Closing Advice

Remote work – key considerations

COVID-19 dramatically accelerated the pre-existing trend toward distributed workforces. While the core principles in this guide hold true in any mode of operation, the tactical execution of great org health should adjust if your team is fully or partially remote. Here are a few key things to bear in mind:

  • Define the rules of engagement: craft a written, “living” document and make it accessible. For example, one ground rule might be asynchronous writing as the default. A shocking portion of real-time meetings are unproductive and disruptive, especially with distributed workforces. Making written communication the default bridges schedules and time zones while removing bottlenecks. It also ensures documentation of important considerations and conclusions from which others can benefit. See Basecamp’s Guide to Internal Communication as a nice example.
  • Get intentional about human connection:
    • Meet up in-person: whether it’s an annual company-wide summit or an ad hoc team offsite, face-to-face interaction is uniquely effective at building trust and rapport. When together, build in time for fun!
    • Insert a little levity: try posing a social question at the beginning of each regular team meeting (e.g. “what song do you hate right now?”).
    • Systemize 1-1 check-ins: managers and their direct reports should regularly discuss individual morale, holistically. Peel back the onion and don’t accept “fine” as an answer.
  • Over-emphasize onboarding: find the right mix of self-training, live tutorials and a buddy system – perhaps by department or team – and hone a tight process. Effective onboarding is absolutely critical to remote success. Set up your new hires for success in this environment!
  • Create a cadence of accountability and acknowledgement: implement daily or weekly pulse checks such as “what will you be working on this week?” with a focus on big picture priorities. This becomes even more important when you can’t swing by someone’s desk or chat by the watercooler. When it comes to acknowledgements, make them public and specific. You might try a “spotlight of the week” from the CEO detailing an individual’s recent contributions. Pro tip: the CEO does not need to pen the full message; this is not deceptive or hollow. In fact, the message will be more specific and meaningful with heavy input from parties closer to the story. Ad hoc acknowledgements should also flow freely within teams.
    When it comes to acknowledgements, make them public and specific.
  • Pick your collaboration “stack” thoughtfully: there are many fantastic software tools out there. Pick what’s right for you. One simple example of a collaboration stack:
    • Zoom for virtual meetings
    • Hive Teams for project management and chat (Vocap portfolio company)
    • Figma for design collaboration / prototyping
    • gDocs for real-time coauthoring
    • Gitlab for playbooks, manuals and knowledgebase
    • Dropbox for shared storage

    Alternatively, the Microsoft product suite can cover most of the above. There are pros and cons of going best of breed vs. single vendor.

    Know Your Team has put together a nice starter list of tools here.

  • Try to avoid hub and (individual) spokes:when you have a center of gravity tied to a physical office, the minority who work remotely will feel isolated and out of the loop. There are various hacks and tactics to address this, but it is an uphill battle and often leads to suboptimal performance and turnover. If possible, we recommend avoiding this flavor of a hybrid model.

Here are some of the best resources on managing remote work (bookmark these!):

Invite the full self

When starting and scaling a business, work often commands more than its fair share of hours and mental real estate. Home health matters, and it affects performance. Get to know your direct team’s spouses / significant others. Include them in the ride. Help them see what this stressful, against-the-odds journey is all about, why you are working so hard for so little near term pay. Encourage your teammates to share life updates, even as pedestrian as regular weekend recaps. EOS incorporates this in its regular check-ins, for example: each person starts with a ‘business best’ and a ‘personal best’. Home life, especially spousal relationships get little airtime in the startup zeitgeist despite the critical importance. Categorically ignoring life outside the office becomes toxic and counterproductive. Encourage people to bring their full self to work. It will foster deeper bonds and help everyone make it through the tough grinds.

Home health matters, and it affects performance.

Gut-check questions to ask on a regular basis

  • Can everyone recite our mission and vision and provide genuine personal interpretation?
  • Are our values invoked on regular discussions? Are they actionable? Am I passing the test?
  • Do exit interviews/Glassdoor/new hire feedback reaffirm that employees are both challenged and empowered?
  • Does our culture fit our true personality, or does is it feel inauthentic?
  • Does a typical meeting include a heterogeneous set of backgrounds and perspectives?
  • Can everyone describe the company’s overarching goals and progress toward those?

If you can answer each of these with an honest and firm yes, then you are on track to building a robust, lasting culture.

Listen and cultivate


As new faces multiply, it gets more difficult and more important to keep a pulse on what it’s really like at all levels. Talk to trusted confidants and lean on your cultural founders. Be visible. Open your door for regular office hours (you can learn just as much as you teach). Are people leaning on your core values in meetings? Do they feel both empowered and challenged? Use every exec meeting to collect feedback from the frontlines of each department. Is your leadership team still drinking the Kool aid? Are their people? Just beware that your managers are most likely going to add positive spin on reality. Ask new employees after their first week what they think your culture is like. Ask them for advice: “if you were me, how would you improve the culture based on your first week”? New employees are great subjects for this.

As you get into Series B and beyond, it might make sense to implement a software tool that helps you keep this pulse (more on this in a later post). Software can augment but should never fully replace personal check-ins.


Beyond good listening, strong culture requires constant tending and reinforcement. Just beware of getting too dogmatic on anything but the mission (even values can change, though it shouldn’t happen often). Remind your exec team that – by nature of their positions – they are culture setters and they need to model how things should be done. Publicly recognize individuals with specific stories of how they embodied your culture code.

When something breaks down (e.g. the wrong people are quitting, you’re failing at your top priorities, an employee does something that truly shocks you), dig several layers deep to get to the root cause. Where did the breakdown happen and what does it say about the strength of your culture? Was the person in question not effectively trained during onboarding on how people talk and act? Did they see the same behavior in their superior(s) and conclude it was okay? Usually, there is something more systematic at the core. Think about the cultural system first and don’t hesitate to terminate individuals for clear cultural violations when necessary. Pruning is part of good hygiene and it also sends a clear message to the organization. As the military adage goes, when you see something below standard and do nothing, then you’ve set a new standard. The same goes for culture.

There are a lot of ways to systematize your culture feedback loop. Ultimately it comes down to what works best for you. However you do it, it needs to become a part of your everyday thought. Make it one of your core mental compartments, right in there with growth strategy and product.