Why Product Leaders Fail

I’ve yet to meet a fellow Chief Product Officer or Head of Product say, “yeah, I’m crushing it right now.” In my conversations with fellow product leaders, there’s even a meme that’s started to form around product leadership roles. Effectively:

“Yeah, you just try to put some points on the board before you inevitably get fired.”

So, if a typical CPO feels their role is about trying to survive a couple of years i.e. long enough to help the business a little bit, what is causing that? Why is it so hard to endure as a product leader?

I would say there are three common failure modes depending on how far along the company is. The earlier stage of a company it is, the more likely the answer is going to be misalignment with the founder/CEO. What no one tells product leaders when they accept product leadership roles is that nine times out ten the founder and CEO still wants to drive the product vision. They want you to help execute that vision. And as founders scale, their founder intuition ebbs in effectiveness in comparison to product expertise in-house, but it takes a long time for founders to accept that. That transition period can be very rocky.

For later stage companies, the more likely answer is that the CPO is really only good at one type of product work, and the type of product work needed for the business changes over time. This can manifest in two ways: The product leader has skills that don’t match the type of job needed today, or as they execute, the skills needed change, and the leader cannot adapt. Not only is the product leader not good at that new job, they are also less likely to be interested in it.

Let’s talk about each of these failure modes and what both product leaders and CEOs can do to make them less likely to happen.

Failure Mode #1: Who Owns Product Vision?

Founders tend to have insanely good intuition about their customers and products because, let’s face it, no one has spent near as much time thinking about them and their problems. When startups tend to hire product leadership, it’s their first time hiring this type of leader. Interview processes can be clumsy or unoptimized, with the founder still figuring out how to articulate the real need. Commonly, what happens during this process is both the founder and prospective product leader end up jamming together on the future product vision. Both sides love this engagement, but for the founder, it’s not an effective test on how much the prospective product leader will help the founder, and for the product leader, it can give a false impression that they will have a ton of say in the product vision.

If at all possible, founders should leverage outside expertise to structure the recruiting and interview process for this type of role. One of the key questions to get explicit on before the process begins is what role will this leader play in setting the product vision? For non-product/eng/design founders, they may be asked to define it. For founders with product, eng, or design backgrounds, that is typically not the case until the company becomes much larger. Product executives usually play a consulting or execution role in a vision that is founder led. Founders need to tell candidates which one it is, and candidates need to ask. Neither of these happen as often as they should. 

Once founders understand their answer to this question, they need to vet for the appropriate skills. If what you really need is help executing on the vision, don’t spend much of the interview process jamming on the vision. Sure, candidates need to understand the vision, but what you really need to learn is are they comfortable receiving a vision from you and bringing it to life in the myriad ways that are difficult. 

Failure Mode #2: Does the Expertise Match the Type of Product Work Needed?

Different companies require very different approaches to their product strategy to be successful over time. Most of us understand there are different types of product work. There is tech and process scaling, there is building new products to find new product/market fit, there’s building new features and iterating on the user experience to strengthen current product/market fit, and there is growth work to get the maximum number of users to experience the product/market fit that exists. Traditionally, product leaders lean toward being experts in one or another. For example, I am definitely most known for my expertise in growth.

Founders often lack the understanding of what type of product challenge they are actually facing when they attempt to hire a product leader. Network effects businesses tend to focus more on growth because more users make the product stronger in a much more meaningful way than new features. DTC ecommerce companies / brands are always launching new products. SaaS businesses tend to need to launch lots of new features over time. Hiring a product leader that wants to build new features all the time into a network effects business likely isn’t going to work that well.

Failure Mode #3: Can the Product Leader Adapt as Needs Change?
Even if founders hire the leader with the right skills at the right time, as companies scale, how much weight they put on these will need to change over time. Today, the product leader’s job is to be what the business needs them to be. So while the old school product leader is a specialist, the new school product leader needs to be a chameleon, who can balance a portfolio across scaling, new product work, feature work, and growth weighted toward the needs of the business, and re-weight it considerably over time as business needs change rather than leave once business needs change. That’s hard, but inevitably how product leaders have to evolve to be successful over the long term within a company.

As a growth oriented leader, I am actually spending more of my time at Eventbrite on scaling, features, and new product expansion work, because that is what the business needs right now.

Product leadership is incredibly hard. Both founders and product leaders can eliminate some of what makes it so difficult by aligning on expectations before hiring roles, and on aligning which problems the organization is focused on right now. It is then up to product leaders to be able to evolve as the product needs change over time. They are both the best equipped to understand when needs change and help the organization change with them.

Currently listening to Rare, Forever by Leon Vynehall.

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