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Understanding the Executive Search Process: A Strategic Approach

  • tcinello
  • May 6
  • 4 min read

Updated: May 8


By Tony Cinello, Founder – Anthony Andrew


Executive Summary

Hiring the right executive isn’t just about who you want—it’s about knowing exactly who you need.

In the mid-market, where leadership gaps can stall growth or break momentum, too many companies treat executive search like it’s just another hiring workflow. But it’s not. It’s a business-critical process that demands structure, insight, and strategic alignment. Especially in moments of change—post-acquisition, leadership transition, or expansion into new markets—getting it right is non-negotiable.

In this article, I break down how a strategic retained search process works, what most companies get wrong, and what separates a recruiter from a true executive search partner.


Why Structure Matters More Than Speed

In a recent Deloitte survey, 84% of CEOs said their company’s future success depends on identifying and developing the right leaders—but only 42% believe their current process is working (Deloitte, 2023). And in my experience, the pain shows up when it’s already urgent:

  • A PE-backed CFO exits mid-fund cycle

  • A VP of Sales is underperforming in a growth market

  • A post-merger integration needs a seasoned operator yesterday

In those moments, companies panic. They move fast—too fast—and start interviewing people who are “available,” not “right.”

That’s where search falls apart.


The Real Cost of Getting It Wrong

According to the Harvard Business Review, the failure rate for new executives hired externally is between 40% and 60% within 18 months (HBR, 2022).

And those failures aren’t just expensive—they’re disruptive:

  • Delays in strategy execution

  • Lost revenue momentum

  • Culture damage and team turnover

  • Frustration from investors or the board

In a $100M company, a bad executive hire can easily cost $1M–$2M in hard and soft costs—if not more.


What a Strategic Search Process Looks Like


Here’s the playbook we use at Anthony Andrew—and what I believe every mid-market organization deserves when it’s hiring mission-critical talent:


1. Role Definition + Success Profiling

Before any outreach begins, we define:

  • The true business problem the role needs to solve

  • Success criteria for the first 12–18 months

  • Cultural and leadership style alignment with the existing team

This phase includes stakeholder interviews, org design considerations, and sometimes even challenging what the “job title” should be.


2. Market Mapping + Research

This is more than just scanning LinkedIn. We conduct custom research into:

  • Competitors and adjacent industry talent

  • Passive candidate pipelines

  • Compensation benchmarking

  • Relocation feasibility (especially in Texas markets like DFW, Austin, Houston)


3. Candidate Outreach + Assessment

With messaging aligned and targets identified, we:

  • Reach out with a high-conversion message strategy

  • Vet for hard skills, leadership style, and cultural match

  • Conduct structured behavioral interviews and scorecards

  • Present only a curated short list of candidates who fit the brief


4. Interview Management + Client Calibration

We partner with hiring execs to:

  • Structure the interview process for clarity and consistency

  • Debrief after every round

  • Align stakeholders on what “good” looks like (and avoid mixed signals)


5. Offer Design + Close Strategy

Top-tier executives are almost never “on the market”—they’re being pulled. That’s why we:

  • Advise on comp structure, equity, and relocation

  • Navigate counter-offers and timing windows

  • Ensure a 360° alignment before close


6. Onboarding and First 100 Days Support

The process doesn’t stop at signed paperwork. We provide a structured onboarding framework and executive coaching access to increase first-year success and reduce turnover risk.


What Clients Often Get Wrong


Here are the most common myths I see CEOs and CHROs believe—and why they hurt:


  • “We’ll just post the job and see what comes in.” → Top executives don’t apply. They’re recruited.

  • “We don’t have time for a full search—we need someone now.” → A bad hire wastes more time than a thorough search ever does.

  • “We’ll hire someone we trust from a past role.” → Familiarity ≠ fit. Especially when the business model or culture has changed.

  • “Let’s go with a contingency recruiter—they’re faster.” → Contingency = transactional. Retained = strategic partnership.


The Recruiter’s Role: Not Just Filling a Seat

When I run a search, I’m not just looking for resumes—I’m solving a leadership puzzle.

That means challenging assumptions, aligning decision-makers, and protecting your brand in the market. Especially in the $25M–$1.5B range, where every leadership hire can shift trajectory, search is a strategic function—not just a sourcing function.


Conclusion


The executive you hire next will shape your business for the next 5 years—or set you back 18 months.

If you’ve underestimated the complexity of executive hiring, you’re not alone. But you don’t have to go it alone either.

If your team is preparing for a transition—or if you’re wondering why your last leadership hire didn’t stick—let’s connect.

Because who you hire isn’t just a decision.It’s a strategy.

—

Tony Cinello Founder | Anthony Andrew Retained Executive Search | Leadership Advisory



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