Hiring for Alignment (The Elephant and the Rider)

Hire leaders who already want to go where the business needs to go

Andrew Wilkinson
I've run 75+ businesses. Here's why you're probably chasing the wrong idea.

Hiring for Alignment (The Elephant and the Rider)

"I've found that hiring CEOs is like they're an elephant and you're the rider. They're going to go wherever it is that they want to go. And so listening incredibly carefully to people's words and their experiences, because generally people will do the thing they tell you." - Andrew Wilkinson

What It Is

This framework helps boards and founders hire executives—especially CEOs—by focusing on alignment rather than attempting to redirect. The core insight: senior leaders will pursue their preferred approach regardless of what you ask them to do. You cannot steer an elephant; you must choose an elephant already heading where you need to go.

The framework applies the principle "to a man with a hammer, everything looks like a nail" to executive hiring. If someone's expertise and passion is enterprise sales, they will pursue enterprise sales—even if you explicitly ask them to focus on organic marketing.

How It Works

The Elephant Principle:

  • Experienced executives have strong convictions about what works
  • They will naturally gravitate toward their expertise and preferences
  • Coaching, directing, or redirecting rarely works
  • They will sandbag or half-heartedly attempt approaches they don't believe in

The Hammer Problem:

  • Enterprise sales expert → Sees every growth opportunity as enterprise sales
  • Organic marketing expert → Sees every growth opportunity as content and community
  • Product expert → Sees every growth opportunity as product improvements

Warning Signs of Misalignment:

  • Candidate keeps returning to their preferred approach despite your framing
  • Interview answers don't match what you need
  • You're thinking "I can get them to try this other approach"

How to Apply It

  1. Define what the business actually needs:

    • What approach does the business require right now?
    • What specific capabilities must the leader have?
    • What would success look like in the first year?

  2. Listen carefully during interviews:

    • What approach does the candidate naturally advocate for?
    • What examples do they cite from their experience?
    • Where do they show genuine enthusiasm vs. polite agreement?

  3. Look for nodding, not redirecting:

    • "I want to be nodding along. I want to go, that's exactly what I would do or that's way smarter than my idea."
    • If you're constantly thinking "but what about..." → misalignment

  4. Don't try to change direction:

    • If their instincts differ from what you need → don't hire
    • No amount of onboarding or coaching will override their convictions
    • "Anytime I try and pull them in a certain direction or coach them... it just doesn't work"

  5. Then leave them alone:

    • Once you've hired an aligned leader, step back
    • Trust their judgment—that's why you hired them
    • Interference undermines both their effectiveness and ownership

Common Mistakes

Mistake: "I can change their approach"

  • Example: Hiring enterprise sales expert but telling them to focus on organic
  • Result: They pursue enterprise sales anyway, or sandbag the organic efforts

Mistake: "They'll adapt to our needs"

  • Example: Expecting a product-focused executive to become sales-focused
  • Result: Frustration on both sides, eventual parting

Mistake: "We'll course-correct in board meetings"

  • Example: Trying to redirect strategy every quarter
  • Result: "They don't really put their heart into it or they're just placating me"

Source

  • Guest: Andrew Wilkinson
  • Episode: "I've run 75+ businesses. Here's why you're probably chasing the wrong idea."
  • Key Discussion: (00:39:39) - Elephant and rider metaphor, hammer/nail problem
  • YouTube: Watch on YouTube

Related Frameworks

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