Human Skills 012 - Crafting company culture

with Wayne Crosby

Jun 13, 2023

Wayne Crosby is one of the most thoughtful leaders I've had the privilege to work with. He has cofounded multiple companies now - The first one, Zenter, was acquired by Google and became what is now Google Slides. While at Google, Wayne won the 'Great Manager Award' in recognition of his dedication, support, and leadership. And I met Wayne at his second startup, Humu, focused on trying to make work better for everyone everywhere.

All that is to say, Wayne has spent a ton of time thinking about how to make companies of various sizes work. And during our interview, I took advantage of that and asked him a ton of questions about culture, environment, and what you can do as either an individual or a leader to make a great work environment.

How do you craft an environment where people are likely to succeed?

It's a good question. And it's a tough one. I can tell you different attributes that make up a good environment. But it's a whole bunch of small steps that end up creating that environment, as opposed to one silver bullet to be like, if you just do x, y, and z, you will have a good environment.
I can tell you some of the things that were very conscious decisions early on in the companies and the teams that I've worked with that I've found create these things. One of them is, you have to pick the values that you're trying to emphasize and invest in those early.
One of the things that I really valued was creating a diverse team. Big believer in good ideas come from lots of different backgrounds. And so in order to be able to get the best out of a team, you need to be able to have those lots of different backgrounds on your team.
If you're not careful when you're thinking about some of this stuff, you can end up building a team, get five or 10 people in to a team and they all look the same and they don't have that diversity of background or experience and it becomes very myopic in its thinking.
And then adding - let's say you're 10 people in and they're all dudes, right? And they're all working on this project. And you're like, "Oh no, I've just created this, this team that's totally not diverse in any way with respect to gender." Finding that first woman who wants to join the team when there's already 10 people on it that don't look like them, or come from a similar background, it becomes exceptionally difficult.
And so you have to seed right from the beginning, the type of backgrounds that you're in, the types of diversity that you're looking for on a team, and then it propagates more naturally over time. But if you, it doesn't take long, especially in the beginning, a string of three or four hires that are all very similar, and then it becomes very difficult to change that pattern. When you're a small N count. The good news is your small N count, so if you focus on it, you can change it quickly, but it becomes very difficult.
So I think that's one of the things is like, bet on your own success, and then build the teams as if you're trying to build for that success, and with the right ratios and the makeup of what you're looking for from the different backgrounds and perspectives.
I think the other thing is you've got to believe in your people. This is a little bit cliche and I know a lot of people say it, but you've got to hire better than yourself.
And then you've got to empower those people and you've got to really listen to them because otherwise you've just wasted an amazing hire.
That sense of autonomy and empowerment I think also fuels a culture of people feeling like they can really own their own destiny.

How do you set up a blameless culture and effective postmortems?

I think there's a couple things that I've seen work well across not only Humu, but other companies that have done this. The first is that you have to have somebody on the leadership team, the engineering leadership team, who exudes these principles of no blame. And once people start to see that they're not gonna get in trouble for an incident and that you're actually going to learn from it as a team and the team is actually going to be better, you create this flywheel.
But this is one of those things that has to come from the top. It's not something that can be a bottom-up type of initiative. If you have a leader at the top who's going to play the blame game, the entire team is going to feel unsafe and they're not going to engage in these processes in a healthy way. They will also play the blame game. And so you have to lead by example on this one. And really hold to it. People should not get in trouble when, if they followed the process in the system, let them down. You should fix the system, not blame the person.

[KBall injection: People make mistakes. You have to start from a premise of people will make mistakes. And if we allow those mistakes to create catastrophic results, that's a system problem.]

Exactly. And as engineers, we should fix the system. That's what we do. So if you treat it as a systems problem, it becomes a lot easier to not play the blame game, and that you should build a system that is fault tolerant enough to be able to handle human error.

How do you create a culture where ideas can propagate easily?

