That Painful Meeting — And How I Became a Curious Product Manager

I arrived at the office bright and early my first day ready to make a difference. I had just started a new job as a product manager and was anxious to get going. My new VP boss, let’s call him John, had spent the last month building out a strategic roadmap for the upcoming year. Now, it was my turn to shine (or so I thought).

Over my first few weeks on the job, my job was to figure out several key features that could help us execute on that roadmap in the first half of the year.

My new colleagues were great. Along the way, many of them sought me out to offer their feedback. They gave several suggestions about features that had already been implemented — but I paid little attention.

I pushed forward and kept my attention focused on what I thought was best for the product.

After a little more work, I was excited to present the plan to John. But then the day of our big meeting came — and I learned a difficult lesson. Here is what happened.

As I went through the slides with him, he had a perplexed look on his face. He finally stopped me about halfway through the deck and asked, “What did the team say when you showed them this?” The question sounded innocent enough. I quickly replied, “Nothing — you are the first one to see it.” Although I still had faith in the plan, my confidence was slipping with each passing moment.

“Well, we actually tried most of this a few months ago,” my boss said. “And it was a spectacular failure.”

I almost sank through the floor in embarrassment — and humbly realized that I needed to change a lot more than my story descriptions and wireframes. The team had been trying to save me from this, but I was too stubborn to listen.

This was the day I realized that I needed to become a more curious product manager.

Curiosity is a fundamental trait that product managers cannot afford to lose. The day you are arrogant and stop asking, ‘Why?’ is the same day that you should start looking for a new job.

I know that might sound harsh. But consider the role of a product manager.

Your core responsibility is to act as a customer advocate. You are expected to know which features they are requesting, the reasons behind those requests, and which requests will drive the most value for the business. That requires a healthy dose of curiosity at all times.

In my experience, curious PMs share a few key traits that help them lead their teams to success. Curious product managers are:

Engaged
I believe that there is nothing more invigorating than building great products. Being a product manager inspires the best people to leap out of bed each morning. They always want to learn more about what they can do to improve their products. And their secret weapon is engaging everyone who has a stake in that product. Curious PMs never stop asking colleagues, customers, and stakeholders how to improve their processes and output.

Insightful
The most curious product managers are insightful because of what they learn and apply from others every day. And they realize that past knowledge does not always translate into future success. Each product is different and each challenge unique. They humbly admit when they do not know something, and ask questions to improve their understanding. Then, they use this collective wisdom to drive future product decisions.

Accountable
Curious product managers are accountable to many stakeholders, even though they often do not have that many direct reports. They must motivate other teams to bring their product visions to life, and remain accountable to the customer at the same time. They cannot succeed in a vacuum.

Humble
No one likes a know-it-all — especially when they are clueless about what they do not know. That is why curious product managers remain humble in both success and failure. And they realize that they need the team to help them see blind spots. Leading product does not mean having all the answers; it means empowering your whole team to build something bigger than you ever could alone.

The best product managers never stop learning from themselves, their colleagues, and their customers. They are in a constant state of growth because they know they cannot lead on their knowledge alone.

This mindset fosters a deep sense of empathy for everyone they must learn from and work with. That empathy drives them to learn more about building products to solve problems that matter.

So, stay fresh and stay curious. Keep striving to gain new perspectives. And keep asking, “Why?” to stay on the right track.

How do you stay curious?

About Ron and Aha!

Ron is a product guy. He is the Director of Product Management at Aha! - the world’s #1 product roadmap software. He previously founded and sold his own company and has been on the founding team of multiple venture-backed companies.

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