How to build a team that can “take a punch”: A playbook for building resilient, high-performing teams | Hilary Gridley (Head of Core Product, Whoop)

If they come to me upset, I try to focus them less on how to litigate another person's impression of you and more on what action you can take to counter-program the narrative you fear this other person has of you. What will you do next to demonstrate that you are the person you know yourself to be?

I always ask myself in these moments, what is one small thing I can do to demonstrate the opposite of what I'm afraid this person thinks of me? I'll give you an example. I was in a meeting a while ago, discussing different things we wanted to start tracking in the Wookie Journal. Our Chief Technology Officer suggested ketamine tracking. I thought she was making a joke and I laughed. She looked at me very seriously and said, "This isn't funny, Hillary."

This concept originates from behavioral activation, a technique used in cognitive behavioral therapy. In my previous role, I worked for Big Health, a company that develops digital therapeutics. These are mobile applications clinically validated to treat behavioral conditions such as insomnia, depression, and anxiety. I was developing a new therapeutic for depression and delved deeply into the subject. I collaborated with an excellent clinical team of psychologists who helped me understand the techniques therapists use when treating individuals with depression.

It's interesting. I think another common complaint in organizations is the need for ten people to sign off on an email before it's sent. The reason for this is that those ten people often have different information, varying contexts, and in many cases, completely different working models for how the CEO and other strategic leaders think. This makes things incredibly inefficient. While people often label it a process problem, it's not a process problem, nor is it an approval problem.

Our CEO obsesses over pixels, which makes getting things through design review challenging. However, this results in a product that is a thousand times better. He doesn't accept small excuses like having to cut scope or not being able to do what was wanted. He sets a high bar and doesn't compromise. This can sometimes be misconstrued, and many might think he just wants maximal scope on everything.

One thing he said to me that really stuck with me is this: When you're reporting to the CEO as a Chief Product Officer, the big mistake people make is thinking the goal is to get what's inside their head and influence the CEO and others to make it happen. If you approach the role this way, you'll fail. Your actual job is to understand the CEO's vision, what they care about, and how they think. Then, you must figure out how to operationalize that vision to create the best possible product manifestation.

Basically, it's one small thing you can do daily. The key here is consistency, so you need to encourage people to do this every day. This involves reducing friction. A common mistake people make when considering how to drive adoption is thinking they must show others how to do their work with these new tools. However, work is often challenging, and if you're on a deadline, the last thing you want is more friction in getting your tasks done.

However, what I believe that misses is the assumption that you complete an analyst job for two years, and by the end, you have someone who excels at building models and a few other tasks. But why should that take two years? And why does that model involve grinding through a task, waiting for feedback, eventually receiving it (whether good or not), then going back to try again? When you consider it, this process is actually very inefficient.