We’ve all read the articles, seen the reports, heard the advice: one-on-one meetings are key to running a startup effectively. So why is it that only a third of managers actually follow that advice and meet with their employees on a weekly basis?

In my experience, it’s because most one-on-one meetings are bad. They’re difficult in the best of circumstances, and that difficulty is often compounded by managers at startups being less experienced on average. The result is meetings that are poorly run, poorly planned for, and really, really awkward.

As humans, when we’re faced with an uncomfortable situation that will theoretically help us succeed in the long term but will be painful in the short term, we’re just not going to do it. This is tru...