The Art of Letting Go




Angie D’Sa: 00:06

Welcome to The Clarifier. In today’s episode, we talk about letting go. We zoom in on the experience of founders and CEOs building out their executive teams. We talk about why this experience can feel challenging, even threatening.

Jeff Hunter: 00:23

We get caught in these perpetual waste cycles instead of perpetual learning cycles. So, how can we learn our way into this? Well, the first thing is to figure out the root cause of why we’re not letting go. The root cause could be the fear of ignorance, as you described. It could be the fear of not knowing how to do this. But in my experience, that’s not the most common reason behind this.

Angie D’Sa: 00:53

At the core of building your team is letting go of control. We’ve learned that founders can undermine themselves and their executives when they don’t acknowledge their own fears of letting go of control. They may either stay too distant or swoop in and grab the wheel instead of having open conversations about what feels scary and confusing as they transition responsibilities.

Okay, Jeff, I’m excited for today’s topic. Thank you for being here on this Monday morning with the lovely construction noise behind me. There’s not much I can do about it since I live in a New York City apartment. So, getting into today’s conversation, I brought this topic to you because I think it’s one where you have a lot of experience advising founders and CEOs. The topic is letting go, specifically letting go of responsibilities that you, as a leader, have held over time as your company has grown to another executive. Whether that executive has grown up in the ranks with you or is someone you’ve hired because it no longer makes sense for you to handle that responsibility for your company. This is a common scenario, right? A CEO who has primarily been responsible for sales because they’ve been the best at getting customers to buy into the vision of the product may realize that they can’t be the only one handling sales if the company is going to grow at the necessary rate. Another example is a CEO who has been completely devoted to product development because that was their inspiration for building the company. However, they may realize that it doesn’t make sense for them to exclusively oversee product when scaling is the mandate, as opposed to just focusing on the initial spark and initiation of the product. These are just two examples, but there are many more. The reason we wanted to discuss this today is because we’ve found that during these transition moments, leaders or CEOs can feel quite uncomfortable. Sometimes they feel challenged or undermined, while the executives to whom they’re transitioning responsibilities may feel set up to fail. It can go poorly. So, I wanted to ask you to share some of your experiences helping leaders through these transitions and give us a sense of how this can be successful and what tends to go wrong.

Jeff Hunter: 03:26

Yeah, great. Once again, Angie, I’m so excited to speak with you. I look forward to our Monday mornings. I’ve been thinking about this topic all weekend. I think the prompt is excellent. I want to expand on the prompt a little bit. It’s about the right time to let go. Because the other phenomenon we see is people letting go too fast, which can become deeply confusing for everybody. I’ve made this mistake many times myself. I probably tend to lean more towards letting go too fast rather than holding on too long. So we can discuss how we think about that. Today, we’ll talk through a couple of different frameworks. We have the 4D framework, which helps us understand what responsibilities you should have as a CEO as everything gets bigger. We’ll discuss the design for people framework, which helps us determine who should hold what responsibilities. And we’ll talk about Big 4, which is how we consider who will be the best at what.

As I was thinking about our conversation this morning, something struck me—a basic, simple truism. On day one as a founder, your job is to work yourself out of a job. That’s really your biggest job. Even if you don’t have the intention to grow the business significantly (although most of us do), there’s a significant distance between where you’re starting and where you want to be. That distance is represented by serving more people, solving more problems, and creating more opportunities. That’s what you want to accomplish. And as you’re building and creating, there are a lot of things you’re going to need—capital, great products, etc. But fundamentally, what you’ll need is people. That’s what it boils down to—more people working for you, more people contracting, advising, investing, etc. It’s all about the people you bring to the table and what they bring—capital, talent, advice, coaching, whatever it may be. So you’re on this path of growth, adding more people. We know that adding the first couple of people to the group is relatively simple, except for co-founder situations, which we discussed in our last session. But overall, it can be pretty straightforward because a small group of people can stay well-coordinated, get to know each other, and learn rapidly together. However, as you add more and more people because you’re serving more people, solving more problems, and creating more opportunities, coordination becomes increasingly difficult. Cooperation becomes more challenging. There’s a tipping point where things start to get really tough, and that point is different for every founder and CEO. Broadly speaking, there’s a concept called the Dunbar number, which suggests that when a business has around 150 people, things start to get complicated. Typically, founders and CEOs struggle with how to design their organizations, how to hire people, and how to manage effectively around that stage. However, this challenge can arise earlier or later depending on the circumstances.

