Building Startup Culture Isn’t Like It Used To Be

When does culture get established in a startup? I’d say the company’s DNA is set during the first year or two, and the founding team should do everything possible to make this culture intentional vs a series of disconnected decisions. Over the years, I’ve seen many great startup cultures that led to successful products and outcomes (and others that were hobbled from the beginning by poor DNA). However, as we plan for our upcoming Causely quarterly team meetup in New York City, I’m struck by how things have changed in culture-building since my previous ventures.

Startup culture used to happen organically

Back in the day, we took a small office space, gathered the initial team and started designing and building. Our first few months were often in the incubator space at one of our early investors. This was a fun and formative experience, at least until we got big enough to be kicked out (“you’re funded, now get your own space!”). Sitting with a small group crowded around a table and sharing ideas with each other on all topics may not have been very comfortable or even efficient. But it did create a foundational culture based on jokes, stories and decisions we would refer back to for years to come. Also, it established the extremely open and non-hierarchical cultural norms we wanted to encourage as we added people.

Once we hit initial critical mass and needed more space for breakouts or private discussions, it was off to the Boston real estate market to see what could possibly be both affordable and reasonable for commutes. The more basic the space, the better in many ways, since it emphasized the need to run lean and spend money only on the things that mattered – hiring, engineering tools, early sales and marketing investments, etc. But most important was to spend on things that would encourage the team to get to know each other and build trust. Lunches, dinners, parties, local activities were all important, as was having the right snacks, drinks and games in the kitchen area to encourage people to hang out together (it’s amazing how much the snacks matter).

Building culture in a startup requires in-person get-togethers

The new normal

Fast forward to now, post-Covid and all the changes that have occurred in office space and working remotely. Causely is a remote-from-birth company, with people scattered around the US and a couple internationally. I would never have considered building a company this way before Covid, but when Shmuel and I decided to start the company, it just didn’t seem that big an issue anymore. We committed ourselves to making the extra effort required to build culture remotely, and talked about it frequently with the early team and investors.

PS: We’re hiring! Want to help shape the Causely culture? Check out our open roles.

In my experiences hanging out with the local Boston tech community and hearing stories from other entrepreneurs, I’ve noticed some of the following trends (which I believe are typical for the startup world):

  • Most companies have one or more offices that people come to weekly, but not daily; attendance varies by team and is tied to days of the week that the team is gathering for meetings or planning. Peak days are Tues-Thurs but even then, attendance may vary widely.
  • Senior managers show up more frequently to encourage their teams to come in, but they don’t typically enforce scheduling.
  • The office has become more a place to build social and mentoring relationships and less about getting work done, which may honestly be more efficient from home.
  • Employees like to come in, and more junior staff in particular benefit from in-person interaction with peers and managers, as well as having a separate workspace from their living space. But the flexibility of working remotely is very hard to give up and is something people value.
  • Gathering the entire company together regularly (and smaller groups in local offices/meetups) is much more important than it used to be for creating a company-wide culture and helping people build relationships with others in different teams and functional areas.

Given this new normal, I’ve been wondering where this takes us for the next generation of startup companies. It matters to me that people have a shared sense of the company’s vision and feel bound to each other on a company mission. Without this, joining a startup loses a big element of its appeal and it becomes harder to do the challenging, creative, exhausting and sometimes nutty things it takes to launch and scale. There are only so many hours anyone can spend on Zoom before fatigue sets in. And it’s harder to have the casual and serendipitous exchanges that used to generate new ideas and energize long-running brainstorming discussions.

Know where you want to go before you start

Building culture in the current startup world requires intention. Here are some things I think are critical to doing this well. I would love to hear about things that are working for other entrepreneurs!

  1. Founders: spend more time sharing your vision on team calls and 1:1 with new hires – this is the “glue” that holds the company together.
  2. Managers: schedule more frequent open-ended, 1:1 calls to chat about what’s on people’s minds and hear ideas on any topic. Leave open blocks of time on your weekly calendar so people can “drop by” for a “visit.”
  3. Encourage local meetups as often as practical – make it easy for local teams to get together where and when they want.
  4. Invest in your all-team meetups, and make these as fun and engaging as possible. (We’ve tried packed agendas with all-day presentations and realized that this was too much scheduling). Leave time for casual hangouts and open discussions while people are working or catching up on email/Slack.
  5. Do even more sharing of information about the company updates and priorities – there’s no way for people to hear these informally, so more communications are needed and repetition is good 🙂
  6. Encourage newer/younger employees to share their work and ideas with the rest of the team – it’s too easy for them to lack feedback or mentoring and to lose engagement.
  7. Consider what you will do in an urgent situation that requires team coordination: simulations and reviews of processes are much more important than in the past.

There’s no silver bullet to building great company culture, but instead a wide range of approaches that need to be tried and tested iteratively. These approaches also change as the company grows – building cross-functional knowledge and creativity requires all the above but even more leadership by the founders and management team (and a commitment to traveling regularly between locations to share knowledge). Recruiting, already such a critical element of building culture, now has an added dimension: will the person being hired succeed in this particular culture without many of the supporting structures they used to have? Will they thrive and help build bridges between roles and teams?

It’s easy to lose sight of the overall picture and trends amidst the day-to-day urgency, so it’s important to take a moment when you’re starting the company to actually write down what you want your company culture to be. Then check it as you grow and make updates as you see what’s working and where there are gaps. The founding team still sets the direction, but today more explicit and creative efforts are needed to stay on track and create a cultural “mesh” that scales.

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