By John Lewis
Principal
Every transit board that has run an executive search has had the same debate. Status quo or change agent? Insider or outsider? How many years of experience, what leadership style, the right vision, the right ethics, the right fit with the culture?
These are reasonable questions. They’re also, by now, a script, and scripts produce predictable outcomes. A board spends months weighing familiar attributes against each other, hiring someone to find candidates who fit the mold, making an offer, and then discovers 18 months later that the agency is no better off than before.
Here’s the uncomfortable part: the problem usually isn’t that the board asked the wrong questions about the candidate. It’s that the board never asked the harder question about itself.
Before you can evaluate who should lead the agency, you must answer something most searches skip entirely: what does success actually look like over the next three years, and does everyone on the board agree?
It sounds obvious. It rarely is. Ask five board members to define success and you’ll often get five answers: ridership growth, budget stability, labor peace, safety metrics, a capital project delivered on time. None of them is wrong.
But an executive hired without a shared definition of success is set up to fail no matter how talented they are, because they’ll spend their tenure managing five conflicting expectations instead of executing one coherent strategy.
The best boards treat the search itself as the forcing function for this conversation. Could your board members, asked separately, define success the same way?
TransPro’s Board Workshop helps transit boards build alignment on agency direction and what real success looks like. It’s essential preparation for a CEO search, but it’s just as valuable for a board that simply wants to lead more cohesively through today’s challenges.
Stop Hiring for Attributes and Start Hiring
for the Next 24 Months
The status-quo-versus-change-agent and insider-versus-outsider framings are seductive because they’re easy to debate in a boardroom. But they’re proxies for a question boards should ask directly: what specifically needs to be true about this agency in two years that isn’t true today, and what kind of leadership gets us there?
That reframe changes everything downstream. An agency facing a structural deficit needs different capabilities than one mid-construction on a capital project, which needs different capabilities than one rebuilding public trust after a hard year. “Change agent” or “insider” tells you almost nothing about whether a candidate can do any of those specific jobs.
Boards that anchor the search to the actual operating context, not to abstract leadership archetypes, end up with a much sharper, shorter list of what actually matters, and a far clearer read on the candidates in front of them. The debate stops being philosophical and starts being concrete, which is exactly where a board wants to be before it makes a multi-year bet.
Labels like “change agent” are easy because they’re vague. The 24-month question is harder because it forces you and your Board to be specific. That’s exactly why it works better.
Try this question on your own board: what has to be true in two years that isn’t true today? If the answers don’t line up, that’s worth knowing before a search begins—not after.
TransPro’s Board Workshop helps transit Boards build alignment on agency direction and what real success looks like. It’s essential preparation for a CEO search, but it’s just as valuable for a board that simply wants to lead more cohesively through today’s challenges.
Success Isn’t a Resume Line. It’s a Contract
So the board has done the hard work and arrived at a real shared definition of success. Here’s the step almost everyone assumes and almost no one makes explicit: that definition has to become terms with the incoming executive, in writing, before they start.
What are the two or three outcomes this person is accountable for in year one? And, just as important, what resources and authority will the board actually provide to make those outcomes achievable? What happens when board priorities shift mid-course, as they inevitably will with elections, funding cycles, and crises?
Too many new transit executives are hired against a general mandate: “turn things around,” “restore confidence,” “modernize the agency,” and then evaluated later against whatever the board happens to be frustrated about that quarter. The evaluation becomes a moving target.
This goes both ways. The executive is accountable for results, and the board is just as accountable for telling the executive, clearly when its expectations change. Boards that hold up their end keep good leaders.
The best boards define priorities and metrics before the executive walks in, revisit them on a fixed cadence, and treat their own side of the bargain as seriously as the executive’s. It’s a demanding expectation of everyone in the room.
Build the Evaluation Before You Need It
Most boards design the search process meticulously and the evaluation process almost not at all. That’s backwards. A rigorous, pre-agreed evaluation framework, built before the search does two things a resume never can.
First, it forces the board to be honest about what precisely it is looking for. Vague criteria are impossible to evaluate against. Building the framework early brings the board into agreement up front while that alignment can still shape the search.
Second, it gives the new executive a clear, transparent basis for how they’ll be judged, which, to a strong candidate. The best people want to know the game they’re being asked to win.
Which brings us to the most important questions. Instead of asking what kind of person are we looking for, the best questions a transit Board can ask is: “Are we, as a board, capable of giving this person a fair shot at succeeding, and do we actually know what success looks like?”
Boards that can answer that honestly are the ones whose searches change the trajectory of the agency. Boards that skip it keep having the same status-quo-versus-change-agent debate, hire after hire, without ever addressing what made the last hire struggle in the first place.
The good news: readiness is testable and fixable before the search begins.
The best searches start with the board, not the candidate. That’s exactly how TransPro works. We’ve partnered with agencies across the country to align boards, define real success, and place CEOs who succeed. Let us do that work with your board. Contact John Lewis at TransPro to get started.
