Leadership Coach for General Manager and Production Manager (Field Services)

The situation I own a tree service company that will do $8-10M this year. Our plan is to reach $20M and roughly 80 people by the end of 2027. Some context that matters more than the numbers. I had stepped back from the business for a stretch. When I came back about ten months ago, I removed my General Manager for cause. There's more to that story than I'll put in a job posting, and I'll walk you through it on our first call. I've been rebuilding leadership from the ground up since, and much of what I found underneath was worse than I expected. Both of the men this posting is about came on after that. Neither has ever seen this company run well. • My General Manager, roughly 50 employees under him. He's been in the seat about three months. Before that he was my Production Manager for four or five months, and before that he led a two-man crew at a one-crew company where the owner was on every job. That is the whole of his management experience, anywhere. • My Production Manager, roughly 25 of those 50, running field operations. He was a Crew Leader until three months ago, when he moved into the job my GM had just left. This is his first management job of any kind. Both are working hard and improving fast. I want it faster, and there's still a lot of basic stuff getting missed. Neither one is in trouble. Expect a lot of fundamentals. The destination is anything but: in two years these are jobs at a company twice this size. I want both of them operating a level above where they are today. Some of the gap is skill, some is mindset, some is a system that decayed while I was away, and some of it is almost certainly me expecting too much too fast. Figuring out that mix is part of the engagement, not something I expect you to diagnose before you've met them. What is driving this Accountability This is the nearest-term problem. My crew leaders have never been held to a standard transparently. My department managers don't yet see the gaps in their own departments that I see, and my GM has only started seeing those gaps himself in the last few weeks. He's trying to work out how to close that without becoming someone he doesn't want to be. He has no model for it here. Whatever the last man in his chair was doing, it wasn't holding people accountable. Leadership transition Both are newly promoted into significantly larger leadership roles than they've held before. Three months in, the habits they'll carry for years are still forming. I'd rather bring a coach in while that's still true. Succession My GM is my succession plan. Closing the gap between "runs the day to day" and "runs the company" is one of my highest priorities. I know that's a large bet resting on eight months of evidence. I'd rather make it with help than alone. How we operate We run on EOS: L10s, Rocks, scorecards, and KPIs at every level. Three of our values bear directly on this engagement: People First, Take Ownership Take Action, and Continuous Improvement. We build into our people, we expect them to treat the business as if it were their own, and we'd rather someone solve a problem than complain about it. I'd rather hear that something is wrong early and plainly than hear the version that's easier to deliver. We're not looking for someone to motivate people. We're looking for someone who changes behavior. The company is the client. This engagement exists to increase leadership capacity and business performance. You'll have access to our leadership meetings, scorecards, KPIs, and the field. I want you coaching the real work, not hypothetical scenarios. The structural question So my Production Manager reports to my GM, and he's in the job my GM held until three months ago. I'm open to two models: • One coach, working with each of them individually. You see the whole system, but you're holding both sides of a reporting relationship. • Two separate coaches. Cleaner boundaries, no cross pollination, roughly double the cost. I don't want a balanced discussion of both options. Tell me which model you'd choose if this were your engagement, and defend it. If you think coaching a manager and their direct report is a conflict you won't take on, say so. That's a legitimate answer and I'd rather hear it now than three months in. What I'm not looking for • A fixed curriculum or program that everyone gets run through • Someone whose first instinct is an assessment or personality profile instead of observing people and doing the work • Someone who considers fundamentals beneath them. Much of this work is going to be basic, and it needs to be done well. • Someone who will tell them, or me, what we want to hear • Someone who has only worked with tech or corporate executives. This is a field business: crews, trucks, weather, real physical risk, an hourly workforce, and thin margins. • A confident diagnosis before you've met them What I'm looking for • A track record with operating leaders in small to midsize businesses, not only Fortune 500 or venture backed startups • Experience developing first time managers, and a real sense of what that curve actually looks like • Experience inside an organization rebuilding after a leadership failure, or a clear view on what that changes • Experience with leaders whose scope is about to double, not just leaders holding steady in the job they have • Familiarity with EOS, or a clear view on how you'd work alongside it • Willingness to challenge all three of us, including me, when that's what the situation requires • The ability to tell a mindset block from a skill gap from a broken system, and to say so plainly even when the broken system is the one I built • The ability to produce observable behavioral change, not just insightful conversations • A 6 to 12 month engagement minimum, with the expectation that it may run longer. I'd like to start with a paid 30 day trial before either of us commits to that. Budget $100-200/hr, or propose a monthly retainer. If you're outside that range, make the case. Estimated cadence is 6 to 8 hours per month across both of them, but I'm open to your recommendation. I intend to start with a paid 30 day trial and then commit to the longer engagement. What success looks like At the end of 6 to 12 months, I should be able to point to observable behavioral changes, not just positive feedback. The point of those changes is capacity: I need leaders who can run a company twice this size. If you can't describe how you define and measure success before we start, we're probably not a fit. How to apply Please answer the six questions below. No pitch deck, no credential list, no proposal template. Short and honest beats polished. 1. One coach or two, for this situation, and why. 2. What do your first 90 days look like? 3. My GM has about eight months of management experience, my Production Manager about three, and the company intends to double in two years. Based on what you've seen, what should I reasonably expect from each of them at 6 and 12 months, where are my expectations most likely to be wrong, and what would worry you if you saw it? 4. Confidentiality. What information comes back to me? What stays confidential? Describe the arrangement you actually use, not the ideal version. 5. A coaching engagement that failed or fell short, and what you'd do differently. If your answer is that this has never happened, we're not a fit. 6. Tell me about a time you declined an engagement, or ended one early. Process A short call with me first, fifteen minutes. If we're aligned, separate conversations with the GM and the Production Manager. Each of them has veto power over their coach. If they don't trust the coach, the engagement won't work.