The leadership lessons nobody prepares you for—and why they made me better at everything else
By Michael DiNapoli
I’ve managed billion-dollar portfolios. I’ve navigated the 2008 financial crisis from inside one of the largest banks on the planet. I’ve sat across the table from some of the sharpest minds on Wall Street.
None of it prepared me for my first month running a division in Florida state government.
Not because government is harder than finance in every way—it’s not. But because the leadership challenges are fundamentally different. And nobody tells you that going in.
I wrote recently about what Wall Street skills transferred to government. That piece was about what I brought with me. This one is about what government taught me—lessons I couldn’t have learned anywhere else. Lessons that, honestly, made me a better leader than two decades in finance ever did.
You Can’t Fire Your Way to Results
On Wall Street, underperformers get managed out. It’s not always pleasant, but it’s straightforward. If someone isn’t producing, you have options.
In government, you lead the team you have. Civil service protections, union agreements, and institutional tenure mean that the people in the room on day one are probably the people in the room on day three hundred. That’s not a complaint—those protections exist for good reasons. But it forces you to become a completely different kind of leader.
You learn to find what motivates people individually. You learn to put people in positions where their strengths actually matter. You learn patience—real patience, not the kind you perform in meetings.
I had a team member at FloridaCommerce who’d been in the same role for over a decade. Half the agency had written him off. But when I actually sat down and listened to what he knew about the state’s economic development pipeline, I realized he had institutional knowledge that no consultant or new hire could replicate. The problem wasn’t him. It was that nobody had asked the right questions in years.
That’s a leadership lesson you don’t get when your default tool is a performance improvement plan.
The Scoreboard Is Invisible
In finance, you always know the score. Revenues. Returns. Basis points. The numbers are right there, updated in real time, and nobody can argue with them.
Government doesn’t work like that. Success is ambiguous. Did the workforce development program work? Depends on who you ask, what you measure, and over what time horizon. Did the economic incentive package create jobs? Maybe—but would those jobs have come anyway?
Learning to lead without a clear scoreboard was one of the hardest adjustments I made. It forced me to define success upfront, to build measurement into programs from the start rather than bolting it on later, and to get comfortable with ambiguity.
That skill has turned out to be incredibly valuable outside of government, too. Most real-world leadership doesn’t come with a Bloomberg terminal attached. The ability to define what winning looks like—and to get a team aligned around that definition when the answer isn’t obvious—is rarer than it should be.
Every Decision Is Public
This one changed how I think about leadership permanently.
In the private sector, you make decisions behind closed doors. Board meetings are confidential. Strategy sessions are privileged. If you make a bad call, your circle of exposure is limited.
In government, every email can be FOIAed. Every budget decision can end up in the newspaper. Every personnel choice gets scrutinized by legislators, advocacy groups, and the public.
At first, this felt paralyzing. Then it became clarifying. When you know that every decision might become public, you make better decisions. You document your reasoning. You pressure-test your logic before you commit. You make sure you can defend not just what you decided, but why.
I’ve carried that habit into everything I’ve done since. Before I make any significant call, I ask myself: could I explain this to a reporter and feel good about it? If the answer is no, I rethink it. That’s not something I learned at Citi.
Building Coalitions With People Who Oppose You
On Wall Street, if a client doesn’t like your proposal, you can walk away. There’s always another client.
In government, the legislators who block your initiative today are the same ones you need to approve your budget tomorrow. The advocacy group that opposes your program this quarter will be your strongest ally on the next one—if you haven’t burned the bridge.
I learned to separate the person from the position. To listen to objections as information rather than attacks. To find the 20% where we agreed and build from there instead of fighting over the 80% where we didn’t.
The best government leaders I worked alongside were masters of this. They could walk into a room where half the people disagreed with them and walk out with enough alignment to move forward. Not by compromising their principles, but by understanding that progress in a democracy is always partial, always iterative, and always requires bringing people along who don’t start where you start.
Try learning that in an MBA program.
Mission Covers a Lot of Sins—And Reveals Them Too
Government attracted some of the most dedicated people I’ve ever worked with. People who could double their salaries tomorrow and chose not to because they believed in what they were doing.
But I also learned that mission-driven culture has a shadow side. When people believe deeply in the cause, they sometimes tolerate dysfunction they shouldn’t—bad processes, poor leadership, outdated systems—because the mission feels too important to disrupt.
As a leader, I had to learn to honor the mission while still insisting on operational excellence. To say “what we’re doing matters, AND how we’re doing it matters too.” That “and” is everything. Drop it, and you either get cynical efficiency or passionate chaos.
What I’d Tell Any Private Sector Leader Considering the Jump
Go. Seriously. Even if it’s temporary.
Not because government needs saving—that’s a condescending framing that gets people in trouble. But because leading in an environment where you can’t control the variables, where the scoreboard is fuzzy, where your decisions are public, and where you have to build consensus with people who disagree with you—that will make you a fundamentally better leader.
The private sector teaches you to optimize. Government teaches you to navigate. You need both.
Today at Marcman Solutions, every leadership instinct I rely on was sharpened in government, not on a trading floor. The ability to read a room. The discipline of making defensible decisions. The patience to build alignment when it would be faster to just dictate.
Wall Street gave me my skills. Government gave me my judgment.
I wouldn’t trade either one.
Michael DiNapoli is President & COO of Marcman Solutions. He spent 23 years on Wall Street at Citi and Morgan Stanley before serving in Florida state government, including as Director at FloridaCommerce and Chairman of the Florida Development Finance Corporation. He writes about leadership, transformation, and bridging the private and public sectors. Connect on LinkedIn.
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