For years as a co-founder, founder, and CEO myself (I’ve been on that journey many times) I was trying to figure out how to design an organization. How do you decide who should be in which role? How do they work together? How do you manage all of that over time? Around 25 or 26 years ago, in the late 90s, I experienced a defining moment. The company I co-founded received a significant Series A investment, and I was overjoyed. But shortly after, I learned about another hot Silicon Valley startup—one that seemed truly special and about to make a big impact. That company was called Google, and they secured a $25 million investment in their A round, which was a record-setting amount at that time. Every founder in the Valley who competed for similar talent, even though we were in different industries, knew we were in trouble. Sergey and Larry were likely going to do something remarkable. Their idea was compelling, and it was evident that they were executing it better. I realized at that point that I needed to think differently about how to design my organization. So I became obsessed with the questions we are discussing today. How do you design an organization? When do I hold onto something, and when do I give it away? What forms can giving it away take? These questions became an obsession for me.

As I sought advice from experts and spoke with people at GE, BCG, McKinsey, and other CEOs, I realized that their answers didn’t make much sense to me. They weren’t grounded in solid evidence but were more based on conventional wisdom or common practices. I saw that my blind spots as a founder/CEO regarding organizational design, assigning responsibilities, and managing them were crucial determinants of success or failure. My competitive advantage was limited by the blind spot I had regarding the questions we’re discussing today. If I hired someone and assigned them a responsibility, and they didn’t succeed, how should I manage that? How should I interpret it? Is it a lack of job knowledge on their part, or am I a bad manager? These questions are often top of mind for the founders and executives we work with. That’s when we started developing these frameworks, driven by the practical need to understand these issues. It became an obsession for me, and that’s how our journey of developing these frameworks began.

One of the things I started to realize was that at least in a high-growth organization, a fast growth organization, where I was really depending on people doing great work. And by the way, I think larger organizations may not have this problem per se because they’re sort of machining out a lot of human difference. But in a fast-growth startup, you’re not looking for the competitive edge. At that time, at that company, I had some of the most amazing technologists working there. What you can see very clearly is that the best technologist was substantially better, even at the same experience level, than many other technologists we were hiring. Of course, Scott Ballmer and others have commented on this, right? In any band of experience, you can get wild variability in performance. When I’m coaching founders, most of the people they’re hiring, that’s the expectation, is like, they’re going to be really, really good. They’re not just going to be average. At another time, we’ll talk about this, but I think the advent of Chat GPT and AI, generative AI, or moving into generative AI, really makes this problem pronounced. Average work will be done by machines, not by humans. Humans will be expected to do exceptional work. There’s not just a talent factor there, about these people are really good at what they do. There’s also the question of how do you manage? How do you give them their responsibilities?

It’s your job to grow this thing. It’s your job to take on more problems and serve more people and create more opportunity. You’re going to do that with other people. Your blind spots as a founder/CEO around how to design your organization, who to give responsibilities, when to give them responsibilities, that is the make or break. Because the final thing I’ll say for this piece is one of the things we believe very, very, very clearly and see again and again, is when you diagnose a big failure in a high-growth company, it has to do with a founder blind spot. It is never about, “We didn’t have the right capital, we didn’t have this, we didn’t have those.” Those are all problems, like, “My strategy was bad. I didn’t have product-market fit.” You can hear all those. However, people knew that stuff was going to be a problem well before it was a problem. And the inability to handle those kinds of things usually came down to a founder blind spot. Of all the founder blind spots that practically impact an ability for an organization to succeed, the one we’re talking about here is probably one of the biggest.

Angie D’Sa: 13:54

Let me take a moment to summarize what I understand you saying. As we enter today’s conversation, one of the things I’ve been contemplating, and I know other coaches have been as well, is how to assist a founder who struggles with giving away their Legos. And what I gather from your remarks is that this is a subset of a larger discussion. It’s essential to consider when contemplating the growth of your organization. It’s not just about how a founder or CEO can hand off previously held responsibilities and set others up for success. It’s also about determining the right design for the organization, the necessary functions, and capabilities over time, and how to set up various individuals for success. This includes your team, potential hires, and so on, in order to effectively address the company’s expanding scope. It’s recognizing that I can’t accomplish everything on my own, but there will inevitably be blind spots that may hinder me. Am I understanding you correctly?

