Founder Transitions: Mitigating Risk and Maximizing Value with Dr. Stacey Philpot and Dr. Ted Freeman.

CEO Hiring: Supporting Founder Transitions with Dr. Stacey Philpot and Dr. Ted Freeman

Hiring a new CEO is a high stakes event, especially when a founder is involved. Roy sits down with Organizational Psychologists Dr. Stacey Philpot and Dr. Ted Freeman to discuss what it takes to successfully navigate these founder transitions. The three walk through each step involved. They share their insights into the challenges and opportunities at play and the unique partnership between a new CEO and founder.

Ted and Stacey have been partnering with Noto Group on these kinds of complex and mission critical VP and C-Level hires for the last few years. Ted has extensive experience as an organization development consultant and executive. He previously served as Culture Officer at EILEEN FISHER, INC and couples this expertise with more than a decade of consulting experience in the areas of leadership development, organizational effectiveness, and executive coaching. Stacey brings over 20 years of experience as an organizational consultant to her role as Managing Partner at Executive Development Consulting. She’s advised Fortune 500 companies and CEOs on how to use leadership development to accelerate growth and increase their competitive advantage. Both will be back in the future to dig further into leadership integration.

Listen to the podcast


  • Why founder transitions happen (3:16)
  • The importance of having a plan in these high risk events (4:00)
  • The kind of support available to organizations (5:33)
  • The distinct partnership between a CEO and founder (7:33)
  • What experts like Ted and Stacey consider when approaching these processes (8:56)
  • How they help companies handle bumps in the road (10:57)
  • Helpful scenarios they’ve worked through with clients (12:30)
  • How these transitions impact existing teams (24:51)
  • Tools and assessments that can inform CEO selection (27:38)

SHOW TRANSCRIPT – HOW I HIRE PODCAST WITH Dr. Stacey Philpot and Dr. Ted Freeman

[00:00:00] Roy Notowitz: Hello, and welcome to a special episode of How I Hire. I’m your host Roy Notowitz, founder of an executive recruiting and leadership consulting firm called Noto Group, where my team and I have spent the last decade helping to build iconic consumer brands, one hire at a time. You can visit us at to learn more.

You can also subscribe to our newsletter to get the latest updates on our jobs that we’re working on and even more hiring insights. I’d like to welcome Dr. Stacey Philpot and Dr. Ted Freeman back to the podcast. They’ve each shared their insight on the show before, and I highly recommend checking out their previous episodes. Today, though, we’re going to talk about CEO searches, but, more specifically, ones that involve a founder transition.

Founder transitions happen regularly in our world, often after a founder reaches a point where they are unable to focus on the areas of the business they enjoy most, or, when maybe they feel they’ve taken the company as far as they can from a leadership and growth perspective. In many cases, there’s a corresponding mandate or desire to scale significantly, which often coincides with an investment of outset growth capital.

Over the past few years, Ted and Stacey have been partnering with my team and our clients to ensure long-term success on the most complex and mission-critical VP and C-Level hires. The stakes are especially high when we take on CEO searches that involve these founder transitions, as there’s a greater potential for failure, if not done thoughtfully.

So, Ted and Stacey have joined me today to share how to support founder transitions the right way, and, in this episode, we’ll talk about all the things that boards, investors, founders, and CEOs can do to minimize risk and ensure success, whether or not the founder is exiting or staying involved in the business long-term. Before we dive in, let me tell you a little bit more about our guests. Stacey is an organizational psychologist and managing director at Executive Development Consulting. Previously, she was head of Deloitte’s Succession & Leadership Consulting Practice, where she guided the firm’s work with clients on matters of talent assessment, leadership development, inclusion, and succession.

Stacey also has held managing partner and principal roles at Korn Ferry and Oliver Wyman. Her impressive client list has included companies such as Apple, JP Morgan Chase, General Mills, Harley-Davidson, Johnson and Johnson, Nike, and PayPal, as well as many more. Like Stacey, Ted brings a wealth of experience to our discussion.

He is also an organizational psychologist and has more than two decades of consulting and executive experience. In addition to his consulting work in the areas of leadership development, executive coaching, people strategy, and culture, Ted was Chief People and Culture Officer at Eileen Fisher, Stacey, Ted, thank you for joining us today and for sharing your experience and expertise on such an important topic.

