In my coaching sessions with CPOs and other senior product leaders, the relationship with a CEO is a frequent topic. Sometimes there’s been a colossal dust-up; other times, merely a lingering sense that the two are not quite aligned. Often, our conversation will go something like this: Client: I’m having difficulties with my CEO and I’m worried that it’s getting worse… [describes the problem that stands between them]… Me: Have you spoken with them about your relationship? Client: Sort of. Well, not really. No. They realize that although they might have talked about the problem, they haven’t ..read more

In a previous newsletter, I reflected on my career in product management and shared some lessons I’d learned. One section, in particular, seemed to generate the most responses: In product management, there’s an art and a science. The “art” gets dismissed as soft skills. When PMs fail, it’s usually because of “The Art.” The most important thing you can do early in your career is grow these skills. Don’t let them be dismissed as “soft skills,” don’t get lured by the promise of tactics and techniques: they’re essential, but the craft depends more on the art over the long term. I want ..read more

I turned fifty earlier this year. The thing about getting older that nobody warns you about is that you always feel like you’re the youngest person in the room until suddenly you’re the oldest. There’s never a noticeable moment where you look around and think, “huh, my age is about average.” You’re the kid, and then you’re old. At some point, about twenty years ago, I moved from engineering to product management. The exact moment is hazy and speaks to how little foresight and deliberation went into my career. I wanted to be closer to the business, so I started doing less and less engineering ..read more

This is the next part of an ongoing series about product culture. Make sure to check out the previous chapters on Airbnb and Stripe. Slack Huddles This morning Slack announced a set of new features intended to help teams stay connected in a post-pandemic world. Included in today’s launch is Slack Huddles, a lightweight, audio-first way to communicate inside a channel or direct message. Huddles addresses the need for fast, ambient, and informal discussions — spontaneous conversations that would happen in hallway encounters or at coworkers’ desks. These chats form the connective tissue of essent ..read more

My previous newsletter was a call to normalize dual-track career ladders for product management, allowing people to choose between advancement in product leadership over people management. I was pleased with the response, which was overwhelmingly positive. Scores of readers saw themselves in my words. Clearly, the piece struck a chord. Hunter Walk wrote a response entitled, Don’t Let Your Best Product Managers All Become People Managers Or Your Company Will Suffer. Please take the time to read the entire post. I want to emphasize a few key points that build on what I wrote: So, in my experien ..read more

? “I look at my peers, and they’re all directors and VPs. Am I behind? Will I risk being seen as unambitious?” ? “My VP’s feedback is always through the lens of performing at the next level [director], but I’m happy where I am, which is frustrating.” ? “I can’t help feeling like my career has stalled. I’m ten years in, and I’m still an individual contributor (IC). But I like my job and want to keep doing it.” ? “As a director, I’m constantly jealous of the product managers on my team. I wish I was still doing their job, and I regret being promoted. I realize there’s very little ‘product’ to t ..read more

This is the next part of my ongoing series about product culture. If you missed it, check out my previous piece about Airbnb and my article on strong product cultures that kicked everything off. Stripe co-founders Patrick and John Collison This month we’re going deep on Stripe. As you’re about to learn, “going deep” is a core product principle at Stripe. The company is now the most valuable startup in the United States, raising a round in March at a breathtaking $95 billion valuation. (Disclosure: I am an investor in Stripe and have a relationship with the company dating back to 2015.)1 I had ..read more

Neil McElroy On May 13, 1931, an up-and-coming 26-year-old Procter & Gamble employee named Neil H. McElroy issued his famous “Brand Men”1 memo [pdf]. McElroy had an ulterior motive: he wanted approval to hire more people (don’t we all). So the three-page letter was effectively a request for more headcount. But his proposed job description was novel for 1931: the new hires should be accountable for an individual brand from top to bottom. This brand- or product-centric approach was a departure from the top-down, functional organizations that typified workplaces in the 1930s. Orienting so-cal ..read more

? Learning to listen, really listen, is a difficult skill to master and takes constant practice. It’s essential to product management—the best listeners engage more deeply with their customers, develop stronger connections with their teams and cross-functional coworkers, and build sturdy bridges to executives. Ximena Vengoechea’s new book, Listen Like You Mean It: Reclaiming the Lost Art of True Connection, is an absolute delight. Ximena is a user researcher who worked at Pinterest, LinkedIn, and Twitter, and she draws from her front-line experiences throughout. She writes with a level of car ..read more

I recently did a five-part podcast series with Rocketship.fm about real-world challenges product people are facing. Each bite-sized episode is set up like a confessional where I confront a series of real challenges submitted anonymously by listeners. Many of these scenarios were familiar from my coaching practice. Here’s the first episode: “what do you do when the board brings in a CPO who has no product experience and is butting heads with everyone internally?” In the other chapters, we deal with unempowered product teams, overcoming our biases during customer interviews, finding success as ..read more