When Your First Executive Hire Doesn’t Stick
Hiring your first C-Suite executive should feel like a turning point. For many founders, though, it turns into a revolving door.
We’ve seen it happen too often. A founder makes that first big leadership hire, whether it’s a CMO, CDO, CPO, CTO, or CFO, hoping this person will “just get it” and instantly lighten the load. But a few months in, frustration sets in. Expectations are missed. The hire doesn’t stick.
The Myth of the Plug and Play Executive
There’s a common belief in startup culture that a great executive should walk in, grab the reins, and start running. No hand-holding. No hiccups. Just instant results.
But here’s the reality. Even the best leaders need context, clarity, and alignment. When expectations are vague or misaligned, even the most qualified hire can flounder.
Founders often assume things like:
“They’ve done this before. They’ll figure it out.”
“I shouldn’t have to spell it out.”
“If they’re really good, they’ll know what to do.”
Those assumptions can lead to costly outcomes. Missed goals. Cultural friction. Sometimes, even a total reset. We've watched it happen and developed a process and approach to counter these costly mistakes.
From Reactive to Proactive
Traditional coaching often waited until there was a problem like burnout, conflict, or turnover. Today, high-growth teams are bringing coaches in early, often alongside new executive hires, to help accelerate onboarding, improve team trust, and align leadership styles.
Methodologies like Conscious Leadership, The 15 Commitments of Conscious Leadership, and Radical Candor are frequently referenced. Many founders are also leaning into group coaching and cohort-based models, which create shared language and accountability across senior teams.
What Great Founders Do Differently
The founders who succeed don’t just hire smart people. They hire with intention. They define what great looks like before the search even begins. They understand their limitations, leadership quirks, and people management challenges. They come to our kick-off meeting open, honest, sometimes vulnerable, as we take a deep dive into their strengths, weaknesses, and use proprietary tools to uncover the blind spots they may not see.
Great founders approach candidate interviews with the following:
Having honest conversations about the company, successes, and failures.
Being upfront about what’s broken and what’s working
Aligning on what success looks like at 90 days, six months, and one year.
Being upfront with how they like to manage and what they expect
Sharing their strengths and weaknesses of their management and leadership style, where they experience conflicts, and how they resolve them.
Recognize that top talent and A-Players want to know the good, bad, and ugly.
Great hiring doesn’t start with a job description. It starts with an immense amount of founder self-awareness. The most successful founders we work with have a deep understanding of their strengths, blind spots, good/bad habits, and leadership gaps. They don’t pretend to be great at everything, especially not people management. Many visionary founders aren’t natural managers at all. Many lead by example. But the ones who thrive are those who know where they need support and intentionally build the right team around them. That’s where great hiring begins.
Final Thought: Expectations Shape Outcomes
Your first C-Suite executive hire isn’t just about taking work off your plate. It’s about evolving your role as a founder. That shift calls for looking within yourself as a leader, strong communication, alignment, and clarity.
If your last executive hire didn’t stick, don’t just chalk it up to “They weren’t the right fit.” Step back and ask yourself: Did I set them up to succeed? Were their goals and KPIs clear and realistic?
Because when you get it right, it changes everything.
Almost 20 years of combined digital and executive search expertise have taught us one fundamental truth: Great companies are not built by job descriptions. They are engineered by visionary leaders who know their limitations and who see around corners.
