They almost always come to me the same way. Sick and tired of being sick and tired. Whatever used to work for them doesn't work anymore, and they're too close to the business to see why.
I usually start close to the founder. Just the two of us, at first. I want to understand the business, of course, the numbers, the team, the roles, what's working and what isn't. But I'm also trying to understand the person running it. What does a normal Tuesday look like? Where does their energy go? What keeps reaching them that shouldn't? What are they avoiding? Depending on the person, Color Code can help me understand how they're wired. I'm trying to see the business and the human being running it at the same time.
That part doesn't really change. I'm trying to build the kind of relationship where they don't feel like they have to give me the CEO version of themselves. The work only gets useful once the founder feels safe enough to bring me the unfinished version, not just the polished one.
But somewhere in most engagements, we hit a wall. I'll ask a question about how the team operates day to day, and the founder genuinely doesn't know the answer. Not because they're hiding it; they're just not in the room. So they'll offer to bring in their integrator, their right hand, their director of operations, whatever the title is at that company. That's usually when I get another part of the picture. Not a more accurate version. Just the view from a different seat. The founder knows things the leadership team doesn't know, and the team experiences things the founder can't see from where they're sitting. Put those perspectives together and patterns start emerging that neither person could see alone.
I want to be clear about something, because I know how this can sound. I didn't decide one day to start coaching whole organizations. I hit a wall I couldn't see past with the information I had, and the only way through it was more of the picture than one person could give me. The founder can't read the label from inside the bottle. Nobody can read their own label from inside it. Me included. And bringing another person into the room doesn't mean they have the truth and the founder doesn't. They have another angle. Sometimes what changes the work isn't finding out who's right. It's finally getting enough angles on the same problem to understand what's actually happening.
There's a boundary here that matters, and I want to name it plainly. Bringing another leader into the room doesn't mean my individual coaching relationship with the founder suddenly becomes open source, and I don't want to become the person carrying messages back and forth between two adults. If we're going to work together, we get clear about what belongs in the shared room, what stays confidential, and what conversations they need to have directly with each other. Otherwise, the coach can accidentally become part of the very system we're trying to fix.
This is why I keep coming back to something I think is a central idea in this whole line of work: personal patterns become organizational patterns. A founder's blind spot rarely stays entirely private. If the behavior happens often enough, the people around them start adapting to it. If I avoid conflict, my team learns what not to bring me. If I constantly rescue people, they learn to escalate instead of decide. If I change priorities every week, they learn to wait me out. Eventually one person's psychology has become somebody else's operating procedure, whether I ever meet the rest of that team or not.
I'd been working with a founder for months, just the two of us. She'd built the business with the same person beside her for a long time, the kind of partnership where they finish each other's sentences. When we hit the wall, she brought him in herself, telling me flatly that I needed to hear how he saw it too. I hadn't asked for it. I've seen this pattern more than once with founders and their longtime second-in-command, people who've worked together long enough to assume they already know what the other person owns.
What came out of it wasn't a story about her doing anything wrong. It was a fuller picture, and not just of how people felt. It was structural. Decisions that got made twice because nobody was sure who actually owned them. Calls both of them assumed belonged to the other person, so neither made them for months. This wasn't a feelings exercise. Ambiguous ownership was creating duplicate work, delayed decisions, and executive friction. Once we could see it together, we could build something around it. We mapped who owns which decision, what gets escalated and what doesn't, and put a standing fifteen-minute check-in in place so a stuck decision gets named the week it happens instead of the quarter it finally turns into a crisis.
There's another reason I sometimes need more than one person in the room, and it took me a while to see it clearly. Some problems don't belong to either person individually. They live between them. The founder keeps stepping in because the second-in-command isn't deciding. The second-in-command stops deciding because the founder keeps stepping in. Each person can give me an entirely honest account of their own side and still miss the loop they're creating together, because you can't see a loop from inside either seat. That's when coaching one person harder isn't necessarily the answer. Sometimes we need to put the pattern itself in the chair.
I know this isn't unique to the people I coach, because it's mine too, from the other chair. I have my own coach, Tony, and after years of working together, she catches things about me I genuinely cannot get to alone, no matter how much work I put in between our sessions. Sometimes she'll remember something I told her years ago. Sometimes she'll ask one question that connects two things I'd never connected. I've gone into a session convinced I had a people problem, only to have her ask one question and realize I had a control problem. I can be completely honest with her and still hand her an incomplete picture, not from hiding anything, just from standing inside my own story the same way every founder I coach is standing inside theirs.
Once both the founder and her right hand were in the room regularly, the work changed shape. Less me interpreting one version of the team for her, more the three of us looking at the same thing and building something out of it together. Decision ownership got clearer. Fewer decisions got relitigated, because there was finally a clear answer to who owned them. Over time, retention improved too, and the right hand stopped quietly managing around problems and started naming them, because there was room and structure where that was safe.
But more voices aren't automatically better. Sometimes bringing another person in too early makes everybody more guarded. I do it when the relationship has enough trust, and when another perspective will genuinely help us understand the system, not simply because I want more opinions in the room.
There's research behind why that room matters when it's earned. Amy Edmondson's early research on hospital units produced a surprising result: some of the stronger-performing teams had higher detected medication-error rates. Her follow-up work suggested one possible explanation: that the better-functioning teams may have been more willing to report and discuss mistakes rather than hide them. That work eventually helped lead to her research on psychological safety, on whether people believe a team is safe for interpersonal risk-taking. The point isn't that healthy teams make more mistakes. It's that healthier teams may be more willing to surface the mistakes and problems they already have, so they can learn from them.
It's not the same thing as executive coaching, but the principle resonates with what I see constantly: information only helps if people feel able to say it. Safety isn't the absence of problems. It's whether the problems can get into the room while they're still small enough to do something about.
I always start with the founder. That's not changing. But there's real value in going deeper into the organization when it's earned, and I want to be honest about what "earned" means. It's not the natural next stage of a growing account. Sometimes the individual work is enough. Sometimes it isn't. When the problem we're trying to solve lives between people, decision rights, trust, accountability, role confusion, and communication, you eventually have to work where the problem actually lives. If the problem lives between people, you can't solve all of it inside one person's head.
Psychological safety can't live only at the top of the org chart. It has to live in how the team talks to each other day to day, not just how they talk to the person signing the checks. And the real test isn't whether everybody can tell me the truth when I'm in the room. That's easy to overvalue. The test is whether they can tell each other the truth after I leave. And I'll say this plainly: it doesn't have to be a coach who builds that room. A mentor could do it. A Forum mate could do it. Sometimes it's just the right person already on your team, someone who already has permission to tell you the truth, if you ever asked them to use it.
If you're the founder reading this: what does your team know about the experience of working in your company that you cannot know from the CEO seat? And who in your company has enough trust, and enough permission, to tell you something you may not particularly want to hear? More importantly, do they need me in the room to say it, or have you built a culture where they can tell you themselves?
Enough safety to tell yourself the truth. Enough accountability to act on it. Sometimes that starts with one person. Sometimes it takes the whole room.
Let's get after it. Todd
P.S. If this one hit close, hit reply. I read every one.