[00:03:12] Ted Freeman: I’m delighted to be here, Roy. 

[00:03:14] Stacey Philpot: Thanks so much, Roy. 

[00:03:16] Roy Notowitz: Well, let’s dive right in. What are some of the reasons or circumstances why founder transitions happen? 

[00:03:22] Ted Freeman: Often, when we engage with founders in these conversations, there’s some kind of inflection point for the company. So, that inflection point could be that there’s a financial transaction — there’s a sale of the company, which is going to trigger a transition. It could be that the inflection point is that the company needs something different to take it to the next level, or the inflection point could be driven by the founder. The founder could be saying, “Hey, my interest lies elsewhere, so I’m recognizing that the best thing for the company is to engage with a different kind of leader.” 

[00:03:59] Roy Notowitz: We all know that founder transitions can be risky and the stakes are high for all parties involved. Why is it not advisable for the board, founder, and new CEO to take a do-it-yourself approach, even when they may feel that they have the right person and a great relationship right off the bat? 

[00:04:20] Stacey Philpot: I think, Roy, there are a couple things to consider. First of all, what’s the level of risk, right? How many things in your business that are high risk, do you leave to chance? Very few, right? And when you bring in someone, a CEO or there’s a founder transition, it’s an incredibly high risk event for the business. So having a plan, a process, a specific way you’re going to engage people and the way you’re going to do it just makes sense from a risk mitigation perspective. So that’s kind of the first thing. The second is founder transitions are really complex processes, you know, they have a lot of emotion in them. A lot of people have to partner well, and they can be kinda messy. So, sometimes when boards are looking at bringing in a CEO, they think once someone’s hired, sort of their job is complete, but really, for these kinds of transitions, particularly when a founder is involved, I find that it’s more of a year long process, at least. Right? And so not seeing it as a process, not putting some structure in place to make sure that process works– a lot of us think that if we just put the right person in a job, things will work out, but in reality, that doesn’t usually happen, and people need more support to get through what can be a really challenging transition. 

[00:05:33] Roy Notowitz: Ted, can you elaborate on the kind of support that an organization might need during this process? 

[00:05:39] Ted Freeman: Yeah, I mean, often it’s– there’s a lot of buildup to this moment, right? The founder’s been thinking about it for a while, they’ve gone through a search process, they’ve met lots of different people, they’ve settled on this person, and that all leads to kind of heightened excitement, right? And, like, a relational excitement, you know? This person’s coming in, they’re going to be so amazing, so on and so on. I don’t mean to disparage that. I think that that’s actually a wonderful part of the process, but what we don’t want to do is misinterpret that as a promise that everything will go smoothly.

Sometimes what happens is both the CEO and the founder, they say, “Well, we’ve hit it off so well, whatever’s around the corner, whatever bumps we may run into on the road, we like each other so much that it’s going to be great.” And, as Stacey mentioned earlier, these are high risk situations. These are high stakes situations.

And, why leave that to chance when we know that that honeymoon feeling wears off? So, one of the things that we really encourage people to do is to step into a process, step into a process where you’re really gonna be able to talk to one another about some of the unspoken assumptions that you have about what kind of role the founder is going to play, about how the CEO’s going to take up their role, about how that change mandate– not only what it looks like conceptually, but what does it look like in practice? What’s it going to mean? What are some of the hard decisions that we’re going to need to make to bring that to life? And make sure that the support is there for it and that the tools and the processes are there so that people can work through those things.

[00:07:33] Roy Notowitz: So this partnership between the founder and CEO is key. Tell me more about that dynamic. 

[00:07:39] Stacey Philpot: For the CEO, they’re often coming in from the outside and they have a really strong change mandate. That’s why you went to the outside. So, they’re coming in and they want to drive change, they want to prove themselves, and, honestly, if they’re wanting to be a CEO, they usually have a strong desire for autonomy and action. And so they can want to move quickly to getting some points on the board. At the same time, they may be worried about how people are going to perceive them. Can they differentiate themselves from the founder, but still be aligned with the brand and the culture?

And that just makes things a little bit more tricky. I think there’s always a bit of a honeymoon period where people are figuring things out, and they’re being really respectful, and they’re learning, and they’re giving a lot of grace to each other, but then sometimes things, you know, start to shift. Something– the business gets under pressure, the new CEO wants more autonomy, a big decision comes up, and it’s not clear who has decision-making authority and things start to get thorny. And those are things you can plan for in advance. You can anticipate how do we want our partnership between, like, the new CEO and a founder to work?

