If you’re navigating a significant transition, it can be tempting to cast a wider net, to contact more recruiters, attend more networking events, and have more conversations. But what if the opposite approach is actually more effective? Today, we’re discussing how senior leaders build market intelligence, narrow their focus, identify opportunities that often emerge long before they’re ever advertised. Whether you’re pursuing a CEO mandate, a board role, investors, or your next strategic client, we hope this conversation gives you a practical framework for thinking differently about your market.
Transcript
Maddie: Maureen, one of the questions that you and I have heard repeatedly is, How do I market myself? And where do I actually find the opportunities? And my question to you is, why do you think that question creates so much anxiety?
Maureen: When a CEO loses a role, or a board candidate wants a new mandate, or a GP, for example, needs new investors, and there’s pressure, there’s pressure from the board, or pressure from other investors, we get nervous. And we think more means better. So cast a wider net, talk to more people, you know, those types of things. But they don’t want to narrow their search because they’re afraid they’re going to miss something. So they expand, they contact more companies, they contact more recruiters, they complete more applications, they do more networking, they have more conversations. Expansion feels a lot safer because that possibility feels like progress. I mean, I’ve been there before myself. I know how that feels because you feel like the activity satisfies you. You think that because you’re busy, that it’s producing results. But often, what I found anyway, is that it creates more ambiguity, more activity and less useful information. So what we suggest is that we narrow the field to produce better market intelligence. So if a CEO says, oh, I’m open to the right opportunity, any opportunity, almost nothing follows from that statement because no one knows how to help you or place you. Who should they meet? What should they research? What recruiter matters? What should their LinkedIn profile communicate? But if they say, for example, I’m targeting 10 private equity backed industrial companies between 500 million and $2 billion that are likely to need commercial transformation leadership over the next 18 months, everything changes.
Maddie: Yeah, I think that makes complete sense. I can think back to being in university and having a lot of kind of like open concept conversations around whatever it is we’re discussing. And a broader question is asked. I think it’s people are a little slower to answer because it’s like, well, where do I start and how do I even…
Maureen: It’s overwhelming, isn’t it?
Maddie: Yeah, it is a little bit. I’m not going to be the first one to raise my hand and take this in a certain direction. But when a specific question is asked and you have a specific answer for it, then you close that gap a lot quicker.
Maureen: It’s the theory of constraints. Study the 10 companies, map their boards and investors, identify likely succession events. It could be an IPO. It could be a number of different things. follow portfolio developments, see who knows whom, test whether their value proposition resonates, and give recruiters a meaningful list and notice patterns. So this constraint of specificity actually creates information. There’s a couple of disciplines sitting underneath this theory. It’s the paradox of choice. So the more options can increase decision difficulty. So it’s around attention economics. Attention is finite, so spreading it broadly weakens the signal. With a hypothesis -driven strategy, so a thesis, you learn faster by testing a defined proposition than by searching randomly. And opportunity cost. every hour spent on a weak fit target is an hour not spent understanding a strong one.
Maddie: I think that that makes complete sense. And what concurrent strategies do you have in mind for those who are amidst a transition?
Maureen: I think what needs to drive That whole strategy, whether it’s a board search, a new CEO mandate, if you’re looking for or you’re looking for an investor is the ideal. client profile or the ideal investor profile or the ideal company profile. We call it in short ICP. So the ICP really represents the bullseye. So, you know, this is the representative type of investor, representative type of board or organization that I am seeking. And that is typically done through some market research. So the three concurrent strategies are comprised of the advertised marketplace, the recruiter segment, and the third one is the hidden market. And this is where I believe most lucrative opportunity resides. So the first one is the advertised market. While that can produce some market intelligence, it’s likely not the best return on time invested because many of those advertised opportunities that you see posted don’t exist. And I have seen this to be the case and others have as well when applications are submitted and there’s no response. you know, candidates are being ghosted. At this level, too, advertisements can be helpful, but they’re likely not going to be the best use of time and energy.
Maddie: Agreed.
Maureen: The second for the CEO and board, not so much for looking at investors, but for a CEO, it could be investors, it could be recruiters. The executive recruiters, board level recruiters who are specialized in your industry can be incredibly helpful. And the third one, I call it the hidden market. This is where a sophisticated CEO learns to identify where a leadership mandate is likely to emerge. really is comprised of all of the opportunities that are in a succession plan somewhere, but are currently not advertised for. So Maddie, as you know, corporations, businesses, they start their their budgeting process in one quarter, and don’t go to market for that resource until the next quarter or the quarter after that. hat represents a plethora of opportunities that are not yet advertised for but still exist on a balance sheet somewhere, on a budget line item somewhere. My point is that succession plans are in progress. for organizations, you know, on a rolling basis. And sometimes they’re not. I mean, that’s where opportunities can pop up as well, when, you know, suddenly the CEO leaves, and there is no one to replace him or her, more so in startups. But nevertheless, it does happen even in you know, mid market companies that have been around for a while may not be an active succession.
