CEOs and Product Leaders
A relationship built on communication, candor, and trust
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 discussed how they talk about the problem.
The CEO and CPO need an open, honest, and frequent rapport for a product to stand the best chance of success. This candor must be present from the start; there should be no withholding or reluctance to share information. You must both be able to voice your opinions in the knowledge that there is mutual respect, safety, and trust. Like any relationship, this one requires constant nurturing.
I’ve touched on this issue of CEO-CPO communication in the past. Take a look at this piece I wrote a while ago, The PM Mind Meld. In it, I look at why—more than anyone else at the company—the CEO and the most senior product leader must be on the same page. You’ll see it’s got lots of practical advice to ensure this alignment happens: you need to address meeting cadence and make time to share unformed ideas, you also need to make sure that conversation is two-way and the CEO listens as much as they talk. And for product leaders, I look at how to develop an intuition around those “third rails” that the CEO is passionate about.
Note that being on the same page doesn’t mean you always agree. And while you may argue that it’s hard to go up against a CEO or founder who’s used to having the final say, you need to be able to push back and disagree with them at times to do the job you’re hired to do. If you can’t disagree with them, what’s the point of having you at the company? If two leaders never disagree, one of them can just go sit on a beach and drink margaritas.
Executive coach Ed Batista calls this healthy tension between CEO and CPO “necessary friction.” As Ed says: “The right amount of friction is necessary not only to generate and select the best ideas, but also to establish a working relationship that lasts. Either insufficient friction or too much friction is a sign that one party is too dominant, and that's rarely tolerable for long.” A relationship based on trust and honesty means that this friction is acknowledged, welcomed, and part of the conversation.
I’ve noticed that strong alignment and candid communication between a CEO and CPO in the early stages can slowly dissipate as a company grows. The multiple daily interactions you have when the company is 25 people turn into weekly 1:1s when you're at 100 people and then into biweekly syncs when there are hundreds of employees. Eventually, the CPO notices that there’s barely any time to talk about things that aren't urgent. One of my clients described it as “feeling like I only get to have one agenda item at a time with the CEO, and it’s whatever’s already been on fire for weeks by the time we can find time to talk about it.”
Counterintuitively, this communication drift is more likely to happen when there was a lot of mutual trust between the CEO and CPO. “We don’t need to be in constant contact because I trust you, and I have too many other things on my plate,” the CEO may say. That can seem like a gift: you’re given the empowerment and autonomy to lead the product team without interference. But I’ve seen again and again that this drift can eventually lead to upheaval and ultimately erode the very trust upon which it was built.
The good news is that I’ve watched CPOs take the initiative with their CEOs to reset this disconnect before it gets out of hand, even when it seems to demand a distraction from the CEO’s other important work. It's always easier to regain alignment than it is to restore trust. Ask yourself, at this moment, what seems important but not yet urgent enough to bother the CEO about? Those are probably the things you need to press for alignment on today to avoid grief tomorrow.
But how do you set the tone for communication and trust from the outset? An approach that worked for me when I was a CPO and has worked for clients is to be explicit about areas of ownership. For example, you might assign different time horizons to the CEO and CPO. At a hyper-growth Series C company, that could mean the CPO takes full ownership for product decisions that affect the next six months, the CEO and CPO take joint ownership of anything in a six to 12-month time horizon, and the CEO takes charge of the strategic thinking for 12 months and beyond. Or you might take the same approach with product surfaces or customer segments.
In my experience, consciously defining areas of ownership can be an effective way for the CEO and CPO to work together. The CEO doesn’t need to be stuck in the day-to-day stewardship of the product, the CPO knows when to involve the CEO, and the CEO understands that it’s their responsibility to shift their attention toward strategy and the longer-term future now that a CPO has been hired. That doesn’t mean anyone has checked out or been shut out. It’s merely differentiating ownership from involvement. “For these things, I like to be involved but trust you fully to make decisions. For these other things, I want us to both be engaged and in constant sync, and we should make important decisions together. And finally, I will try to involve you as much as possible for this last set of things, but I am taking ownership.”
And if you find your CEO wants someone to do the grunt work and isn’t interested in sharing ownership at all? Hopefully, you can discover that before you join. Everything I suggest here is something you can discuss with a potential CEO when considering an offer. I would insist on it. Walk through sample problems or product decisions—how would the CEO imagine this working? Who is responsible for what? How will they handle it if the two of you disagree? Are they open to different points of view? What’s the ideal forum for disagreement? Are they comfortable with dissent and discussion in front of the team, or do they see it as undermining their authority? Their receptivity to this discussion will give you some important clues about how they perceive the CPO role and how much ownership they anticipate giving away or sharing. I’ve looked at this division of responsibilities in this newsletter, Product Manager Zero: When should you hire your first PM?
Here are some excellent reads on improving the CEO-CPO working relationship:
This First Round Review piece, A Tactical Guide to Managing Up: 30 Tips from the Smartest People We Know, is a nice review of some tricks and tips that can be applied immediately to manage upwards. One that made me smile: The Rule of Seven Dippings. As Ralph Loura puts it, “Don’t save up a big topic until you feel you have all the answers—anything worthwhile takes time to build. An old manager of mine had a ‘rule of seven dippings,’ which essentially means that anything sufficiently complex or abstract takes multiple exposures (in his case, seven) in order for someone to internalize the concept.”
Here’s a lovely little video from The Conscious Leadership Group, Candor: Are You Revealing or Concealing? It gives a quick run-through of the risks of withholding, why leaders need to have a joint commitment to candor, and why this should be established from the start of the relationship.
Get comfortable taking responsibility for initiating tough conversations. One of the best classes I ever took was an internal course at Google called “Having Difficult Conversations,” run in conjunction with the Harvard Negotiation Project. It taught me to explore the “third story” before walking into a charged discussion—the invisible story that a keen impartial observer might tell. Everything we covered in the course is available in the book Difficult Conversations: How To Discuss What Matters Most.
How have you improved communication and alignment with your CEO?
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