you as a founder? These are the crucial questions we're diving into today with Evgeny Shadshanev, a founder who has lived through this very journey. Evgeny is an author and co-founder of Makers, a coding bootcamp that has trained thousands of software developers. After nearly a decade at the helm, he made the difficult decision to step down as CEO in 2020. In our conversation, we talk about the complex emotions and strategic challenges of this process.

1:37Evgeny shares how he knew it was time to move on, the importance of planning ahead, and the pitfalls to avoid when hiring and onboarding a successor. We also discuss the surprising commonality of founder transitions and why they should be seen as a mark of success rather than failure. Evgeny's story illustrates that sometimes the best thing you can do for your company is to get out the way, and that new adventures await on the other side. Okay, my conversation with Evgeny Shadshanev. Let's get into this. Evgeny, welcome to London. Thanks for joining me. Thank you for having me. How did you know when it was the right time to leave your company?

2:25I was reflecting on it for way too long. I was sitting on the fence for about two years, but the specific moment when I really committed to it was the day we closed the funding round in 2019. I sat down with my chair. It was Friday morning, but we were at Granger in Clackenwell, where we usually met for breakfast, and cash literally hit the bank as we were ordering our coffee. And instead of celebrating, I frankly felt like I ran out of options because my marriage had collapsed. I was utterly exhausted by that point and I was seeing a psychiatrist that afternoon to speak about my mental health.

3:01And so we raised a glass of water to celebrate the funding round and then I said to my then chair, Claudia, that we probably need to talk about me stepping down one day. So it wasn't a resignation. I wasn't like saying I need to leave by the end of the week or anything. I was happy to stay as long as it takes for the transition but that was the moment when of things started moving. How do you know what happens in that moment? So, you know, we're going to talk obviously about how to recognize these moments yourself as a founder in the journey. What did you notice in yourself?

3:39For me, it was just a combination of things. It wasn't just one particular reason. It was the pressure of fundraising, a sense that I'm doing something, or rather I was not doing something that I should be doing for a living, so there was some sense that I'm somehow fundamentally misaligned with my job and this sense had been there for a good couple of years before that, if not longer. And I also was mindful of timing because to orchestrate the CEO transition, even though I had no experience of doing it at the time, it's not a two or three months journey. So we need to consider fundraising timing.

4:20We need to figure out who the successor is going to be. It can easily take a year or a year and a half. And so my realization was also that we need to start this conversation today if I want to see it happening, let's say two years later, if we want to plan things properly. Okay. So how did your transition go? What did you learn that you did right or did you learn that you did wrong? I'm really, really proud of how we as the board navigated the transition. We did a lot of things right, even though as a CEO I've made plenty of mistakes. But as far as the transition go, the things that we've done right were, first, we allowed it enough time.

4:5914 months passed between that conversation at Granger until I shut down my laptop and went surfing, not being a CEO anymore. So we allowed it enough time to do. The second thing is we found the right candidate. And of course, there is a huge factor of luck present here because we got lucky that we had an insider who turned out to be just right for the business. And spoiler alert, it's Claudia who was then my chair and then she took over as a CEO. So we had a really good trusted relationship. And also when Claudia and I were orchestrating the handover because there were several months between us agreeing to handover and me actually getting out of the way, we planned it very well.

5:52So by the time I closed my laptop and said, I'm not a CEO anymore, I was pretty confident that everything that needed to be done before the transition was done, all the document systems and so on were prepared. Although there was a small case of fraud that I had no idea about at the time, which came to the surface four months later. When we did the head over, when I stepped down as a CEO, I had no idea that someone inside the business was about to commit fraud. and it could could have easily take down the business but I had no idea and so when it came to light four months after the fact Claudia called me and briefed me on the situation effectively saying Evgeny this is what's going on I said oh my god and we connected the dots and in hindsight we jumped into action notified the police work to secure our financial systems recover the cash pay the team in time by Christmas.

6:53So we've done all of this, keeping the team involved and updated on a daily basis about what's going on because they didn't know if we would be able to pay them because for a while, we didn't know if we'd have access to our bank accounts. So it's quite a major fraud. Yeah, it was interesting. But we navigated it pretty well and there are two things that are relevant here. The first one is that we built a lot of trust between me as an outgoing CEO and Claudia as an incoming CEO, which allowed us to collaborate efficiently on solving this. But more importantly, in hindsight, I realized that we could have and should have done a bit of a formal due diligence when Claudia was taking over.

7:40Because as a chair, she, of course, knew a lot about the company. As an outgoing CEO, I thought I knew a lot. but this financial fraud, it could have been picked up if we did a bit of financial, if we did the proper due diligence like investors do when they're about to invest in the company and later when I was interviewing other CEOs about their transitions, other stories came up of CEOs taking over and then realized, oh my God, I wish I knew this. So hardly anyone does due diligence when they take over as CEO. And there are several cases of people who regret they haven't done it. Wow. I didn't know that about the fraud.

8:24It sounds like fraud with a big F, not a small F. Yeah, it looked scary at the time, but we got away lightly. We recovered all the cash. So is there a blessing in disguise for an incoming CEO to be dealing with a crisis straight up? It's probably not what they would like, but it's a great test to see, can they handle it? It's a great question because actually after taking over, Claudia, my successor, later told me that it was a blessing to step in during a time of crisis. Although she didn't mean that fraud. She meant a slightly different one. Because it allowed her to hit the ground running and make progress and show that she is a builder and she can make a difference straight away.