Jeff Hunter: 15:04

Yes, that’s right. Those blind spots can take various forms. For example, you might believe you’re excelling as a manager when you’re actually performing poorly, or you might think you’ve hired the perfect person for a role when that’s far from the truth. In a future episode, we can delve into the topic of hiring mistakes, which is always significant. We can discuss the insight we’ve had for a long time that all hiring mistakes stem from post-hire management mistakes, not pre-hire assessment errors, for instance. But yes, when we’re talking about blind spots we could be talking about one of the following. You know the problem, but you’re afraid to deal with it. Or you’re not aware of the problem. Or, you know the problem and you’re dealing with it, but you’re doing it really badly.  So there are different ways blind spots can manifest. But yes, what you just said is exactly right.

Angie D’Sa: 16:03

One of the things you hinted at regarding the design of the organization, beyond yourself and in service of growth and scalability, is knowing when to hand things over. I also believe I heard you mention how it might look different if someone other than yourself is handling that responsibility. Would you like to further elaborate on either of those points?

Jeff Hunter: 16:26

Yeah. So I think the conventional wisdom when we talk to managers, founders, and anyone who is in a managerial role with multiple direct reports is that there is this ingrained belief, which I think stems from business school and classic management thinking. It’s the idea that organization design is independent of the people within it. It’s this mechanistic thinking from the early 1900s where you design something and then fit the pieces into that design, without considering that the pieces themselves can influence the overall design. This mindset originated from mass production theory, where you could simply place anything that meets certain specifications into a designated role and the design would work. However, in practice, as many people going through the growth phase have discovered, this belief is far from true. In fact, it’s catastrophically untrue in many cases. One common mistake I observe is that people adhere to this mental model, believing that certain roles are well-defined and there are known jobs to be done. For instance, the notion that every organization needs a CFO is pervasive. We also assume that there are clear boundaries for each role and that we should aim to hire the biggest and best candidate for that role. However, all three of these assumptions are incorrect, and their practical implications can be significantly flawed and vary depending on the circumstances. If I could debunk this conventional wisdom, I would consider it a lifelong achievement. In reality, at any given stage of organizational growth, there are specific problems that need to be solved and opportunities that need to be created. These give rise to associated responsibilities. Let’s consider the example of a CFO. Every founder knows that they need to be aware of the cash in their bank account. I haven’t encountered a single founder who isn’t aware of this, and those who aren’t are no longer be founders. Understanding the cash flow is crucial because without cash, there is no business. However, as the organization grows and you have more people on board, the amount of cash in the bank becomes less of the big thing on your mind. It remains important, but it’s no longer the primary focus. So, you recognize that managing cash is a problem that needs attention. How do you address it? Well, at day one, it’s likely just you and a small team, and you know exactly how much cash is in the bank. But on day 365, with a larger team, the cash in the bank is no longer your primary concern. You need it to be managed well, but it’s not the main thing on your mind. At this stage, there are different people who can handle cash management. Some organizations have office managers who handle cash, while others may have external accountants. In some cases, internal Chiefs of Staff take on the responsibility. There are various designs for this. The goal is to figure out the next stage of growth and identify the best person available to take on that responsibility. At a certain point along the growth curve, there may be a cluster of responsibilities related to money, treasury, and related functions that logically make sense to group together, resembling a CFO role. However, even in creating a so-called CFO role, it won’t be exactly the same as everyone else’s CFO role because it’s specific to your organization, reporting directly to you, and influenced by unique aspects of your business. Additionally, when it comes to hiring for such a role, I frequently witness a common mistake—hiring a big-name CFO and expecting them to seamlessly fit into the organization. This often ends in disaster. While there are exceptions, most big-name CFOs have experience in larger organizations, operating in different cultures and contexts. Simply having the title and a certain set of responsibilities at that level doesn’t guarantee success in your specific context. Let me bring up an example where someone holds onto a responsibility, such as cash management, longer than they should because they’re uncertain and feel they can’t afford a big-name CFO. They may think, “I don’t know what to do, so I’ll just retain control over the cash management.” This mindset prevents them from considering the possibility of finding someone who could manage cash better than they can and finding a way for that person to handle it, freeing up their own attention. I’m highlighting cash management because it’s a critical aspect for many organizations and can become a sticky point for founders to let go of. They believe they have to be constantly on top of the finances or cash. However, that constant attention comes at a cost—it diverts their focus from other crucial areas such as product development, market fit, sales, and organizational growth. If they get trapped in the belief that they can’t afford a CFO or other solutions due to conventional wisdom, they hinder progress in delegating the responsibility to someone who can perform just as well, if not better, and reduce the attention they need to dedicate to that particular task.

