Author: John Lewis, TransPro Principal
What Do I Do Now? A Challenge to New Transit Executives Before Day One
I remember my first day as a new executive at my first transit agency. I had just survived a grueling interview process — panel after panel, scenario questions, a deep dive into my record, a negotiation over salary and benefits that felt like the finish line. And then I sat down at my new desk and thought: What do I do now?
I knew the agency only through what I’d learned preparing for interviews. I didn’t actually know what the board wanted from me. I didn’t know what they considered success, for the agency or for me personally. I spent most of my first two quarters quietly trying to answer those questions — reading budget documents, sitting in on committee meetings, taking board members to coffee one at a time — all while trying not to look like someone who had walked in without a map. Looking back, that scramble was avoidable. The time to get those answers was before I accepted the job, not after.
The negotiation you’re not having
New executives negotiate hard over salary, car allowances, deferred comp, severance terms. Almost none negotiate for clarity. But clarity is the thing that actually determines whether you are successful or not.
Before you sign, you should be able to answer: What does this board believe success looks like for the agency over the next two to three years? What does it believe success looks like for me, specifically, in year one? How and when will I be evaluated, and against what? If you can’t answer these with confidence, you don’t yet have enough information to know what you’re agreeing to — no matter how attractive the opportunity and the compensation package looks.
Ask the question directly, even if it feels risky
It can feel presumptuous to ask a board, mid-negotiation, “What does success look like for me after twelve months?” It can feel like you’re implying they haven’t thought it through. Ask anyway. In my experience, boards that bristle at the question are telling you something important: they haven’t done the work of aligning on priorities themselves, and you’re about to inherit that gap. Better to find out during negotiation, when you still have leverage, than during your first performance review, when you don’t.
You’re not just asking for your own benefit. A board that’s forced to answer this question before you start day one has to do something many boards skip: agree among themselves on what they actually want. If five board members have five different pictures of what your first year should accomplish, you need to know that now — and so does the board.
If the board doesn’t have an answer, that’s your first project
Sometimes you’ll ask and get a thoughtful, unified answer. Often you won’t — you’ll get vague generalities, or five different answers from five different board members, or a polite version of “you’ll figure it out.” If that happens, don’t treat it as a red flag to walk away automatically. Treat it as a request for help and make it your explicit first project.
Propose, as part of your onboarding — and ideally before you start — a structured process to get the board aligned: a facilitated session, a written set of priorities, a shared scorecard for year one. If the board doesn’t have the internal capacity or objectivity to do this itself, say so plainly and suggest bringing in a third party to facilitate
it. An outside facilitator can ask the uncomfortable questions and surface disagreement among board members in a way that’s much harder for a brand-new executive to do on their own, especially before they’ve built trust with anyone in the room.
This isn’t a sign of weakness on your part. It’s the opposite. Walking in and immediately identifying that the board’s alignment is the actual first obstacle — before ridership, before budget, before capital project delivery or anything else — is executive judgment, not naivety.
Don’t let day one be a surprise
The version of me on that first day, quietly trying to reconstruct the board’s priorities from context clues, lost real time and real capital. Every meeting spent guessing what the board wanted was a meeting not spent building the plan to deliver it.
You don’t have to walk in blind. Ask for the definition of success before you accept the offer. Ask how you’ll be evaluated at twelve months. Ask what the board’s priorities actually are, in writing, agreed upon by the board as a whole — not assembled by you after the fact from hallway conversations. If the answers aren’t there yet, help the board build them, with outside help if needed, before your first day arrives. Your first quarter should be spent executing a shared plan, not discovering there wasn’t one.
Helping boards align on priorities before a new executive’s first day is exactly the kind of work John Lewis and the TransPro team does. If your board could use an outside facilitator to build that shared definition of success, contact John Lewis today.
Media Contact: Natalie Cochran at natalie.cochran@transproconsulting.com.
