Caricatures by Ryan Wooley

I have a good relationship with my boss. We’ve worked together now for 13+ years. I respect the work he has done to make our school better and to improve education in general. I think he appreciates the work I have done to contribute along the way. As one of the most senior members of his administrative cabinet, I am proud of all of the things we have accomplished together.

We had my annual review conversation yesterday. It was a good conversation. I think we are still on the same page about most of the essentials. I am completely aligned to his agenda. However, there is typically a “less comfortable” moment in these conversations, and this conversation was no different. Like clockwork, he mentions how our contrasting work styles have contributed to the long-standing stasis in my upward mobility in the school. He sees himself as a real-time processor and me as a private deliberator who has to go away from the group and perseverate and then come back two days later with a plan, two days after he has moved on to other things.

Every time I hear him give this explanation, I have the same thought: “The volume of things I must process in real time every day is probably significantly higher than almost any other administrator at the school.” I’m literally doing this constantly—sometimes as a solo decision maker, sometimes with partners, sometimes with groups. I don’t spend much time admiring problems, and I can point to a number of mission critical decisions that I had to make quickly that I hit just right. In fact, I have done this kind of thing with him a number of times.

I wouldn’t necessarily disagree that our styles are different. I just have a vastly different sense for how deeply or sharply they contrast. Deep down, I know that working chemistry cannot be, and almost should not be, explained. He either feels it or he doesn’t, and that is all that matters. And, the truth is, there are only 1-2 organizational rungs above the one I’m on, and this is a small organization. Chances are I would have trouble moving upward even if our chemistry was pitch perfect. I am not really worried about it or focused on it.

However, because it has come up so many times over the years, I have naturally had to try to develop an internal explanation for our differing impressions. I know that once or twice over the years I may have responded to a design challenge in the way he describes, and I wonder if his irritation at my style in these moments has assumed a disproportionate amount of his impression. I am certainly a thinker and an internal processor. And, I like to put things down (in a document, in a presentation, etc.), because, frankly, I’ve been in hundreds of meetings that were less than productive because nothing was recorded or because no one came to the meeting with any pre-formed thoughts. Watching a group of disparate thinkers try to develop a coherent plan with a blank whiteboard can be painful. Please watch this video for a great enactment of the kind of frenetic, disjointed conversations that tend to lead to less than stellar results.

But still, I do frequently lead and participate in productive strategy and design conversations with others in real time. So, why does he see me as someone who can’t or doesn’t do so? The answer I tell myself is tied to an observation I made some time ago about certain leaders. Here it is: some, maybe even many, leaders see the people around them as caricatures of themselves, rather than the nuanced, complex people they are. Steve Jobs was notorious for classifying people as either morons or geniuses, with nothing in between.

Let’s face it, working at the strategic level of an organization probably requires some kind of short-handing. Too many decisions and choices need made to get caught up in nuance. Add to this reality that leaders are probably constantly justifying choices they make (at least in their heads), so they are apt to repeat their arguments back to themselves—building a mental case for their choices. They replay the image of a subordinate doing something irritating or doing something great. I have seen many leaders and managers refer to the same criteria and instances again and again and develop, what I perceive to be exaggerated versions of the reality. These supervisor observations are not always negative or limiting—not always warts. Sometimes the short-handing and case-building is favorable. I see these tendencies in my boss as well.

So, if there is anything to this observation, if it is a common characteristic of leaders to see the world in caricature, what does it matter? What can we do about it? If any of this rings true for you, or if you have been the victim or beneficiary of caricaturization, I have two pieces of advice:

  1. If you are in a position now or in the future when you lead, try to remember that your colleagues are likely way more complex than your short-handed impression of them—whether they be positive or negative.
  2. The more independent you become, the less any of this matters. If you feel you have been held back by a boss’s impressions of you, that impingement goes away when you become your own boss.  Conversely, if you have been built up by someone, you will lose some of that buoyancy when you break away. You will need to find it inside yourself.

My boss has been immensely effective in his job, and I am a fan. I don’t begrudge his short-handing. I’m sure to a certain extent we all have mental caricatures of people, of events, of environments. Leadership and progress may frequently depend on it.

Regardless of how much or little it may be affecting you, it will likely change in your next act, and you may want to start to prepare for that change. Caricatures or not, we are affected by perceptions of those around us. We need to listen to those impressions but not be beholden to them. New environments and new relationships give us an opportunity to reset our identities. Being ready for these changes may help us find opportunity in them.