Angie D´Sa 23:47

I’m hearing at least one common pitfall and some practical steps. So I want to highlight what I’m hearing. I think the pitfall that I also hear so often and I’ve fallen prey to it myself is responding to advice or input from somebody outside my company that I need a CXO or VP X as though that title means the same thing to everybody in every company and can simply be dropped into my organization to make magic happen. The gap in thinking that happens when one just accepts, “Oh, I need a CXO or a VP X or a senior director y or whatever it is, insert function here,” is not going through the steps of really granularly articulating what are the responsibilities I need this person to hold in my company because of our current size and stage, because of our most important imperatives, and also because of what I’m like as a leader? Right, because of my idiosyncrasies. Because of the things I’m going to swoop in and do that I shouldn’t be bothering to do.

What I’m hearing you say is the common pitfall is assuming, “Oh, I’ve hit this magic number. Now I need a CFO,” rather than taking stock of what do I actually need somebody to fulfill today, and maybe a year from now? And what would it look like to hire for that responsibility set in the context of my company? So, that’s the first thing that I’m hearing. And then the question I guess I would have for you, Jeff, is, what about for those founders who are doing this for the first time, who don’t really know? They know, “Okay, I don’t really want to be the person who’s managing cash anymore. But I also don’t know what the upside could be here. If I had somebody who had expertise in this function. And in this field, I don’t know what the line items of responsibilities are. I don’t know what excellent looks like. And in fact, I’m a little afraid of having to manage this person once I bring them in because they know how to do the job better than I do.” What would you suggest for those founders?

Jeff Hunter 26:03

It’s a very, very common problem. And it’s well stated the way that you stated it. And I just have to reflect for a moment, I just love doing these with you because as I was talking, I was like, I think this is like spaghetti salad. I don’t think I’ve actually have a through line on anything I just said, and then you cleared it all up. So thank you very much.

You’re not going to know if it’s your first time. Let’s say it’s not your first time, but you’re in a different sort of industry or a difference. You’re not going to know. And so the question is, how do you learn into that problem, as opposed to try to fix it? And I think, again, the conventional wisdom is, either I have to just go pick the biggest name I can who does that thing, turn everything over to them, back away, give them space, and hope for the best, which is almost always a failure pattern, or I don’t let it go at all. Because I don’t know, and how would I know how to do that? And all those kinds of things, which is another failure pattern, both of those things typically lead to some sort of failure. And when I say failure, by the way, I just want to be clear, like those failures can become productive. You can learn from them. But we shouldn’t ignore that there’s a better way to do this, they can give you much smaller failures or mistakes that are much more productive for learning along the way. As opposed to, I just recruited the biggest CXO in the world for this job, it took me six months, I burned a ton of money with a retained search firm, I paid a ton of money with a sign-on bonus. And now like, now I’ve got the real problem. Now you think you’ve got the real opportunity. But now actually, you’ve got the real problem. So that’s a very common pattern of like, wow, once you’re there, it’s going to be difficult to unwind that decision, it’s going to be difficult to unwind to that cost. It’s going to be incredibly wasteful when you don’t succeed because it’s difficult to figure out what went wrong, where. We get in these perpetual waste cycles as opposed to perpetual learning cycles. So what would be a way that we could learn our way into this? Well, the first thing is, we have to figure out what is the root of why we’re not letting go. The root could be the fear of ignorance, as you described, it could be “I don’t know how to do this.” But my experience is that isn’t the most common root cause of this. That is one of them, and it comes up. But the most common root cause is fear of lack of control. That is where we see the most common root cause of these problems. And listen, it makes sense because founders actually have serious control issues. One of the things I know about every founder I’ve ever worked with is they’d much rather be working for themselves than working for others. That’s because there are lots of reasons for that, the belief that they can create more wealth for themselves, whatever. But one of the big reasons is they don’t like being told what to do. They often have very intuitive paths to success that are difficult to describe to other people. I definitely have this a ton of this issue. So it’s very difficult to describe to other people. It’s very difficult to manage other people in somebody else’s context, inside a large organization.