9:03And even though it wasn't easier, it was a good idea. It worked out well in hindsight. And the crisis I'm referring to is that we did a handover in 2020, the COVID year, first year of the pandemic, which is a whole different story because when we first reached a handshake deal that Claudia is going to take over for me, COVID hasn't hit yet. and then the country went into the lockdown in March 2020 for a while we thought that we wouldn't have a business anymore because we've got two student campuses in London and our business is in recruiting or placing junior software developers and the entire country stopped placing developers so for a while we thought oh my god what if the company is not going to exist by the end of the year and at that moment I called Claudia and said look no one knows about this.

9:56If you don't want to take over if we're going to shut down the company, that's my job to do and I'm going to stay and do it. And that must have been around April or so. And Claudia thought for a second and then said, Evgeny, I thought I would be taking over on a high note, but if I'm going to be a good CEO, I should be prepared to lead in good times and in bad times. And I'm still in. And at that moment, I absolutely knew I just could feel that we found the right successor that I could really rely on. And needless to say, Claudia took the company through successive lockdowns and various challenges, and she's still running the business better than I ever could.

10:35Okay. But could she write a better book about founder transitions? So let's get into that. The answer is no, obviously, Evgeny. So that's your experience. And obviously your experience, you know, sparked this curiosity for you, which is, I'm guessing, you know, well, not even guessing, we've spoken about it, right? So it's a very normal part of many founders journey. Indeed. And not really that openly discussed. Unfortunately, no. And founder CEO transitions, situations when a founder CEO chooses or thinks about stepping down are very common, surprisingly common. And no one really talks about it, Because there is a narrative that the only role model is someone like Jeff Bezos or Mark Zuckerberg taking the company from an idea to first sale, first employee, and then all the way to global empire 20 years later.

11:29But this is not what happens in the vast majority of companies. And this is not what's right for the vast majority of founders. And so there are plenty of people who choose to step down. And it's really important to understand this is not a failure. However, taking the company from an idea to the point when a different scale up CEO or just a different person can take it to yet another level is a mark of success. And this is not how we think about it today as an entrepreneurial community. So yeah, you're absolutely right. It's not widely discussed. Okay. And what prompted you to go out and interview other people?

12:09So after I stepped down as a CEO in 2020, I started coaching other founders as a founder coach. And I noticed that people or other founders are reaching out to me because of my experience of stepping down. The conversation often went along the lines of, hey, you stepped down from your role as a CEO. I'm in a similar position. Can we talk about it? And over time, I realized that first, I know something about the area because I spoke to many other founders about it. But second, I've got my own experience. And looking back, I think we navigated it pretty well when I think about some other transitions that didn't go so well.

12:52And long story short, I thought there is a book here. I could write it down and hopefully it will be useful to other founders. So there's a great saying, which is the quality of your life is determined by the quality of your questions. you must as a coach as a founder coach you must have an incredible arsenal of deep and penetrating questions that you've been asking founders about their journey that helps them understand where they are in that journey and how to navigate the next step so what are some of the useful questions that we as an audience of founders can start to think about with regards to this transition Yeah.

13:30So maybe the most useful question is the one that we ask every day. How are you? But actually answering this, how are you really? How do you feel? How are you deep down? How do you feel running this company day to day? And then going from there to maybe some deeper questions, like what is it that you feel you're meant to do in this world? And then maybe go into fears. What are you afraid of? What feels scary about this transition? Or what's your idea of good life? What are you looking forward to? And where do you see yourself in the next 10 years? So there is plenty to explore with every founder.

14:08How much do you think money is the big limiting factor in all of these questions? And I guess just asking on the basis of most founders have equity. Equity is tied up in the value of their business. It's all future promise. It's not actual real wealth. But of course, they take a salary from the company. So one thing that I've learned by talking to founders myself is this mismatch. You could be a really successful founder and be on a big salary and all of those things, but you still have your mortgage and you have everything until the big payday, the exit or whatever. And so if you do step down and you lose your salary, you are actually poor again until something great happens with the right successor.

14:49It doesn't change the reality. You're still technically the same as any other employee who depends on a salary. So has that come up a lot? This is a huge topic. And if people don't talk about transitions in general, they talk even less about money when it comes to transitions. So let's talk about money. It's important. Let's talk about money. First, you're absolutely right. There is a stereotype that founders or CEOs are rich, which can be true if they had previous exits and so on. But in many cases, just as you described, the company is doing well. 99 % of their net worth is in illiquid equity and they've got a comfortable salary.

15:23But having a good salary is different from being able to afford a few months or half a year or a year or two not working, especially if you've got a family to support. However, the first thing I want to say is that it can be genuinely helpful to have this conversation with the board. If you stay as a CEO out of fear that you don't know how you will make money if you step down, it's a lose-lose situation for everyone. You are probably miserable in your position as a CEO. the company is probably not getting the best leadership it can get. The company prospects are probably suffering as a result.

16:00And it's just a lose-lose situation for everyone. And the truth is that the amount of money that is meaningful for the founder is relatively insignificant in the context of the financial situation of the company, which is why I advocate founders and boards to have a conversation about financial security for the founder so that the founder CEO knew that if they choose to step down, they will not worry about money. In practice, it effectively means things like settlement agreements, share buybacks. But the point is that the founder should be thinking about what's best for the business, knowing that if the best thing for the business is to get out of the way right now, they can afford to do it and keep paying their mortgage.

16:49Can you get specific? Give us some examples. What are the different structures in which an outgoing founder can literally continue to make money without actually turning up to work every day? So one possibility is negotiating a settlement agreement with the company where the company just pays a lump sum of money so that the founder doesn't worry about the bills for the next year or two. Is that common? Not super common, but it happens. And again, going to some examples, how does one negotiate that? So the founder and the board are aligned around the success of the business. In order to make sure that the business is run well, the founder CEO needs to stay committed for as long as needed, but no longer than necessary.

