Rob Ott was a founding member and SVP of Business Operations at ACT Oncology, a pharmaceutical services company that grew from 2 consultants in a garage to 3,500+ employees across 15 countries. Earlier in his career, he was part of the team that helped get Herceptin, the first monoclonal antibody for breast cancer, approved by the FDA. ACT Oncology was acquired by Precision for Medicine in 2016.

Today, Rob coaches executives navigating a world where AI is reshaping what leadership even means.

When I sat down with Rob for the Coach as Entrepreneur podcast, I wanted to understand something specific: what happens when a decisive, problem-solving entrepreneur has to stop giving answers and start asking questions instead?

Because that transition is where most experienced leaders-turned-coaches get stuck.

Starting in the Garage (and Surviving the 2008 Crash)

Rob didn’t set out to build a company. He and his founding partners started consulting in the late ’90s because pharma companies and their contract research organizations were talking past each other. Rob’s skill was translation. He could sit between a biotech and a CRO and make each side understand what the other actually needed.

That interpreter role turned into a business. Word of mouth brought clients. Clients brought hiring. Before they knew it, they were scaling.

Then 2008 hit.

Their business depended on biotech investment. When the financial crash froze capital markets, Rob’s client base dried up overnight. They had to scramble, rethink, and rebuild.

One thing that saved them: they’d built the company around people, not offices. They were fully remote in 2000. Laptops and air cards. If the best quality person was on the West Coast, they hired them. If the next hire was in Indiana, their HR leader had to learn a new state’s regulations. The flexibility to assemble a dream team regardless of geography gave them resilience when everything else was uncertain.

The “Wet Blanket” Problem: When Your Strength Becomes Your Ceiling

About ten years into building the company, Rob hit a plateau. He’d always played the role of devil’s advocate on his leadership team. Contingency plans, worst-case scenarios, risk mitigation. He thought he was being strategic.

His team saw it differently. To them, Rob was the wet blanket. Every time momentum built, he was the one pulling everyone back down.

“I thought at the time I was awesome,” Rob told me. “I had everything covered. But I was starting to develop a reputation for not being as strategic as I could be.”

The remedy was hiring a coach. And that first coaching relationship changed everything.

Rob still works with that same coach, twelve years later.

The pivotal moment came at a Dunkin’ Donuts. Second or third session. His coach hit him with a simple choice: absorb the feedback and grow, or we stop.

“It probably wasn’t that harsh,” Rob said. “But it felt like your whole earth moved three inches to the right. Everything lurched.”

That’s the moment of coachability. You can’t manufacture it. You can’t predict when it’ll happen. But until a leader owns the feedback instead of defending against it, nothing changes.

From Giving Answers to Holding the Flashlight

The biggest adjustment Rob faced when he became a coach wasn’t learning frameworks or getting certified through Columbia’s coaching program. It was stopping himself from solving problems.

For 25 years, he was the decisive one. Someone brought him a problem, he fixed it. That was his value.

Coaching requires the opposite.

“I’m walking on the path with you with a flashlight,” Rob explained. “I’m not in front of you. I’m not leading you. I’m just showing you some things that you may not have seen.”

This is where Rob’s Columbia training shaped his approach. Total person coaching. The solution is already inside the client. The coach’s job is to help them reveal it. Build trust, earn permission to push, then let them do the work.

Some clients just want the answer. Rob gets it. But if he solves the problem for them, they leave the engagement with a solved problem. If he helps them solve it themselves, they leave with a skill they’ll use for the rest of their career.

That’s the difference between a consultant and a coach.

The Chemistry Call: Why Client Selection is a Skill

Rob doesn’t use a formal coachability assessment. No questionnaire. But he takes the chemistry call seriously.

His filter is straightforward: Can I connect with this person? Is what they need inside my skillset? Do I believe I can help them?

If the answer to any of those is no, he refers them to a colleague. And he has plenty of colleagues to refer to, because he invested heavily in building his coaching community through his Columbia cohort and beyond.

“Some people drain energy and some people radiate,” Rob said. “When I first started, I was out there like, I’ll coach anybody. That’s just not a really good recipe for success.”

This is something I hear from nearly every coach I talk to. Early on, the pressure to accumulate hours and build a client base pushes coaches into working with anyone who says yes. But the coaches who last are the ones who develop the confidence to say no.

The Last Generation of Human-Only Managers

This is where our conversation got interesting. Rob runs the AI and digital health team for a life sciences trade organization in New Jersey. He works with everyone from vibe-coding startup founders to enterprise leaders at IBM and Johnson & Johnson.

His perspective on AI and leadership is specific: this is probably the last generation of leaders whose sole job is managing humans.

The next generation will manage agents, multi-agent setups, robots, hybrid teams. They might even be managed by AI themselves.