I’ll give you an example. I was giving a presentation at an event in Manhattan back in November, and I had done some research in advance. This was for a group of CTOs in the capital market. So they were buy side, sell side professionals. And there were three different cases in which the CEO of a technology company, it was a mortgage company, I can’t remember the name of the company in the United States, young man, only 54, tragically killed last year in an ATV accident. He was the founder of the company, had done really, really, really well, was just beloved by everybody. wonderful family man, and he died suddenly, and there was no successor for him. And I’m not sure who stepped in to replace him in the short term, but it does happen. And the whole point, which was kind of a sad side of the story, is that when you are in an organization, and you are You know, maybe at a senior level, you’ve reached a ceiling, perhaps, and you’re thinking, well, you know, now’s the time for an exit strategy. Don’t forget. Positioning yourself as the next leader in your division or your organization can be very helpful in terms of positioning and preparation for the next opportunity, whether it is internal or external. So these things happen and another gentleman, it was actually in Toronto, it was a hedge fund in Toronto and the young man, another young man in his 30s passed away very suddenly and he was the only person person who had signing authority for his organization and bank accounts. There was no backup person for that role. I believe it was the Canadian equivalent of the SEC who came in and had to shut down the business. these individuals were, you know, significantly impacted I guess the point of my illustration here is thinking ahead to what you’re seeking next. And if we go back to the ICP for a moment, the ideal company profile. So our ICP, as an example, is I’m a CEO for mid market $1 billion medical device manufacturing companies within, and that’s my ICP. And so that’s where I know that I do my best work. I have the networks, I have the industry knowledge, and so on and so forth. So that’s the ICP, just speaking, there’s a bit more to it than that. But that’s an example of one. And so your question might be, well, how do I use an ICP to tap into this hidden market? And so this is a very practical example. There are many ways to do this. But one is doing a simple search using your tool of choice is, you know, I’m seeking companies that match this ICP within a, let’s say, 100 mile radius of Atlanta, Georgia. that produces a list of, let’s say, 10 companies. So if we go back to the bullseye analogy, that is our ICP, we have these 10 companies that match the criteria, what do we do next?
Maddie: Yeah. And before we get into next steps, someone might ask you, you know, if I’m only focusing on 10 organizations, is that reducing my chances? Because again, going back to that kind of fearful, anxiety driven, motivation for your next opportunity, whatever it might be, I think we see a lot of kind of grabbing at too many things. So when you get asked that question, your point is that actually focusing on 10, probably maximum, I would argue, is more than enough because the work that we’re going to do and what we’re going to drill into in terms of raising your visibility in your search is going to is going to be the bulk of the work and 10 organizations is plenty to position yourself in front of.
Maureen: I think so. I mean, far better than, you know, 25, 30, because then it becomes diluted, the effort and return on time and invested becomes diluted. And so the specificity and the containment, the constraint of 10 companies is going to produce the clarity that you’re going to need or that is required to deepen the relationships that you’re going to need within these organizations. It doesn’t mean that you can’t pursue other opportunities, especially if a recruiter or a hiring organization or a family office contacts you
Maddie: I think that makes sense. So you’re working on. Getting clear on on the ICP and clearly drawing a line between yourself and that ICP so you’re putting in the work to do so, but that doesn’t necessarily mean that during. that time, you’re not also just tapping into some other networks. And you can be surprised where that contact can come from. When you’re looking for a new opportunity, naturally, you’re just going to be open to having more conversations. I mean, really, that is important as well. And you just never know where or who you’re going to be speaking to. Oh, so -and -so is looking for a certain kind of opportunity. I was speaking with them the other day. It’s just like it can have a ripple effect. But I think in terms of time spent during this transition and search, definitely working on your own visibility and getting very clear on your ICP is the most important thing. Going back to the recruiters, where specifically in the journey do you see recruiters fitting in?
