Confessions of a Millennial Marketer
What starting over at the top actually asks of you.
Three weeks into the new job, I’ve already stepped on toes I didn’t know were there, asked questions everyone but me apparently knew the answer to, and called a thing by the wrong name in a room where the name mattered. I’m telling you this on purpose.
Everyone expects a particular version of a new executive: walks in, surveys the kingdom, announces the plan by Friday. It’s a fantasy, and a dangerous one. The truth is messier, and I think better. The first month of a big new job is mostly learning, out loud and in front of people, how little of your old map still applies.
It’s a strange time to be the new executive entering a role. I’ve spent a decade running marketing functions, and have arrived in my new seat when the function is repositioning underneath all of us: the dashboards we trusted no longer holding, the measurement layer coming apart. So I’m not only learning a new company; I’m learning a job that’s changing shape while I hold it. Some nights that lands as dread. Most days, honestly, it lands as the most interesting problem I’ve had in years.
The thing I do trust is narrower than my title. I can see how a team actually operates — where the work bottlenecks, where the revenue leaks, where the whole system is held together by one person’s memory — and I build the engine that makes it scale. That’s the part I’d bet on in the dark. It’s also completely useless on day one. You cannot build the system for a team you don’t understand yet. So the bumping into walls and stepping on toes isn’t in the way of the work. For the first thirty days, it is the work.
Because learning how a team really operates is on no onboarding doc. It’s in who gets cc’d and who gets left off. It’s the workaround everyone uses and nobody wrote down. It’s the meeting that looks pointless until you realize it’s the only room where a certain decision actually gets made. You learn it by bumping into it, which is a polite way of saying you learn it by getting some of it wrong first, on purpose, where people can see.
Early in my career, I thought the goal of a first month was to look like I already belonged. Now, I know the goal is to earn the right to build, and you earn it by being genuinely, visibly new for a while — by asking the dumb question instead of nodding past it, by letting the team teach you the thing the org chart can’t.
If you’re about to do the same thing
A few things I wish someone had pressed on me harder, for anyone walking into a new management or executive seat.
Operate in it before you try to fix it. You can’t lead a function from the conference room, and you definitely can’t redesign one you’ve only heard described in welcome meetings. Sit in the standups. Read the dashboards nobody cleaned up for you. Learn how the work actually moves before you move it.
Read the situation before you prescribe. A team that needs steadying and a team that needs a turnaround look identical on the org chart but require opposite things from you. Get that read wrong and your first big move lands as a wrecking ball.
Have the awkward conversation with your boss early. Not the polished one. The real one: what does a good first ninety days look like to you, what can’t break, what would you do first if you were me. Aligning on what “good” even means is the most useful hour of the whole month, and almost nobody spends it.
Earn one real win before you announce anything. Pick something genuinely broken, fix it where the team can see, and let the fix talk. One real win buys more standing than a reorg you can’t yet defend. The reorg is usually just what we reach for to look decisive before we’ve earned the right to be.
Hold the playbook that got you here loosely. The instincts that made you great in the last seat are those most likely to mislead you here. You haven’t seen this before. You’ve only seen something that rhymes.
None of that is about moving slowly. It’s about spending the first month earning the only thing that makes the next eleven possible: enough understanding of how this specific team works so the systems you build for it actually fit.
I don’t have the tidy ending where I’ve got it all figured out. I’m three weeks in. I’m going to step on more toes and may accidentally propose some sacred cow is sent to slaughter. But the fear that I’ll get something wrong is just the flip side of caring if I get it right, and the day I stop feeling either one is the day I’ve stopped being any good at this.
I’ll keep bumping into walls a while longer. On purpose. It’s how you find out which ones are holding the place up.
Willing to be a beginner again, at the exact moment it’s least convenient to be one?
Of course I am.
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