On “Founder Mode”, deep collaboration, and execs who “manage up”

Like everyone in Silicon Valley, I read Founder Mode with interest this week. I won’t pretend I have much to offer Brian Chesky or Paul Graham on the subject of running companies with thousands of employees. The largest company I’ve run was about 150 employees, a fraction of the size of Airbnb. 

But there was one part of the essay that resonated with me, and that was the experience of hiring fancy executives and then being told to butt out of their affairs while they simultaneously worked to reduce my expectations of their teams’ outputs. PG describes this feeling as being “gaslit.” I’m not sure I agree with that characterization, but I do agree that watching a team’s performance degrade while hearing things like “As CEO of a Series B company, you shouldn’t be spending time on these details” is disorienting. 

Sadly I did not respond by hulking out and engaging in “Founder Mode,” though if Brian Chesky ever records his talk, maybe I can learn how! But I did learn a few things as I went through a journey of figuring out how to keep expectations high and outputs strong while adding management layers.

So, to add to the zeitgeist, a few thoughts on collaborating deep in the org chart, and dealing with execs who are “managing up” to you.

Great execs don’t push back on high expectations or founder collaboration. I made a lot of mistakes at Periscope Data, and that included hiring some leaders who weren’t the right fit and who we had to move on from. From this experience, I learned that great leaders are eager to collaborate with the founders on improving their team’s execution. Great leaders are not threatened by you working directly with their teams. This is because great leaders just want to win, and are genuinely excited by any and all ideas, collaborations and bar-raising standards that help the team win. We ultimately got to an exec team at Periscope that, IMO, worked well together and wasn’t threatened by deep collaboration, either from founders or from peer teams. This taught me most importantly that such a thing is possible. If you feel like your team is pushing you to butt out even though they’re not succeeding, consider making changes to the team.

Objective benchmarks are great for setting performance expectations. Every year as part of annual planning, I would pick the most successful comparable companies in one of our big VC’s portfolios, and ask for that company’s historical growth data from the years when they were our size. This historical data would be a key input to our planning. This added a ton of clarity to the goal-setting process: “Look, we’re all here because we want to be as successful as Twilio or Snowflake. Here’s what they were doing at our size. So, now we know, that’s where the bar is if we want to win.” Again, great execs aren’t here for the paycheck, they’re here for the outcome, so they welcome this.

Know the numbers cold and expect the same of your team. It’s pretty common in my experience for the founders to know the details of the company’s key metrics and how they’re calculated. After all, they ran those calculations themselves for many years. Retaining this knowledge, and asking enough follow-up questions of the data that you continue to understand your company’s performance at a deep level, is critical. And it’s a bad sign if, say, your sales leader doesn’t know the details of the sales numbers at least as well as you do. It is absolutely reasonable to expect your leadership team to live and breathe their performance metrics, and strong leaders will welcome smart, detailed questions on the numbers.

You have strengths and weaknesses. Know them and play to them. If you’re a great marketer and built an incredible community around the company from scratch, you should absolutely not compromise on your level of engagement with the community management team, even if it’s a couple levels down on the org chart. But it probably does not make sense for you to dive deep with the platform engineering team, and trying to do that if you don’t have the chops just grinds the org to a halt while they try to awkwardly work around you.

Engagement needs to be consistent. If you’re going to dig in on UX designs, then dig in! This means at least weekly and sometimes daily engagement with the team, enough that they start to know you, know what you care about, how you think about tradeoffs, and where you will and won’t compromise. Showing up once a month or quarter to upend everything with a bunch of specific directions that you don’t follow up on doesn’t help. Pick your spots and dig in deeply with those teams. Then change these spots over time depending on what’s going well and poorly.

Steve Jobs’s success is not a reason to act like a dick. Too many founders do this, and I worry PG’s essay will lead to a spike in bad behavior. Here are some things to emulate about Apple in the Steve Jobs years: They had a strong and remarkably stable management team. They had very high standards for product quality. And, yes, Steve famously collaborated directly with the hardware design team on prototypes – which, by all accounts, they were excited to do! Many great leaders are detail-oriented and have very high standards while treating people kindly. Aspire to that. 

I found the framework of CEO as “Editor,” I think originally attributed to Jack Dorsey, to be helpful. Ultimately the founders bear personal responsibility for the company’s outputs: Its products, its marketing materials, its customer support, the things salespeople say on calls, all of it. When one output of the company – e.g. the marketing copy – is sub-par, then you as a founder should be editing that output by giving specific feedback directly to the team. If this is an area where you personally did the work before the company got bigger, then it can absolutely make sense for you to directly collaborate with the copywriting team, up to and including contributing your own work, to bring the quality up.

But repeated “edits” of the same type to the same team without consistent improvement probably indicate that a change needs to be made on the team. And once the copy is consistently excellent, you no longer need to spend time editing on that team. You can then relax and ultimately eliminate the process you used to collaborate with the team and edit their work, so they can run fast and do great work while you focus elsewhere.