I mean, the biggest one is just psychological safety. At the end of the day, this is the unlock to so many things. To people feeling safe at work, to good idea creation... so fundamental to any culture, creating that space where people feel like they can be exactly who they are, show up to work as themselves. And if you are successful in doing that. That's the right foundation for all of this stuff to proliferate.

[...and what did you do as a leader or what should a leader do to help create that sense of psychological safety?]

For me, it's about the people. It comes down to... projects have timelines that are a lot shorter than work careers. And it's easy to get caught up in a timeline on a project scale. And sometimes, especially with new leaders that are trying to prove themselves, it's easy for them to lose sight of the fact that there's going to be many, many more projects and the more important throughline in order to create success and create that right experience for workers and employees is to treat the person first and foremost. Support them if they're struggling.
I've been a part of teams where the deadline for something was the thing that, that defined success for everybody. Only to reach that deadline and not have the product be as successful as people expected because things were rushed or, people weren't fully in it because they were wrestling with personal challenges at home. And so the the output wasn't as good as expected.
There's all of these things that happen and if you come back to focusing on the individual and the relationship with that individual and making sure that they're in the right mindset to be able to do their best work, the right things will happen.
And I find that you actually have a lot higher chance of hitting project goal deadlines over a longer time period if you're able to focus on the person and make sure that they're in a good spot, before you start working on delivering on any particular project.
So focus on the person. Don't play the blame game. Because as soon as you start playing the blame game, everybody starts shutting down and not wanting to contribute anything because then it's going to be their fault.
Being able to identify who has good ideas and be able to support them no matter where they're coming from in the organization. That's another huge one in order to create that right balance of people feeling like they can contribute and that they're valued for who they are.
The failed state on that one is that you see organizations where people feel like they have to do X, Y, and Z in order to be able to get the promotion, in order to be able to... There's a checklist that people are going through. They're not being authentic to themselves. They're just following a checklist in order to get the reward at the other end.
And while that may be true for some jobs, the vast majority of knowledge jobs, if you're authentic to yourself and who you are, and you're passionate about it, that's going to lead to a faster outcome in terms of your own success than following any particular checklist.
It's also gonna lead to a lot more happiness for yourself. Just at the end of the day, I think too many people define success by a title and it's just not healthy for most people. What I've found is that the happiest people tend to be the people who are working on interesting problems with interesting people, regardless of title. And they're all contributing, and they're all trying to build something that they couldn't build by themselves.
That's the fundamentally human part of work, that when you're in it, you feel great, regardless of whatever your title is. And I think that's what more people should be striving for and looking for. And through that journey, you will also create these spaces that are safe, that you can build upon, that you can actually create amazing cultures and work friends throughout that entire journey that where that relationship lasts so much longer than any particular project.

Recommended Resources

Straight from Wayne

From a leadership perspective, the three books that have been most influential in my thinking have been Good to Great by Jim Collins (get the right people on the bus and then figure out where the bus is going), and Drive by Dan Pink (even though it's a bit pseudo science, the model of autonomy, mastery and purpose really resonate), and of course Nudge by Richard Thaler and Cass Sunstein (be thoughtful about your environment, we are hardwired to react to it). On the podcast front, I wish I had more hip/indie podcasts to refer to, but I love the storytelling of Snap Judgement, 99% Invisible, and This American Life.
If you want something a little more fun and in honor of pride month, I draw inspiration from an unlikely show, RuPaul's Drag Race. Every show ends in the same way, RuPaul says "The time has come for you to lip sync. For… Your… Life! And don't f**k it up!" Everytime I hear it, it reminds me we're all just lip syncing to a song as we move through our day and trying so hard to not mess up — and quite frankly taking ourselves way too seriously. And then, the show concludes with the juxtaposition of one of the most authentic affirmation statements ever said, "If you can't love yourself, how in the hell you gonna love somebody else? Can I get an amen up in here?". Yes, RuPaul you can. Amen!