How to Master Startup Leadership & Execution

Colleen Connors has run funds, founded a tech start-up, served as COO of a digital identity company and now coaches leadership teams through Coaching Leaders Global. In this episode of The Humans Behind the Tech, she talks to Old.St Labs co-founder Rob Woodhead about her non-linear career, from bond trading at Schroders to an entrepreneurship MBA at Babson.

Colleen explains why founders misdiagnose their own problems around 80% of the time, and why the real issue is usually structural rather than personal. She describes the trust gap that holds back highly capable, self-reliant founders, and the discipline of staying focused when a prospective customer offers revenue for a detour. On AI, she sees teams saving real time with tools like Claude. She also argues that experience and human judgement are still what separate good output from plausible-looking mistakes.

Along the way she covers compartmentalising under pressure, firing clients who mistreat your team, and finally pulling on a Team USA shirt at 40.

Key takeaways

• Founders usually misdiagnose the problem. Colleen estimates that around 80% of the time the issue a company calls her in for isn't the real one. What looks like a people problem is often an outdated structure built for a smaller company.
• Strategy fails at the handover to execution. Talented leadership teams can drift slowly out of alignment, so their day-to-day actions no longer serve the goals they say they share.
• Self-reliant founders have to learn to trust. No hire will care about the company as much as its founder does. Founders who expect that will struggle to delegate.
• External opportunities are the hardest distractions to resist. It's easier to say no to your own new ideas than to a prospect offering money for a custom build.
• AI is a tool, not a replacement. It speeds up templates, admin and code review, but you still need experience to recognise when the output is wrong.
• High standards include who you work with. Colleen learned at 23 that you can fire a client, and she has kept that standard ever since.

Chapters

• 00:00 Introduction
• 01:15 From Penn to fund management at Schroders
• 05:45 What finance teaches you about service and standards
• 10:27 Leaving corporate for an entrepreneurship MBA at Babson
• 13:22 The emotional rollercoaster and learning to compartmentalise
• 18:09 Hockey, from Penn Division I to the US Masters team
• 21:45 Founding a sports equipment matching start-up
• 24:24 COO in digital identity: fraud, privacy and control
• 28:16 Trade finance consulting and the move into coaching
• 29:13 Closing the gap between strategy and execution
• 32:16 Why founders misdiagnose their own problems
• 34:03 Being the outside voice that holds founders accountable
• 39:49 Where AI is showing up in leadership teams
• 45:01 Experience, AI and knowing what good looks like
• 49:49 Trust: what holds smart founders back
• 55:23 Shiny objects and the discipline of focus
• 58:49 Firing clients and protecting your team
• 01:01:32 The impact Colleen wants to make next
• 01:06:39 Fractional work versus going back in-house
• 01:09:06 If your business were an artist

A career built on non-linear moves

Colleen started her career in finance, as many University of Pennsylvania graduates do. She spent around eight years at Schroders in Philadelphia and London. Moving from a small municipal bonds unit to global fixed income at headquarters threw her in at the deep end. It also showed her what she wanted from work: pace, change and no two days alike.

Meanwhile, friends starting businesses kept asking for her advice over coffee. She set up a monthly group for women entrepreneurs, then began hosting events that brought her finance contacts together with that network. When she decided to leave finance, she chose an MBA at Babson, which is known for its entrepreneurship programme. A hockey teammate had suggested it. Colleen wanted a classroom full of people who would all start companies one day, and she wanted to make fewer mistakes once she started her own.

Finance sets the bar for client service

Rob and Colleen both started in finance, and both say it shaped how they treat clients. As a fund manager, Colleen says, performance was everything, and her personal credibility rested on it. She has carried that standard into her coaching. Early exposure to CEOs and CFOs also gave both of them the confidence to advise senior leaders as peers. Colleen adds that confidence only lasts if it rests on experience, and two decades of experience include plenty of things going wrong.

