It's one of the most common questions I hear from senior leaders, HR professionals, and founders navigating their next stage of growth: "Should I invest in coaching — or just send people to a training program?" It sounds like a simple either/or but of course in reality it's more complicated than that. And getting this decision wrong is expensive - not just financially, but in time, momentum, and trust. After 11 years at Google leading teams across sales, partnerships, Cloud,

I sat across from a founder last year. Series B, backed by a well-known fund, team of 60. From the outside, everything was working. Valuation up. Press coverage good. Investors pleased. He looked at me and said: "I have never felt more alone in my life." I have heard some version of that sentence more times than I can count. From founders. From VPs who were just promoted. From CEOs who are, on paper, at the peak of everything they worked for. The success arrives — and the iso

Most countries celebrate their national day on the date they declared independence, won a war, or became a republic. France has Bastille Day. The United States has the Fourth of July. Ireland does something different. St. Patrick's Day, held on March 17th, marks the feast day of Ireland's patron saint — the anniversary of his death in 461 AD. Not a revolution. Not a founding moment. A death. And the man being honoured wasn't even Irish. Born in Roman Britain in the late 4th c

I am currently reading   Hamnet by Maggie O'Farrell . You probably know the premise by now: it is the story of Shakespeare's son, who died at eleven, told entirely through the eyes of his mother Agnes. What strikes me every time I pick it up is the structural audacity of the thing. The most famous writer who ever lived appears in these pages as a peripheral figure. He is never once named. The novel insists, quietly and firmly, that the woman history forgot is the one worth kn

After 13.5 years in Ireland — and counting — I still smile every time I see a Dublin Bus display its gentle regret: "Sorry, Not in Service." Even the buses apologize here. It's such a quintessentially Irish moment that perfectly captures something deeper about this island nation's culture, one that every leader working in Ireland needs to understand. The Weight of History: How Emigration Shaped a Culture To understand Ireland's communication culture, we need to understand its

Most leaders think growth problems are strategy problems. They're not. They're communication problems that only become visible once the organization starts to scale. When teams are small, things "just work." People fill gaps. Context lives in conversations. Decisions happen quickly because everyone knows what everyone else knows. Then the company grows. More people. More layers. More complexity. And suddenly the same leadership style that worked before starts to fail. Not bec

I’ve bombed more interviews than I care to admit. Some of them I only realized   after   the fact.   Others I felt in my body the second I walked out of the room. Through my coaching work, I keep seeing brilliant people tie themselves in knots before interviews. Imposter syndrome. Over-preparing. Second-guessing every answer. That familiar mix of nerves and self-doubt. It’s made me reflect on my own track record - the mistakes I made, the things I misunderstood, the moments I

Don't get me wrong. As a leader, you should be strict about your time. Ruthless, even. Your calendar is one of your most strategic assets, and protecting it matters. Boundaries matter. Saying no matters. And yet. Some of the worst leadership decisions I see are made by people who are constantly telling people they "don't have time." Not because they're lazy. Not because they're careless. But because they're operating from a place of deep psychological scarcity. The Time-Rich,

We shall not cease from exploration  And the end of all our exploring  Will be to arrive where we started  And know the place for the first time. — T.S. Eliot I’ve been thinking about this poem a lot lately. Exploration is rarely the glamorous, expansive thing we imagine it to be.   Most of the time, it’s disorienting.   It strips away labels.   It removes the scaffolding that once made life feel coherent.   It asks uncomfortable questions long before it offers any clarity in

Three months after my Google career came to an end, someone asked me at a dinner event: "So, what do you do?" I hesitated before I started answering. It wasn't that I didn't have enough going on for me to be able to give a coherent answer. I was building my executive coaching business and working with a few exciting businesses as an advisor / consultant.   I hesitated because none of them felt fully-baked yet. It all seemed too hand-wavy.   For 11 years, the answer had been e

You've done the prep.   You know your achievements.   You've researched the company.   You walk into the interview room (or log into the Zoom) ready to impress. And then it happens. "So, tell me about yourself." You hear yourself say:   "Well, I'm   sort of   passionate about... " "I   think   I could be a good fit because..." "I've been   trying to   develop my skills in..." And just like that, you've undercut yourself before you've even started. The Power of Words The words

Congratulations. You got the promotion. The title changed. The compensation went up. Maybe you got a new team, a bigger scope, or a seat at a different table. Most people think the hard part is over. It's not. It's just starting. Here's what usually happens: People spend months (sometimes years) positioning themselves for a promotion. They work extra hours. They take on stretch projects. They manage up. They do everything right. Then they get the promotion — and promptly take

Stepping into a management role is already a shift in identity. Stepping into a management role over people who used to be your peers is a different kind of stretch. This is where many new managers get stuck. They know how to do the work. They are less sure about how to lead people who knew them before they were “the manager.”

A few months ago, a founder I coach said something I hear almost every week: "I feel like I'm juggling twenty balls, and none of them can drop." She runs a fast-growing startup.   Her calendar is a wall of back-to-back meetings.   She's managing a team, closing deals, mentoring, hiring, fundraising, fixing ops issues. If this sounds familiar to you, you are not alone.   Whether you're a founder, an executive, or a people manager, the reality is the same: You're constantly pul

You spent six weeks finding the perfect candidate. She nailed every interview. The team loved her. The offer package was ready. Then came the email: “I’ve decided to pursue another opportunity.” It’s easy to blame compensation, timing, or “the market.”   But most of the time, candidates aren’t rejecting your offer.   They’re rejecting your process. When the Process Sends the Wrong Signal I had coffee recently with Marcus, a VP of Engineering who’d lost three senior hires in a

It was 2:07 AM and I was staring at the ceiling, replaying two paragraphs of feedback in my head for the hundredth time. Earlier that...

Eight years later, she still remembered the message. It was 2016, and I was preparing to welcome a new hire to our team at Google. She...

How diversification, flexibility, and strategic design are redefining executive careers. When I shared recently that I'd taken on a...

(And Why You Might Be Looking in the Wrong Places) Whether you're a founder building from the ground up or a corporate executive scaling...

Startups are built on extremes.   You’re either scrappy or bloated.   You’re doing it all yourself or over-hiring too soon.   You’re...