Episode 39: The Messy Middle: Why Your Growth Is Hiding in the Hard Parts
I often say, “Growth always comes out of the messy middle.”
Not the planning stage. Not the retreat. Not after you've figured it out.
In the mess. Through the mess. In fact, I think that’s the purpose of the messy middle.
The hard part, however, is that this is the part most leaders try to resist, instead of allowing themselves to sit in it. And sitting in it means not rushing to a resolution. Not jumping to the perceived happy ending (because there is no such thing). But actually staying present to what the mess is trying to teach you, train you for, or strengthen in you.
When you avoid the mess? You limit your growth edges and undermine your growth opportunities. And ultimately, you stay exactly where you are.
That’s what we’re going to unpack in this episode, and we’re going to do it through the lens of a few of my guests from this season of the podcast: Shawn Donaghy, Donishea Martinez, and Traci Rossi. As I reflected on their episodes, I felt that each showed me a different version of their messy middle and what becomes possible when you stop trying to get out of it and instead allow yourself to go through it.
Let's start with the messiness of conflict.
Now, when it comes to conflict, I'm not talking about the dramatic kind, like the huge blowups that ultimately end up in HR. I'm talking about the everyday subtle kind. The disagreement in the room that nobody names. The tension between two people on a team that everyone can feel, but nobody addresses. The feedback that needs to be given keeps getting pushed to next week. The toxic positivity of niceness is because you don’t want to hurt anyone’s feelings. The conflict that has built up more in your mind than in reality.
Most of us were taught, explicitly or just by watching leaders around us, that conflict is bad, it’s evil, and something to get through as fast as possible. Something to smooth over. To manage down, and especially to avoid at all costs. In fact, most leaders feel that if their team is engaging in conflict, they’re doing something wrong, not realizing that healthy conflict is a sign of psychological safety.
Somewhere along the way, we picked up the message that conflict means something is broken. That if you're in conflict, something is wrong with your communication or your leadership.
But that’s not true, and Shawn Donaghy, the CEO of North County Transit District, confirmed that for me.
In fact, he doesn't try to eliminate conflict. He actually recruits for it.
Shawn said, "If we don't have disagreements (speaking of himself as the leader), then you're the wrong person in that chair, I'm the wrong person in that chair.”
Now that’s not something you’d read in a leadership book.
Disagreement isn't a sign that something's broken. It's a sign that two people are actually thinking.
When Shawn arrived at North County Transit District, one of the first things he noticed was that people didn't feel comfortable raising concerns, issues, or problems. They'd see something was off, something that needed to be addressed, and they just stayed quiet. They didn’t speak up because the culture had taught them that raising problems was risky. That raising problems was causing conflict.
So as a result, problems festered.
His response wasn't to demand more candor or hope for the best. He decided to put his leadership team through crucial conversations training. Not to teach people how to fight, but how to build conflict fluency. The ability to stay in a hard conversation without collapsing, avoiding it, or letting it turn destructive. To get comfortable with conflict and not see it as something bad or to avoid.
Conflict doesn't live in a vacuum. It requires something from the leader before it can exist safely in the organization, and that’s vulnerability.
Having hard conversations takes vulnerability. Sitting in discomfort takes vulnerability. And admitting when you got it wrong — publicly, clearly, without hedging — takes vulnerability. But that willingness to be exposed is exactly what signals to people that it's safe to do the same. When a leader models it, they're not just sharing a moment of humility. They're giving the entire organization permission to disagree, object, raise concerns, and tell the truth.
Shawn understood this. Before any of his people could show up with candor, he had to go first. Standing in front of 300 employees and saying I got that wrong — here's what I was thinking, here's where I missed it, now help me fix it wasn't just an act of accountability. It was an act of trust-building. He was laying the groundwork for an organization where people don't have to hide what's not working, because the person at the top doesn't hide it either.
That's what makes conflict productive rather than destructive. Not a policy, not a process, but through a leader willing to admit and be seen in the mess first.
Now, let me talk about the messiness of learning in real time. This one can be particularly hard to admit to because it can feel like you’re losing footing, your north star, the thing that has always defined you, what you believed you could always count on.
That story you build up in your head that says you've been successful. You've built a track record. You have a leadership style that works. You have a winning combination. And then the context changes. There's a new structure, new complexity, new ambiguity. And then suddenly everything you thought you knew doesn’t work anymore. That playbook that made you successful just isn't landing the same way.
And at that point, you’re faced with a choice. Do you keep running the same playbook that always worked for you before? Do you keep pretending that you have all the answers and know exactly what to do?
Or do you accept the fact that what got you here won’t get you there? And it’s time to embrace the role of learner again?
That's the messy middle of adaptive leadership. And Donishea Martinez, an executive leader at Genentech, lived it.
When her entire field team shifted into a new matrix model, she walked in as someone who had earned her authority. A track record of building high-performing teams. She knew how to lead.
But the environment demanded something she hadn't fully practiced.
Not leading from her experience. But leading from curiosity.
She told me: " You can’t lead out of fear, but that's what she was doing.
When the ground shifts under you, your instinct is to grip tighter. To lean into and default to what you know. Prove you belong in the room by performing the version of leadership that got you there. But when you do that, you’re leading with fear and ego.
But that fear-driven default to the old playbook is exactly what prevents growth. In both yourself and in the people around you.
What Donishea did instead was harder. She got still. She got honest about what she didn't know yet. She stopped trying to perform expertise and started practicing curiosity.