Right? Who’s going to have decision rights here? Who’s going to be at what meeting? You can plan those out so that you’re not having them go sideways and then trying to fix it. You can actually anticipate it and plan for it, which makes everything easier. 

[00:08:56] Roy Notowitz: With that relationship in mind, what are your considerations as you approach a founder transition?

[00:09:02] Stacey Philpot: So, Roy, what I would say is, you know, there’s not just obviously one type of founder. So it’s also important to think about what type of founder are we working with? Each of those types of founder are going to approach the process differently and have a different experience, right? It’s much more emotional when it’s someone who’s really grown up, it’s the only company they’ve worked for, it’s sort of their baby, and they have to let go. That is usually a lot more challenging than someone who maybe has done this a couple times and really just wants to make sure they work with the right person and kind of is very thoughtful about the process. When it’s a founder who they’ve really grown up in the company, so much of their identity about who they are is embedded in the company. Often their name, right, is a big part of the company. And so, how do they unwind from that without too much risk, too fast and being really mindful to the sequence of the transition? That tends to be really helpful for them. How do they know what to let go when, so it doesn’t feel too fast or too slow? 

[00:10:06] Ted Freeman: And along that way, along the path that those founders are on, they’re going to be dealing with a lot. On the one hand, they’re going to be very excited, they’re going to be enthusiastic, they’re going to see this new person coming in as a big opportunity.

Opportunity for them to let go of things and dedicate their time to whatever’s next for them, opportunity for the company, because it’s getting something that, um, you know, it needs at this moment. So those are all positive feelings and then they’re usually coupled with some more challenging feelings, some feelings around letting go and feelings of loss and transition.

So, helping the founders productively manage that as they manage also the operations of the transition is important. 

[00:10:57] Roy Notowitz: So what do you do when issues emerge or friction starts to happen?

[00:11:03] Ted Freeman: So a starting place is just to make sure that everybody knows that bumps in the road are part of the process, and it’s totally normal. So, getting them to expect that they’re going to happen, not freak out when they happen, but instead, manage them productively. What we’d like to do is give the founder and the incoming person a language, a vocabulary, for understanding what each of their styles are, for understanding the ways in which that can be complimentary or potentially conflictual, and then, give them some tools for how they can best manage that. What we don’t want is surprises. We want them to know what they’re getting, we want them to understand how it’s going to be aligned with or be different from their style, and we want them to have all the equipment that they need to be able to work well with that. 

[00:12:08] Stacey Philpot: Life happens and, you know, people get upset at mistakes made, or people trip over each other, and you need a place where you can have a conversation to clean it up. Where’s a place where we can reflect on how it’s going, and if there were some missteps or we stepped on each other, how do we kind of clean that up and learn from each other so it doesn’t, you know, mess with the dynamic? Right? That’s part of the process too. 

[00:12:30] Roy Notowitz: Have you dealt with situations when conflict between founders and CEOs escalated? 

[00:12:35] Stacey Philpot: I was working with, um, a CEO and a founder, and the founder was really excited about the CEO that they brought in. Part of it was the CEO’s team, they, they looked at the market in the same way, they thought about consumers in the same way, they really clicked sort of intellectually in how they thought strategically about the business. And so the first couple of months were really exciting, particularly as the CEO was getting to know the business, right? They did a lot together to understand the business, and it worked really well. Where things started to go south a little bit was at about the five month mark where the CEO said, you know, I’ve kind of learned the business, I’m ready to go. Now I want to start making some decisions. And the founder started to feel more threatened and really nervous about that — wasn’t sure that the CEO was ready to make those decisions, and they started getting into some conflict. 

[00:13:25] Roy Notowitz: So how did you handle that? 

[00:13:27] Stacey Philpot: What we did, right, was, first of all, we took the CEO and the founder offline because some of the tension was starting to show up, even in the management team, and said, let’s have a conversation.

What are the decisions that each of you wants to make, feel you should make, individually and together? And help them understand that there were some decisions that they actually needed to both sort of make together, versus just separating everything. And also helping the founder say, okay, these are the decisions the CEO can make right away, and I’m okay with; these ones, I’m not quite ready. Can we have a couple of milestones so that I’ll know I’m ready to do it? So that would be an example of where we kind of clarified a little bit. 

