Dave O'Connor Start a conversation

Executive coaching for founders, CEOs and owners

A thinking partner for the long game of leadership.

Founders, CEOs and owners bring me the decision that keeps slipping and the team that's outgrowing how they run it. Every other week we sort what's real from what's noise, and you go back out pointed at the thing you care about most.

I ask a lot of questions. I also tell you what I see, from twelve years of selling and from running a private-equity-backed company that grew from 4 people in 6 markets to 16 people in 12.

Start a conversation See what clients get
Dave O'Connor standing outside a stone arcade, hand in pocket, looking at the camera
"He knows me, he knows my business, and he knows what I'm trying to build."

Tim Bradley, Founder and Executive Producer, Team Pennant

What you get

A reset every other week.

You arrive with the week still on you. You leave ready to walk back into your company and lead it on purpose.

Someone who remembers.

I hold the thread across months: what you said mattered in March, what you promised yourself two weeks ago. From inside the week you can't see those patterns. I can, and I'll name them.

Structure built for your operation.

Frameworks fitted to the business you have now and the one you're growing into, not a borrowed template.

A check against your North Star.

You decide what matters. My job is to notice when the week pulls you off it and say so.

Calls from recent sessions

Coaching often hides behind questions. I'll ask plenty, and I'll also make a call when I see one.

  1. A first-year CEO was being pushed by his board and supporters to announce a signature initiative while he was still rebuilding the organization's HR and donor systems.

    The callShielding the organization's limited resources from loud, outdated expectations is the job. No big new thing until the foundation holds.

    He took that framing to his board.

  2. An owner was preparing to announce his general manager's promotion at an all-staff kickoff and worried the room would read it as his exit.

    The callSay what the change is. This is role clarity, so everyone knows what they own and the whole company performs better.

    He made it a central point of his remarks.

  3. A studio owner had capped his growth expectations because a growth mandate at his old agency had worn down its culture.

    The callI don't accept that belief. Test the assumption against what you value in the team, not against someone else's history.

    He redefined growth around depth and margin, with a clear target size for the studio.

  4. A CEO was making faster decisions by thinking out loud with his deputy, and had never said so.

    The callMake that partnership explicit. Ask your number two to ask what's on your mind, because that speeds up every decision downstream.

    He did, and leaned on that partnership to make his next hard personnel decision.

Dave O'Connor smiling, leaning on a railing on a city street
"I've been working with Dave for several years now, and one of the things I value most is his ability to help me see the bigger picture when I'm buried in the day-to-day. He knows me, he knows my business, and he knows what I'm trying to build. He's remarkably good at making sure I don't lose sight of that, even when things get messy. Every couple of weeks, I show up carrying some combination of big ideas, complicated decisions, and the general chaos of running a growing business. And somehow, I always leave with a little more clarity, a little more conviction, and a better sense of where I'm headed."
Tim Bradley Tim BradleyFounder and Executive Producer, Team Pennant Pennant Video Co.

Who I work with

My clients run a video studio, a nonprofit, a finance desk, a family business. On paper they have little in common. In the room they share four things.

  1. 1They think before they act, and they want someone to think with.
  2. 2They carry real responsibility and take it seriously.
  3. 3They are crazy about the thing they're building.
  4. 4That thing shapes other people's lives: the people on their team and the people they serve.
"Working with Dave has fundamentally changed how I lead. I'm more confident navigating complexity, more thoughtful in my decisions, and better able to hold the full system, including people, politics, and purpose at the same time, which has elevated my impact as a CEO and community leader."
Stephen J. Kerrigan Stephen J. KerriganPresident and Chief Executive Officer, Kennedy Community Health Center, serving a community patient population of 34,000+ Edward M. Kennedy Community Health Center

When they call

  • A decision on personnel, product, partners or positioning that they want to make and haven't.
  • A business growing past the systems that got it here.
  • People who used to execute are being asked to delegate and lead, the founder included.
  • A good quarter that is costing more than it should.

If you want three calls and a quick win, I'll point you to the book. The coaching is built for people who plan to keep building.

How we work

Every other week, for as long as it's useful.

Sessions run an hour. Some clients have worked with me for years, and the longer we work, the more of your history I can bring back to the table when you need it.

Between sessions, you execute.

We work a decision through, you go make it, and we come back to study what happened: how you decided and what you'd do differently next time.

A shorter way in.

Decision Day is one deep-dive session on the decision in front of you, for leaders who want a defined start and finish.

Book Decision Day

Scale of Impact

Every other week, a leader thinks out loud with a partner who knows the business and its history. Self-trust grows. Decisions come faster and in greater number, and each one reaches further into the company and the people it serves.

1 2 3 4 TIME IN PARTNERSHIP SCALE OF IMPACT
An illustration of how the work compounds, not a measurement.
  1. 1

    Thinking partnership

    The leader brings the decision that keeps slipping to someone who knows the business and remembers what they said mattered.

  2. 2

    Self-trust

    Each decision worked through, made and studied afterward becomes evidence. The next call comes sooner and from the leader.

  3. 3

    Velocity and volume

    More decisions get made, faster, and fewer of them wait on the founder. Action follows closer behind each one.

  4. 4

    Impact on and through the company

    Those decisions reach the team, the clients and the community the company serves, and the team starts deciding faster too.

Why I do this

My professional role model is Shep Gordon, the manager behind Alice Cooper, Blondie and George Clinton who later invented the celebrity chef, combining his passion for the culinary arts with his expertise in representing talent including the world's best chefs. But along the way Shep was the man behind the talent, a position I love to be in too. He cared so much about his artists' work that he would do whatever it took to help them make more of it. I want to be that for my clients: in it for the long haul, finding ways for you to build more of what you want to put into the world.

What clients have built

  • Production studios and films, built from the ground up
  • Revamped executive leadership teams
  • Original IP and B2B and B2C products
  • Sales and operations SOPs
  • Internal mentoring and coaching initiatives

"When I started working with Dave, I was racked with interpersonal battles. The tools, the strength, and the comfort I have now in negotiating and leading feel so much better. I'm communicating with my group in ways I couldn't have a year ago.

Instead of weighing every possible decision, I focus on three a day. I've become a better delegator.

I came to Dave for one thing: relief from the leadership scenarios that had outpaced me. What I got wasn't relief, exactly. It was the ability to do more, and to do it differently, when the stakes were highest."

Dr. David Tawfik Dr. David TawfikChief of Service, Hospitalist Department, Kaiser South Bay Medical Center Kaiser Permanente
Black-and-white portrait of Dave O'Connor seated on cathedral steps

Start with one conversation

Tell me what you're building and what's on the table right now. If I can help, I'll say how. If I can't, I'll say that too, and I'll point you to someone who can.

Book 30 minutes

I'm in downtown Chicago most Thursdays. If lunch suits you better, say so.

Not ready to talk? Start with Ways of Being: Leadership, Questions & Quotes for the Reflective Leader, the frameworks I use with clients, built to work on your own.

Get the book
"I had a crazy day with a lot in my head, big stuff on the table, and I got deep into thought looking at your book. Super helpful to give me some perspective. It's a great tool."
Tim Whitehead Tim WhiteheadFinancial Planner with Northwestern Mutual, former professional rugby football player Northwestern Mutual