And the messiness of this is hard; I've seen leaders struggle with it. It can cause an identity crisis, a questioning of all of their successes, and wondering if they were ever a good leader or could be a good leader in the future. It feels like weakness. Like failure. It’s a tension most leaders would want to avoid, and to get out of it, they may start to avoid their responsibilities or allow others to take up the slack, or worse, quit.
But it’s not failure. It’s just messy. And actually, the most advanced leadership move you can make is to sit in this messy middle of your leadership.
Because real adaptive learning, not the compliance training kind, requires a leader who is willing to be uncomfortable. Who can sit in not-knowing without pretending otherwise. Who can model for their team that growth is not a destination you arrive at. It's a practice you return to over and over again. It’s an iterative approach to leadership, a cycle of learning, applying, discovering, and then learning, applying, and discovering again and again.
Every time the context changes. Every time the old playbook stops working. And yes, it’s scary, and yes, it can feel messy, but on the other side is your new level of leadership. An evolved level of leadership.
What Donishea described on the other side of that season wasn't just that she was a stronger leader. It was that her team trusted her more, precisely because she had shown them what it looked like to keep growing under pressure.
That's the return on staying in the messiness of adaptive learning. Not the performative leader pretending as if they have all the answers, but the growth leader you’re modeling through the mess.
The third kind of mess is the quietest, and often the most dangerous, because it doesn't announce itself. It grows slowly, in direct proportion to your success.
I call it the messiness of maintaining trust.
It usually starts with growth in the organization. More complexity. More responsibility. More time spent in rooms with boards, executives, and partners, and less time in the hallways, the informal check-ins, the conversations that aren't on anyone's agenda. Before long, you’re nothing more than a title, instead of a leader. A function. A mystery. And the people closest to the work stop feeling seen and known by the person at the top.
And here's where it gets costly.
When people don't feel connected to their leader, they stop trusting the direction. When they stop trusting the direction, they disengage from the mission. When they disengage from the mission, you start losing your best people first, because high performers always have options. And the ones who stay? They start filling the silence. Rumors form. Silos harden. People stop raising issues because nobody's listening anyway. The leader, now further removed, starts interpreting this as a performance problem, and employees begin interpreting leadership's absence as a lack of caring. Each side blames the other. And neither is entirely wrong.
What you're left with is the full spiral of low engagement, high turnover, a fractured culture, and eventually a reputation that precedes you, in the worst way. Basically, a mess.
And the most painful part is that leaders either don’t see it coming or, when they do, don’t want to deal with it. They're not pulling away intentionally. They're just managing up, trying to execute strategy and solve the problems right in front of them. Distance isn't the decision. It's just become the default.
Which is exactly why catching it and choosing differently, choosing not to ignore or avoid the mess, is such a defining leadership act.
That's what Traci Rossi, Executive Director of Friends of the Children Portland, did. She leads one of the most admired nonprofits in the region, eleven consecutive years of being the most admired, to be exact, and at some point, she looked up and noticed a distance had started to grow. Her responsibilities had expanded. The informal touchpoints were disappearing. She knew she had to do something different, noting: "I don't want my leadership to be this mystery.”
So she reinstituted what she calls her Friendly 15s. Fifteen minutes, with every member of her staff, on a regular cadence. Not to check on performance. Not to move work forward. But to stay in a relationship.
She did this because she knows that you cannot build a culture where people tell you the truth if your only contact with them is task-based. Trust isn't built in all-hands meetings and performance reviews. It's built in the fifteen-minute conversations that most leaders think they're too busy to have.
It was a nod back to the story she shared about the community her grandmother fostered in her beauty salon.
It's remembering what someone told you six months ago and asking about it. It's being present in a conversation that has no immediate deliverables.
I know this creates tension between leaders who want to be available and those drowning in legitimate demands. There is always something more urgent, more visible, more measurable pulling at their attention. Relationship-level work rarely screams loudest. So it gets deprioritized, not out of negligence, but out of the relentless math of a packed calendar. And over time, when it starts to build up, avoidance just gets easier. You get used to the distance.
You build workarounds. You tell yourself the team is fine, the work is moving, and things are holding together. But what you're really doing is choosing the short-term comfort of not diving in over the long-term return of actually doing it. Because when you do go in, when you stay in a relationship, when you make the time, when you show up for the fifteen-minute conversation that wasn't on your calendar, you come out more connected, more informed, and a better leader as a result. The mess becomes the medicine.
The Friendly 15s aren't a program. They're a leader diving into the messy middle, refusing to let organizational growth become the excuse for why she stopped showing up for her people.
So here's what I want to leave you with.
The messy middle isn't a sign that something is wrong with your leadership. It IS your leadership, at least the part that actually develops you into a great leader.
The ridiculous notion that you always have to be right, always have to have the answer, always have to look like you've got it together, that’s what keeps you from not just facing the messy middle, but being okay while you’re in it.
Shawn stayed in the conflict mess and built a culture of truth-telling. Donishea stayed in the learning mess and came out as a leader her team trusted more. Traci stayed in the trust mess and chose relationship over convenience.
All three of them could have taken the easy exit. None of them did.
And that's the question I want to leave you with today:
Where are you taking the easy exit right now? What tension are you smoothing over, what discomfort are you rushing past, what messiness are you trying to avoid or clean up before you've learned what it has to teach you?
That's where your next level of leadership is. Not on the other side of the mess, but in the willingness to stay in it.
Thanks for joining me.
Until next time, keep leading people-forward. I’ll see you soon.
