New in the Chair: Lessons from a First Year Leading a Fleet
When Rachel Darken became Fleet Service Superintendent for the City of Madison, she thought she knew what to expect. She had already spent nearly two years helping fill the role while her predecessor was on leave. She understood the organization, knew the people, and had already been making many of the same decisions.
“But I definitely thought things wouldn’t change,” she says. “And they did.” The biggest surprise wasn’t learning how to run a fleet. It was learning what changes when the final decision belongs to you.
For fleet professionals stepping into a leadership role, Darken’s first year offers a practical playbook built around one idea that surfaced repeatedly throughout our chat: leadership is less about having all the answers than making sure people know they have a voice.
Invite Input
One of the first things Darken noticed after becoming superintendent was that conversations changed. The people who had been her peers became more hesitant to offer opinions. “They started kind of backing away and kind of being like, ‘Well, it’s up to you to decide that. It’s up to you to make that decision,’” she explains.
During her time as interim leader, interactions had been collaborative. Once the appointment became official, colleagues became more inclined to defer to her judgment. She realized she would have to work harder to draw people back into the discussion because good decisions still depended on hearing different perspectives.
Instead of accepting the shift, she made a point of inviting people back into the decision-making process. “I was still making that space and asking for that,” she says, “Like asking, ‘From your perspective, what does this do? What does this impact? How would that change things?’”
For Darken, earning the title of superintendent didn’t mean relying less on the people around her. It meant relying on them more intentionally. “I would not be in this role without people giving their expertise and their experience and helping teach me along the way, too,” she says.
Maintain the Mission
Darken realized early that employees were observing more than just her decisions. They were trying to understand what kind of leader she would become. She notes, “When a team sees that leadership spot change, they’re feeling out, ‘Okay, what kind of a leader are you?’”
That realization shaped her approach during her first months. Rather than introducing sweeping changes, she directed her efforts on helping employees regain a sense of stability after a period of transition. “I really focused more on listening and just kind of bringing the team back to ‘What is the vision for our division now?’”
She reminded employees that while leadership had changed, the mission had not. “We’re focusing on the fact that we are a fleet service division, and that means service,” she says.
Re-centering the division on service was more than just a slogan for Darken. She wanted employees to think beyond the shop walls and remember the people depending on their work, from public works crews to police officers to parks employees.
Take It Slowly
Like many fleet professionals, Darken describes herself as someone who likes solving problems. “I’m someone who definitely wants to have an answer right away and deal with the thing,” she says.
But stepping into the superintendent role taught her that leadership sometimes requires slowing down instead of speeding up: “You really have to just pause.”
When new requests and ideas started flooding in after her appointment, she resisted making immediate decisions. Instead, she asked what those decisions would mean over the long term and invited her team to help evaluate the options.
Communicate Consistently
One lesson that surfaced repeatedly during Darken’s first year was the importance of communication. Her approach is built around more than just meetings and memos. “I like to think the more ways people can hear things in different formats, it helps reinforce the message,” she explains.
That means emails, consistent connection with managers, weekly chats with shop leadership, and open sessions where employees can ask questions directly. One of the first initiatives she introduced was holding dedicated conversations with different groups throughout the division. “We’re going to sit down. You can ask me any questions. You can talk to me about your concerns. And that will help shape what we’re going to be doing going forward,” she says of her approach.
It’s just as important for employees to see that their feedback influences decisions. Communication, Darken believes, doesn’t end when a decision is made. Employees want to know their ideas were heard, even if the outcome isn’t exactly what they hoped for. Explaining the reasoning behind a decision builds trust and reinforces that their input genuinely matters.
Leave the Office
Leadership comes with meetings, budgets, reports and deadlines. Darken intentionally schedules opportunities to get out on the shop floor because she knows it won’t happen otherwise. “I hold dedicated time on my calendar for it,” she says.
The resulting interactions have become one of her most valuable indicators of organizational health. “The willingness for staff to engage in those conversations is a metric that you should also be tracking,” she notes.
She says operational data matters. That’s why Madison closely watches out-of-service rates, preventive maintenance compliance and repair trends. But she insists relationships matter just as much: “If employees stop talking, leaders should pay attention.”
Darken lights up when the topic turns to Madison’s apprenticeship program. “This is one of my favorite programs that we do,” she says.
What she didn’t anticipate was how much structure successful workforce development requires. “The thing that’s worked the best for us is making sure that we have a mentorship model.” Experienced technicians volunteer to mentor apprentices, and the city has strengthened that process with more systematic onboarding and regular check-ins.
Madison also recognized that being a great technician doesn’t automatically make someone a great instructor. The division introduced “train-the-trainer” education to help experienced employees become better mentors, strengthening the apprenticeship experience for both people involved.
For agencies struggling to recruit technicians, Darken believes establishing apprenticeships is well-worth the effort. “It does take time and investment, but even just a small program can really help in the long run,” she says.
Darken has learned that being available doesn’t have to mean being constantly connected. Outside of work, she’s raising two young children. Family time often means playing outside together, whether riding bikes, kicking a soccer ball around or shooting baskets. When she does find a quiet moment, she’s likely to be working in the garden or getting lost in a good book.
That balance doesn’t happen by accident. “I intentionally protect my time at home,” she says. Work email lives in a separate app on her phone, and notifications are turned off so every incoming message doesn’t interrupt her personal life. Her staff and fellow department heads know how to reach her if something truly needs immediate attention.
“They know to call or text my cell phone if it’s an emergency. Otherwise, it can wait,” Darken insists. For new fleet leaders, it’s an important reminder that taking care of your team also means taking care of yourself. Fleet management is a profession where there is always another issue waiting for attention. Creating healthy boundaries allows leaders to return each day with the focus and energy their teams deserve.
Note to Self
Asked what she would tell herself on her first day as superintendent, Darken didn’t mention budgets or fleet strategy. “Breathe,” she advises. “You don’t have to have all the answers right away.”
Darken acknowledges that stepping into the superintendent role came with moments of self-doubt, even after serving as interim leader. Looking back, she realizes she was more prepared than she gave herself credit for. Trusting her own judgment, while continuing to lean on the experience of those around her, became one of the biggest lessons of her first year.
“Trust yourself,” she says. “You have a team around you; trust your team.” For new fleet leaders, that may be the most valuable takeaway of all. The responsibility may ultimately rest with one person, but the strongest organizations are built when employees know their ideas and concerns matter and they have a meaningful role in shaping the road ahead.
