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Welcome to July!
Happy Q3 and/or New Fiscal Year!This first half of the year has felt like a bit of a blur, but also has been so very full. And this June gave me a small taste of the insanity parents face at the end of the year- my niece had her first dance recital ad her 3K stepping up ceremony and my nephew graduated Pre-K (I unfortunately had to miss the ceremony due to a fridge that stopped working— but did make the post-ceremony festivities). Apparently, their pre-K had a “senior week” which I found adorable though I wasn’t the one running around getting him themed outfits. To those with kiddos- bless you. I hope you are getting some rest (though likely not with summer vacations).
I’ve got a few summer plans coming up, including finally sitting for my ICF certficiation and completing my Astro certification (yes, I love astrology- and have some ideas about astrology and leadership formulating currently). I also have a trip to London and Bath. I’ve been before but always welcome any good recs so send them my way!
What are you up to? Rest? Travel? I’d love to know.
The Questions We Should Ask Before Calling Someone "Difficult"
Every Fourth of July I post the same James Baldwin quote: "I love America more than any other country in the world, and, exactly for this reason, I insist on the right to criticize her perpetually.” At this point it's basically a seasonal tradition for me.
This year, though, I found myself thinking not just about America, but also organizational culture.

You see, I'm working with a social impact organization right now on its culture of feedback, and it's made me wonder what Baldwin's idea actually looks like inside a team. Criticism as an act of love sounds clean in theory. It gets more complicated when you really respect the other person. Or know they're going through some big life challenges. Or it's the third time you've brought something like this up and nothing seems to change. And it feels different from the receiving side.
Here's the mistake I see organizations make over and over: they treat pushback and "not a team player" as the same thing. But they're not.
Someone naming a misalignment because they care about where the work is headed is doing something fundamentally different from someone who's decided the relationship is adversarial and approaches every conversation through that lens. Leaders don't get into trouble because people disagree with them. They get into trouble because they stop asking what kind of disagreement they're looking at.
I've been in meetings where someone raised an issue that made half the room roll their eyes. You could almost feel everyone thinking, We're really doing this again? I've learned to put my own frustration aside and get curious.
Why is this still coming up? What's underneath it? Are we hearing the same concern for the tenth time, or are we finally hearing the concern we've been talking around?
More than once, the answer was that we'd never actually resolved the issue. We'd deferred it, assumed everyone was aligned, or solved the surface problem without addressing what was underneath. It wasn't the tenth complaint. It was the first real conversation.
I've been on the other side of it, too.
After years of watching leadership pendulums swing back and forth in education, there were times I couldn't hear a new concern for what it was. Someone would raise a completely fair point—or revisit an issue we'd wrestled with years before—and I'd hear the last battle instead of the conversation in front of me. That's unresolved history dressed up as a personnel issue.
One of the advantages of consulting is that I walk into organizations without the history everyone else is carrying. It's striking how often two people describe the exact same interaction completely differently. One sees someone who cares deeply about the mission. The other sees someone who's impossible to work with. Before I decide what's actually happening, I usually want to know what happened six months ago.
That distance has helped me separate the signal from the noise. I came up with three questions I still use before deciding whether someone is the problem—or whether the organization has one.
1. Is this about the mission, or about me?
If the concern keeps circling back to strategy, resources, priorities, or the work itself, that's a stakeholder talking.
If it's shifted into commentary about you personally, that's a different conversation. Better to have it directly than pretend you didn't notice.
As I used to tell my team when we got hard feedback: Let's separate the form from the content.
2. Is this the tenth time because nothing changed—or because nothing ever got named?
Repetition by itself isn't a red flag. Repetition without resolution is.
If someone has raised the same issue nine times and you're only now deciding they're "difficult," it's worth asking whether the concern was ever actually addressed—or whether everyone kept talking around the real issue.
Sometimes the problem isn't resistance. It's that a values conflict, strategic disagreement, or unclear expectation has been sitting in the room unnamed.
3. Is this new, or is this old?
Some frustration doesn't belong to you. It belongs to whoever sat in your chair before you, and you're just the nearest surface for it to land on.
That doesn't mean you ignore it. It means you name what it actually is before you react to what it looks like.
None of this means every dissenter is secretly a misunderstood visionary. Sometimes the tenth time really is just the tenth time. Sometimes what's dressed up as candor is simply hostility.
The hard part isn't deciding whether conflict is good or bad. It's figuring out what kind of conflict you're actually looking at.
These three questions help me make that distinction. They're the beginning of the conversation, not the end.
Once you know what you're dealing with, you still have to know what to say—how to respond to a legitimate concern, and how to redirect someone who's crossed into unproductive territory without shutting down future dissent along with it.
I've shared the actual scripts I use for both below, for paid subscribers.
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Stepping Into a New Leadership Role?
If you've been here for a bit, you know how much I care about leader onboarding. Starting a new role isn't just about learning systems or reading documents. It's about making sense of a new organization, building relationships, and figuring out how you want to lead.
That's why I'm teaching two workshops this fall, both designed to help leaders step into new roles with greater clarity and confidence. If that's you—or someone on your team—I hope you'll join me.
On September 9th, I’m hosting Start Strong: Your First 90 Days as a Leader. During this session, you'll create a practical roadmap for your first 90 days. Together, we'll clarify what you're actually being asked to solve, identify the stakeholders who will have the biggest impact on your success, uncover opportunities for meaningful early wins, and build a plan for turning insight into action.
On October 7th, I’m hosting Building Your Leadership Operating System. Clarity comes from within. This session will focus on translating your values in to behaviors, mapping out decision making rights and roles, and outlining the meeting cadence that keeps the work moving.
And if you’re looking for something else? I offer several 1:1 coaching packages for those looking for a bit more individualized support- just hit reply and share what you’re looking for. And for those on a budget? Check out my paid subscription.
1% Solutions
Trying to build more honest conversations? This week, thank someone for disagreeing with you—especially if they made your thinking better.
Trying to understand someone’s decision? Replace one "Why did you...?" question this week with "Can you walk me through your thinking?" You'll usually learn more.
Trying to launch a new initiative? Before launching something new, ask: What will people have to stop doing to make room for this? Every "yes" requires a "no."
What I’m Reading & Listening To
Reinventing an Organization to Do More with Less (HBR Ideacast)- many of us (especially in the social impact space) likely cringe at hearing “do more with less.” But two things: first, the title is a bit of misnomer because this is really about how to lead while being under resourced. Second, the guest is Kelly T. Clements, Deputy High Commissioner at the UN Refugee Agency and if anyone is going to tell me anything, it’s someone who is navigating the world of foreign aid. I found her to be thoughtful and clear while never once diminishing how hard the people in her sector and the people they serve have been impacted.
How Great Leaders Create Shared identity- When I canvassed in PA back in 2024, I was trained to say “Thank you for being a voter,” not “Thank you fo rvoting. Why? Because if something is your identity, it is that much more likely you’ll do it. (I leared something similar in teaching- “Thank you for being a helper” will have much more impact on your class culture than “Thank you for helping). While there’s a negative side to this- as we see in current politics- used judiciously it can transform a team. This article shares how to do so (I’d also share this with my midlevel leaders!)
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The Scripts for The Conversation
A framework tells you what you're looking at. It doesn't tell you what to say once you know. So here's the actual language, scenario by scenario.
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