[00:14:08] Roy Notowitz: What are some other scenarios you’ve helped founders and CEOs work through? 

[00:14:12] Stacey Philpot: Another challenge we’ve seen is when the CEO says, “Well, you know, I kind of want to stay involved. And I, you know, I’m going to really focus on the brand, but I don’t want to do the operations.” And sometimes, in that situation, what it’s like is the founder sort of saying, “I want to do what I like to do, but I don’t want to do what I don’t like to do anymore. I want to change my job.” And, in that situation, helping them anticipate together, the founder and the CEO, what are the problems and trade offs that they’re going to have to make so that they don’t get polarized.

So, for example, one time we’ve worked with a CEO and founder in that situation, and the founder really focused on growth because that had been his strategy for success. And growth can hide a multitude of sins in a company, but then they needed a CEO who was much more operationally minded, more fiscally responsible. But, not looking at the problems they were solving together to see how they made those trade-offs kind of created some polarization between the two. So, part of what helps is talking about the different types of CEO/founder relationships. What are some of the patterns? And helping to anticipate what might be problems for the individuals in this specific case.

[00:15:19] Roy Notowitz: Thank you for mentioning those examples. They really illustrate common challenges that arise during founder transitions. Ted, do you have any others you can share? 

[00:15:29] Ted Freeman: Another challenge that we see can be more on the CEO side of things. So there’s a lot of pressure for them to demonstrate their value quickly. They’re being paid a lot of money, they’ve gone through a very competitive search process, there are a lot of expectations on them, they have a lot of expectations on themselves. Usually these are people who are, you know, very ambitious, and they want to succeed, and they want to show that they’re strong executives and all those kinds of things.

And so they come in and they really want to drive their changes — drive the things that they’ve been asked to make happen. And one of the things that they can overlook is what has been going well in the company that has brought it to this point. What are the things about the brand and the culture that, to an outsider, might seem a little funky, but actually have real value? And, to have the discernment to know what is it that we need to preserve? And what is it that we need to reshape? What is it that we need to let go of? 

[00:16:38] Roy Notowitz: Yeah, this is especially true in a lot of the cases that we work on together. So what else can you do to support the longevity of these partnerships? 

[00:16:48] Ted Freeman: So, this is not something that’s going to be one and done, there’s not a quick fix, there is not a silver bullet. There’s some work that needs to be done over time to build a partnership between the CEO and the founder. So, I realize in this conversation, we’ve sometimes said the relationship between the CEO and founder, and what do we mean by relationship? It’s not just about being friends, it’s not just about being excited about this new person who’s going to come into the organization, fix all the things that we haven’t been able to fix. It’s more about a partnership. And I think we’re really intentional about that because, particularly in founder-led organizations, there can be a culture that’s very relationship-driven.

So, oftentimes founders, at least, particularly in the early stages, they surround themselves with people that they know, people who are their friends, people who live in their apartment building, people who may be family members, people who they went to school with. All of those kinds of things. And that can set a tone where the currency in the organization, the way that things get done through the organization is through personal relationships and interpersonal relationships. That can be a wonderful, wonderful thing, and there can be blind spots to that. And so what we’re talking about is how you build partnerships that start with clarity around goals for the business and alignment around roles and on how they’re going to work together.

I think the other thing that I would add, ’cause you know, we’ve talked so much about this idea of a process and getting roles clear and so on and so on. We don’t want to do that on the person’s first day. I think Stacey said earlier, one of the mistakes that could be made is people think, oh, you know, we found just the right person, now we’re good.

And I think the next mistake is, “We hired the right person, they had their first day, they know where the bathroom is, they know what the strategy is, they’ve had lots of conversations with the CFO. We’re good. And, actually, that’s not where things tend to come up. So, it’s almost like clockwork that you see certain patterns at 60 days, you see certain patterns at 120 days when we’re starting to get into the rhythm and the cadence of the business.

That’s when we start to see more of these wrinkles turn into fissures. So, you know, Stacey and I often think about making sure that we have the right timing for this intervention. We do want to do things right away. We do you want to do things while this honeymoon period is going on, but also, how do we spread out our engagements with founders and CEOs so that we are both able to give them some of the equipment that they need, and we’re also able to work in real time on some of the challenges that come up. 

