Almost every week I sit with a founder who’s decided they need to hire a head of sales or a VP of engineering. They’ve never held the role themselves. They ask me where to start. I tell them: before you talk to a single candidate, learn what great looks like in this role. Not the job description version. The real version, from people who’ve done the job and watched others fail at it.

See: The MOC The framework this card feeds into. Draft it first, then use calibration calls to sharpen the gaps.

Here’s what I find quietly hilarious about this moment. The same founder who obsesses over every pixel in their product, who wouldn’t ship a feature without user testing, who has a near-spiritual conviction about craft and quality? That person is about to wing one of the most expensive decisions they’ll make this year. They’ll spend months perfecting a button color and then hire a VP off vibes. A calibration call is a brutally simple thing.¹¹ Hiring for a new role/function? Do this. Liz Wessel coined the name. I’ve taught this practice for over a decade; she gave it the label that stuck. Her questions are worth reading alongside this card. You get on the phone with a few people who are great at the job, you ask them what good looks like and how people fail, and you put it into a document. This is not rocket science. But founders who have done it a dozen times still freeze up when a new role shows up, as if they’ve never been here before.

That’s what a calibration call is for. Draft the MOC first; you’ll see the gaps immediately. Then do the calls to fill them. You’re not replacing your thinking. You’re pressure-testing it against people who’ve already lived what you’re about to go through. If you know a role is on the horizon, start these calls before the pain becomes acute. Three conversations when you’re not in a crunch will teach you more than six when you are.

Lead with failure questions

Here’s the technique that makes calibration calls work: don’t start by asking what great looks like. Start by asking what failure looks like.

There’s a quirk of human psychology behind this. When you ask someone “what does great look like in this role?” they often aren’t very good at answering. You get polished, vague descriptions. But ask “what does failure look like?” or “what mistakes do people make?” and something shifts. People get specific. They get vivid. They get honest in ways they never would about success. Our brains are wired to catalog what can hurt us, and that wiring makes failure questions the fastest way to learn what you need to know.

Those answers warn you what to avoid. If three people tell you the last hire “spent the first quarter reorganizing the team instead of learning the product,” you know what not to let happen.

But they also show you what to pursue, because the shape of failure, turned inside out, is the shape of excellence. If every failed hire “couldn’t make the plan,” you now know that plan-making is what great looks like at this level.

Navigate to the right people

Most founders skip calibration calls because they don’t know who to call. They don’t have a network yet in the function they’re hiring for. Work toward it rather than grab for it.

Go to your investors, other founders, and anyone whose judgment you trust in this space. Ask two questions:

1. “Who do you know who’s best in class at this?” One hop: a direct introduction to someone excellent.
2. “Who do you know who would know a lot of people who are best in class at this?” Two hops: a connector whose network runs deep in this function. When you meet that connector, ask them the first question.

Almost everyone asks the first and skips the second. The second is the one that gets you past your immediate network.

Three groups to talk to

Once you’ve navigated your way in, you want conversations across three groups:

1. People who’ve done the job well at companies you admire, at roughly your stage. Two to three here, not one. Experts disagree, and a single conversation gives you a single lens.
2. People who’ve hired for this role: founders and executives who’ve run this search before. They’ve made mistakes you haven’t made yet.
3. People who’ve worked alongside someone excellent in this role, not as their boss, but as a peer or partner. They saw what a genuinely great hire did differently, what problems that person solved that average people never noticed.

What to ask

Lead with failure questions in every conversation. Then layer in questions about excellence and process.

For people who’ve done the job:

• What do failed hires in this role have in common? What are the behaviors, the patterns?
• How does this role change as the company scales, from 1–20 people, to 20–50, to 50–100?
• What do the best people in this role do that average people don’t?
• What mistakes do people typically make in their first 90 days?
• The question that surprises most founders: what roles does this person need around them to succeed? A great head of sales almost always needs a sales operations person alongside them. If you’re hiring your first head of sales and haven’t thought about sales ops yet, you’re about to learn about two roles at once.

For people who’ve hired for this role:

• What mistakes did you make during this search?
• What do you wish you’d known before you started?
• What question do you now ask every candidate that you didn’t ask early on?

For people who’ve worked alongside someone excellent:

• What did that person do in the first 90 days that set them apart?
• What was it like to work with someone genuinely great in this role versus someone average?
• What did they do that you didn’t expect from someone in this function?

What you walk away with

You now have a benchmark for this role built from real experience, not your own guesswork. If you’ve done these calls right, you feel uncomfortable and grateful at once. You were about to step on mistakes you didn’t know existed, and now you know where they are. The MOC you write with that picture in your head will be sharper than the one you’d have written alone. The ladder was right there the whole time. Go sharpen the MOC.