The Worst Part of the Week

Years ago I read in The New York Times1 that when asked, people said talking to their boss was the worst part of their week. As a longtime manager, this was a blow. I’ve certainly been frustrated by my bosses at times, and I am also self aware enough to know that I’ve frustrated and confused the people who report to me as well. Even so, this still stood out as a pretty damning indictment of management as a profession. This assertion (it wasn’t well sourced enough for me to call it a fact) has bothered me ever since.

The founding principle of this newsletter is that we should demand any structure of authority prove its worth. If, almost by default, interacting with one’s manager is somewhat harmful, the implication is that the amount of value we create as managers has to be that much higher.

The other question I’ve been asking myself since reading that article is … why? What’s the characteristic of these interactions that so often makes them unpleasant for the person who’s on the subordinate end of the stick? I have a hypothesis.

I suspect that people are uncomfortable talking to their boss due to cognitive dissonance. Simply put, cognitive dissonance is the discomfort caused by dealing with contradictions. Wanting to do something you know is unhealthy is the classic example — I love to eat cake even though it’s bad for me, and when I do, I experience cognitive dissonance. Fortunately, I have my old friend rationalization to help me out. That particular cake is one of the specials and if I don’t try it now, I’ll probably never have the chance again. Or, if I decline, my brain reminds me most cake looks better than it tastes anyway. Thanks, brain.

There’s a particular uncomfortable contradiction that frequently arises when people talk to their boss. Pretty much everyone feels like it’s a bad idea to upset or disappoint someone who wields power over us, so when we talk to our bosses, we want to be the bearers of good news. At the same time, nothing is ever going completely smoothly. What this means is that pretty much every conversation with our boss comes with a little dose of cognitive dissonance. We can either be honest with our boss, and worry that we’ve upset them, or we can leave out (or worse, lie about) the bad stuff, and worry that we’re just going to have an even more stressful conversation later if we can’t resolve the problems we skipped over before our boss finds out.

It seems like there’s a solution to this for managers — psychological safety. There are about 3,000 pages on the Harvard Business Review site that mention psychological safety; people are clearly onto this already. You totally should do whatever you can as a manager to build a relationship of trust with your direct reports and establish psychological safety on your team. Doing so can to some degree mitigate the problem described here, but the discomfort I describe can’t be fully avoided or mitigated.

As managers, the threat of perceived failure lives within many of the questions we must ask our direct reports. “Do you think we’re going to hit our growth goal for the month?” “Have we interviewed any good candidates for the staff engineer position?” “Are people using the new metrics we came up with in their reports?” “How did that meeting with marketing go?”

These questions can’t be avoided any more than I can avoid being confronted with the opportunity to eat cake. All of those questions have answers that look like success, and answers that look like failure, or at that at least reveal the possibility that failure is an option. As managers it’s our job to ask these kinds of questions all the time, and even when we don’t, our reports fear that we will ask them about something they’d prefer not to discuss every time we chat. This stresses people out.

I have some ideas about how we, as managers, can improve the chances that we won’t be the worst part of the week, but I think it’s really important to first accept that this discomfort is a fundamental aspect of the managerial relationship. Everyone feels that being honest with their manager carries some risk2. The first thing we can do as managers is be understanding when our reports seem a little defensive, or evasive, or they leave out some of the details when describing a situation. We’ve put them in an uncomfortable situation just by discussing the topic.

I’m not a reader of the relevant management literature, but my friend Jason Wong is, and when I asked him for feedback on this newsletter, he shared some useful references with me. Pioneering work here was done by Amy Edmonson, most specifically in her paper “Psychological Safety and Learning Behavior in Work Teams,” published back in 1999. The broader subject of this newsletter falls under the impression management research topic.