17:41So if the founder or CEO is thinking about what job they're going to go next or they're interviewing or they're being distracted, it's not a helpful position for the company. From the company's perspective, the founder should be able to get out of the way when the new CEO becomes available. And the new CEO, the timing of their start date is also a big unknown because they're difficult to find, they've got their own notice period. It can be literally anything between a month or two to a couple of years. And during all this time, the founder CEO should be able to effectively extract themselves out of the business on a possibly short notice.

18:22The way to square the circle is to say to the board that, look, I'm happy to keep running the business as long as necessary. I'm happy to get out of the way as quickly as necessary. But in order to make it possible, Let's agree that we're going to sign a settlement agreement, the company is going to pay a reasonable sum of money that is going to facilitate the transition. And usually it's a win-win scenario for everyone. It doesn't have to be a settlement agreement. Share buybacks are also possible when the company or some investors buy some shares of the founder. So these are some of the options.

19:02Got it. What's the most common? The most common is that founders don't talk about it. Boards don't talk about it if founders don't talk about it. Everyone is stressed about money. Everyone is pretending it's not an issue. And what's most common is a lose-lose situation for everyone when founders are worried about money and investors are worried about the CEO transition. Yeah, okay. Okay. So actually, typically, what happens is the founder just stays in the role as a CEO way too long anyway. Either stays way too long anyway, or tries to stay in some other role, for example, advocating that they get a paid role as an executive chair or a CEO.

19:47It depends. Not no, but it depends for reasons. If you are trying to get the role on the senior team just to cover your expenses and you don't actually know how you will genuinely add value, that's less helpful. At the same time, there are plenty of genuine examples when there is a great next move for the outgoing CEO as an executive chair or head of strategy or someone else.

20:19I guess the thing that I'm confused about is if you are if you've been the CEO and you've been successful up to a point and there is cash available in the company because you've done a decent job you're just no longer right to be CEO isn't it fair to assume that with some of the right intention you'd be very capable at doing one of the other jobs it's just not full-time it um it depends so let's take a job of an executive uh chairperson as an example um A good example here is Jeff Lin, founder and the first CEO of Cedars, a crowdfunding marketplace. He got out of the way and negotiated to stay as an executive chairperson with his board.

20:59But he is a bit of a special case because he had multiple board positions before that appointment. In other words, he had experience on multiple boards, which enabled him to be a genuinely good executive chairperson at Cedars. Most founders don't have extensive board experience. There, we are busy running our startups, and at best we are on one other board, and even then not as a chair. So going from very little board experience other than your board, all the way to being an executive chairperson coordinating the board, may be a step too far in some situations. I know it would have been for me.

21:37So when I stepped down, I didn't even try to open the conversation because I realized we can find far more capable chair people, chairperson. And we did find an excellent chair who is now chairing our board. Got it. Okay. So there's technically three scenarios, right? Or four scenarios, but the three would be that you step into another role inside the company, you have a share buyback, or you get some compensation from the company, or the most common, you don't talk about it. Yes. Or, of course, what also happens is that you just get a job elsewhere. And here, it might work out financially, which is good news.

22:20But there are also good reasons not to rush into another job as soon as possible. A client of mine, Orvin Reed, founder and first CEO of Whereby, said that his biggest risk when he was stepping down as a CEO of Whereby was that he's going to jump into something else. His problem was not money because he was constantly headhunted for other positions and he knew that something would be available instantly if he wanted to. But he spent years running the business. He was understandably very tired. And for him, the challenge was to step back, slow down, take a deep breath and think deeply about what he wants to focus on over the next 10 years in his career.

23:06And eventually he started another CEO job that he's doing right now. But allowing that period of reflection was also really important. Can you take us through in your experience so far, how you go from the moment of clarity that maybe this is time to move on and the steps that you advise people to take from that moment? Yeah. So when you first notice you're having doubts about whether you should run your business or not, my advice is... So week one of starting as a founder, think about leaving. Well, maybe not week one, but if you notice maybe a few years in that you're seriously thinking and maybe you've been thinking for a few months that you should step down, take it seriously.

23:53Can I just interject? Yeah. You and I both know, and this is what's so hard about this, the peaks, the troughs, for most people the imposter syndrome and doubt it's so hard to tell what is an emotional response what's a rational response to a tough time and what's just like i should give up i'm not good enough for this it's so genuinely hard to tell which one of those is an authentic thought that actually deserves validation and which one given a few days is gonna bugger off again until the next like peak and drop. Yeah. So you're absolutely right. Some of it is normal just because the job is bloody difficult, as both of us know.

24:34But it's also really genuinely important to bring some clarity to this because sitting on the fence thinking, should I step down? Should I not? But maybe I shouldn't. Maybe I shouldn't. And living like this for months and even years, as was in my case, is not a good idea for two reasons. First, it's highly distracting. There is just no peace of mind if you don't know if you want to stay in your job. Second, in order to do your best job as a chief executive, your full attention needs to be on the job. The job is hard enough if you want to do it. The job is so much harder if you are not sure if you want to do it in the first place.

25:11So from a purely objective perspective, for the company to have a high-performing CEO, this chief executive needs to be committed to doing their best. It can be hard, it can be very difficult at times, but the commitment should be there. And so if there is a sense that you're sitting on the fence and you're not sure whether you want to do it in the first place, take it seriously as a business problem, not just a personal issue. Okay. So that's if you don't want to do it necessarily. But what if you don't think you can do it? If you don't think you can be a good CEO going forward. Well, for the next stage of the company.

25:51Fair enough. It probably means that you've done an amazing job making the company so successful that it requires a skill set which is beyond yours. So that's a mark of success. So first of all, congratulations. That's a good result. And it's probably a really good topic to discuss with the rest of the board. Because here, the perspective of the board, perspective on your performance, but what's just as importantly what the company needs going forward can be really relevant. I mentioned external perspective because our own sense of how we are doing as CEOs is not most reliable because we are under a lot of pressure and as a CEO I often felt like I was doing a shit job.

