This article is part of our Leading in the Middle: 2025 series. Throughout the year, we will share Thought Leadership articles by UNC Executive Development Senior Associate Dean Dave Hofmann on how to lead effectively from any position in an organization.
You can read the 2024 series by downloading Dave’s ebook, Leading in the Middle: 2024.
Ever since I launched my MBA course entitled “Leading in the Middle,” I have joked that it might be one of the few MBA courses with a theme song: “Stuck in the Middle with You” by Stealers Wheel.
I’m sure you’ve heard it. The chorus repeats:
Clowns to the left of me
Jokers to the right
Here I am, stuck in the middle with you
Do you ever feel like that? Clowns on one side and jokers on the other? Or maybe more related to leading in the middle of an organization: clowns and jokers in every direction.
What might be a few things making you feel this way?
- Decisions coming from leaders above you that do not make sense, where little or no context is provided, and maybe that you disagree with.
- When working in a matrix, you might have two bosses who tell you to do different things and want you to optimize conflicting metrics.
- You might have peers who are not collaborative, seem to be working at cross purposes with you, and only advocate for their perspective and how it is more important than yours.
- Or you connect over dinner with a professional colleague, and they spend two hours talking about themselves and answering all your questions while not asking a single question about you or your work. Well, let’s just say, if they are sitting on your left, they are a clown, and if on the right, a joker.
So what to do? Here are a few tips:
Check Your Assumptions
First, check your assumptions and attributions. It is easy to think, “They don’t have any idea what they are doing,” or worse, “They are not smart, clueless, etc.” I think it is best to assume that most people are trying to make the best decision possible given the information and vantage point they have. Now, some people will, over time, cause you to move away from this assumption (i.e., “They really are evil 👿”), but they are far fewer than our initial attributions might suggest.
The movie Eye in the Sky offers a helpful example of why it’s essential to check our assumptions. Although the film is set within a military drone team, its core focus is on how a complex organization navigates a single, high-stakes decision. The script consists of all the conversations that must happen to make this decision: more than 100 (yes, I have counted). You can watch a breakdown of the stakeholders and this complex web of decison-making in this video.
Amid all these conversations, there are two that I find particularly interesting. The first involves the operational leader (played by Helen Mirren). The situation meets her limited criteria for carrying out the mission, but for reasons not relevant here, the decision is escalated to the next level. The following scene depicts the escalation meeting, where the team evaluates the decision from a much broader and more complex perspective. They explore various options and consider how the media, other nations, and other stakeholders might react to each potential outcome.
The point here is that as you move up in an organization, the criteria set and stakeholders you are trying to optimize or satisfy become significantly more complex. So, senior leaders don’t lose their minds when they get their roles; they are just trying to optimize for a much more complex situation. More complicated than how we see it in our limited domain.
Similarly, cross-functional peers and matrixed bosses have different information and vantage points than you do. And you should assume that they are acting rationally given the information, vantage point, and incentives at play for them. If their behavior doesn’t make sense, try to generate at least three potential hypotheses about what information, vantage point, or incentives would make their behavior rational.
So, the first step is to check your assumptions and attributions, generate alternative explanations for the actions of others, and assume positive intent. Generating these alternative explanations sets you up nicely for the next step: seeking to understand.
Seek to Understand Before Seeking to be Understood
One of Stephen Covey’s 7 Habits of Highly Effective People is, “Seek to understand before seeking to be understood.” I’ve been helping teams overcome the obstacles to cross-functional decision making for well over a decade and have similarly concluded that one should lead with inquiry before advocacy.
For your cross-functional peers, seek to understand how they would define success in the decision or on the project. Ask, “If this initiative were successful, what would be different/changed, and how would you know it?” The first part of this question will get them talking more abstractly about goals while the second part gets them talking about metrics. You need to understand both.
Don’t forget the second part of Covey’s advice: “Seek to be understood.” Make sure to answer the same questions yourself so the other person understands what success looks like to you and how you will measure it.
This advice also applies to decisions coming from senior leaders. Ask questions. Be curious. Because you owe it to your team to seek clarity, begin by gaining clarity for yourself about the situation and its context.
But keep in mind that clarity may not always be readily available. In these situations, it’s your responsibility as a leader to help create that clarity for your team. You may have to take your understanding of the company’s strategy and do the best you can to make sense of the decision. This conversation could start this way: “Although I don’t have context for this decision, here is how I am making sense of it given my understanding of the strategy and what we are trying to accomplish…” Then continue to try to seek clarity.
Offer a Little Grace and Provide Feedback
No leader gets it right all the time. We don’t. They don’t. Perhaps the rollout of a decision is clumsy, or maybe several key stakeholders weren’t consulted.
Once I rolled out a decision and realized after the fact that a very key stakeholder, who should have been given a heads up on what was coming, was surprised and caught off guard. As we planned to roll out the decision, we simply overlooked this key individual. I know it seems hard to imagine that this could have happened, but it did. When we realized it, I immediately went to his office, apologized to him, and owned my mistake. I didn’t make excuses. I said it shouldn’t have happened. Period. Full stop.
So, we should offer a little grace that none of us gets it right all the time. The leaders of our organization won’t get it right all the time, nor will our cross-functional peers. And neither will we.
But offering grace is not enough; we also need to offer feedback. We should see leaders improving over time and not repeating the same mistakes. If we do not see that progress and learning, then it is fair that our grace will begin to dissipate.
We also need to be willing to receive feedback, learn, and improve ourselves.
Seeing Beyond the “Joker”: Preparing for Meaningful Dialogue
These recommendations will help you lay the foundation for constructive conversations in all directions. Often, these conversations are challenging, which is why they are called “difficult conversations.” But one of the most important ways to make these conversations less difficult is to prepare thoughtfully. That means moving beyond our own assumptions and beginning to understand the broader context and others’ perspectives.
Challenging yourself to consider what information, vantage point, or incentives might be at play for others will help you generate alternative hypotheses about their actions. When you have multiple possible hypotheses, you can then test them. This means starting with inquiry before advocacy and, in the process, laying the foundation for more constructive conversations.
By doing this, you might find that those around us aren’t really “jokers” or “clowns.” Instead, they are well-intentioned individuals doing their best within the context, information, and incentives they have. And they may come to see that you aren’t a joker or a clown either, but someone equally well-intentioned.
P.S. The one situation I’ve not addressed is the work colleague, or “friend,” who prattles on about themselves for two hours (“Enough about me, what do you think about me?”) Here are just a few of the many options for handling this challenge.
First, you could say, “Hey, I want to jump in here to make an observation related to what you were just talking about.”
Second, ask them to reflect: “Wow, that sounds like a full week. What was one thing you learned or that you would do differently if you could?” This often slows down the speeding train of word salad and triggers a two-way conversation.
Third, make a game of it to just see how long the conversation can go without them asking you a single question. My record is about 2 hours. I was sitting next to a businessperson on an international trip with a non-profit organization. I learned about where he lived, his entire family, a detailed story about his connection to the organization we were traveling with, the nature of his business, the challenges of the supply chain, the positioning of their product in the market, the name of his dog, cat, and pet gerbil (well, maybe not this last one). He learned that I worked at the University of North Carolina. 🤷️
Fourth, don’t have dinner with them again because they are a joker or a clown.
