Stop Hiring for the Company You Want to Be

You just landed a big hire. Impressive resume. VP of Product at a Fortune 500. Led teams of 40. Managed a portfolio worth nine figures. They interviewed great, said all the right things about wanting to "get back to building," and now they're yours.

Give it four months.

I've watched this play out more times than I can count, and it almost always ends the same way. The impressive hire flames out, the founder is back to square one (minus six months and a pile of cash), and the company is worse off than before because now everyone's demoralized.

When I was at Suzy, we hired two product executives at roughly the same time. One came from a large enterprise company—the kind of place with formal processes, experienced teams, and org charts that actually meant something. The other was a senior director I'd worked with before and brought over because I knew he could operate in chaos.

Here's the thing about the senior director: he'd never been a director before. He'd been an IC his whole career, with maybe one brief stint managing a single person as a group PM. On paper, the enterprise exec had the leadership track record. My guy had almost none.

The enterprise exec was my peer. He lasted about five months before they let him go and gave me both roles.

Here's what happened.

He came in expecting a certain level of discipline. Experienced product managers who knew how to write PRDs, maintain roadmaps, run prioritization frameworks. What he got instead were scrappy operators who were great at getting things done but had never worked in a structured environment. They didn't document things the way he wanted. They didn't follow his processes. They just shipped.

He didn't know what to do with them.

I watched him spiral. He'd come to our one-on-ones and complain about his team. They wouldn't listen. They wouldn't provide the documentation he asked for. He was trying to fit people into boxes they'd never been in, at a company that didn't have boxes yet.
Then he fucked up the easy stuff.

He had a director on his team who was struggling as a product manager. She was clearly a subject matter expert in market research, and he had the right instinct: find her a role where she could thrive. But instead of leading with "where do you want to go?" he led with "you're not working out as a PM."

She thought she was being fired.

It created chaos. Her morale tanked. Her direct reports felt it. She eventually had to be moved under me because she couldn't work for him anymore. A conversation that should have been positive turned into an organizational wound that took months to heal.
That's what flopping looks like. You start screwing up the easy stuff because you're operating from a playbook that doesn't fit the environment. He was having performance conversations like he was still at a company with HR infrastructure and formal career ladders, not at a place where everyone was doing ten jobs and figuring it out as they went.

Meanwhile, the senior director I brought over was thriving.

He had the right mindset. He understood that doing the work was only the first part of the job. The second part was building a process others could follow and teaching his people how to run it. He respected structure even when there wasn't any, and he created it as he went.

The company was constantly in chaos. The founder-CEO had a new idea every week, usually with no business justification. My guy knew how to handle it. He'd break down whether the idea had product-market fit, whether users actually wanted it, whether it was worth the engineering investment. He didn't just say yes or no. He translated founder intuition into operational reality.

And when he didn't have a PM to work on something, he'd figure it out himself.

He once discovered that 85% of our fraudulent user accounts were registering with VoIP phone numbers. Nobody had thought to look for that pattern. He implemented a fix that blocked VoIP registrations and saved the company almost a million dollars a year in fraud costs.

He just figured shit out.

That's the difference. The enterprise hire needed infrastructure. He needed experienced PMs, documented processes, clear lanes. The senior director could build in chaos. He didn't need an org chart to function. He created order where there wasn't any.

After watching this pattern enough times, I've learned to look for a few things.

First, ask what their first 90 days would look like.

Listen carefully to the mental model underneath their answer. Some people will talk about assessing the team, setting up one-on-ones, establishing a cadence. Those are all reasonable things to do. But that answer assumes there's already a team to assess and a structure to optimize.

What you want to hear is someone who starts with getting their hands dirty. Learning the landscape. Doing the work themselves before they try to delegate it. The person I look for has a sequence in their head: do the work, build a process around it, teach it to others, then step back. If I hire someone on January 1st, they're doing the work on January 2nd. But by July 1st, their team should be handling most of it.

The enterprise exec who flopped had a different sequence. He came in ready to lead a team that does the work. He was prepared to mentor, develop, guide strategy. All the things a good executive should do. But his model assumed the infrastructure already existed. When it didn't, he had no fallback.

Second, ask them about a time the company strategy changed suddenly, or a key client threatened to walk unless they got a specific feature. Anything that would knock a bigger company off balance but happens every Tuesday at a startup.

Listen to how they respond.

If their answer is some version of "I'd push back and protect the roadmap," that's a problem. That works when you have leverage. You don't have leverage.

If their answer is "I'd do whatever the client wanted," that's also a problem. You can't build a product by chasing every request.

What you want is someone who can navigate the middle. Someone who understands that the client request might be unreasonable but the underlying need is real, and their job is to find a solution that works for both sides. Someone who's been in that situation enough times that they have pattern recognition, not just principles.

Third, ask when they last got their hands dirty. When did they personally dig into data, fix a process, unblock a problem that wasn't technically their job? If they can't give you a recent example, they've been managing too long. They're not going to suddenly rediscover that muscle at your company.

The mistake founders make is hiring for the company they want to be instead of the company they are.

You're at $2M ARR. You don't have departments. You don't have clear handoffs. You don't have documentation. You have a handful of people who are each doing eight things, six of which aren't in their job description.

The person who thrived at a $200M company with clear roles and established processes is going to drown at yours. They're not bad at their job. They're bad at your job, which is a different thing entirely.

After Suzy let the enterprise exec go, he sent me a message on LinkedIn. "The company just wasn't ready for executive leadership," he said.

He was right, actually. Just not in the way he meant it.

The company wasn't ready for executives who expected a ready-made situation. They were ready for leaders who could build the company into one that would eventually need that kind of leadership.

He wanted the finished house. What they needed was someone who could pour the foundation.