In retrospect, I kept shooting myself in the foot.
Not because I lacked talent or drive or the ability to figure things out. I had plenty of all three. But through every major career transition, every high-stakes decision, every moment when the pressure was highest and the margin for error was smallest — I did it alone.
Not completely alone. I had a brilliant husband who is one of the sharpest thinkers I know. I had friends I trusted. I had mentors inside my industries who had seen a lot. But every single one of them saw the situation through my lens, with my framing, and with a deep emotional investment in how things turned out for me. None of them could see the whole board. None of them could see me.
I wonder sometimes what I might have done differently — what I might have become sooner — if I'd been a little humbler. If I'd been clear-eyed enough to recognize that what I needed wasn't more smart people who loved me. What I needed was a coach.
The Reactivity Chapter
In 2003, I stepped into my first marketing leadership role at Reactivity, a network appliance company, mid-crisis.
Two major industry bakeoffs — one in eWeek, one in InformationWeek — had evaluated the competitive field before I arrived. The criteria had been set, the testing done, the analysis written. By the time the results published, I was already in the seat. Reactivity's product came out rated most usable and most flexible. And slowest.
For a network appliance, slow isn't a footnote. It's a disqualifier.
What made it complicated — and what made the communications challenge genuinely hard — was that the performance testing was conducted at volumes that didn't exist anywhere in the real world. Not a single customer, anywhere, was pushing web services traffic at the levels those bakeoffs used as their benchmark. We had more than enough speed for every live use case that existed then, and probably for the next two years of projected growth. The other appliances were faster on a test that had no analog in production.
That's a nuanced argument to make in a market where "slowest" is already the headline.
Patrick Corman, the owner of the PR agency Reactivity had retained before I arrived, became my closest thought partner through that period. I kept him when I took the role, and that was one of the better decisions I made. He was a gifted strategist — someone who understood how to shape a narrative under pressure, how to protect a company's credibility while buying time for the engineering team to close the performance gap. The leadership team was rattled but supportive. The board was watching. And Patrick and I worked through it together.
Three years later, Cisco acquired Reactivity.
I look back on that chapter with real gratitude. And one question I've never fully stopped asking: what might I have done with a coach alongside me? Not a PR strategist who was also navigating the situation. Not my husband, who wanted me to succeed more than almost anything. An outside coach — someone with a framework, someone who knew how I was wired, who could see my patterns without being inside the pressure with me.
I kept shooting myself in the foot. Not in that job only. Through the career. Doing the hard things, making the big calls, taking on the new challenges — and never once stopping to ask for the kind of help that would have been most useful.
Rory McIlroy’s Team
Rory McIlroy just defended his Masters title.
Last year he won it for the first time — completing the career Grand Slam after more than a decade of painful near-misses at Augusta, the one major that had eluded him while the rest of his resume quietly became one of the greatest in the history of the game. The golf world exhaled. The burden was finally gone.
Then he came back and won it again.
The coverage has focused on the back-to-back. The dynasty conversation. The comparisons to Tiger. What the coverage has mostly skipped: the team.
Rory McIlroy does not walk onto Augusta National alone. He walks on with Michael Bannon, who has coached his swing since he was eight years old — not someone he calls when something breaks, but a constant presence who knows his mechanics better than anyone alive. He walks on with Dr. Bob Rotella, a sports psychologist who helps him manage the game between the ears, which at Rory's level is as technical and trainable as anything he does with a club. He walks on with Brad Faxon, a former tour player who works specifically on his putting. And he walks on with Harry Diamond, his caddie since 2017 and close friend — who is, among other things, a real-time strategic advisor making course management decisions under tournament pressure alongside him.
Every one of those people has a framework. A methodology. A point of view developed over years of working with elite performers. None of them is emotionally neutral about whether Rory succeeds — they're all invested. But every one of them brings structured expertise that his wife, his friends, and his instincts alone could not replicate.
He didn't build that team when his game fell apart. He built it when he was already good, and he kept building it as he got better. And when he finally won the thing that had haunted him for eleven years — he came back the next year and used that same team to do it again.
The High-Performer Paradox
That's the part that most high-performing executives get backwards.
The leaders I talk with who are most resistant to coaching are, almost without exception, the ones who have built real careers on their ability to figure things out. Strong instincts. Proven track records. The identity of someone who doesn't need a map because they've always found their way. That identity — "I'm the one who solves problems" — is precisely what makes the idea of a coach feel unnecessary, or worse, like an admission of something.
But Rory McIlroy didn't keep Michael Bannon for forty years because he couldn't swing a club. He kept him because he wanted to swing better than anyone in the world.
The worst time to find a coach is when something's on fire. By then you're reactive, defensive, making decisions from a contracted place. The coaching has to work twice as hard just to get you back to steady.
The best time is right now. When you have to perform before any negative feedback has arrived. When you're stepping into something genuinely new — a bigger role, a different kind of organization, a market that's rewriting its own rules underneath you.
Navigating the Shift
Which is exactly the moment we're all in.
AI isn't a tool upgrade. It's a role redefinition. The leaders who navigate it well won't be the ones who worked the hardest or knew the most. They'll be the ones who figured out how to lead differently — how to communicate across an increasingly fractured culture, how to make decisions when the data is moving faster than the org chart, how to hold their people together through fear and uncertainty without pretending it isn't real.
I worked with a GM for eight months as she stepped from a leadership role at a small, fast-moving startup into a general manager position at a large multinational — a different culture, a different scale, a different set of rules, with a compressed runway to prove herself in a highly competitive environment. She told me recently that our work together both grounded her and elevated her. That she came away with focus and perspective at the same time.
She made it through her first 90 days. She made it through her first year. She's running a region now, on a growth trajectory, still building toward the balance and boundaries the role demands. She was talented when we started. Coaching didn't create that. What it gave her was a place to think clearly — outside the noise, outside the politics, outside the version of herself that shows up when the pressure is highest and the stakes feel most personal.
The True Cost of Going Alone
I spent years being the person who figured it out alone. I had smart people around me, and I had real successes. I also left things on the table I didn't have to leave.
The question I'd ask any high-performing leader reading this — or any CEO or board member thinking about where to invest in their best people — is a simple one:
What's your honest instinct about coaching? And how much is that instinct costing you?
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