[00:19:46] Roy Notowitz: Speaking from experience, organizations can really set themselves up for a successful transition by ensuring the executive search process is thoughtfully carried out. If the incoming CEO isn’t well aligned in the first place, it can be difficult, even impossible, to work through some of these challenges. With that in mind, who should be involved in that vital search process?

[00:20:11] Stacey Philpot: I mean, what I would say is any big decision in a business, you want to hear from multiple perspectives, right? I think what’s challenging is it can be an emotional decision, but it’s such a risky one that really what we encourage founders to do is get a lot of perspective. Right? So much kind of bias can come in for founders. They either want someone who’s just like them, or they’ll kind of go the other pendulum swing. So getting a lot of perspectives on the candidate– if they’re investors, certainly investors are going to want to have a point of view, but, whoever is advising the founder, we encourage them to use those advisors in this process and get multiple perspectives. It’s a really tough choice for a founder to make and getting a lot of inputs to mitigate their bias can really help. 

[00:21:00] Roy Notowitz: If you’re enjoying our conversation, check out our previous episode with Stacey. In it, she shared three things that hiring executives and boards should be thinking about as they reset and rebuild their leadership teams. We also talked about how a data-driven hiring approach can mitigate points of failure when filling complex leadership positions. 

So, in a lot of the cases that we’ve worked on together, the founder has wanted to stay pretty active and involved in the organization. And then you had mentioned in other cases, not so much; they’re ready to just hand over the torch and move on.

So, is there a difference, in your opinion, between those two scenarios, as it relates to the type of process for onboarding and transitioning? 

[00:21:49] Stacey Philpot: You know, people have a lot of complicated feelings around the transition. And so, even if they say things like, “I definitely don’t want to be with the business, I’ve always wanted to spend more time on vacations. I want to go be with my family. I don’t want to be in the business.” You know, you have to go forward knowing that there is probably a part of them that still wants to say they’re connected to the business. And so helping them really be conscious of both those parts and talking about them so that they don’t get kind of acted out, can be really important.

I think, for founders, what’s important in a transition is making sure they have other things that are going to fill the space and give them a sense of fulfillment and not just leaving that to chance either. Helping them think about not just what do they want their legacy to be, but what else is in their life that they really want to contribute, grow, develop?

Or what gives them energy? If you don’t do that, it’s really difficult for the founder. So I think that’s really important.

[00:22:43] Ted Freeman: And I do think that that adds another layer of complexity. I mean, think about, you know, a director-level person who’s been reporting up to the founder for many, many years. Now, this new CEO comes in and the founder is staying on in an executive position, but not the CEO role.

How does that person figure out how to navigate that, right? Like, they’re saying, “Well, I, I know that, like, this is the CEO, but, at the same time, like the founder’s still here and they’re– of course, I guess, who am I going to pay attention to? Who am I going to follow here? And it’s not an untenable situation, but it does add complexity.

And I think it heightens the need for all the things that Stacey and I are talking about around role clarity, around decision-making clarity, around how you communicate that to people. And here’s a story that– it’s not a founder transition, but it was something that happened to me that was enormously helpful to me.

So, when I moved into an executive role at Eileen Fisher, I overlapped for a number of months with my predecessor. At one point, I was proposing that we do something around, you know, some development for our executive team. One of the other members of the executive team said to my predecessor in a leadership team meeting, “What do you think about what Ted’s proposing?”

And I knew that this isn’t how she would have done it– I knew it. It’s just not her style, it wasn’t the way that she would have approached this problem. But what she said, which I found to be enormously helpful, was, “Around this, I don’t think my point of view is relevant. I would probably do it differently, but the most important thing is this is Ted’s decision, and this is Ted’s recommendation.”

That was enormously helpful for me. And I think one of the things that I really appreciated about her was that she had done a lot of work to be able to let go of her role in an organization so that she could support me in having that happen. 

[00:24:51] Roy Notowitz: That’s a great example, Ted. Stacey, what are some typical scenarios that you see relating to the leadership team’s dynamic with an incoming CEO?

[00:25:00] Stacey Philpot: Roy, I think there are two tangible problems that almost always come up about four months into CEO/founder transitions and sometimes, much earlier. And one is: who goes to the leadership team meetings? Does the founder go? And what is the relationship of the founder to the leadership team?