Maureen: Great question. So essentially having an ideal company profile to share with a recruiter is a tremendously helpful. I’ve done a number of recruiting projects over my career. I don’t, I don’t do that anymore, but having that clarity and specificity can be incredibly helpful. The list, the ideal company profile and the targeted list of 10 companies can be used with recruiters to demonstrate and illustrate the types of companies that you’re best aligned with. It could be that maybe the recruiting firm has relationships with these companies and can ultimately open doors that way. Ultimately, the recruiters become a member of your team. And while you can certainly seek advertised opportunities, you know, the recruiter can become part of that ecosystem. And while they’re representing the company, their client companies, they can advocate for you.
Maddie: So we’re talking also not just about an executive search strategy, like we are talking about different situations. You know, you mentioned a GP, a CEO, different titles, different levels, different ICPs, ultimately. And now we’ve discussed different strategies that are kind of holistically going to put things in motion. What does direct outreach actually look like at the CEO or board level? And at what point in this strategy do you think is the best in terms of timing?
Maureen: Great questions. So direct outreach can look like a number of things. What I recommend if you once you have this list, is do some research, go to LinkedIn, and have a look at the five people in the organization that could be the chair of the nom gov committee, it could be the CEO, depending on the role that you’re, you know, targeting. It could be another committee chair, maybe it’s the audit committee chair, connect with those five people. And connecting with five people in an organization on LinkedIn will trigger the algorithm to raise your profile in their feed. So suddenly that person will becomes known within that organization. This is very, very top of the funnel activity, but it’s intended to introduce you at a very, you know, cursory level. Then take it another level and contact your own networks and find out who knows people in your targeted organization. So ABC company, maybe you have people in your network that have affiliations with that company and can arrange an introduction to those organizations. Does that make sense so far?
Maddie: Definitely. And I can attest to this approach as well, because it has worked for me.
Maureen: You know, it’s not a perfect science. You know, there are a lot of marketing principles and sales principles involved here, but ultimately it’s raising visibility, it’s building rapport and building relationships, but doing it methodically and intentionally with a list.
Maddie: With a list, absolutely. And I think, you know, sometimes we do get asked, doesn’t this feel transactional? Um, you know, outreach can feel very unnatural for people and I absolutely understand why that is. I think it’s pretty common for people to feel uncomfortable to talk about themselves. You know, especially when you’re getting used to the language that, that you have gotten now clearer on and, and, okay, I do know what I want to go after and I’ve figured out the language and I’ve gotten clearer, but you may not have been speaking about yourself in that way up until now, so it can feel new. But ultimately, if you’re aligning your goal with an ICP, and you’re starting to have conversations with people strategically, it won’t feel transactional, because ultimately, you’re just talking about what you’re capable of doing and what you’re passionate about doing. If you’re not aligned with your goal, and something that you actually value and care about, then it’s definitely going to feel unnatural. But I think that if you’re, uh, having conversations with people, just sharing your experience in a certain area, very specific, we call them success stories and or signature stories. You know, when you’re talking about those two people, it’s not transactional. It’s. relevant, and it’s a good conversation to have. So there are ways to approach conversations that doesn’t feel unnatural, transactional.
Maureen: No, I agree with you. I have something else I’d like to share with you and get your feedback on. So there are two principles in this world of what I would call business development, job search, board search, that a golden thread. that actually become the catalyst to that engine. And the two principles are one of consistency and persistence. So consistency, once you have done the outreach, and you’ve engaged with the chair of the nom gov committee, maybe you’ve had a couple of emails, and all of a sudden, things go quiet. And that person doesn’t respond to you, they’ve ghosted you, I guess is the word that we would use these days, the term In that situation, you could read it as the signal is, oh, we’re not interested. We’ve moved on. We’re not interested in having another conversation. Nothing could be further from the truth most of the time. And by being consistent, what I mean by that is being methodical in your follow up with these individuals and ensuring that you haven’t lost track of the conversation. You can use a CRM or use your calendar to do the follow up, but having a systematized approach to that follow up. can produce powerful results. I’ll give you an example. And I think you’ve heard this story before, Maddie. About 12 years ago, I met the CEO of an organization at a chamber dinner. And she approached me and asked me if I did a specific type of work. And I said, yes, absolutely. She said, would love to have you in, would love for you to do this work with us. And I was excited. It was early on in my business. And I didn’t hear from her. I didn’t have her card. She had mine. I managed to find her phone number. And over a period of nine weeks, I had left her seven voicemails. Wow. And because I couldn’t quite figure out, you know, why I wasn’t hearing back from her. She was very, very interested. She sought me out because I was sitting at the head table and they had announced me as part of the head table. So she knew who I was. By the ninth week, I had left seven or eight voicemails. She finally called me back. She actually called me back the same day I left the last voicemail to say, look, I’m so pleased that you followed up. She said, we’ve had our board has had a major crisis. And we’ve been working 18 hours a day for the past six weeks. Really pleased that you continue to follow up. I may not have remembered to follow up with you. And I was in their office the next week. And I was there for the following number of weeks working on a project with them.
