When companies reach out to me to help them with executive search, they often describe their open role as “pretty straightforward.”
“We just need someone who’s run a sales org before.”
“It’s a backfill—we’re not looking to reinvent the wheel.”
“We want a strategic partner, but someone who can roll up their sleeves.”
At first glance, it might sound like a standard search. But in my experience, there’s no such thing as a truly simple executive hire. Because behind every job description is a company with a unique mix of personalities, politics, expectations, and history—and that’s where the complexity lives.
As someone who often combines executive search with leadership coaching, I specialize in reading between the lines. I listen for what’s not being said; I pay attention to where people hedge. I ask the questions that surface the real tensions and then I help clients get clear on what kind of leader will actually thrive in the role.
Because when you misdiagnose a hiring need, it doesn’t just slow you down; it sets you back.
What looks simple on paper is often complex in practice
Here’s a story I’ve seen play out more than once:
A company comes to me looking for a new Chief Marketing Officer. On paper, the brief is clear: They want someone who can build the brand, drive demand, and lead a small but mighty team. It’s positioned as a plug-and-play hire.
But as I dig in, I start to uncover layers. The last CMO was beloved by the team but lacked a strategic edge. The CEO wants more “rigor” but isn’t quite sure how that will land culturally. The sales org is hungry for tighter alignment with marketing, but they don't have a seat at the hiring table. The internal brand is stronger than the external one. And there’s a new board member quietly pushing for someone with direct-to-consumer chops—even though that’s not in the job description.
Now we’re in different territory.
It’s no longer a “simple” hire. Now we’re looking for a transformational leader, a culture translator hire. This is a role that demands emotional intelligence, backbone, and strategic vision in equal parts — and hard skills the client didn’t initially identify.
Complexity hides in plain sight—if you know where to look
Most clients don’t come out and say, “There’s political tension on our leadership team.” Or “We’ve got a high performer who’s quietly sabotaging the search.” But those dynamics shape the success of every executive hire and spotting them is part of the work.
During the discovery process, I use coaching techniques to gently surface hidden dynamics. I listen for contradictions—like when someone says, “We want a bold, visionary leader” but also mentions how the last person got fired for “moving too fast.” Or when they say, “We’re open to fresh perspectives,” but they seem to be most interested in candidates from their industry.
These aren’t red flags—they’re breadcrumbs. And they help me uncover what kind of candidate will thrive not just on paper, but in practice.
This is also why I create customized interview questions for my clients. Instead of pulling from a routine, recycled list, I design questions that get underneath each candidate’s intrinsic capabilities and motivations. It’s how we uncover whether someone can navigate the specific challenges of your organization—not just do the job anywhere.
The high cost of misdiagnosing a hiring need
According to Harvard Business Review, nearly 50% of executive hires fail within 18 months. And research from SHRM shows that the cost of a bad hire can reach up to five times the person’s annual salary when you factor in lost productivity, team disruption, and the cost of restarting the search.
I’ve seen it happen. A company hires a CFO thinking they need a tactical operator—someone to clean up the books and tighten up reporting. But they overlook the need for strategic partnership, someone who can hold their own in the boardroom and within six months, the CFO is sidelined, the CEO is frustrated, and the finance team is demoralized.
That’s why I tell my clients: even if you think the hire is straightforward, it’s worth digging beneath the surface to get it right. Because the stakes are too high to treat a leadership role like a transactional fill.
How a boutique process solves complex hiring problems
One of the benefits of working with a boutique search partner like TKJ Leadership is that we’re not bound by rigid processes or “off-limits” constraints. I don’t have to protect client relationships at Pepsi or Ford or Pfizer—so I can recruit top talent from companies other search firms can’t touch.
But beyond the logistics, it’s about approach. I don’t start with a generic job spec. I start with a conversation. I ask about what’s worked, what hasn’t, what’s changing, and what’s quietly keeping your team up at night. I talk to stakeholders across functions. And I pay attention to what the role represents—not just what it requires.
Then I go find someone who can step into that complexity—not just survive it, but shape it.
Our process is also fast. Most of our searches wrap in 1–2 months, compared to the 3–5 month average at large firms. That means less disruption, lower opportunity cost, and faster momentum for your team.
We also help clients onboard new leaders thoughtfully and effectively, ensuring they have the context and support to succeed. 3 months of onboarding is included in our search process. Because even the best hire can falter without the right runway.
What great hires are really made of
At the end of the day, great executive hires aren’t just about competence. They’re about clarity (what do we actually need?), chemistry (who will thrive in our culture?), and courage (are we willing to choose the person who can truly lead us forward—even if they don’t look like what we first imagined?).
That’s what I help my clients navigate.
It’s never just about filling a seat. It’s about building the kind of leadership team that can carry your vision forward—through the messiness, the transitions, and the unknowns.
So the next time you find yourself thinking, “This should be a pretty straightforward hire,” I’d invite you to pause.
Ask yourself:
What’s actually changing in the organization right now?
What kinds of leadership styles have succeeded—and failed—here?
Where might there be hidden friction or unspoken expectations?
And then ask a partner like me to help you think it through. Because hiring is rarely simple.
But when it’s done well? It’s transformative.
“TKJ Executive Search takes a uniquely thoughtful approach to finding the best person, not only for a position but also as a match for our organization and culture. To be able to collaborate on the important nuances makes all the difference. They are highly intuitive, deliberative and thorough, and they are authentic partners with their clients.”
