NEW Book - Reimagining Blue: Download Your FREE Chapter Today

November 21, 2020

Leadership is about Disappointing People at the Rate They Can Absorb



I went to Harvard. That statement is true(ish) because I was fortunate enough to spend three weeks attending the Harvard Kennedy School of Government “Executives in State and Local Government” program. But I still love saying I went to Harvard and pausing before I say…. for three weeks. It was the most academic of the training I’ve ever attended and I left there with my mind blown beyond its original dimensions.

The reason it was so good was because the instructors didn’t allow you to give a canned answer and then move onto the next person. And, unlike most classrooms, they didn’t wait for you to raise your hand. The notion that you could be called upon at any moment to offer your opinion about a discussion or an assigned reading meant that we were all at the ready.

One instructor in particular was terrifying. Marty Linsky would stand in front of the large audience and toss out a cerebral question and when he scanned the room, I found he normally chose the person to call upon who was attempting to avoid eye contact. I was never that person because I always have something to say and I’m not usually afraid to say it. But this was different. After someone made a comment, Professor Linsky would gaze at you and press harder. “Why did you answer the question in that way?” Or “What did you mean by that?” Or perhaps, “Why have you come to that conclusion?”.

I’m usually good for about one answer that makes me appear of average intelligence but the more he dug deeper, the more my classmates and I struggled to answer the question. We would often become flustered but he remained relentless in his pursuit of the “why”. In the moment, I wanted to punch him in the throat but now that I am able to see clearly, he was doing what so many people fail to do – dig deeper for meaning.

I can regurgitate talking points that I’ve heard from a news correspondent or from a colleague and even feel strongly in alignment with those opinions. But when you start asking seemingly simple follow-up questions, most people can’t go beyond their canned answers. It forces you to dig deeper and when you’ve hit the bottom, most people find that they know very little about a particular topic.

Marty changed me. He made me do research to support my position and my greatest motivation was not to look foolish in class. Fortunately, that lesson has transcended outside of the classroom and I have learned to carefully construct my position based on facts. I have also learned to challenge my own position. That’s my biggest take-away. When he forced us to peel away the layers after parroting an answer, it actually caused some of us to change the way we looked at something on which we once felt immovable.

But the day Marty literally blew my mind was when he spanned his gaze at all of us and he uttered these words:

“Leadership is about disappointing people at the rate they can absorb.”

What the hell does that mean? He saw the confusion on everyone’s face and he repeated the same phrase as though the repetition would be cause for enlightenment.

“Leadership is about disappointing people at the rate they can absorb.”

Nope. Still nothing, Marty. Leadership is inspiring people to align with a vision. It’s about taking people where they need to go but otherwise wouldn’t. It’s about setting clear goals for your people and getting work done through others. Great leaders do the opposite of disappointing people. Dammit Marty Linsky, YOU HAVE LOST YOUR MIND.

I went to Harvard in 2011 and on February 1, 2017, I was sitting at my desk reflecting upon several decisions that I’d made during my one year as the Chief of Police in the 2nd largest city in the State of Illinois and it hit me. Sitting alone in my office, the lightbulb went on and I got it. I freaking got it! I wanted to call Marty to tell him that I finally understood what he meant. When you are the top person in an organization, you can no longer point to someone above you and shift responsibility. That means that every decision is yours and yours alone and even if you’ve collected other opinions and data and made an informed decision, it’s still not going to please everyone.

Even with the best of intentions, a leader is going to upset someone. Whether it be through a policy decision, a choice for promotion, or administering discipline, leaders disappoint people. Even when attempting to implement something new and big that will change an organization for the better, people resist because it’s different than what they are used to. People are creatures of habit and they don’t particularly like to be forced out of their comfort zones and when their environment shifts, they stand their ground in defense of it.

I had only been the chief for one year in my organization when I became conscious of all the people I had already disappointed. Even though I believed I could see things so clearly that needed to be changed or people that needed to be disciplined, others did not agree.

Marty was right. Being a leader who actually transforms an organization invariably means that some people are going to get left behind. It also means that you have to find the precise amount of transformation because people who walk in and decide to scrap everything are making a mistake. Every organization has a lot of wonderful in it and those things should be left exactly as they are. But the things that need to be changed should be changed even if it means that people are disappointed in the process. I have found that it’s the transitional part of change that people cannot tolerate. But once you get through the part of change that’s uncomfortable and you get to the other side, people are appreciative and even wonder why we didn’t do it sooner.

So carry on in disappointing people but make sure it’s at the rate they can absorb.


Media Appearances

Let's Chat

Fill out the form to inquire about media appearances.