Your Best Hire Might Be Your Worst Mistake

Most CEOs obsess over finding the “right” hire. But as Shannon Swift reminded me on The Scaling CEO, the wrong cultural fit, no matter how talented, will cost you more than you think.

Shannon is the founder and CEO of Swift HR Solutions, a firm she’s run for over two decades after leading HR at fast-growing companies like Zillow. She’s also spent more than 13 years in the Entrepreneurs’ Organization, advising and learning from hundreds of CEOs. Few people know the people side of scaling like she does.

Hired for Skills, Fired for Who They Are

Shannon didn’t mince words.

“People are hired for what they know and fired for who they are.”

That’s why CEOs must build culture screens into hiring. Skills shift. Priorities change. But values endure. If you compromise on alignment, your best-looking hire on paper may become your most painful mistake.

Culture Exists in Language and Stories

Culture isn’t posters on the wall. It lives in how leaders talk and the stories employees share.

Shannon said integrity at her firm doesn’t just mean honesty. It means being predictable. Your words must match your actions. And when leaders share stories of employees living values in action, those values stick.

As CEO, ask yourself: what stories are circulating in your company? They’re defining your culture whether you like it or not.

Settling Is the First Step Toward Decay

Every CEO faces pressure to fill roles quickly. Shannon’s warning is blunt: don’t settle.

When you make one “good enough” hire, you send a message that values are negotiable. That compromise compounds until the culture frays. If you wouldn’t both hire and fire based on a value, it’s not really a value.

The Hidden Cost of Turnover

Turnover doesn’t show up on a P&L, but CEOs feel it everywhere. These include exiting employees, lost productivity, recruiting fees, onboarding time, and even reputational damage on social media.

The smartest CEOs work with their CFOs to quantify these costs. Seeing the real numbers makes it clear: prevention through careful hiring is far cheaper than constant replacement.

Impostor Syndrome in the Boardroom

Behind closed doors, Shannon hears the same confession from many CEOs: impostor syndrome.

“Executives and CEOs are wondering how the hell they got here… feeling like they don’t deserve to be in the room.”

This self-doubt is more common than you think. For CEOs, the key is acknowledging it, surrounding yourself with peers and coaches, and recognizing that growth requires discomfort.

When the Job Stops Being Fun

Scaling often changes the CEO’s job into something they no longer enjoy. Some founders thrive early but struggle with later-stage demands. Shannon advises leaders to be honest about where they add the most value and when it’s time to bring in a COO or even a new CEO.

The message: don’t confuse stubbornness with leadership. Sometimes the best decision is to redesign your role.

AI Frees You to Be More Human

Shannon has seen HR transform with automation. What once took hours of paperwork now takes minutes. That frees leaders to focus on onboarding, culture, and connection.

AI won’t replace empathy. But by removing repetitive tasks, it gives CEOs more time to lead.

Final Takeaway

Your best hire might be your worst mistake if you ignore cultural fit. Scaling requires discipline: define values, enforce them through hiring, and never settle. The costs of turnover and cultural decay are far higher than the cost of patience.

I’m Glenn Gow. I coach CEOs who want to scale with the right people in place. On my podcast, I reveal the strategies elite leaders use to hire for culture and grow without regret.

Listen to the full episode of The Scaling CEO with Shannon Swift for candid lessons on hiring, impostor syndrome, and scaling with the right people.

Table of Contents
Glenn Gow
Privacy Overview

This website uses cookies so that we can provide you with the best user experience possible. Cookie information is stored in your browser and performs functions such as recognising you when you return to our website and helping our team to understand which sections of the website you find most interesting and useful.