How to Avoid the Most Common Onboarding Mistake

Hiring a new executive is just the beginning—onboarding them well determines whether they thrive or fail. Learn the critical mistakes to avoid and the proven steps to build trust, alignment, and momentum from Day One.

Key Takeaways

• Most exec onboarding fails because CEOs “hire and forget.”
• Early adjustments cost less than late-stage clean-up.
• When things go wrong, it’s often because trust was never really built.
• Start in the details—step back later as trust grows.
• Onboarding isn’t control—it’s an investment in momentum.

Imagine you finally found the hire you've been looking for.

After months of searching, interviewing, and backchanneling, you meet someone who says all the right things.

They seem like a perfect fit.

At last, you can delegate the role you've been carrying for too long. You’ve got other fires to fight.

So you pat yourself on the back and let out a sigh of relief…

But before you ride off into the sunset, here’s what usually happens next.

The Ugly Truth About Exec Onboarding

Most founders are so excited to make a hire that they fall into the classic trap: hire and forget.

You give them space—after all, they’re experienced. So you say something like this:

“Take a few weeks to settle in. Think through your priorities. Come back with a plan.”

They nod. They disappear into the calendar, and you get back to your to-do list.

Then, a few weeks pass and they present you their plan. It’s... different than what you expected. But they’re the expert, right? So you roll with it. After all, you don’t want to micromanage—you want them to own it.

Things move slowly... slower than planned. But again—you’re busy with other priorities.

Then, around month four or five, you start asking more probing questions. And as you dig into the weeds, your heart begins to sink.

“This is going in the wrong direction.”

“I forgot to tell them about X.”

“Why didn’t they show me this earlier?”

You panic. You jump in... hard.

They’re confused. From their perspective, you’ve been hands-off and all of a sudden you’re throwing a grenade into the plan you approved.

“You clearly don’t trust me anymore,” they say.

And they’re right.

Because the trust was never really built.

You lean in harder. They get demotivated. You get anxious and start to avoid them.

And just like that, you find yourself in a toxic relationship.

What happens next? Either they quit—feeling smothered—or you fire them.

Then it's down to you to clean up the mess: undoing their systems, unpicking their hires, and refocusing the team on the new (and original) vision.

You’re back to square one. Rehiring. Looking after their role. And completely maxed out.

Sound familiar?

The Better Way to Onboard New Execs

Most CEOs want to give their new exec space. They want to show respect and empower them.

However, the best CEOs do something different: they invest in the relationship upfront.

It’s easier to start with intensity and soften over time than to start soft and suddenly tighten the reins. So they set clear expectations from Day One.

Setting Early Expectations

When you bring on a new exec, you need to set them up for success. So rather than being laissez faire at the start, start in the details.

Here are a few of the expectations I set with my senior recruits that help me avoid some of the common issues later on.

1. We’ll sync daily for the first 2–3 months. Even if it’s just 5 minutes, frequent check-ins help us stay aligned as new topics and challenges emerge.

2. You’ll come with lots of questions. Being proactive in mining my knowledge is the fastest way to get up to speed on how things work here.

3. You’ll be curious about my standards and vision. One of my core responsibilities as founder is to hold the company’s vision. One of yours is to align yourself—and your team—to that vision.

4. We’ll build the plan together. If there’s a clash of vision early on, we’ll go with mine, because I have context you don’t. Failing to plan is planning to fail.

5. You’ll shift to async updates as trust builds. I prefer short Looms over scheduled meetings to reduce the coordination burden and protect focus time.

6. You’ll schedule a monthly conversation to surface misalignment. Misalignment is normal. Let’s assume it exists and make it our shared responsibility to find and resolve it.

You can (and should) ask about their expectations too. But be honest with yourself and with them about which you can realistically meet—and what needs to be earned over time.

Early Adjustments Cost Less

It’s tempting to delegate fast. But that instinct can cost you.

Giving too much autonomy too early wins you time in the short run, but the long-term risk is high—very high. Instead, you need to go against your instinct and spend more time upfront.

And if you ever doubt whether that investment is worth it, ask yourself: 

What would it cost to rehire this role in a year?

The answer isn’t just time and money. It’s lost momentum—and in a startup, momentum is critical.

Done right, onboarding is not about handing over the keys. It’s about building trust—deliberately, explicitly, and together.

Related readings

• How to Run Exceptional One-on-Ones
  
• How Smart Leaders Respond to ‘I Don’t Know’
  
• How to Ask Your Team the Right Questions