That’s almost always something that comes up. And a second issue that almost always comes up is: how, and when is the founder allowed to make requests for resources? Because, you know, that’s kind of what happens, kind of comes in: “Well, I’ve got this project,” or “I need this money,” or “I need this person,” and the organization doesn’t feel like they can say no to the founder.

And, you know, Ted’s example earlier was about being authorized, right? Having your predecessor authorize you so the organization knows you’re the decision maker. These are examples, right? The resource allocation, and who goes to the meetings. Those are really about role clarity. Right? What is the CEO’s job? What authority do they have on the leadership team? And who gets to decide how money gets spent? So those are just things you can anticipate that you want to map out in advance before you get into a problem. 

[00:26:11] Roy Notowitz: Thinking about this and what you’re saying, one other key thing that came to mind for me, for CEO’s coming in is assessing existing leadership teams, and sometimes, they may or may not see that leadership team in the same way that the founder does. And so, how does that work itself out? And what do you do to support that when there’s different perspectives potentially on who should be part of the move forward versus maybe finding other opportunities within the organization for somebody?

[00:26:40] Ted Freeman: I think that is a wonderful example of a kind of potential conflict that an incoming CEO and an outgoing founder, or a founder who’s moving into a different role, will face. And, you know, just to go a little bit further with it, Roy, you know, very likely, the founder has had confidence in those people. Probably have had close personal relationships with those people. And yet, it is the CEO who needs to think about what is the team that will help her or him move the organization forward.

And that may or may not be the team that’s there. So, this is exactly the kind of thing it’s like, okay. So how are we going to make those decisions? Is the founder going to be ready to authorize the CEO to move forward on those things? Those are exactly the kind of things that need to be worked through. If we don’t have agreement and transparency about how we’ll approach those, we’re sunk. 

[00:27:38] Roy Notowitz: Exactly. Along the same lines, we always recommend using the Hogan to inform the CEO selection process. I’m curious how that information can also be utilized to support a founder or new leader integration process. 

[00:27:53] Ted Freeman: One part of the Hogan helps to understand what kind of culture the leader is going to create if left to their own devices. What are the natural ways of interacting with people? What are the natural ways of approaching problems that they’re going to gravitate toward? So, if we give the founder a vocabulary for understanding how they would do that, and also give them a vocabulary for understanding how the incoming CEO would do that, they’re able to very quickly see when there’s some kind of difference in the way that they approach these problems. They’re able to talk about that much faster, much more efficiently to figure out, okay, well, how are we going to move forward on this? 

[00:28:42] Roy Notowitz: Stacey, do you have anything to add with regard to the benefits of a Hogan or leadership assessment in general?

[00:28:48] Stacey Philpot: You know, I think it’s hard for people to describe their leadership style. And yet, when you’re working with someone– people’s leadership styles, when they conflict, it, it’s, you know, it’s a dynamic in the relationship, but it’s hard to know how to put it into words and talk about it. So, one of the things that assessments will do is, as Ted was saying, it gives language to things like: what are your strengths? What do you value? What type of culture do you create? And how do you show up when you’re stressed so people don’t take it personally? Assessments can give you language so you can talk about it in a really easy, even sometimes kinda funny way where you can get to know each other really quickly.

And when you, when you work with leaders about giving them feedback and giving them language, it just makes things easier and they can work through conflict faster. 

[00:29:36] Roy Notowitz: I agree. Everyone is unique and a product of their experience, and they bring distinct ways of leading, influencing, communicating, relating, and making decisions to achieve business goals. This transition work is powerful and effective because it takes into account a lot of that variability. It’s like an insurance policy to avoid catastrophic outcomes when bringing in a new CEO. Are there milestones or indicators that tell you whether a founder transition is on the right track for any board members, CEOs, or founders who are listening to this podcast? How might they take a pulse on their own situation?

[00:30:17] Ted Freeman: Well, this may not be satisfying as a hard metric in terms of, you know, whether it’s working in success. But, I think the truth, having been in executive roles and having worked with many, many executives, people know when it’s working and when it’s not working. They just know. I mean, when they find themselves going home and talking excessively to their partner or their spouse about things that, you know, are happening with the other person, when they’re lying in bed, strategizing about, you know, “How am I going to have this hard conversation with the person?” They know, right, that they have not forged the partnership that’s needed. And you know what? That’s just, that’s just waste in the company. And you’re just destroying value in the company when people are spending their energy focusing on those kinds of things, rather than on moving the business forward. Now, I think on the flip side, people know when it is working. People know when they have gotten clarity around things, they have worked through the possibly difficult process of figuring out decisions and roles and all those kinds of things, and that things are moving smoothly, and that the incoming person is successfully preserving what needs to be preserved, the incoming person is also moving the business forward in the way that the business needs to move forward. 

