The "One More Thing" That Tells Candidates Everything

Last week I came across a job posting for a founding sales lead at an early-stage AI company. I'm not going to name them, because this isn't really about them. It's about a habit I'm seeing more and more from leaders hiring for important roles.

Most of the posting was good, better than most. They were upfront that sales is founder-led today and there's no proven ICP to inherit. Whoever takes the job will be selling and figuring out the market at the same time. That's the kind of honesty candidates rarely get.

Then came the application. A résumé. Two or three examples of deals you built, with the starting point, the result, the timeframe, and what you personally owned.

Screenshots of pipelines and sequences welcome.

Fair enough. Then this:

"Then do one more thing: Pick a company you think should buy [our product]. Tell us why, and write the exact outbound you'd send them. That matters more to us than a polished cover letter."

"One more thing." Tacked onto the end of a long list, like an afterthought. But it's the biggest ask on the page.

Think about what the company already has. Two years of building, customer conversations, demos, and learning where the product lands and where it doesn't. All of that sits inside their walls. The candidate gets a website and a job description. With that, they're asked to pick the right buyer, explain why, and write the message. And this is in the same posting that admits the company hasn't nailed its ICP yet.

So what comes back? Most candidates will read the website, run it through ChatGPT or Claude, and polish the result. AI lets you do more with less. But without the context the company is holding, there's a very small chance the answer is right. You end up grading guesswork and prompting, and you learn almost nothing about how the person actually sells.

The bigger issue isn't the test itself, though. A hiring process is the first thing a candidate learns about how you'll treat them. Asking for real strategic work, for free, before a single conversation, sets the level of respect you'll give that person going forward. The company collects the thinking. The candidate carries the risk.

I've seen this from the other side. When I was at Fresh Tilled Soil, free work came up here and there to win business. A prospect would ask for a workflow or screen to see how the team "thinks." It never sat well. Even when it paid off, the relationship started on the wrong foot. One side was giving and the other side was deciding.

Not every ask crosses the line. A 30-minute discovery call is fine. That's two sides figuring out if there's a fit. Asking about previous projects and work history is fine too. That's the candidate's own story to tell.

Asking for your go-to-market thinking, on spec, in a vacuum, is different.

If you're hiring a sales leader, talk to them. Ask about deals they actually built: where they started, what got hard, how they closed. Pay attention to how they tell it. A seller's storytelling shows you how they'll run discovery, how they'll handle your buyers, and whether they'll fit your team. That's a better signal than any cold email written from your homepage.

If you want to see how they'd think about your market, do it together. Share some of what you've learned, ask how they'd approach it, and have a real conversation. You'll see how they think with real information, and that's the job anyway.

This goes well beyond sales. It applies to designers, marketers, engineers, whoever you're hiring. Candidates are evaluating you as closely as you're evaluating them, and the good ones have options. The way you ask is the tone you set, so set the one you want to keep.