26:36And then I would go to my chair or other board members and ask, okay, how am I doing as a CEO? And they would say, well, there are some pluses and minuses and things to improve, but by and large, you are doing okay. And inside, it would feel anything but okay. So there can be disconnect, and it's probably quite normal. So external perspective matters, but also the skill set really matters. The skill set of a founder and the skill set of a CEO are two different things, and some people are able to cover both, but there is nothing wrong with doing the founder bit and then handing over to someone who will run a functioning, scaling company, as it happens quite often in startups.

27:19What do you see as the main difference between a founder and a CEO? The job of a founder is to make sure that the company survives and finds their product market fit. The job of a CEO is to build a company that builds the product. So a founder focuses on the product, the CEO focuses on the company that builds the product. It may feel like a theoretical difference, but in practice it makes all the difference, because a founder does things like leading sales personally and being in every detail, knowing everything about the company, managing by intuition and moving very fast, maybe even without having necessary support systems all across the company.

27:56A CEO manages and builds a machine that delivers the product in a repeatable way. They've got a proper senior management team they can rely on, high quality systems across of all businesses and their focus is on the machine itself that builds the product that serves the customers um okay so you you've decided that you're going to move on whether you can do it want to do it don't want to whatever that's the moment it's been decided now what so uh when you are still thinking that whether you should should or shouldn't move on i would advise getting not escalating this conversation to the board level just yet talk to your trust that because it's a bit like a box you can't close again yeah a little bit yeah uh so even though i do generally advocate speaking to the board earlier rather than later leaving it too late is generally not a good idea uh if you are not sure uh whether you want to step down or not or why basically all your personal psychological matters talk to your friends coaches family loved one, therapist, whoever.

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29:05But get some sense of what's happening inside you. But once you get some sense of clarity of what's happening inside me, it's the time to start talking to the board. And here, the earlier, the better. So if you leave it until the point of, I can't do it anymore, I'm quitting next week, and my co-founder is going to be the new CEO, it's probably very late. You really want to open it much earlier when you say, okay, I'm happy to run this company for another year or two, but I think there are reasons to consider hiring a new CEO. Or even, I have decided to step down, but I'm completely open regarding timing.

29:42Let's discuss how to orchestrate the transition in the best interest of the business. Okay, so you've decided? Yes. Then what? Take charge of the process. And by this, I mean, don't wait until the board makes the first step. if you are thinking about stepping down as a CEO, there is a certain chance that the board might also be thinking about replacing you as a CEO. And if you raised venture funding, they probably have the power to fire you. So in this situation, you will probably have more options and better options if you proactively start a conversation with the board about what's happening, why it's happening and how you want to orchestrate it.

30:27At some point when you've got some clarity on that you certainly want to step down, speak to the board one by one, individually it's probably best practice, then together at a board dinner or a board meeting, again to make sure that everyone had the chance to process the news and think what it means for them. And then together as a board, work on it as just another business challenge. Yeah, it's interesting. I suppose it's sort of similar to any negotiation, like leverages everything. And so whoever makes the first step and how you navigate that conversation, which is a difficult conversation, you know, being in control of the communication because you've thought about the next steps gives a huge opportunity to having the outcome that you're looking for versus basically accepting what someone else does.

31:25Exactly. So leverage matters. And this is why I suggest in most cases, wait until you've got clarity and then start the conversation. And the more clarity you've got around your performance, your feelings, your plans, the company needs, whether the company needs a founder skill set or the CEO skill set, how the board sees your performance, which is a whole different topic. The more clarity you've got about around all of this and how you see it working, the easier it will be to orchestrate the transition that's going to work well for you and the business. So how do you go and find someone that's right for this role?

32:05And what does that person really look like? So there is no answer that's going to fit every company because every startup is so different. Where your company is on the product market fit scale matters. If you've got a strong product market fit, it's generally easier to bring an external scale-up CEO into the business. If the company has a weak product market fit or is even at an earlier stage, it's probably going to be difficult to find an external candidate. So you're probably looking at your co-founders or early team members. so that's one consideration an executive search can be genuinely helpful but the real important bit is to find someone you can deeply trust and people who we really trust are people who we have known for years and so they're probably coming from either your network or inside the company or the investors network.

33:07So by the time it gets to an executive search, you probably have exhausted the supply of trusted people inside your business. But finding someone you can really trust your company to, someone you can't wait to give the keys to and look what they do with your business is genuinely important. So how have you seen this go wrong? It goes wrong in plenty of ways. First, sometimes founders leave it until too late and they just want to get out as quickly as possible at all costs and they hire the first candidate that looks okay. This would be a mistake. It's such an important transition. It will have a huge impact on the future of your company and on when and where you retire even if this moment is decades away.

33:59So it is absolutely worth planning it carefully and giving time. So one mistake is just hiring the first candidate that looks good. Another mistake is sitting on the fence too long. This was my mistake. I spent two years thinking, should I do it? Should I not do it? But I like the company, but I'm very stressed, but it's okay to be stressed. And it was just going on in my mind for too long. I really should have acted sooner for the benefit of the business. Another very common mistake is not clarifying your role after you step down. So you hire a new CEO and then you hang around as a founder without a clear role.

34:39So a good example here, in my book I quote James, founder of Sanctus, who hired a new CEO and then stepped down as a founder with an unclear job spec. And as he later told me, he felt like other people didn't know what he was doing. His work was not as important as people with real jobs. And it was just an uncomfortable place to be. And it's really important to get out of the way, which brings me to another possible, another common mistake, not getting out of the way. It's really important to get out of the way and not undermine the new chief executive. A really good example, a case study I describe in the book is a transition at Opus Recruitment Solution, a mid-sized recruitment business in the UK where the founder, Darren, hired his successor, Amy.

