WHAT THE RIGHT HIRE NEEDS TO KNOW

There’s a moment in most founder-led companies when things start to feel more stable. You get traction, a team, maybe even some breathing room.

That’s also when it’s easiest to let your guard down and make a hire that slows everything you have in motion.

I’ve seen it happen again and again. With the best of intentions, a founder brings in someone who’s run big teams or scaled a company they admire. On paper, they’re perfect. But pretty quickly, it becomes clear they’re not built to work in a business that’s still taking shape.

What early-stage companies really need is people who can build while the ground is still moving. People who understand that clarity doesn’t come first. It gets created along the way.

Read more in What It Really Means to Work with a Founder.

When you hire someone who doesn’t see that, they start asking for structure when what’s needed is judgment. They slow things down without meaning to. And if you don’t catch it early, you lose more than momentum. You lose the edge that made the company work in the first place.

PERSPECTIVES

“A startup is not a smaller version of a large company."
— Steve Blank, entrepreneur and author of The Four Steps to the Epiphany

MARK MY WORDS

One of the hardest parts of 2025 was realizing that some of the hires we made in years prior weren’t what we needed, and it caught up with us.

They came from structured, well-established companies. They were used to what I call Professional Mode — where clarity comes first, systems are already in place, and the playbook is clear. But at Ninety, we were still operating in Founder Mode.

We needed people who could act without certainty. Who could move fast while things were still taking shape. Instead, we found ourselves explaining, clarifying, and translating when we should have been doing meaningful work.

In Stages 3 and 4, the founder’s intensity isn’t a gap to fix. It’s the force that holds everything together. When you try to professionalize too soon, it creates confusion, misalignment, and more work than before.

ONE MORE FOR THE ROAD

In case you missed it, here’s more from Founder’s Framework:

The Real Reason Founders Burn Out

It’s not the hours. It’s the lack of structure around them. This blog unpacks how intensity without consistency breaks even the most driven leaders.

[Read Now]

The soundtrack for every founder who’s second-guessed a hire halfway into onboarding.