The Boomerang Employee Dilemma 

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(And Why “Never” Isn’t Always Right) 

“Your dead to me.” 

“They left once.  

They’ll leave again.”  

“Nothing’s changed.”  

“We’ve moved on.” 

But here’s a different perspective:  

What if we’re asking the wrong question? 

The Emotional Response 

Most leaders react with: 

  • Hurt pride 
  • Wounded ego 
  • Sense of betrayal 
  • Fear of repetition 

And miss the strategic opportunity. 

The Reality Check 

Before saying “never,” consider: 

  • What they learned elsewhere 
  • How they’ve grown 
  • What perspective they gained 
  • What networks they built 

Sometimes the best training Happens on someone else’s payroll. 

The Strategic Questions 

Instead of “should we?” Ask: 

  • What’s really changed? 
  • What new value could they bring? 
  • What problems have we fixed? 
  • What’s different now? 

The Analysis Framework 

Consider these factors: 

  1. Exit Context 
  • Why did they really leave? 
  • Has that issue been addressed? 
  • Could it happen again? 
  • Should it matter? 
  1. Growth Assessment 
  • What have they learned? 
  • How have they developed? 
  • What new skills do they bring? 
  • What connections have they made? 
  1. Cultural Impact 
  • How will others perceive this? 
  • What message does it send? 
  • How will it affect morale? 
  • What precedent does it set? 

The Professional’s Choice 

You can: 

  • Hold firm to “never” 
  • Close doors permanently 
  • Miss potential value 

Or: 

  • Evaluate each case 
  • Consider strategic fit 
  • Make rational decisions 

Because here’s the truth: Sometimes the best hire Is someone who knows exactly What they’re coming back to 

Next Steps 

  1. Create clear rehire criteria 
  1. Build evaluation processes 
  1. Remove emotion from decisions 
  1. Focus on strategic value 

It’s not about second chances.

It’s about smart business. 

This article was developed from real client questions. Our most insightful content comes from working professionals wrestling with actual market challenges. 

Have a Sales or Marketing Question? 
We answer one reader question each week, turning real-world challenges into actionable insights. Submit your question about sales, marketing, or business development to colin@salestriage.com. 

 

Previous Reader Questions Tackled: 

  • When Your Best Salesperson Leaves 

  • The Price Objection That Isn’t About Price 

  • You Don’t Have To Do It Alone 

 
 

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