The 5 leadership lessons from running for Congress that no one talks about

It was 6:45 on a Tuesday morning in Waukesha County, and I was standing outside a Kwik Trip shaking hands with people who had zero interest in talking to a congressional candidate before their first cup of coffee.

One guy looked at my campaign sign, then at me, and said, “You’re running for what? In this district?” He laughed. Not mean, just genuinely surprised. Wisconsin’s 5th Congressional District hadn’t elected a Democrat since 1958. I was a Black construction business owner trying to change that.

He bought his coffee. I kept shaking hands. And I learned something that morning I’ve carried into every leadership role since: the people who are hardest to reach are usually the ones most worth listening to.

In 2016, I ran for Congress against Jim Sensenbrenner, a 38-year incumbent. I won the Democratic primary. I lost the general. What happened between filing those papers and election night taught me more about leadership than 20 years of running a construction company ever did.

These are the lessons from that campaign nobody talks about. Not the obvious stuff about “finding your voice.” The uncomfortable ones that actually changed how I lead.

TL;DR: Running for Congress in Wisconsin’s 5th District in 2016 taught me leadership lessons that transfer directly to business and life: listen to people who disagree with you, make decisions with incomplete information, lead people you can’t pay, tell your story before someone else does, and know when losing is actually winning.

The best leadership skill is listening to people who think you’re wrong

Every candidate prep guide says to focus on your base. Rally the faithful. That’s smart electoral strategy. It’s terrible leadership advice.

Some of the most important conversations I had during the campaign happened at doors where people told me straight to my face they weren’t voting for me. A farmer in Jefferson County spent 20 minutes explaining why my position on trade policy was wrong. He had specific numbers. He knew more about soybean tariffs than anyone on my policy team.

I didn’t change his mind. He didn’t change his vote. But I walked away understanding something about rural economic anxiety I’d been getting wrong in every stump speech for two months.

I used to surround myself with people who validated my decisions. I’d hire consultants who told me what I wanted to hear, read the positive reviews and skip the one-stars. The campaign broke me of that habit fast.

When you knock on 10,000 doors, you don’t get to choose who answers. You hear from the angry, the frustrated, the skeptical, and the exhausted. If you’re actually listening instead of waiting for your turn to talk, you get information no focus group will ever give you.

I use this now. When I walk into a struggling market, the first thing I do is find the most frustrated people on the team. Not the ones happy to see me. The ones with complaints, the ones who think it won’t work. They’re the ones who know where the real problems are.

You never have enough information and the decision still needs to be made

Three weeks before the general election, I had to decide whether to spend our remaining $12,000 on TV ads in the Milwaukee media market or on targeted digital and ground game in the western counties. My campaign manager said TV. My digital consultant said online. My volunteer coordinator said neither, spend it on yard signs and door-to-door.

Everyone had data. None of it was conclusive. The TV buy window was closing by end of day.

Nobody romanticizes this part. You don’t get a clear answer. You don’t get to wait for more information. You get conflicting advice from smart people, a deadline, and the knowledge you’ll be judged publicly for whatever you choose.

I went with a split: $8,000 on digital targeting in suburbs where our polling showed movement, $4,000 on ground game in Waukesha. Nobody was fully happy with it.

Was it the right call? I honestly don’t know. We lost by a wide margin regardless. But the ability to take in conflicting inputs, commit to a direction, and own the outcome without having certainty first, that’s something I draw on every week.

Running a construction company, I’d gotten comfortable waiting until I had enough information before making big calls. The campaign taught me that’s sometimes a luxury you don’t have.

Leading people you can’t pay or fire

I had over 200 volunteers during the campaign. Not one was on payroll. They showed up at 7 a.m. on Saturdays to knock doors. They made calls after putting their kids to bed. They donated lunch breaks to stuff envelopes.

If any of them decided they’d rather sleep in, there was nothing I could do. No performance review. No raise to dangle. No consequences for quitting.

That is the most honest version of leadership there is: getting people to show up when they have every reason not to and no obligation to stay.

Speeches didn’t keep them engaged. Showing up did. When volunteers arrived at 7 a.m., I was there at 6:30 setting up. When we knocked doors in the rain, I knocked more than anyone. When someone had a rough interaction at a doorstep and felt discouraged, I sat with them and talked it through.

People don’t stay because of titles. They stay because they believe the person in charge is working as hard as they are and actually cares about the same outcome.

I have positional authority now. I can set expectations and hold people accountable. But the teams that actually perform, the ones that go beyond what’s required, they do it because they trust the mission and the person running it. That trust doesn’t come from the org chart. It gets built the same way it did on the campaign.

If you don’t tell your story, someone else will tell it worse

Two weeks before the primary, a local blog published a piece about my construction company that got three major facts wrong. They said I’d gone bankrupt. They said I had no political experience. They implied I was running as a vanity project.

My instinct was to ignore it. My communications director nearly tackled me. She said something I’ve never forgotten: “The high road is where narratives go to die. If you don’t correct this now, by Friday it’s the truth.”

She was right. We put out a detailed response within four hours. The story died. If we’d waited two days, it would’ve been the first thing voters found when they searched my name.

I see this in business constantly. Leaders let a bad review sit unanswered. They let a competitor define their reputation. They assume their work speaks for itself. It does, but barely. Your story needs to be told clearly, consistently, and before someone else fills that silence with their own version.

I’m not talking about spin. I mean knowing what you stand for, having the receipts to back it up, and being willing to say it out loud. I tell my teams: document your wins. When something goes wrong, get in front of it with honesty. The vacuum you leave by staying quiet gets filled by someone with less context and less goodwill toward you.

Sometimes losing is the most important thing you can win

I lost the general election. Not close. I didn’t come close to beating a 38-year incumbent in one of the most conservative districts in Wisconsin. On paper, the campaign was a failure.

Here’s what actually happened after.

I got invited to speak at the 2016 Democratic National Convention. I became a DNC Representative for Wisconsin, a position I held for six years. I built a network of community leaders, organizers, and advocates across the state. I joined the board of Planned Parenthood of Wisconsin. I became an Everytown for Gun Safety fellow.

Every one of those things came from the campaign. Not from winning it.

Outcomes and impact aren’t the same thing. You can fall short of the goal and still move things in ways that matter more than the original objective. I grew Penebaker Enterprises from $1.5 million to $15 million. I grew Roofed Right America past $35 million. Both had years where we lost bids, lost clients, and lost money. Those losses built the capability that made the growth possible.

The campaign taught me to measure success by what I’m building, not just what I’m winning right now.

What the campaign trail teaches that the boardroom can’t

Running in a district you almost certainly can’t win strips away every buffer between you and the people you’re trying to lead. No corner office. No title that commands automatic respect. No budget big enough to cover up mistakes.

Just you, a message, and thousands of conversations with people who owe you nothing.

If you lead anything, find something that puts you in that position. Run for school board. Chair a neighborhood association. Organize something in your community. Somewhere that your only tools are your words, your work ethic, and your willingness to listen.

You don’t have to run for Congress.

That guy at the Kwik Trip in Waukesha County, I saw him at a town hall three months after the election. He recognized me. He said, “You didn’t win, but you’re still here.” He meant it as an observation. I took it as the best compliment a leader can get.

I’m still here. Still showing up.