Maddie: Yeah, it’s a good one. It’s important. I think everybody has experienced and can relate to Follow up fatigue. It’s real for sure. It’s especially when it’s happening at the same time that you’re still in your transition and your search, it can feel exhausting, but to what that story demonstrates and the reality is. that in so many cases, something has happened internally that you’re just not aware of, and it has nothing to do with you. If somebody is getting irritated by your consistency and persistence, they will let you know. And then you’ll have an answer. If they’re not answering, it’s going to be something that has nothing to do with you and they will appreciate the dedication.
Maureen: I agree. I mean, you know, I appreciate that my myself, there’s just times there are times when you know, you’re simply not a priority for that other person. That doesn’t mean that you won’t be. It’s so important at the executive and board level, to be consistent in your follow up and to be politely persistent, because that is what is expected at that level.
Maddie: Yes, I think that that’s a very good point. And to round out the call and sort of bring everything that we’ve talked about today into one final question. If someone listening feels like they’re on the brink of a transition or amidst a transition, and if this conversation in general is speaking to them, what is something that they could be doing tomorrow morning?
Maureen: Oh, that’s a good question. I really think it depends on what stage you are in a transition. You know, are you planning a transition over the next 12 months? Are you planning a transition tomorrow? When’s the best time to start a succession plan or an exit plan? Well, ideally yesterday or five years ago. But realistically, if you are planning an exit in a year’s time, start thinking about your exit strategy. Start thinking about the ideal next organization. What does it look like? If you’re unsure, think about all of your previous board opportunities, investor opportunities, business opportunities. Where did you thrive? Where, you know, did you do well? Where were you challenged? That can help your thinking around an ideal company, client or investor profile. If you have the luxury of time, I think thinking about the ideal company profile, and then creating a targeted list of organizations that align with your ideal profile can be tremendously helpful. There is a principle that we didn’t talk about today, but it is specific to narrowing the field And when you have time, this is particularly helpful. We don’t always have that luxury, but it’s called the reticular activation system. This is not going to be a scientific definition, but you’ll get the gist of it. My daughter, when she was in university, bought a green hatchback Hyundai. After she bought that green hatchback Hyundai, I saw all of the green hatchback Hyundais on the street. Everywhere I went, I saw those green cars. What this does, and I’m sure that there is a scientific explanation for it, but what this does, this process of creating an ICP and a targeted company list creates the reticular activation system. You now see those green cars everywhere. And it’s because it’s now relevant to you. It’s clear. it produces a degree of certainty in the outreach and the search. So if you can take some time to sit down with your colleague, with your spouse, with a friend, and take an inventory of all the opportunities that you’ve had in your career or business so far that have really resonated with you and create a profile, what does it look like? What are the features? And then you can you know, begin to create an ICP that aligns with your interests, your goals, and your values. Remembering too that if you are in transition and you don’t have time, still use this methodology, but what you might want to do to amplify a transition as soon as possible. So for example, if you’re a CEO without a mandate, and you’re seeking a new one, what I would recommend doing is looking at the marketplace from where you came. So your most recent CEO mandate, the closer you can align with that mandate in the future, the faster you will land. So We’ve talked about industry changes before. This is not a good time to change industries, because what we want to do is to target organizations that require the skills, capabilities, and achievements that you have just produced for the company or organization that you’ve recently left, if that makes sense.
So those are my two answers.
Maddie: Yeah, I think that that’s really good advice for first next steps. And yeah, I think this was a good conversation, Maureen. Is there anything else you’d like to…
Maureen: Just that I think that this conversation aligns really well with a number of podcasts that we have been syndicating over the past little while that focus on business transition, companies that are getting ready to sell for family businesses, CEOs and others who are transitioning into fiduciary board roles, maybe concurrent with their current CEO mandate, or as a succession, you know, post CEO mandate, I think this will be really helpful for individuals who are planning a transition or who are in transition. And I hope that if any of you principles and ideas resonated with you, we would love for you to give us the feedback. You can reach out to us at maureen @ westgatebranding .com or maddison @ westgatebranding .com. Leave a review for us and we look forward to presenting more valuable insights in episodes to come. Yeah. If you found today’s conversation valuable, we’d be grateful if you would share it with someone who may be navigating a similar transition.