Fight for Outside Perspective

To build a product, you need to talk to people. You need to talk to potential customers, and to potential employees. People whose expertise you could use, and people who could use yours.

Any leader that isn’t getting outside perspective is going to eventually get stuck.

Unfortunately, with our own teams getting first crack at our calendars, and the shift to remote work sweeping away many a business lunch or chat over coffee, a lot of leaders are getting stuck. Here’s how it goes down.

The War on Meetings

Let’s say you find yourself with a calendar full of meetings. Purely hypothetically, of course.

If you’ve got back to back meetings – 5, 6, 7 hours in a day – then you’re gonna have a bad time. You’ll be coming in underprepared, feeling and acting disengaged, and struggling to find time for focused and thoughtful work. It’s a bad scene.

Luckily, you’re a smart and perceptive person. So you crack down on meetings. You get more disciplined, putting more attention into a smaller number of well-prepared calls. You say yes to the most important meetings, and say no to the least important ones.

Or at least, that’s the idea.

We intend to say no to the least important meetings. But in practice, we tend to say no to the meetings that are easiest to avoid.

Consider two ways you could spend 40 minutes:

1. Catching up with an awesome someday hire. Easy to avoid, high importance. Tends to fall by the wayside under calendar pressure.
2. Agendaless weekly status update. Harder to avoid, questionable importance. Tends to stay on the calendar.

Perversely, some of your best long term time investments – building new relationships or getting your assumptions challenged by outside folks – tend to get crowded off your calendar. Your manager might ask to talk to you Tuesday. Your next senior hire probably won’t. You might get a calendar invite from a team that wants a status update – but a team at some other company that knows exactly how to solve your biggest problem doesn’t even know who you are yet.

If you let your calendar be driven primarily by whomever has asked for meetings and whichever meetings were set to auto-repeat, your schedule will get more and more inward-looking over time. The bigger your company, the worse it is.

So here’s what you need to do: regularly review your calendar to ensure a healthy proportion of your meetings are with outside people.

Iterating who you know

When you’re considering how you spend your week, especially any item that repeats weekly, ask yourself whether that time might be better spent talking to:

• A potential future team member
• A potential future customer
• A professional coach
• A professional therapist
• Someone you look up to who can hold you accountable to your goals
• An expert on a topic that’s important to you right now
• Someone who is building a team bit bigger than yours
• Someone who is thinking about things in a totally different way than you are, and can ask a damn good question you didn’t know you needed asked

These people can, in 30 or 50 minutes, make a huge impact on your week, month, or even life. But they won’t seek you out.

Even if you could really benefit from a coach – and you probably could – no coach can detect that. They can’t just book a recurring meeting on your calendar. You need to keep an eye on these kinds of needs, gauge how much external perspective you’re getting on a regular basis, and put in the work to seek it.

Of course, that’s easy to say. If you’re anything like me, your brain really does not want to reach out to a bunch of people you don’t know very well, and ask if they can bless your calendar with yet another zoom call. So in the last few months, I’ve accumulated a few tricks for this:

1. There are platforms like Lunchclub that match folks up pseudo-randomly to talk shop. They can be surprisingly worthwhile.
2. Try to participate online somewhere where you’re in touch with like-minded folks in a low stakes context. That might be Twitter, a Slack group, or other written medium.
3. When you’re inviting somebody to catch up, try suggesting an audio call. Video has its benefits, but for catching up with somebody you know, try shutting off the camera and getting away from your desk.
4. Try reaching out to people in chunks. I used to set a goal like “Reach out to one potential hire a week” and I would struggle to keep it up. Now I set a goal like “Reach out to 5 potential hires” and during one of my focus times I buckle down and do it in one go. For me that ended up being less hard.
5. There are a lot of talented coaches, therapists, consultants, and others out there who are practiced at asking you good questions and helping you get perspective. Research a few, reach out to multiple, and don’t feel bad about trying multiple before you settle in with one for a while.
6. In addition to blocking out focus time on your calendar, block out times to get outside perspective. Maybe you have 40 minutes once a week for “Go for a walk with somebody smart” or “Talk to a potential customer” or whatever you need most right now.

Together, these approaches have helped rebalance my perspective diet for the better. Obviously your team and business deserve the majority of the time, but if they get too much of your time, you could be doing them a disservice.

Of course, that’s just my perspective.