Outsourcing the One Decision You Can't Outsource

The right hire already showed up. Your sales leader passed on them. The right hire already showed up. Your sales leader passed on them.

You’ve never built a sales team. This is your first one.

You do the reasonable thing. You bring in a sales leader to lead interviews, and you trust their judgment. You’re technical. You’ve never sold. Who are you to overrule the person you hired? You need to empower them, right?

I get it. It feels like the responsible move. Trust your people.

Here’s the part you might not be thinking about. The leader you brought in has often never built a team from scratch either. Not at a startup. Not at this stage. Maybe they’ve built one at Salesforce. But building a team at Salesforce is nothing like building before you have proof that this works. There you had a brand, a playbook, inbound leads, and a name that got meetings. Here there’s none of that. The leader you have is often a player coach. They speak confidently. But building the machine that hires and ramps other sellers from nothing they haven’t done before. You outsourced the decision to someone who’s making it for the first time and they know less about the business than you do.

So you wait. Weeks go by. The role isn’t filled. You start to wonder if the right person just isn’t out there. Lots of excuses why no one has been hired.

They’re out there. You’re passing on them.

Here’s how it shows up.

The expectations aren’t real. The leader can’t tell you what the role actually requires. How would they know? They just joined the company and any hiring experience they have is often at a company is completely different. You think the problem is candidate quality. It isn’t. Nobody built the system the candidate was supposed to walk into. You’re waiting on a leader to find the perfect candidate vs setting up a process that strong candidates could follow.

Then the screening starts working against you.

I watched a leader pass on a candidate who fit almost everything they said they wanted. Six years of experience. Promoted four times. Had been at a company that went from $1M ARR to $10M ARR. One company. The leader said, “I don’t think they’d work in our environment. They’ve only been at one place.”

Sit with that.

One company that started at same ARR startup is at now. Grew through the exact motion the startup is trying to run. 4 promotions at one company this is a top performer, every year. Staying at one company isn’t a person who can’t handle ambiguity. It’s a person who stays when things get hard. That’s what you need for a first seller. And the leader passed without taking the meeting.

Then there are the quiz questions.

The leader asks a candidate, “What’s your approach to prospecting?” Candidate says, “I make cold calls and I use Sales Navigator.” Vague question gets vague answer. Leader hears a bad answer. Unoriginal. They immediately check out of the rest of the interview. Candidate has no shot after that.

But the leader didn’t ask the only question that matters. What results did your approach generate?

Because if cold calls and Sales Navigator are filling that person’s pipeline, there’s nothing to fix. You don’t need creativity. You need repeatability, and they have it. A leader who knew what they were looking for would’ve followed up. “What does that get you?” “If it stopped working here, what would you do next?” Now you’re learning how the person thinks.

But here’s the bigger issue. That leader is looking for a seller to come in and solve a problem the leader doesn’t know how to solve themselves. If you’re running sales at a seed or Series A company and you don’t have a recommended way to build pipeline that a new hire can follow, that’s the problem. Not the candidate’s answer. You’re grading them on creativity because you don’t have a system to hand them. So you disqualified a good seller to avoid admitting the pipeline motion doesn’t exist yet.

Notice what both have in common.

The one-company pass. The quiz. Both are screening to keep people out instead of screening to find someone to build with. When you don’t know what good looks like, saying no feels like rigor. It isn’t. It’s hedging against making a mistake.

There’s one more thing these leaders miss. Hiring is a two-way street.

The best candidates have options. They’re evaluating you while you evaluate them. But a leader who’s never hired at this stage runs the process like the candidate should be grateful to be there. Take-home tests before you’ve earned it. A series of interviews with no end in sight. Long gaps with no knowledge if you are still being considered. Every one of those steps tells a strong candidate the same thing: these people don’t know what they’re doing.

The top sellers need to be sold. Spend as much time answering their questions as asking your own. Many leaders conduct a 45 minute interview where they ask questions for first 40 minutes and leave the last 5 minutes for candidate questions. This fails for 2 reasons. 1) The candidate doesn’t feel valued. 2) The interviewer doesn’t hear the level of questions the candidate comes up with which can be an important data point for interviews.

The fix isn’t a better candidate. It’s the part being skipped.

Get clear on what the role actually requires before you start speaking to candidates. Know which skills are non-negotiable and which ones a good hire picks up in ninety days. Build the system you’re putting someone into, and run a process that makes them want in. Do that, and the candidate who “only worked at one company” stops looking like a risk and starts looking like the person you were waiting for the whole time.

Stop completely outsourcing this decision and find a way to support.