Founders have a lot of autonomy issues, they want to have freedom, they want to have space, they want to be able to control things within that space. When you start hiring people and giving them work, you’re letting go of control in some ways. Mostly, you’re giving up control, you’re going to give up some level of information. Because if you’re doing it, you have more information, you’re going to give up at least a start some level of speed, you can probably do it faster yourself than go through all the effort to hire someone else and give them the job. You probably think at least you can do at a higher level of quality. Most founders have big quality buttons, like, “I don’t want crappy work, and I can know I could do it well.” So these are all control issues, right? Like, if I could control this thing, then I could do it faster, I could do it better, I could do it cheaper, why would I give this to someone else? And that control issue is a fundamental fear, which blocks success. It is an insidious sort of blind spot, a cancer that builds inside of an organization. Because the fear demonstrates or is represented as virtue. It is represented as “I am doing the right thing, I founder am uniquely capable, I founder, and the only one who can save us, I’m founder and the only one who can do this.” And let’s just be clear, if that’s true, that you are uniquely capable, blah, blah, blah. There may be some instances where that’s true, but for the most part, that just means you’re a bad manager. That’s what that means. It is a fear that then is because it’s difficult for us as humans to see our fears, we feel them, but it’s hard to articulate them. We give ourselves Virtu narratives. Really but inside, we’re sort of feeling impostor like and last. And then we exhibit those fear narratives to others as virtue narratives that are, “I’m going to be better at this, etc.” And if you as a leader, don’t have someone by your side, as a coach, or advisor, or somebody you trust, who can point this out to you. And really hold that mirror up to you, you are going to make a lot of really terrible hiring decisions. And once even if you make good hiring decisions, you’re going to manage atrociously. So that fear has to be identified, “Listen, you’re still in control, you still have control, you still have ultimate higher fire, promote demote authority, that didn’t go away, just because you put somebody in the role. They won’t be as good as you on day one, they can’t be mostly because you didn’t know how good you are, and you don’t know how good they are. And you will filter that to the belief that you are better than them. Even if they object objectively that isn’t true. So on day one, it’s going to feel uncomfortable. And day one, they won’t be as good as you are, they won’t be as fast as you are, and they won’t be as cheap as you are. And yet, if you don’t go through this process of helping them find and unleash their potential, you can’t grow the organization, because you ultimately can’t hold everything. So the question is going to be first of all, how do you identify that fear? And second, how do you start to deal productively with that fear? And the way you deal productively with that fear in the hiring situation is to talk openly about them. Don’t hire somebody who doesn’t have a view into that and doesn’t have success dealing with founders like that. And once you hire them, stay close, and do the handoff well. Onboard them purposefully. Don’t just throw things in, because what we see happen again and again with founders with these control issues is they back away. They’re still nervous, and something goes wrong, which it always does. Then they fly back in and pounce. Then the person who has hired, who is the quote-unquote expert to do the job, feels under threat, belittled, micromanaged, that reduces their productivity and performance, which validates the founder’s belief that they were right in the first place not to hire somebody. As you can easily see, it cycles downward from there. If you stay close, ironically, if you have a good onboarding plan, if you make sure that you’re doing these handoffs well, as we’ve learned with principles like ski in front, ski beside, ski behind. Employing those sorts of techniques, you actually significantly reduce not only the probability of a bad hire or bad management situation, but you also start to learn to deal with your fear more productively.

Angie D´Sa 34:57

So, I think what I’m hearing you say here is, it’s going to be really hard to actually see and do in practice. But you’re asking founders and CEOs to recognize that in most instances when they’re setting up a new executive or an internally promoted executive to take on a responsibility, there is a fear of losing control that colors interactions with that person. And that also colors the diagnosis of what’s going on if and when that person screws up. They do something differently than you would, they achieve an outcome that doesn’t make sense to you. And the first thing to do is to get help to see the way that fear of losing control might be manifesting in ways that one is blind to oneself. So that’s sort of the headline that I’m hearing you offer us. And then I think, you know, the interesting thing to look at is in those situations, I can hear so many founders in my head saying, “Yeah, but what if that person actually isn’t good enough? I have limited time, limited money, and limited bandwidth to make this thing work, right? And what if I let the person stay in the role too long? The implications of that for my organization could be terrible, right? Wasted time, money, resources, we go in the wrong direction. And so how does one balance that challenge between self-awareness, self-skepticism, could I be the one who’s setting this person up for failure, and actually being vigilant and fast enough to fire if needed, and move on to the next person, learn the lesson, and move on to the next person? How does one balance those two things?

