Executive Coaching From Someone
Who Has Done the Job
The best leaders I know share one habit: they keep working on how they lead long after they’ve stopped needing to prove they can. Coaching is where that work happens. A dedicated space to step back from the noise, look honestly at how you’re showing up, and sharpen the judgment everything else depends on.
I’m David Dressler. I spent over a decade as an operator, co-founding and scaling Tender Greens to 1,200 people and $100 million, which meant leading executives, being one, and learning the inner game the hard way. I coach senior leaders on the part of the job no one hands you a manual for.
If you’re a founder or CEO, you’ll want the page built for that. Start here instead.
For the organizational side of a transition, see leading change.
What Executive Coaching Actually Does.
Technical skill gets you promoted. It’s rarely what holds you back later. At a certain level, the constraint isn’t what you know but how you lead: how you decide under pressure, how you handle the conversations you’d rather avoid, and how steady you stay when everyone’s watching how you react.
There’s an outer game of strategy and execution, and an inner game of patterns, triggers, and the gap between how you think you land and how you actually land. Executive coaching works both, because they’re not separable. This isn’t soft. It shows up in retention, execution speed, and the quality of decisions your team makes when you’re not there.
A Common Starting Point.
An executive gets promoted over former peers. The work is suddenly less about the function and more about the relationships around you: a friendship turning complicated, a strong performer testing the new authority, a boss watching how the transition lands. Nobody inside the company provides a safe place to think that through. That’s what executive coaching is for.
The same pattern shows up whenever your circumstances shift faster than your habits do: a bigger role, a new leadership team, a restructuring, an AI implementation, a stretch of rapid growth. The informal ways of working that once made things easy start creating drag. What looks like resistance is often uncertainty about competence, identity, or what the change means for someone’s role, including your own. The strategic part is usually the easy part. The harder work is adapting to who you need to become in it, and coaching creates the space to see what’s actually happening beneath the surface and respond without defaulting to the habits that got you here.
A Coach Who Has Carried Operating Weight.
There are a lot of coaches. Fewer have operated inside fast growth, held a culture together while it strained, and been the executive under pressure rather than the consultant beside one.
When you bring me a situation, I’m drawing on having been there, not theory I’m applying secondhand.
There are a lot of coaches. Fewer have operated inside fast growth, held a culture together while it strained, and been the executive under pressure rather than the consultant beside one.
When you bring me a situation, I’m drawing on having been there, not theory I’m applying secondhand.
How I Work.
One on one and confidential, built around your real decisions. Usually twice a month. A monthly retainer, no long-term contract, because the work should feel like relief, not another obligation. Sessions run in person or online.
The work can stay focused on you as a leader, or expand into leadership team work and support through organizational change when the situation calls for it.
If you’re carrying more than you’re talking about, let’s talk.
Frequently Asked Questions.
Are you a certified executive coach?
My foundation is operating experience: building and exiting a 1,200-person business, and doing the inner work that demanded. For the leaders I work with, a coach who has actually carried the weight matters more than a credential. That said, I am a certified executive coach by both CTI and ACE and a member of ICF.
What does executive coaching cost?
It runs on a monthly retainer scaled to the level of support you need. The honest answer is that fit matters more than price, and a short conversation settles both. Schedule a call
How often do we meet, and how long do engagements last?
My company would sponsor the coaching. How does confidentiality work?
Simply: what we discuss stays between us, and any reporting back is agreed with you in advance. This is a key part of any executive coaching program.
Do I need a coach or a mentor?
A mentor gives you their path. A coach helps you see yours clearly, especially the patterns you can’t see from inside. If you already get plenty of advice and still feel stuck, that’s usually a coaching problem. I help clients navigate top executive coaching challenges.