Compartmentalising is a survival skill for founders

Colleen hasn't had a truly consistent salary since 2011, and she's candid about the emotional cost of entrepreneurship. What helps most, she says, is the ability to compartmentalise. She draws on sport for this: what happens on the pitch stays on the pitch. Her most striking example came just before a major contract meeting. She learned she was pregnant, composed herself, went in and closed the deal, and only then sat down with her business partner to work through what it meant.

Most company problems are structural, not personal

At Coaching Leaders Global, Colleen works in the space between strategy and execution. Founders, leadership teams and sometimes VCs bring her in because something isn't working. The diagnosis is usually different from what they expect. A sales manager who seems to be underperforming may simply lack the process and accountability to do the job. A founder may have become the bottleneck without anyone noticing, so the business slows down whenever they go on holiday. Structures that worked for a 10-person team rarely survive growth intact.

Because she's an outsider, Colleen can say things no one inside the company can, including telling a CEO that their behaviour is unacceptable. Many founders have no board to answer to, so she is often the only person holding them accountable.

Trust and focus are the two biggest blockers

Colleen sees two patterns again and again in ambitious founders. The first is trust. Founders who built their success on self-reliance struggle to hand over ownership, partly because they expect hires to share their level of commitment. The second is focus. Founders are natural ideas people, and the hardest distraction is an outside prospect asking for a custom build. Moving engineering resources to chase one customer is a major strategic decision, she argues, and too many companies make it lightly.

AI saves time but still needs a human with experience

Colleen sees AI everywhere among her clients. Individuals use it for emails, meetings and admin. One client gave Claude two years of well-written code to bring a dormant product back into production. Engineers use it as a QA assistant to check the day's work, and one company now requires every employee to use AI daily.

She is just as clear about the limits. AI is only as good as what it starts from, and she has never had a generic output she wouldn't change. Rob points out a generational risk: if you've never learned what good looks like, you can't tell when the AI has got it wrong. Both agree it's a tool, not a replacement.

About the guest

Colleen Connors is a leadership advisor and executive coach who helps founders and leadership teams turn strategy into consistent execution. She began her career as a fund manager at Schroders in Philadelphia and London, then completed an MBA in entrepreneurship at Babson College. She founded a sports technology start-up and later served as COO of a digital identity company, where she remains on the board. She now runs Coaching Leaders Global, helping scaling companies build clarity around KPIs, alignment, accountability and operational performance. A lifelong hockey player and coach, Colleen has represented the US Masters team at the World Cup.

About the host

Rob Woodhead is co-founder of Old.St Labs, a London-based AI software development agency that has spent six years turning founders' ideas into working products. Before Old.St Labs, he worked in corporate finance advising on mergers and acquisitions. He hosts The Humans Behind the Tech, a podcast about the people, careers and decisions behind the technology industry.

Frequently asked questions

What does an executive coach do for a scaling company?

Colleen Connors describes her role as working in the gap between strategy and execution. She diagnoses bottlenecks, leadership misalignment and outdated structures, then helps leadership teams build and deliver a plan to fix them.

Why do founders often misdiagnose problems in their business?

According to Colleen, founders are usually too close to the business to see the root cause. Around 80% of the time, what looks like a people or alignment problem turns out to be structural, such as processes or accountability that the company has outgrown.

Who holds a founder accountable if there's no board?

Often no one, Colleen says. In those cases an outside advisor can fill the role, because they can raise difficult issues without internal politics getting in the way.

Why do some founders struggle to delegate?

Founders whose success has come from self-reliance often find it hard to trust others with ownership. Colleen says part of the fix is accepting that new hires won't share a founder's level of commitment, and that this is fine.

How are leadership teams using AI today?

Colleen sees it mostly at the individual level so far: emails, meetings, admin, code review and QA. Some companies are going further, using tools like Claude to take actions or revive old codebases.

Can AI replace experienced professionals?

Neither Colleen nor Rob thinks so. Both see AI as a time-saving tool that still needs an experienced person to check its output, because you can only spot an error if you know what good looks like.

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