35:34And Darren and Amy made an agreement that the only time Darren would override Amy would be when he would justify her. And he never did. Seven years later, she took the business to an incredible exit. So it's a really, really positive story. But it was very important for Darren to get out of the way and give his successor complete freedom over the business, even though it was a bootstrapped business. And so Darren was pretty much the only or major shareholder. So there was no board of investors. And I suppose that's, you know, there's two sides to this always, right? There's the founder, the founder's ego, how the founder resolves a lot of this pressure and tension and what they want to do next and all that stuff.

36:23And obviously the psyche of the incoming person, there needs to be psychological safety that they can do the job properly. Otherwise, presumably it's just really not that attractive and they will do a bad job. Yeah. And there is a good example of a founder CEO who hired a new CEO, linda it's it's it's a buy the company beautiful business i thought you're gonna talk about twitter no no no no no definitely elon's out linda's in no you don't think it's going well nope different linda uh and linda left after a year and a half uh not because she was a bad ceo the business genuinely needed her skills and she made good progress and she's proud of what she's done but what happened is that the founder stepped down to join the senior management team but he effectively tried to continue running the company.

37:10And for a year and a half, Linda was technically in the CEO position and she was the CEO. And then there was the founder who was ex-CEO and the entire team who knew the founder as the ex-CEO. And he was still trying to have his way. And a year and a half later, Linda effectively said, you know, we need to find a different arrangement. And so she stepped down and the previous CEO stepped back into the role. My point is, it's okay to quit. But if you do quit, get out of the way. If you hang around undermining the new CEO, it will be a lose-lose situation. If you want to keep running your business, don't step down.

37:50If you step down, get out of the way. It's really that simple. But you've studied this space and interviewed loads of people. So what's What's the most common process that happens?

38:01I think most commonly people actually get out of the way, but they leave the company. They go and do something else, which is a bit of a loss because founders are genuinely helpful. They know the company, they build the company. The best solution in many cases is to find a way to stay involved, but genuinely crafting your role for yourself, not undermining the new chief executive. This way, the company can leverage your skills, experience, everything you learned about running this business, but with a new CEO having full freedom to run the business. But what happens in most cases is that founders leave and go and do something else.

38:51And when they do that, and having a conversation and they're trying to hire the new person and all of this stuff. So give us some examples of how to hire the right person. We've talked about how it can go wrong. How can we set people up to succeed? How can we ask the right questions? And that's beyond trust. So outside of your ideal network. Yep. So first, be clear on who you are hiring. do not hire like for like. The goal is not to hire a replacement for the founder CEO. The goal is to hire the right CEO for the next five, 10 years. And maybe it's a scale app CEO, maybe it's a CEO who is going to get the company to an exit.

39:31Maybe the job is to optimize for free cash flow if this is the goal. So it's important to stop and think, what does the business need going forward? Not what the CEO used to be doing up until now. And presumably you need a feedback process in that right so because you are going to be the one stepping away yeah so it's no good you being like well i've had a look and i've decided that this is what the company needs so that's who i'm going to hire and then i'm going to bugger off because the board and everyone else might be like absolutely what the no way is that what this company needs that's exactly what's going to happen if you don't get the board involved this is why it makes sense to get the board involved earlier and then instead of jumping into interviewing people straight away spend a lot of time thinking about what do we want to see happening, align the board around the vision for the company, make sure that all key decision makers are on the same page, discuss the mandate for the new CEO, what do we want from the new CEO, write it down on paper, job spec, and all of this, and figure out what the process for hiring the new CEO is going to be and who is going to run it.

40:39somewhat counterintuitively, it's actually surprising when companies hire non-CEOs, basically everyone else, there is an HR team and they have process and best practices and whatnot, and when it comes to hiring the CEO somehow all of this sometimes goes out of the window and one of the board members says oh I know someone I met last week, let me introduce you and you interview them, so basically the entire process all best practices go out of the window this is a mistake Think about what's important, write the job spec, design the process, figure out who is going to run it. It's probably a chair if you've got a chair or a lead investor, maybe even the outgoing CEO, but they are understandably biased.

41:21And then run the process. So in one example of one of my clients, he designed a beautiful process. and it's really important for him to get very diverse talent at the top of the pipeline, just to make sure that he doesn't hire yet another white man like him. And then he's got an investor who kept sending him WhatsApp messages along the lines of, hey, I met this guy yesterday at a networking event. Could you please interview him tomorrow? It's already in your calendar, which was highly frustrating for them both. It would have been much easier. Basically, what happened is that they sat down and had a conversation about, how are we going to run the process?

42:02How are we going to add candidates? How are we going to interview them? And aligning on the process itself and figuring out who is running it can take a lot of frustration out of the experience. What are the horror stories that you had? There were definitely few. One horror story is a founder who raised venture money, basically. So she raised Series A, then the company didn't make enough progress. And the investors panicked at the first sign of trouble and said that we will invest more money to effectively bail out the company, but only if you get out and we hire a new CEO. And the founder felt like she had no other choice, so she stepped down.

42:53than what she described as a slow motion car crash. Investors brought in a new CEO. He quit after half a year. Investors brought in another person, and he wound down the company another year later. There were no winners in this scenario. Investors, clients, the team, founders, everyone lost. And when I look at this horror story, I think again about the importance of trust. I'm not trying to say that the company would have been fine if the founder stayed as a CEO. Ultimately, we don't know. But there was a complete lack of trust at the top level, which absolutely didn't help. And another horror story, which I probably wouldn't mention if it weren't just too common is discrimination at the level of the CEO.