“They don’t necessarily need to code,” Rob said. “They don’t necessarily need to be on the front lines with it. But they need to understand it enough to run an organization that’s going to be impacted by it.”

The fear is real. Leaders in their forties and fifties are too young to retire but too established to start over. The technology is moving so fast that what they understood yesterday is already changing by next week.

Rob’s approach is what he calls “on-ramping.” Finding each leader’s entry point into AI fluency. For some, it’s writing a better email with AI assistance. For others, it’s rethinking how work creates value in their organization. The on-ramp is different for everyone, but everybody needs one.

AI Will Close the Performance Gap (and Expose the Lazy)

Rob shared a perspective backed by McKinsey and Gartner research: AI won’t supercharge the top performers. They’re already optimized. What it will do is close the gap between mediocre performers and high performers.

The middle tier gets lifted. The people coasting get exposed.

“It’s gonna expose a lot of laziness,” Rob said. “But the high performers are not gonna get super charged. They’ll get incremental benefits. The people in that middle performance tier will close the gap using AI.”

And the companies that threw money at AI tools without preparing their people? They saw personal productivity gains. Better emails, better organization. But no organizational transformation. Because they didn’t rethink the work itself. They just bought a tool and expected magic.

Rob pointed to companies that got it right. They spent the first three to six months building what he called a “resilience reservoir.” Getting people ready for the transformation before introducing the technology. Change management first. AI second.

Marketing is Not Selling. It’s a Responsibility.

Near the end of our conversation, I challenged Rob on something I challenge every coach on: the relationship with marketing.

Rob is honest about it. He doesn’t love marketing. He’s the guy behind the guy. He’d rather sit down and coach someone over a beer than write a LinkedIn post about it.

I hear this from 95% of the coaches I talk to. They just want to help people. The business side feels like a necessary evil.

Here’s what I told Rob, and what I’ll tell you: if you’re an ethical person, and you believe the work you do genuinely helps people, then it’s your responsibility to let people know you exist. That’s not selling. That’s service.

Most people don’t know what coaching is. They don’t know they need it. If you’ve got the skills to change someone’s trajectory and you’re hiding because marketing feels uncomfortable, you’re not being humble. You’re withholding help.

Rob’s response was immediate: “That’s the gem I’m gonna walk away from with this.”

Rob’s Weekly Structure (for Coaches Building a Practice)

Rob segments his week deliberately:

  • Monday morning: Lead engagement, social media prep, content planning for the week
  • Tuesday through Thursday: Client work, coaching sessions, meetings
  • Friday morning: Personal development, AI learning, reading, podcasts
  • Friday afternoon: Weekly reflection. What did I learn? What am I applying? What am I taking forward?

He used to put business development on Friday afternoons and realized his energy was wrong. So he moved it to Monday mornings. Eat the frog first.

Structure beats motivation. Every time.

Frequently Asked Questions

What is the difference between executive coaching and consulting?

A consultant diagnoses a problem and delivers the solution. A coach helps the client discover the solution themselves. Rob Ott describes it as “walking on the path with a flashlight.” The coach isn’t leading. They’re illuminating things the client might not have seen. The distinction matters because consulting creates dependency on external expertise, while coaching builds the client’s own capability. When a coaching engagement ends well, the client has new skills they’ll use for the rest of their career, not just a solved problem.

How does AI affect executive coaching and leadership development?

AI is creating a new category of leadership challenge. Current leaders need to become “AI fluent” without necessarily learning to code. They need to understand how AI reshapes where value is created in their organizations, how work gets reorganized, and what new skills their teams will need. Research from McKinsey and Gartner suggests AI will close the performance gap between mid-tier and top performers while exposing leaders who were coasting. Coaches working with executives in this space focus on change management fundamentals, systems thinking, and building organizational resilience before deploying AI tools.

How should new coaches approach marketing if they hate selling?

Reframe marketing from “selling yourself” to “letting people know you can help.” If you genuinely believe your coaching changes lives, withholding that from people who need it is not humility. It’s a disservice. Start with a simple structure: dedicate specific blocks of time each week to business development. Track the activity, not the outcome. Build a community of fellow coaches so you can refer clients who aren’t a fit and receive referrals in return. The confidence to market yourself grows with practice, just like the confidence to say no to wrong-fit clients.

What makes a leader coachable?

Coachability requires professional maturity and the willingness to own feedback rather than defend against it. Rob Ott describes hitting a plateau where his 360 feedback revealed he was the “wet blanket” on his leadership team. His breakthrough came when he stopped justifying his approach and started absorbing the feedback as fuel for growth. The key indicators are humility, willingness to take action on difficult changes, and the discipline to sustain those changes over time. Leaders who can separate their identity from their current behavior are the ones who grow the fastest.

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