Every founder I have ever coached on fundraising has, at some point, looked at me and said some version of the same thing: "I had no idea it would be this hard." Not the first time. Not the fifth time. Not even for founders who have done it before and know exactly what is coming. Fundraising is one of those things that looks clean and logical from the outside and feels chaotic and deeply personal from the inside. The TechCrunch announcement is the last paragraph of a very lo

An Honest Guide for Senior Professionals In the last few weeks I have had quite a few conversations with people who have left or are planning on leaving their corporate careers. Former colleagues. Old Google network connections. People who found me through LinkedIn. Prospective clients referred by people I used to work with. They are reaching out because they are standing at a crossroads and they are not sure about which way to go. Some of the profiles are: A Senior Di

Some time ago, my client — let's call him Steve — came to me disappointed, angry, and confused all at once, which is a particular kind of exhausting. Steve is a founder. Sharp, self-aware, genuinely good at what he does. Some of the people he had invested most in — developed, advocated for, stayed late with, comforted when they confided in him about personal issues — had left the company the minute a competitor came calling. Not just left. They brought some of his client book

A few years into a senior role at Google, a more senior colleague pulled me aside after a meeting. "You're the smartest person in that room," she said. "But you're not landing the way you think you are." That sentence stayed with me for a long time. Not only because it stung (it really really did) but because I knew she was right, and I had no idea what to do about it. I had the skills, the track record, the ambition. What I didn't have was anyone who could help me see myself

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

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

I work with a lot of B2B sales leaders. Founders still running founder-led sales. VPs trying to professionalize chaos. Sales managers inheriting teams that look busy but don't reliably convert. Most of them say the same thing: "We have strong people, but something isn't clicking." They're right. And the problem is almost never talent. Great sales teams don't outperform because they hustle harder or chase more activity. They outperform because they operate differently — wi

Every year, I look back not just at the metrics and milestones, but at the cultural touchstones that colored my days — the books that shifted my thinking, the films that stayed with me, the podcasts that became companions on long walks, and the experiences that reminded me why all the hard work matters. Here's what made the cut this year: 🎥 Favorite Movie: About Dry Grasses Nuri Bilge Ceylan's latest masterpiece. Slow, deliberate, and devastatingly human. It's a film about i

As the year winds down, I’ve deliberately slowed my pace to reflect. I’m writing this from the USA, far from my own home, and that distance has been surprisingly helpful. Being away has given me perspective — on what worked, what didn’t, and what I didn’t do this year that I want to be doing more of. 2025 was a strong year. Productive, expansive, and intellectually stimulating. The work grew in scope, the rooms got sharper, and the range of what I delivered widened meaningful

Earlier in my career, I flew to Orlando for what was supposed to be a global offsite. The agenda looked ambitious — strategy sessions, team alignment, big-picture planning. We were pumped. After we landed and checked into the hotel, we walked into the conference room for the opening ceremony. That's when they told us: our teams were being disbanded. Our roles were no longer going to exist. I still can't decide what was more absurd — the fact that they flew us across the world

A few months ago, a client came to our second session. She'd always been composed, strategic, the kind of person who thinks three steps ahead. That day, she was exhausted. "I quit," she said flatly. "Sent the email this morning. No backup plan. Just done." She'd been at the company for six years. Senior role. Respected. Good at what she did. From the outside, everything looked fine. But when we unpacked it, nothing had been fine for months. She'd been drowning in admin work t