43:50In one specific case, investors did not include the founder CEO in the options round. She was the only person not included in the round of new options when they learned that she was pregnant. It's discrimination. It's immoral, illegal, and wrong on every level. And I wouldn't be mentioning it if it just wasn't still happening today in 2024.

44:15In that situation, the founder didn't want to step down. She wanted to keep running the business, but effectively she felt like she was being pushed out of the business by her investors who decided that apparently it's not okay to have children if you're running a business. And I know it's not right on every possible level. and unfortunately such horror stories also happen. So listening to a lot of what you've said, it sounds like, you know, fortunately the job of a CEO is often strategy. However, founder job is different to CEO job. So maybe founder is not the best at strategy. It feels like there's a lot of strategic pieces on the chessboard to move along here.

44:57You've got maybe an incoming funding round. You've got your intentions to step out externally and leave the company. and you either need to bring someone up from the company to take over your role or go for an external process and find a way to communicate all of this at the right time without creating a toxic environment. How the hell do you do all of that? So this is a really interesting question. So the timing of fundraise really, really matters because if you're running a venture startup, you're probably raising every 18 to 24 months. Stepping down as a CEO right before the round is difficult because you might not close the round.

45:30investors want to know who is going to lead the business. If you try to live right after the round, it's also difficult because the investors will ask, why didn't you tell me last month, which will be a bridge of integrity and a difficult conversation. So ideally, you want to live right in the middle of the round. When you raise the round, maybe made some progress, and there is still another 6, 9, 12 months of runway for the new CEO to step in. Now, the timing this transition is difficult because you don't know when you will find your successor. They've got their notice periods, search, who knows how long it's going to take.

46:07So one possible way to navigate all this is to do what Adam Fudakovsky, the founder of Switchy, did at his business. So when he started thinking about stepping down one day, he hired his future successor, Tom, as a head of strategy. The intention was twofold. First, to get to know each other and to get some experience of working together before actually promoting Tom as the CEO, and also control the timing. The board got to know them. Then he raised the round together with Tom, so the new investors got to know Tom. And then I think six or so months later, he said that he would step down and promote Tom to the top position.

46:54And by that time, he was in control of the timing. Tom was a known quantity and he knew the company. The investors, previous investors from the latest round also knew Tom, so there were no surprises. And the transition went very, very smoothly for all of them. So, you know, what I've just written down the note here is just tons of awareness around timing. Yeah. Timing is critical and very important. It's interesting because if you think about in life, so outside of work and stuff, you know, things happen and you get very emotional. And when emotional things happen and you have an emotional response to stuff, you're not necessarily thinking clearly in that moment.

47:41And this almost feels like the perfect example of the exact opposite, like leaving your company can not in any way really be an overly emotional experience because you need to keep it together long enough to turn up to work every single day for another nine, 12, 18 months from the moment you've made that decision with genuinely great intention. Yes. And that is like a very mature, very strategic, very calculated and very unemotional way to behave in general, which is difficult because leaving the company that you founded is a hugely emotional thing. This is difficult. And this is what you described is precisely why it would be a mistake to leave it until the last moment when you feel like you just can't do it anymore and you need to get out of it by the end of the week at all costs.

48:32so you really need to start acting while you've got while you can see yourself doing it for another year or two and yes it's not easy it is an emotional question which by the way I why I do recommend taking time away and basically clearing the space and mind space to really think through this decision. For me, I spend a lot of time going to Chamonix in France and Scotland, just be alone hiking or on my motorbike to slow down, not be distracted by email or slack, and just think about what's going on. Feel my feelings, reflect on the situation. Be fucking cold. Be a bit cold. It's a good distraction.

49:19Scotland and mountains, got it. Yeah, but it's really important given the magnitude of the decision. Taking a week offline when you are going to do nothing but reflect on what's going on can be a great investment. What are some helpful questions then that you can ask yourself in this period of reflection? What's going on really and how do I feel? And what am I afraid of? Exploring fears. And ideally exploring them with someone else. because fears are, well, scary, at least in my case. And exploring the fears with a trusted person who doesn't have the skin in the game in terms of whether you step down or stay can be tremendously helpful.

50:09Okay. So you've stepped aside and things have all gone well. Yeah. What next? First, take a break. Don't rush into it. If you can at all afford it, slow down, think, reflect. You're probably more tired than you realize. If you ran your company for years, it must have been very stressful. You need some rest. It's probably measured in months, if not years, the amount of time you really need. But then start thinking about what's next for you. There are a few traps to fall into here. The first one is founders often think that they can't do anything else. They think, and I've been doing this for the last decade, so they think that the only option is to go and start another business.

50:58Yeah, you feel unemployable. You feel unemployable. You've got all kinds of wrong ideas about what's possible out there. So it's very easy to conclude that I'm a founder, so of course I'm going to start another company. In fact, there are seven different career paths available to founders or seven common career paths that founders tend to take after they leave their businesses. And starting another business is only one of them. And then another potential trap is to fall into doing what's easier. Let's say you're not worried about your bills and you've got some money in the bank. and then it's very easy to just wake up in the morning, watch Netflix and have a pint at four o 'clock and feel like it feels a bit empty inside and my life is drifting in the wrong direction.

51:48This would be a mistake. If you're resting, plan it like work. Figure out what you want to do, how much screen time you want to have. Do you want to spend more time with your parents or nephews or doing that big trip or meditation retreat you always wanted to do? So plan your rest responsibly. But another trap that founders sometimes fall into is getting busy with what is familiar to them. Like joining panels and getting various volunteering positions and helping other startups and doing the same things that they've been doing for the last 10 years. Or maybe they never had time to do what they could do.

