Make work a place worth working in by addressing the core tension.

Q: I’m three months into a challenging leadership role with a start-up company. The company and its business are very promising, and everything I’ve learned in the past three months just continues to prove that true. 

But the environment is confusing and chaotic. 

Execution doesn’t match the vision; the executive ranks have shifted more than six times in three months. The different teams are working in different directions. This is not conflict – we are not working at cross-purposes. This is either a lack of leadership or a lack of communication of leadership, or—most likely—a lack of clarity. 

My biggest challenge is sorting out how to bring my unique set of insights and abilities— my Onlyness—to this team to help create clarity and direction and keep the proverbial ship on course. How can I learn to bring my Onlyness to the efforts to influence decisions and practices as they are getting clarified?

Dear Clarity Seeker

While there are many ways to create value, there are just a few ways to destroy it. 

Confusion surely tops the shortlist of destructive ways.  

I once joined a promising team, and the Head of Finance Howard, was my co-conspirator. From day one of working together, we respected each other and got each other. Laughed, even. 

But within weeks, we weren’t connecting. 

Was it me? Was I not communicating well, or did I do something wrong, like overstepping my scope? Was it him? He kept taking longer and longer to respond to my requests, even though his office was next door. 

This ickiness spread, infecting the extended team. People started checking with him and with me, but separately. Most wrote emails to document critical decisions for fear something would bite them in the butt. And many looped the bosses into CYA conversations, creating more and often unnecessary work for everyone. 

The confusion seems interpersonal, inconsequential at first. But it takes down teams.   


It’s a lack of understanding, yes. Uncertainty, surely. But confusion cuts deeper than that. Confusion blunts one’s sense of purpose and spins one around enough that they don’t know what they should do next. 

This is why the confusion in the firm is not unrelated to the firm’s prospects. It’s a sign and signal that the needed conversations and debates—the things that create a shared understanding among people to create an executable strategy—are missing. I’ve previously described this as an organizational “Air Sandwich,” like a PB&J sandwich without any of the PB&J. 


One does not have a great strategy if one also has confusion. One cannot execute well when there is confusion. One does not have great teamwork if there is confusion. If you have this disorder, you have a dysfunction.


So, I’m sorry to break this news to you since you asked the question the way you did. But there is a conflict. It’s just invisible right now. 

The dynamic between Howard and me? It turned out that we were being told slightly different stories about priorities. And each of us wanted to do our best, so we adjusted our approaches accordingly. We didn’t check with each other because we assumed our bosses were aligned. But they weren’t. The CFO had been cynical about a recent company acquisition, and because he didn’t feel heard or valued in that process, he was now asking hard questions about whether the right things were in place. He was adding pressure to “prove his point.” The Head of Product was now in charge of the new big thing, so he felt frustrated that not enough was being done to make that work successful. His career was on the line, too. 

But our team couldn’t see all that. 

It looked like so-and-so wasn’t being supportive. Or that we were not doing enough. 

None of us asked, “what is that’s dividing us, and how do we solve it?” 

And I readily admit that I would have been uncomfortable asking this question way back. 

Like nearly every one of you who writes to me, I had an internalized sense that leaders should know where they’re going and be mature enough to talk with each other. I also questioned if I knew “enough” to ask a valid question. I wasn’t raised to believe in my voice.  Combine these beliefs—and we know what kept me from asking relevant questions. 

These beliefs are more common than we’d like to admit. The preponderance of these beliefs means that the “call is coming from inside the house.” The same beliefs that keep us from upsetting the apple cart are the same beliefs that keep us from adding value that only one can. 

If no one asks, what is putting us at cross purposes? Nothing has a chance to be solved. 

You see this everywhere. 

The person who reports to one person, but has a dotted-line relationship with another, is often told they need to be a “better communicator.” But the issue is rarely words. When executives aren’t aligned on priorities, a junior person is put in the middle.

Or how we ask middle managers to “just navigate the ambiguity” vs. fixing the darn ambiguity. 

Or when we are asked to do work against two competing goals when there’s only enough energy and resources to do one thing well. Instead of deciding which one, teams are asked to “figure it out.”

These “solutions” make people the Band-Aids instead of stitching the open wound of an organizational conflict. It’s how we fail: depleting energy and slowing the business.


Innovative, alive work is about how a group gathers together to turn nascent ideas into new realities. The keyword in the last sentence is how

But most of us are operating in a different how. One so well known I’d bet that if I write just one word of the three, you’ll be able to fill in the entire phrase. 

Ready. ___. ____. 

This beloved sequence of operations is often used to lead a team towards hitting an objective. 

The logic of the adage is linear. That one thing follows the other. First, you prepare, then decide, and finally, execute what has been resolved. The “ready-aim-fire” logic is a tried-and-true operational maxim that many people still value. It gives people a (false) sense of predictability.  

But I’d like for you to reevaluate it for two reasons:

First, if you accept this premise, it’s easy to think of your job as one of the three. We’re either the planners and resource folks (readiness), the strategizers (aim), or execution folks (fire). So let’s say you show up at a firm where the strategy is already “decided”; you can think your job is to execute what others have determined, even if you think it’s off by some measure. Which, by definition, denies Onlyness where each has a perspective to offer, regardless of role.  

The second reason is more abstract but relevant. Just ask yourself: Is anything this linear? How exactly does one prepare for something before you decide what it is? What if one finds new information while executing? Wouldn’t you need to reevaluate the decision? It sounds so appealing to think of work as predictable, but nothing I’ve ever experienced works this way in real life. Have you? 

In the Social Era, we create (or rather, co-create) value via relationships. Modern work is interrelated, instead of isolated handoffs that the “ready-aim-fire” construct suggests. How we ask what the issues are, how we stay curious, and how we learn together. Business results, including revenue, are not tied to isolated or individual efforts but to how connected we are. 

Not naming the conflict for what it is ….denies you all a way to connect and solve it.


If the company keeps overturning its leadership team, it’s a sign that they think new players will fix a broken strategy. So, as the newbie, you can be the one to ask that. “Sometimes, people hire new teams because they think the issue has been execution. Before we become the (next) team that must be replaced, let’s take the ten days to ensure we’re aligned on the strategy.

Or, if the execution doesn’t match the vision, someone is signaling that it’s okay to change the playbook. So you’ve gotta learn to ask questions that get at that. Ask, “Hey, this is hard for me to ask because it seems like I’m challenging someone. But I see that execution doesn’t match the vision, and I worry that we’ll never get on the same page if I don’t ask.

And even more specifically, to get the team to address what they want MORE THAN other things. This is the conflict that Howard and I faced but never named. And based on my 20 years of experience since then, it’s nearly always the issue. We want different things simultaneously but don’t want to name the inherent conflicts. We don’t want to disagree, which leaves us in a check-mate situation. Unable to move forward, unable to win. Confused.

To be clear, you’re not raising conflict to create discomfort—yours or theirs. 

The reality is if we don’t ask and author those meaningful questions, the company won’t have a chance. You’re raising the issues because you want the very thing it wants for itself: success. 

As Phillip Roth once put it, “Life is, and.” He meant that we don’t live in a linear world. We live with many things at once. Everything is connected to everything. And that’s your work, too. Connect your voice to the thing causing everyone to suffer. Connect with your peers to name what drives a wedge between all of you and winning. Connect them to the work you all need to do, together.  

I am rooting for you as much as this drummer is pounding away. 

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