[00:31:38] Roy Notowitz: Stacey, is there anything else that you want to share about how you know when it’s working or not working?

[00:31:42] Stacey Philpot: So, a lot of times the people who feel the pain of the relationship not working the most is the leadership team. The people on the leadership team, because they feel sometimes caught in between. They’re the people who get different messages, like if the founder wants something or legacy culture in the way that the CEO wants something new.

So the first thing that, you know, I want to do when I go into working with a CEO and a founder is not just hear things from their perspective, but talk to the leadership team. And understanding that helping the founder and the CEO understand how they’re impacting the team can be something that really helps bring the CEO and founder together because they both care about the executive team being a high-performing team.

So that’s the way that, you know, if things are working, and it’s also a point of helping things get better, right, if they’re not. 

[00:32:31] Roy Notowitz: Ideally, organizations will follow a proactive and thoughtful founder transition process from the outset; however, sometimes that’s not the case. Can you still step in, even after significant challenges emerge to get things back on track? 

[00:32:49] Stacey Philpot: You know, it’s never too late. There are always things that you can do. Sometimes that means kind of working through some tough spots that might’ve happened to get things off track, but there’s definitely things that you can do to help these transitions go better. Even if it’s a little bit late in the game. 

[00:33:03] Roy Notowitz: How have the events of the last couple of years factored into the way CEOs and founders are envisioning their culture moving forward?

[00:33:10] Ted Freeman: I mean the single word for it is inclusion. I think people have been transformed in terms of understanding that idea, understanding the potential for it, understanding the need for it, and, you know, we just don’t have conversations with clients anymore about the business value and the, the business upside of inclusion and diversity. People know it.

It’s a question of how do we get there? And how do we do that? How do we do it faster? It’s not a question of whether we should. 

[00:33:48] Roy Notowitz: Well said. Stacey, what are you seeing with your clients? What are they thinking about as they look to the future? 

[00:33:56] Stacey Philpot: I’m privileged to do a lot of work right now with CEOs and their executive teams. I think that what’s on the minds of CEOs and other leaders right now is: really what is going to be different as we return to work, and what has changed, and what’s different? What I often hear is when people use the word ‘return to work,’ what CEOs and even executive teams mean, and what most employees mean with that same phrase, is radically different.

And so there’s this disconnect happening. And a lot of my work is helping people explore what does that mean? And so my work has been helping CEOs think about how do they have that conversation. How do they connect with people? And some of it is exploring what have been some of the trade-offs and sacrifices they’ve made?

Right? And how do they really feel about that now? Because if they don’t explore that it can get in the way of them being able to have the right conversations with their people and really know how to make the right decision about what their workforce is going to look for in the future. 

[00:34:54] Roy Notowitz: That’s great. You both have the most interesting jobs, and the work that you do really helps to amplify the impact of individuals and teams.

I’m so honored to be able to collaborate with you both, and I’m always in awe of your talents. I’m looking forward to sitting back down with you to dig even deeper into some of this work. Next time we’ll go beyond the CEO and founder dynamic to discuss new leader integration and acceleration, specifically at the VP and C-Level. Until then, thank you both so much for being on the podcast. 

[00:35:26] Stacey Philpot: Thanks, Roy. 

Thanks, Roy. Glad to be here. 

[00:35:29] Roy Notowitz: Thanks for tuning into this special episode of How I Hire. Ted and Stacey will be back to continue the discussion about leadership integration, and there’s so much to dig into there. Until then, you can learn more about How I Hire and our guests by visiting You can also find a full transcript of this episode and others there. If you know somebody who might be interested in the topics and discussion you heard today, please share this episode with them. It’s a great way to support our show and to spread the word about the latest in the executive hiring.How I Hire is created by Noto Group Executive Search. To find out more about Noto Group, visit You can also find us on LinkedIn. This podcast was produced by AO McClain, LLC. To learn more about their great work, visit