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 and they're upset, I try to focus them less on how you litigate another person's impression of you and more on what is the action that you can take to counterprogram the narrative that you are afraid that this other person has of you. What are you going to do next to demonstrate that you are the person that you know yourself to be?

And so I always ask myself in these moments, what is one thing that I can do small that will demonstrate the opposite of what I'm afraid this person thinks of me. And so I'll give you an example of this. I was in a meeting a while ago and we were talking about different things that we wanted to start tracking in the Wookie Journal and our chief technology officer suggested ketamine tracking. And I thought she was making a joke and I laughed. And she looked at me very seriously and was like, this isn't funny, Hillary.

A lot of where this comes from is a concept in cognitive behavioral therapy called behavioral activation. In my former job, I was working for a company called Big Health. We make digital therapeutics. So these are mobile apps that have been clinically validated to treat behavioral conditions like insomnia, depression, anxiety. And I was working on a new depression therapeutic, and went very deep on this and was working with a really wonderful clinical team full of clinical psychologists who helped me understand the techniques that therapists use when they are working with people who have depression.

It's interesting. I think another thing I hear a lot of people complain about in organizations is the why do 10 people have to sign off on this email before I send it? kind of problem. And I think the answer to that is because those 10 people all have different information, different context and in many cases completely different working models for how the CEO of the company and other strategic leaders in the companies think and it makes things super inefficient. I think people will often say it's a process problem, it's not a process problem, it's not an approval problem.

So our CEO is somebody who obsesses over pixels in a way that is challenging to get things through design review. But I think results in a product that is a thousand times better than it would be if he were accepting of small excuses here and there for, oh well, this we had to cut scope here. We couldn't quite do what they wanted here. Like he sets a high bar and he holds it and he doesn't compromise. And I think this can sometimes get misconstrued. And I think a lot of people might think that he just wants maximal scope on everything.

One thing that he said to me that really stuck with me is when you're reporting to the CEO as a Chief Product Officer, the big mistake that people make is they think that the game is all about getting what is inside their head and influencing the CEO, influencing the people around them to make it so. And if you go into the role trying to do that, you're going to fail because, actually, what your job is to understand what the CEO's vision is and what they care about again, how they think about things and figure out how to operationalize that in a way that results in the best possible manifestation of it in the form of product.

Basically, it's one little thing you can do every single day. And the key with this is consistency. So you need to get people doing this thing every day. Reducing friction. I think a mistake a lot of people make when they start thinking about how to drive adoption is they're, oh, we have to show people how to do their work with these tools. But I'm, well, work is hard and if you are on a deadline for something, you've to get something done. The last thing that you ever want is more friction associated with getting it done.

But what I think that misses it assumes that you go and you do this analyst job for two years, and at the end of it, you have a person who knows how to make models really well and knows how to do a few things really well. But why does that have to take two years? And why does that model of you grind over this thing, you wait for feedback, eventually you get that feedback. Maybe that feedback's good, maybe it's not. You go back, you try again. It actually is really inefficient when you think about it.