Resilience

Why the Worst Product Managers Expect the Best

With each product I’ve built, things rarely come together exactly as planned. But it’s not the inconveniences, technical challenges, or misguided people that are the problem. It’s that we ever allow them to catch us off guard in the first place.

Anyone can operate under ideal conditions. But ideal conditions are the exception, not the rule. Eighty percent of your time building product will take place in a maelstrom of ambiguity and obstacles.

It’s naive to expect that the world should bend to your favor and promote ideal conditions. Most reasonable people acknowledge this. But when it comes down to it, many of us cling to expectations that our work should progress without pushback and our lives should follow a neatly charted map. We forget how much of life is negotiating egos and hidden variables along the way. 

The best teams embrace imperfections beyond their control and create great products anyway.

The worst teams self-destruct because they’re too busy obsessing over inconveniences. 

It’s easy to pick out the product teams who struggle with this. Each challenge appears to catch them off guard, demoralizing the team and throwing people into a state of anger or despair. This type of reaction points to two things: inexperience and fragility.

Improvement comes from experience and perspective–you’re prepared to face a wider range of potential scenarios. In turn, this allows you to develop a deeper well of resilience and resourcefulness.

Creativity and resilience

At age 23, I started working for a healthcare startup, building out a web-based patient portal. Each setback caught me off guard because I expected things to just work–a laughable statement for anyone who has worked in technology for more than a week. When I went on-site for the launch with our first big client, I was unable to anticipate the ways I was about to get torched. 

There were technical challenges inherent to a complex healthcare organization and integrations with its existing software that we had to sort through. But the technical challenges were only half of it. The true test was handling stakeholders–internal and external–as well as the people who create noise and thrive on passive-aggressive emails.

Anyone who has worked in product is familiar with these challenges. There’s nothing unique about them. But I struggled to adapt because my expectations were off base. I lacked perspective. I was focused on perfection in our product and people pleasing–both impossible tasks–rather than creativity and resilience. 

The best product managers are able to cycle through dozens of permutations and anticipate certain situations through dimensional thinking. But no matter how good you are, at some point you’ll get hit by something you didn’t see coming. Whether the feature you’ve been working on breaks or a “senior leader” steps in and changes the rules at the last minute, you will encounter situations that test your limits. 

Your job isn’t to prevent these mistakes or eliminate every obstacle. Rather it’s to develop the ability to continue moving forward when the inevitable occurs. Leading product requires that you establish an unwavering sense of perspective and imbue this quality in your team. Then, and only then, can you build the resilience and resourcefulness to adapt, imagine creative solutions, and bring them to life. 

Resilient teams who cause a few more quality issues will always beat out fragile teams who are only able to operate under perfect conditions. The difference is self-awareness and being able to step back to put things in perspective. This means assuming responsibility instead of feeling sorry for yourself because something you built didn’t work or someone criticized you. 

This is not to say that you shouldn’t focus on promoting favorable conditions. You can’t create a complete shit storm for yourself and hope to come out better for it. But you should also understand that you’re never going to get ideal conditions. There are going to be things beyond your control. And that’s what keeps life interesting–the challenges and obstacles you have to learn how to overcome along the way.

Each team meeting, one-on-one, and retrospective is an opportunity to develop these qualities in your team. By challenging each other to maintain perspective and reflect on experiences, you can turn things back to what’s within your control–your attitude, the effort you put into your work, and the guiding principle that propels you forward.

Opportunities for reflection

In my experience, few things are more valuable to the morale and resilience of a team than holding retrospectives every few weeks. These are best done with your immediate team (keep things small so everyone can have their voice heard) in a low-stress environment, outside of work. There are multiple formats, but each person should have a chance to discuss what’s gone well and what hasn’t. 

This provides a valuable outlet for everyone to air their frustrations, without judgment or repercussions, and remind each other of recent accomplishments. It also allows the team to come together and consider how you might frame challenges in a more productive light and course correct the things within your control.

Retrospectives are just one outlet to discuss experiences and rediscover perspective. And with the right perspective, you can begin building the resilience to navigate the conflict and uncertainty inherent to challenging work. 

Creating more opportunities for reflection is the best way to harness experience and build perspective. It’s the first step towards realizing that imperfect conditions are where the majority of life takes place. Knowing this, you’ll be able to lead better teams, build better products, and live a better life. 

Expect challenges. Expect unknowns. Expect ego. When you set your expectations accordingly, you’ll waste less time consumed by the things that have happened to you. 

Anyone can operate under ideal conditions. But the best product teams don’t sit around waiting for the stars to align. Instead, they embrace the imperfections inherent to life, create their own momentum, and make things happen for them. To steal a line from Charles Bukowski, “What matters most is how well you walk through the fire.”



*This article was originally featured on Mind the Product.