52:30Basically busy work. Basically busy work. And this would equally be a mistake. Plan your rest, plan your recovery, do different things, do new things, get immersed in new relationships, get to know yourself, and then slow down, reflect and think, okay, there are many different options available to me, which of them is going to be my next professional step? You mentioned the seven career paths that we can take. I didn't know that. What are they? Actor, dancer, ballet? Well, only for some of us. So the seven are joining your own senior management team. You step down as a CEO, you join as an SMT member.

53:14Starting a new startup, joining someone else's startup as a member of a senior team, or joining a corporate, which is quite a different story. Some people go freelance. That's my case. I went into founder coaching, effectively building a freelance career. Some people go into investment. And finally, it's fairly common for founders to go into an executive chairperson position. The transitions to the corporate world and to a senior role at someone else's startup are particularly not obvious. So I'm thinking of an example of Nick Eels, who sold his startup back. And then he wanted to get the job of a VP of product at some other company.

54:07But he never did anything other than running his own business. So he was competing with people with 10 years of product experience on the resume. And as he told me, he updated his LinkedIn to make it look like all his career was leading up to this moment. The way he described it was that he had to fake it until he made it. He was learning about the product and eventually after several crazy interviews, he got the job as a VP of product at one company and then the other one. And right now he's in his third VP of product role. And looking back, he said that this process helped Nick realize how valuable his CEO experience is.

54:50Because for a founder CEO that he's working for right now, he's the only person on the SMT who really sees the situation from a CEO lens. All other members of the senior team, they might be experts in sales or technology or someone else, but he's got a holistic founder view as a CEO. And this can be tremendously helpful if he becomes effectively a right-hand man to another chief executive. Right, because he has empathy and he can also connect things up to the higher purpose, the vision, etc. Yeah, exactly. That makes sense. One of the things that founders get wrong, hiring, and certainly hiring processes, especially onboarding processes.

55:38and the best companies have the best teams, right? The best hiring processes, et cetera. So extrapolating that all out, how much extra time do you need to put into place for the hiring process of a CEO and onboarding and like getting them up to speed, all of these things? I mean, it sounds exceptionally hard. So how do you design something amazing? So it's slightly different compared to all other employees. So the difference is that first, proper hiring and onboarding process matters. Often boards don't really pay attention to it because every board member is part-time on that board and their old CEO is gone.

56:18So there is no manager, so to speak, to really take care of the onboarding process. And this is generally a mistake. But what's also relevant is that much of the onboarding for the new CEO can and should happen before they take on the role. Usually onboarding happens after you show up at the office, get the new laptop and all the stickers and the onboarding begins. The new CEO should be able to hit the ground running on day one. On day one, they should have a good idea of what's going on, why it's happening. The old CEO should be out of the way. And so the transition of knowledge and all relevant systems and so on can and should be done while the old CEO is technically still the CEO.

57:02but they know that the new person is going to take over in a few months. So this is what we've done with Claudia, for example. At my business, we effectively co-ran the company for a few months before she took over. So by this, I mean that I was running the business, making day-to-day decisions, but I was also very aware that Claudia would be living with the consequences of my decisions. And so I would do my best to align with her on how both of us think about the future of the business and make sure that I don't do something that Claudia would need to revert in the first week that she's a CEO.

57:46And so in the process where we're aligning on decisions, handing over all the important systems changing, access passwords. And there are also some in this process, there are sometimes non-obvious points like, for example, I almost forgot that I've given personal guarantees to one of the lenders in the early days of the business. It happens. Lenders sometimes want personal guarantees at early stage companies. But the trouble is that when you step down as a CEO, if you retain this personal guarantee, then you're on the hook for someone else's actions. So you really want to negotiate a personal guarantee way before you step down because the new CEO will not be keen to take on your personal guarantees.

58:31And fortunately, in our case, it was possible, I effectively made an argument that the business is so much bigger and more stable and is in a good position. So it wasn't necessary. So we just canceled it. But I almost forgot about it. Yeah. Okay, it's probably quite a long checklist, I imagine, of things. Yeah, it's a long checklist. And given that CEO transitions in the company don't happen often, it's not like it's a reusable checklist. So you can't go to HR and say, hey, give me a checklist for a new marketing hire that we used two months ago. It needs to be prepared carefully. There are lots of things like bank mandates.

59:14And in our case, updating bank made it with our old boring high street bank with a blue logo took a long time. Have you created a checklist? Yeah. Can you share some of the things from the checklist we should watch out for? All the systems, like domain names, for example. Domain names happen to, I bought our domain name, I think, under my own name in the early days of the business. It's kind of obvious when I say it, but there are lots of small things like this. Who credit card is registered for, banking access, biometric systems, notifying financial services authority about the change of a key person, notifying some of our industry bodies because we're a regulated business, so we needed to notify others.

1:00:06If you are stepping down as director, you need to notify companies house. So again, all of this is obvious when you look at it, but there are dozens of things like this that you need to write down and then have a proper handover document that will probably take several pages. Right. And it might be like the one time you do it in your whole life and the whole company does it once. So actually what you're developing is a really useful cheat sheet for those single instances across the industry. Yeah. Nice. Just a question on communication. Yeah. How do you navigate the question of communication with your team?

1:00:42And how did your experience of how you did it compare to the people that you've interviewed in your book? So in general, it's a good idea not to let the team know until there is a clarity on what's going on and what it means for them. If you go to the team and say, I'm stepping down as a CEO, but I don't know when, I don't know who is taking over, and I don't know what it means for anyone, it will just create a bit of chaos for no good reason. So I told the team only when there was clarity that I'm stepping down, Claudia is taking over, it's happening on the 1st of September, and this is what's going to happen between today and the 1st of September, which is how I think most companies do it, and for good reason.