Angie D´Sa: 36:46

Oh, I can’t hear you for some reason.

Jeff Hunter 36:50

Okay, there we go. So the first thing I’d say is you’ve connected into what I would say is the second root of this situation of failing to let go, which is the “what ifs?” What if I make a bad hire? So first of all, we know, you know, without going into this, the mind is a forecasting machine. That’s really its evolutionary advantage. It’s its job. It’s so it’s playing downfield all the time. What if, what if, what if? Lots of fear, lots of FOMO, lots of all that stuff. We hear those as reasonable decision criteria, reasonable ways to judge something, but they’re not. They’re fear, an irrational, unreasonable fear, sort of poking its head out into your consciousness, and you post hoc rationalizing it with smart words and concepts. So you have to understand this fear exists. And one of the reasons the fear exists, I believe, is because people are terrible at firing other people. I mean, it is truly astonishing. I’ve talked about this many times. And by the way, I don’t think getting good at firing people is something that anybody should try to do or should put on their goal list. Because it means you failed miserably as a manager to get to that point, just to be clear. But, if you think about it, at least the experience I’ve had is if I took a look at the hundreds, maybe even thousands of use cases of being by a manager while they were firing someone or thinking about firing someone, or even at the beginning of that performance anxiety of like, “I don’t think this is working out.” And then you look forward and you say, “Okay, here are all the people who ended up getting fired.” In how many cases did the manager say, “I did that well, and they did it in about as much time as it should take”? How many managers say, “I did that poorly. I went way too fast. I regret getting rid of them.” And how many are saying, “I did it poorly. I took way too long”? I have literally never heard anybody say anything in the first or second category. It’s always the third. It always takes way too long. You know, at month six, that something is deeply profoundly wrong. There are going to be lots of reasons for that: your bad management, whatever. But you know it’s profoundly wrong. You will find in many cases a year later, things haven’t gotten better and the person is still there. And when a manager or a leader is going to be in that position of not being able to deal with their fears productively, and be able to figure out a path to an exit, or figure out a path to a better job or a different manager or something else, a demotion or a movement or an exit, yeah, it makes sense that you’re going to be scared about hiring someone. And it makes sense that you’re going to be scared about giving somebody responsibilities. Because you yourself are locking yourself in that present. This is not about the person you’re hiring. This is not about the reality of this thing. It’s the reality of you being unable to deal with your fears. And the fears start with you can’t have an honest conversation about your confusion. You can’t say, “I expected one thing, and I’m experiencing another and I’m confused.” That feels conflicted to you. So you don’t say anything. Instead, you just bury the signal, you bury the conversation, and you keep going. Unsurprisingly, every time you bury that, you get worse. And the situation gets worse. If you create a mental model that this person isn’t good at their job and the person gets worse because they’re not getting feedback or information they need to get better at their job. So again, there’s this thing of there is this fear that underlies the hiring, there’s this fear that underlies the management, and an inability to give voice to that fear. In, by the way, you can do it whatever way you want. You’re like, “Hey, I’m not going to be able to fire people who suck” or whatever. Give yourself whatever bravado you need to be able to state this, but state it and see it and get help on it. Have a conversation during onboarding when something doesn’t go right, when you still have it in the honeymoon period and you believe things could work out well. Don’t bury that conversation until the honeymoon period is over. That will have a massive effect on the relationship. So the same sort of pattern holds if you’re not giving away a responsibility quickly. And that’s because you have a fear of control, fear of letting go, or fear of a problem once you hire somebody. Then you have to deal productively with that fear. And you’re going to do it in two ways. One is you have to get help giving voice to the fear and working through it. And second is you have to do lots of little things to get familiar with the practice, not do big things, and then sort of get stuck with the result.

