• Transparency is paramount. Make sure there are stated objectives (even if they’re inaccurate), daily check-ins, and quarterly reviews.
  • Flexibility empowers your people to do the best work they can. Have a bias against policies, rules, and meetings.
  • Trust is your most powerful tool. Get a bunch of good people together, point them in a direction, and get out of the way.

One of the myriad benefits of having spent so much time working as a contractor is the variety of cultures, work practices, and methodologies employed by various companies. I’ve seen dozens of companies succeed and fail first-hand, and I’ve learned a lot about what works well and what doesn’t, both for the company and for the team members.

The purpose of this letter is to form an outline of the things I look for when considering new opportunities, and it comes down to a few over-arching themes with specific practices to help build and support a culture that embraces those. A lot of what I have to say is similar to Netflix’s culture docs, and my early beliefs were shaped by that, so I wanted to give credit where credit’s due.


The more open, honest, and candid the team can be, the better.

Daily “Standup”

I’ve been known to give flak to certain elements of formal agile methodologies in the past, but after seeing things go wrong so many times, I’m going to toss my hat in the ring of some sort of daily standup. There’s a key to maximizing value in these, though: make sure the people involved are relevant to each other and keep it brief. The benefits I’ve seen from doing this are increased visibility into what everyone else is working on (duh), but also a certain serendipity every now and then where either two people are working on something similar enough, or somebody’s already done/tried something, and can make a quick recommendation.


There are also fringe benefits in getting new members up to speed and overall accountability. Nobody wants to show up to your daily check-in multiple days in a row with nothing to add. Ways to optimize performance are to have everyone put together their update ahead of time, and give everyone else a few minutes to read through those updates. I’m particularly fond of Zapier’s model.

Quarterly Reviews

Another incredibly valuable practice that, on the surface, looks way too bureaucratic is one I picked up from MobileIgniter: quarterly reviews. I’m sure I’ll get a few eye rolls when reading those words, but hear me out. The structure was the same, and it was pretty straightforward. Reviews always happened at the end of a work day, and were always held offsite (a coffeeshop or, more usually, a bar). Each review gives the employee an opportunity to talk about what’s going well for them and what isn’t going so well. We were also asked to give ourselves a performance score based on a set of criteria we agreed upon when we were hired (and was up for revision every review). After that, whichever co-founder you were meeting with did the same - talk about what they think you’re doing well with and what could use some work, and then gave you their score and justification. At the end, come up with a list of action items and areas to focus on for the upcoming quarter.

At first, I was reluctant, but after seeing the value, I fell in love with the practice. It’s become even more painful having worked with other companies that don’t have anything like this in place. The most important part about it is the candor. Everything has to be on the table, and you can talk about whatever you want. There were times were we talked about bonuses, or about new experiments we were trying, or about other teammates. The purpose is to clear up anything that might be slowing things down or causing any unhappiness. The work environment it created was incredibly positive - if something wasn’t working out, everyone had the chance to discuss it. Nobody ever left that company without it being obvious far ahead of time, whereas I’ve been completely blindsided by changes in other companies.


Let people do their job when, where, and how they’re most productive.



While there’s something to be said about being able to make assumptions about general availability, I’ve never understood companies that insist on having strict business hours. One of the main reasons I left ZebraDog was the insistence that a work day started at 8:30am and ended at 5pm. Sure, I can be in the office at those times, but those definitely aren’t my most productive hours. I’d much rather show up around 10am and leave around 6pm, or maybe some days stay later and then leave earlier on other days. As I told their founder, if you want me in the office at 830am every day, then schedule a meeting for 830am every morning (side note: don’t. Schedule your daily check-in at a time that makes the most sense for everyone).

Nextt, MobileIgniter, and AmFam have all had a much better understanding of flexible scheduling. Wednesday-Friday I get out of rehearsal for Kanopy at Noon, so my schedule was typically to put in 10ish hours Monday and Tuesday, and then do 5 or 6 the other 3 days of the week. Everything that needed to get done got done (usually ahead of time), and nobody seemed to mind.


Remote work is becoming more and more common, and while I haven’t written exclusively about it yet, it’s currently one of the strongest deciding factors in picking my next partner. Aside from the benefit of having a much broader talent pool to draw from, it also gives your people the freedom they need to work wherever they work best, whether that’s a remote island beach or a bustling Bay Area coworking space. Some days, being in the office with other people is great. Some days, cozying up in a small coffeeshop gives me the energy and inspiration I need. And some days, I lock myself in my room at home and carve through piles of work.

When people are forced to be in the office all day every day, it can actually be detrimental to morale and culture. If somebody works extremely well in quiet, isolated conditions, and you have an open office format, you’re either slowing them down or causing undue stress. If somebody doesn’t want to be in the office that day, everyone else can tell. There’s no need to add extra negativity.


I’ve already written at length about how policies and process can get in the way of progress, so I won’t go into much depth here. Basically, err on the side of freedom, letting your people do what you ask them to in whichever way makes the most sense for them.

Netflix seems to have the right idea here: provide context, not control. Instead of trying to force people to do certain things, give them the understanding they need to make the best decision for the team at every step.

This extends to equipment, as well. Don’t force your employees to use one machine versus another. Don’t even force them to use a company machine. It’s 2017 - you can do things that let people work in their own natural environment without jeopardizing the company. Even forcing new hires to get set up on a new machine results in days of lost productivity, and then having to manage having two machines (one for personal use, one for work) is extra hassle, especially when traveling.


Hire good people, assume performance, and proactively prune.


One of my favorite practices from working with MobileIgniter was our policy on policies. There was no formal vacation policy, there were no set work hours, and aside from things required by HR, we didn’t really have policies on anything. Our policy was simple: don’t be the reason we need to create a policy for something.

While a little cliche in the startup world (and, admittedly, a lot easier to maintain with a small team), the statement that makes to your team is incredible. It’s basically this: we trust you. We hired you based on character and aptitude. You don’t need to be told what and how to do.

Trust also is the subtext to a lot of what’s mentioned above: flexible scheduling requires you to trust your people will put in the time they need to. As does remote work. Standups, retrospectives, and reviews are all trust building exercises. Outside of those agreed upon practices, I have a bias against standing meetings (and, really, against most meetings). There are certainly times when getting a group together to talk about things live is productive, but in general, meetings are there because somebody doesn’t trust somebody else (and it’s usually a manager not trusting team members).

If there’s one thing I wish more companies took after Netflix on, though, it’d be what I’m calling “proactive pruning”. Essentially, every team member should be expected to be performing at a high level, and if they’re judged by their peers and supervisors to not be for too long of a time, they’re given a generous severance package. That’s not to say everyone should be constantly worried about their job, but one of the most valuable things you can do for your company and culture is to surround everyone with people they can learn from and they respect.

Nothing, and I mean nothing, can kill performance and motivation like having team members that aren’t pushing everyone forward. Some of my most enjoyable work experiences have been when the team is constantly facing new and hard challenges but everyone is great to work with and we know we can rely on each other to do what needs to get done. The worst are always when there’re individuals on the team that aren’t performing up to par and nothing can be done about it. Those are the situations where I’ve made the decision to remove myself from that environment - aside from it not being a great work experience, it’s not pushing me or helping me grow.

Obviously this isn’t an exhaustive list, but I wanted to get some thoughts out around what I look for when considering new opportunities, as well as things I’ve learned that seem to work well. I’d love to chat more about these points and more, and to see how we can improve your company’s work environment.

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