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The importance of self reflection and what it means for founders

DocSend's COO and co-founder, Dave Koslow, on how ritual self-reflection can help startup leaders stay on track.

I remember the earliest days at DocSend when we had our first meetings as a fledgling team. They were awfully exciting, partly because conducting a meeting lent validity to the young corporation we were operating, and partly because they stood as a break between long periods of solitary software development. How things changed so quickly…

How did I get here? Importance of self reflection
Image credit: KnowYourMeme

Whose calendar is this?

As a leader, you inevitably reach that point where you wake up in the morning and look at your calendar to find that your day has been fully booked, one meeting running straight into the next. I call this inevitable because as you excitedly build your team, you want to ensure their success. So, any free time on your calendar becomes fair game. And eventually if it’s not your team grabbing free slots on your calendar, it’s your customers or prospective customers.

With all this “doing,” there remains precious little time in the day to reflect. What’s working? What isn’t? If you’re not careful, suddenly you’re a passenger in your own company, reacting instead of acting, playing defense instead of playing offense.

And that’s incredibly dangerous. Who’s flying this thing? Suddenly you may be surprised to look down and find the steering wheel in your hands. Failing to deliberately block time for thought and reflection, you miss the forest for the trees. Lots of work is getting done, but it doesn’t tie neatly into a coherent strategy because you’re in the weeds, with your eyes on a patchwork of initiatives rather than the road ahead.

Warning signs that you need to get your eyes back on the road:

  • Your strategic decisions drift back to “the best of what’s around.” Classic example: your marketing team has an annual events and sponsorships budget, but you constantly seem to be deciding among the opportunities that land in your inbox. Yikes. Especially since you’re a startup, you’re likely not on every conference sponsorships lead’s target list. So have your team do the research, figure out the best opportunities that are out there, and then decide among them, not just the ones that are pitching you.
  • Company vision starts to blur. Suddenly everything feels like it’s “on-vision.” Yes, let’s build everything! We’re taking over the world! Not so fast. Related: Your team starts to suffer from extreme near-sightedness. You start to have the feeling that in two to three quarters, the product will be “complete.” That’s as good a sign as any that you have no opinion on where the future should go. And if you don’t, how is your team supposed to? Imagine your team for a minute gathering with their family and friends over Thanksgiving. How are they describing your business and the big idea you’re pursuing?
  • Left hand stops talking to right hand. Example: Marketing is focused on one set of target personas while product builds for another and sales focuses on yet another. A startup’s greatest asset is its speed. In order to move quickly, though, you have to focus. If you’re focused on every persona, you’re focused on no persona. Without you at the helm coordinating efforts, the likelihood of departments operating independently — and disjointedly — is far too high. They may succeed at their own departmental goals but be out of step with what other departments are doing, compromising the force multiplier that occurs when everyone is pulling together. Gather your exec staff and make a hard call on what matters most right now, and do just that.
  • You literally just spent an entire day in your inbox. Ok, so you’re at inbox zero. Great job. But if all your brain space is devoted to responding to others, you’re operating fully in reactive, not proactive, mode. Think back to when you first got your business off the ground: If you had spent all day in your inbox, then you never would have gotten to where you are now. And spending all day in your inbox now won’t get you to where you want to be.

Times such as the present with the COVID-19 crisis only make matters worse. The desire to help, to enable, to fix, to act is so natural. To pick your head up, or, for a fresh slap in the face, recall the words of psychologist Viktor Frankl:

Between stimulus and response there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom.

If you’re so busy that you’re sparing yourself that space, you’re compromising yourself, and the fate of your company.


Image credit: nick via Giphy

Make space, and get back in the driver’s seat

Commit to yourself — now — that you’re going to earmark the time required to think each week. I’ve had much success borrowing the “No-Meeting Wednesday” concept from Facebook, blocking off my calendar each Wednesday for zone work and plenty of thinking time. Wednesdays tend to work the best for me as they’re situated between the beginning of week coordination meetings on Mondays/Tuesdays and the more reflective 1-1s and retros I have later in the week.

Whichever day you choose, it’s even better if you can encourage others in your company to do the same. This will help reduce the temptation to accommodate someone else’s schedule. (I still, however, make exceptions for existing and prospective customers.)

But even if you have a no-meeting day as a standard practice, you’re still liable to get pulled down into the weeds and devote the day to doing, not reflecting. That’s wonderfully productive, for sure, however, without space specifically allotted for reflection alone, higher-level thinking won’t happen.

So go ahead, and on that no-meeting day you designate, start by blocking off one hour for thinking. Consider the following when thinking about what hour would be best:

  • When am I clearest?
  • What time do I have the most energy?
  • When am I least likely to get interrupted or tempted to dive back into other work (or Slack, etc.)?

Don’t worry about it being the perfect time slot. You can always experiment.


Image credit: Reddit via Giphy

Now for the fun part: The importance of self reflection

Just as effective 1-1s have a solid agenda, I find it helpful to have a default agenda of 3-5 questions to ask yourself in your ritual reflection in case there isn’t anything specific front-of-mind for the week.

Some ideas:

Theme: Company Performance

  • What’s going really well right now?
  • What’s not going so well?
  • What am I worried about?

Theme: My Performance

  • How am I performing as a leader?
  • I communicated well when…
  • I could have communicated better when…
  • What are my personal knowledge/experience gaps that the business needs from me right now? In 6-12 months?

Theme: My Feelings

  • When do I feel most productive? Most unproductive?
  • What’s nagging at me?
  • What’s a difficult conversation I’m avoiding?
  • How are my energy levels? How do I feel physically?
  • Am I loving and nurturing my body, if so, how well?

Theme: Getting Help

  • What work am I doing that someone else on the team would do better?
  • What low-leverage work am I doing that I should hand off to someone else?
  • Who can I ask for help?

Log your thoughts in a running Google Doc so you can reference them later.

Self reflection: Taking a fear inventory

If ever during your reflection you’re feeling a general sense of anxiety, tenseness, or negativity without a clear reason why, I highly recommend taking a “fear inventory.”  These negative emotions can bubble up from one or two issues that you may not realize are nagging at you under the surface. Without introspection, you’re left to wade through experiencing the nasty symptoms with no clear path to feeling better. Taking a fear inventory, on the other hand, guides you to unpack those feelings by finding their root causes. In the process, you often realize that these root causes are fears of something very specific happening that, in fact, are quite unlikely, or can be addressed head-on. With this in mind, you’re already on your way to feeling better.

This practice can be done in a very simple form: Just set aside ten minutes to write down as many endings as you can to the sentence “I am fearful that…” as you can think of. Some of these fears will be much greater than others — hopefully this will guide you to pinpointing which are causing you the most trouble. From there you can set to work on addressing them, one by one, much more deliberately.


Image credit: peteneems. via Giphy

Never stop exploring…yourself

Building a startup entails trying to make so much happen in so little time. As a result, it can often feel a bit like a sprinted marathon. But in that pursuit of go, go, go, as founders, it’s too easy to over-index on a Leaders Eat Last framework. The result: Routinely missing the opportunity to slow down, get our bearings, and thoughtfully consider our next move. If pressing pause for an hour a week can increase the likelihood that those are the right moves, that seems like time very well spent.