1:01:26At the same time, I also learned that senior members of the team will probably figure out what's going on much sooner because there will be some signs that something is changing. So one senior team member at my business later told me that he figured out that Claudia would take over as a CEO because she started to attend more meetings and ask more questions and generally got more involved. So it also happens. But what's also important here is to align communication at both companies. One company is obviously your company, but the other company is where the CEO is coming from. Because the chances are that they had a CEO job or another high-profile job elsewhere.

1:02:12And the change of a leader should be communicated by that leader and not by a post on Twitter. So the way to do it is to have two all-hand meetings back-to-back, probably online because it's easier and everyone is hybrid anyway right now. So in the first meeting in one company, the outgoing CEO announces they're stepping down, introduces the new CEO. Next meeting, the same thing happens. and afterwards both companies share it on social media, send emails to key partners, trusted suppliers, and basically notify everyone. So having a written communication plan for the day of the announcement is really important because it's easy to forget someone, like people who are on holiday or out of the office or who are about to join but haven't signed the contract yet.

1:03:07So it's important to think about every audience and manage it quite tightly, which is not difficult, but it still needs to be done carefully. I find there's a really strange dichotomy in general as CEO, where really one of your jobs is to control the flow of information and make sure that everything that is being communicated, that people have awareness of, is contributing to the best outcome for the company one way or another, aligning people, not causing chaos and confusion, like you said. And sometimes that can be really misaligned with someone's own personal desire to be transparent, authentic, friends, family, all the words that come up, you know, with how you feel with your colleagues and stuff.

1:03:54And ultimately, that can eat away at you. And I know it's a perfect example is when you know you have to let someone go. Yeah. And you know, you have to let that person go. And even worse, when it's for financial reasons, actually nothing to do with their job. You think they're great. You really like them. They've been loyal, all of the things. And you know this information for sometimes weeks before you have to have that conversation. You still have to turn up with them. You still have to interact with them every day. It's a horrendous feeling. It's a horrendous feeling. And you're talking about doing this for 18 months.

1:04:28Well, hopefully less, because part of those 18 months is the period where you already know when the new person is taking over, which is when you can announce it. But in my case, it was definitely a few months between I firmly committed to getting out of there and we started interviewing candidates and when we announced it to the team. Right, but that's still the longest. I mean, that's longer than any that you'd hold other information, right? So how does that feel? That doesn't feel particularly nice. It feels, yes, there is a natural instinct to be open with the team and to share everything. And at the same time, being a CEO is a lonely job for a reason.

1:05:17It's stressful for a reason. It can be more or less stressful, but this is one of the aspects that makes it particularly difficult. We just can't be, as CEOs, we can't be transparent about everything with everyone all the time. So it's part of the job. Okay. Fair. Sounds terrible though. All right. I want to do a nice closing question. So

1:05:49you've been around Europe asking people this question. What is the most surprising thing that you've learned about how to step down as a founder CEO? What is the thing that you might have learned that would have changed how you did it? The most surprising thing I learned is that it's far more common than it may seem. When I was going through it myself, it felt like everyone else is committed for life or until the exit and I'm the only one who is thinking about it. It's common. Nearly every founder or CEO either thinks about it or considers it at some point. and so when I started talking to other people I realized how much how much is there to discuss to share to uh to learn from and this conversation hardly ever uh happening uh in public and here uh there is an interesting parallel with you know 10 years ago it felt like the founder community did not talk about mental health everyone was pretending that I'm killing it everything is fine I just closed the funding round and hired a great candidate as my new chief revenue officer.

1:06:55And they are slaying. And they are killing it every single day. And I would feel like I'm the only one who's got no idea what I'm doing. And over time, this changed. Today, founders are so much more open in the meeting that sometimes it is really difficult to run a startup. And it doesn't make us bad founders. It's just how things are. and I really, really hope that the conversation about founder-CEO succession will also become more open because it's happening. It's there. Lots of founders are thinking about it. Lots of founders are going through it. And in many cases, as I've said in the beginning, it's a sign of success, not failure.

1:07:36You took the company from an idea to the point when it's possible to bring in a professional CEO. This progress is success, not failure. Well done. getting the company successful and getting out of the way. Beautifully said. Evgeny, thank you so much for your time on Secret Leaders. Thank you, Dan. Okay, that's it for this episode. And thanks for tuning in to this one on Secret Leaders. If Evgeny's story resonated with you particularly, then share this episode with someone who you think you could have an open dialogue with, an honest conversation about these kinds of challenges and the opportunities that present themselves from stepping down from your company and moving forward.

1:08:22I know I've personally taken a lot from it and it opened up a lot of difficult but important conversations that needed to be had in one of my companies as well. So if you found value in the insights we shared today, the simplest ways to support our work is just to subscribe to the podcast and check us out on YouTube at Secret Leaders Podcast. Don't forget to like and subscribe. Thanks for listening.

1:08:53You

From the publisher

Imagine building a company from the ground up, pouring your heart and soul into it for years, only to reach a point where you realise it's time to step aside as CEO. 
How do you know when it's the right time? How do you navigate that transition while setting the company up for continued success? And what comes next for you as a founder?
These are the crucial questions we're diving into today with Evgeny Shadchnev, a founder who has lived through this very journey.
Evgeny is an author and co-Founder Makers, a coding bootcamp that has trained thousands of software developers. 
After nearly a decade at the helm, he made the difficult decision to step down as CEO in 2020.
In our conversation, we talk about the complex emotions and strategic challenges of this process. 
Evgeny shares how he knew it was time to move on, the importance of planning ahead, and the pitfalls to avoid when hiring and onboarding a successor.
We also discuss the surprising commonality of founder transitions and why they should be seen as a mark of success rather than failure.
Evgeny's story illustrates that sometimes the best thing you can do for your company is to get out of the way - and that new adventures await on the other side.
…

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