Angie D´Sa 42:15

So let’s see if we can sort of put a practical wrapper on the conversation we’ve just had. I’m hearing you say that one of the core reasons that a founder, with, by the way, I don’t like to use the word “control freak,” I like “control enthusiast.” So, a founder with control issues might be motivated by a very real lived experience, which is, it’s hard to fire people. And so I’m daunted by making this hire, I’m daunted by transitioning this responsibility because in the back of my head, I have this fear, what if it doesn’t go well? If it doesn’t go well, then I have to deal with giving the feedback, firing the person, and finding someone new, and whether that’s explicit or not, that concern lives inside. And so it’s heavy to bring someone new on. And I know having spoken to so many founders, that there is this worry of, “Okay, I want to let this person flourish. I want to let them do their thing. I don’t want them to feel micromanaged.” And so I feel a little bit gagged when I see something that I don’t agree with or doesn’t make sense to me. And the mind can say, “Oh, I’m just letting this person do their thing.” Whereas I think what I hear you saying, Jeff, is that’s a great justification for why you’re sitting back and you’re not actually closely managing the person you’ve just hired. But the reality is, there’s some motivation in there that’s coming from fear, from fear of saying something that’s going to produce conflict, from fear of saying something that’s going to cause a separation. And now you have to start all over again with hiring. So the most important thing to do is not sort of grit your teeth and give feedback anyway, the most important thing to do is to create an environment where you actually expose that fear. “Hey, new hire that I’ve just made, I want to have a conversation with you. But before I can jump into it, I have to take ownership of the fact that this is scary ground for me, right? Managing senior-level executives who expect a lot of autonomy is something that I’m not great at. And I’m worried I’m going to piss you off. I’m worried I’m going to push you away. But there’s no way we can have a healthy management relationship if I don’t face that fear for myself and say the thing: ‘What you’re doing doesn’t make sense to me.'”

Jeff Hunter 44:28

That’s right. And, by the way, the only thing I adjust on any of that is, you don’t know whether you’re great at it or not. So don’t judge yourself in that way. You just are unpracticed at it. I use this with my clients all the time. They’ll say, “I’m terrible at this.” I’m like, “Have you really practiced it and you’re bad, or you just haven’t practiced it? If you haven’t practiced it, then you don’t know whether you’re bad or not. You just know you don’t have a playbook from your own experience. So you’re gonna have to be really careful stepping through this. That’s all you.”

Angie D´Sa 45:01

Okay. Well, like so many of these conversations, it seems like the advice is, it comes down to just say a thing. Search for the fear, acknowledge it, and say it out loud to the person you’re most afraid to say it to, whether that’s your co-founder or your new executive hire, whoever it may be.

Jeff Hunter 45:19

Yes. And so, that will be the recurring theme, obviously, because we believe that the thing that stands in the way of great organizations, great businesses being built is founder or executive blind spots. Those blind spots are largely based on a lack of self-awareness, self-skepticism, and the courage to face things. And we are trying to lead to practical sorts of suggestions where you can practice little things, so that you can get better at solving what we call the personal mastery problem. These are all personal mastery problems, and we believe they’re at the very root of why organizations fail. It isn’t all the other stuff that people talk about, like the lack of capital; all those are problems, I live it, I get it, it’s painful. But this personal mastery thing is really the root cause of a lot of this stuff. You can learn through a personal mastery challenge, just like in learning through a skill challenge, you have to do it while the bus is driving, you can’t pull over to the side of the road, go on a little learning adventure, and then get back on the bus. So we’re just trying to say that’s the thing you’re trying to learn. You’re trying to learn the one square foot between your ears and how to use that effectively to make your dreams come true. And we’re talking about little practical ways that you can lean into what you’re like and how you’re dealing with your environment. And rather than go for the big bang, Courage moment, practice these things, so that you actually get better at yourself, which will lead to a better business. When we’re talking to leaders, that’s what we’re looking for.

Angie D´Sa  47:01

Okay, great. So, my key takeaway is this: when you’re hiring and onboarding new leaders, it can feel scary to let go of responsibilities that you’ve held or never delegated before. The real trick is to practice openness and say, “Hey, this is scary for me, but this is what’s not making sense.”

Jeff Hunter  47:24

That’s right. 

Angie D´Sa  47:25

All right. Thank you, Jeff.

Jeff Hunter  47:28

You’re welcome. Always a pleasure.

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