The 2 questions I always ask
In my work, I mainly work with senior leaders: Executive Directors, someone with Chief in their title, the Principal of a campus—you get it. My decades of experience as a senior leader myself means I deeply understand what it is like to sit in that seat, the myriad of challenges that a leader faces and the considerations when deciding when to act.
When I begin working with a leader, I’m thinking a lot about two questions in particular:
To what extent is this leader clear?
While what they need to be clear on depends on the specific problems they are working to solve—it could be their vision, their beliefs, a theory of change, about what needs to happen, etc.—the leader needs to be clear.
2. To what extent is their leadership team helping or hurting?
I’ll talk more about the first question next week, but for today I want to focus on the second question.
I know that some of you, after reading “To what extent is their leadership team helping or hurting?” recoiled a bit at that binary language: helping or hurting. I can hear people now, “Can’t it be somewhere in the middle? Does it have to be one of these?” While I am all for nuance and shades of gray in thinking in life, in this case I think it’s helpful to have a forced choice. The answer doesn’t have to be scientific—it can be a gut reaction. Are they helping… or hurting?
Helping or Hurting?
Some people may think “Well, they’re not helping but they’re not hurting.” This is where I tell you the unfiltered truth: If the leadership team isn’t helping the leader, that is hurting the leader. A leader of any size organization is still only one person—there’s only so much they can do. An effective leader is like an octopus—they are at the head and they have eight tentacles extending in every direction, making sure that their reach extends far beyond them. If a tentacle is limp, or not doing much, then it’s not helping!
Sometimes we think about the toxic actions like backstabbing, gossip, not putting the necessary level of effort into any task… and if we mentally scan the list and none of that is happening on our team, it’s a relief (which is an appropriate reaction; of course it is). Those actions are so damaging to a team’s trust and culture that they need to be addressed immediately by the leader—which from a leader’s perspective can be frustrating because this is a group of adults, not a group of middle schoolers. I work with leaders all the time on how to address these situations—it can be complicated based on the particulars of the situation, how the organization has historically dealt with conflict, where the organization is relative to goals—a whole lot of things.
As part of any initial data analysis I do, I always ask the leader for their perspective. Leaders are human so they come into this with varying amounts of baggage, pet peeves, etc. so I always do my own data gathering and analysis to confirm or contest the leader’s perspective.
What’s interesting, though, is often when I ask a leader to tell me about their leadership teams, I get a pause. Responses can vary—from, “I haven’t really thought about it before” to, “Welllll” or a lukewarm response like, “it’s fine.” All of these tell me that the leadership team could be much better. Now, if I ask you about your team and you start singing their praises, talking about how all the individuals contribute to the greater good, how in sync people are, how healthily people handle conflict… then, as my dad says, we’re cooking with gas! Things are working!
Here's the thing: I almost never get this response. Leaders come to me for help with adult problems getting in the way of reaching the mission, and almost always, there is something with the leader or the leadership team that is contributing to that. The particular diagnosis varies—it could be that people are afraid to disagree, or they are less than enthusiastic about something and that shines through. People could be struggling with time management, their own prioritization, ambiguous strategies or unclear priorities. There are literally thousands of potential contributing factors. It makes sense—when we think of teams as made up of groups of humans, and knowing that humans are messy, complicated, multi-faceted, and ever-changing---well, it’s no wonder that almost all leadership teams have some room to improve.
The good news is—as the senior leader, you are well positioned to fix this.
This too can be fixed.
Taking some time to think, reflect, diagnose and act is important—whether that’s on the quiet of your commute or on a mini-retreat day with yourself. Sometimes getting outside help, like a consultant or coach, makes a big difference—you get an objective perspective, dedicated time to think about this issue and an accountability-buddy in making sure that the team moves closer to helping on the continuum.
If your team needs a reset, it’s always the right time to do it—no matter if it’s October, January or March. What I love about the next few months for anyone who’s working off the academic calendar is that the summer break/upcoming school year gives everyone a time to reset: it’s a natural part of the rhythm of the year. This time of year is perfect for pushing your team to level up, whether that’s from good to great—or from hot mess to functional.
As a way to help leaders out in this busy time of year, I’m hosting a free masterclass on Wednesday, May 17 at 4PM CT. It’s called “How to reset your leadership team”—and whether you want to tweak your team or do a massive overhaul, you’ll walk away with ideas you can put into action immediately. If you are reading this after the masterclass, you can join the waitlist here to know the next time I teach this.
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