Most marketing leaders take a job and then figure out what they walked into. I do the diagnostic before I commit. The questions I ask upfront are the same ones that determine whether a build will work, and the answers tell me more about the role than any job description.
The failure mode I've watched repeat
The typical pattern goes like this: a growth-stage company brings in a marketing leader. The leader builds the function, runs the programs, produces the metrics. Twelve to eighteen months later, the CEO is frustrated, the marketing leader is defending their results, and nobody can agree on what went wrong. What went wrong was almost never the execution. It was the setup.
Only about a quarter of CEOs say their marketing leader's performance exceeded expectations. And only a third of CEOs and their marketing leaders actually agree on what marketing's role is in driving growth. This is a clear symptom of a shared failure to establish shared definitions before the work starts.
What I look for
The first thing I try to understand is whether the ICP is real or theoretical. A real ICP is specific enough that a sales rep could pull a list from it. If the answer I get is a broad category like “mid-market SaaS” or “enterprise healthcare,” the targeting work hasn't been done fully. A GTM built on top of a theoretical ICP will generate motion but will lack traction.
The second thing I look for is whether sales and marketing have any structural relationship, or whether they're operating as separate functions with separate mandates. If the sales leader and the marketing function don't have a shared definition of a qualified lead, a shared read on pipeline health, and a shared accountability structure, the build will generate internal conflict before it generates revenue.
The third question is harder to ask but more important than either of the first two: what does the CEO actually believe marketing does? This matters because the CEO's mental model of marketing determines what gets resourced, what gets credited, and what gets blamed when results don't arrive on the expected timeline. Getting explicit about this before the engagement starts is not a negotiation. It's a prerequisite.
The fourth thing I look to understand is the budget relative to stated ambition. A GTM build requires investment in people, tools, programs, and time before it produces measurable returns. If the budget conversation produces vague answers or numbers that don't support the stated goals, that is a signal about organizational commitment.
What the answers tell me
A company with a defined ICP, a sales organization that wants a marketing partner, a CEO who understands the sequencing of GTM investment, and a realistic budget is a company where a GTM build has a real chance of success. The execution is still hard, but the conditions exist for it to work.
A company missing two or more of those things needs foundation work before it needs a marketing function. Sometimes that's a conversation I can have with the CEO before we start. Sometimes it means the timing isn't right. Marketing leaders who succeed in early-stage builds are the ones who asked these questions before they started.