The Best Product Managers Fear This One Thing

I learned a tough product management lesson a few years ago. My startup product team and I had spent the past six months working on our new software product in beta before we were ready to launch it. It was our biggest launch yet, with several prominent blogs and news outlets planning to cover it. No pressure, right?

The new product launched and initial signs looked good. The first customers raved about our functionality, and we gave ourselves pats on the back. But things quickly shifted in the wrong direction. Two of our earliest customers canceled the next month, followed by a few more who told us the following week that they would not renew their monthly plans either.

As we talked with these soon-to-be ex-customers, it became clear that while there was a lot of initial excitement around the launch, customers were not finding these updates useful enough for long-term adoption. They would poke around within the application, then leave their accounts dormant after a few weeks.

I knew our product would not survive as it was. So, I set out to make a bold strategic change.

I outlined a new vision and strategy for the product. And the following week, I presented my suggested pivot to the leadership team by describing the core problems we were facing.

But before I could continue, the VP of Sales snapped:

“I don’t see why you went through all this trouble. Why are we changing direction so drastically instead of staying the course?”

I felt my stomach sink to the floor. The one thing I feared most as a product manager had happened.

My product management skills — and, by default, my leadership and my judgment — were being second-guessed.

I see how this happens. Instead of corporate boards, product managers have stakeholders — colleagues who are often more senior than we are and are heavily dependent on our products’ success. These stakeholders need to know how a product will enhance their business. If there is a lack of clarity, questions and doubts can quickly arise. And it is painful for product managers.

I felt inclined to give up on the spot. But then I took a deep breath and thought about the VP’s question. I realized that this was a crucial moment for me. So, I responded and:

Answered the “why” I reiterated why I was suggesting that our product should head in a new direction. I achieved this by referencing the operating plan that our whole organization — including stakeholders — had reviewed at the end of the previous year. Then, I explained where our product fit into that plan. Finally, I aligned the new product strategy that I was proposing back up to our business-level objectives.

Although I had shared that our current product direction was not working, I realized that I had not been specific enough. That left room for doubt about the true state of affairs — and it was my job to remove that doubt. Sharing the direct truth about our status reassured the VP that we needed to shift our product strategy.

Considered other concerns I sympathize with product managers who have been second-guessed. It feels rotten and can wear you down. But you must show respect if you want to receive it. And a big part of being a leader involves answering hard questions. So, when that VP snapped at me, I resisted my urge to do the same thing. Instead, I put myself in his shoes to try and understand the reason for his doubt.

When I asked him what his concerns were, the VP revealed that the root of his question was fear. He was worried that I had abandoned the team and was going rogue. Once I showed him that I was working with our shared business goals in mind — and explained how I planned to help us achieve those goals using our new product strategy — he was much more considerate.

Kept stakeholders informed That VP’s doubt revealed one of my blindspots. I realized in hindsight that I had not been including him on important product updates to my product team. So, when he walked into that meeting and was bombarded with new changes, he felt thrown out into left field. And I saw how I had let him down by not communicating as often as I should have.

So, I left that meeting and reassessed my communications plan. I chose to hold weekly standups where everyone with a stake in our product was included. This gave us all more clarity about what we needed to achieve each week — and why it mattered in the long run. These standups showed me that the VP of Sales was not the only one who had been confused — other members of my product team had felt lost as well. So, his doubt was a blessing in disguise. It showed me where I had room to improve as a product leader and helped me get better moving forward.

Being questioned does not feel good — but it can be a good thing. It forces you to think more deeply about your decisions as a product manager. And if you are grounded in what you aim to achieve, it also gives you a chance to strengthen your leadership.

Make no mistake: being second-guessed can cut deep and break down your confidence. But it is important to think thoroughly about your product strategy and develop a strategic plan. You should also acknowledge that there will always be doubters and you will benefit from them keeping you on your toes. Their doubt might sting sometimes. But if that doubt grows your skills as a product leader, then it serves a strong purpose.