Just got back from a remote sensing company where I was talking to their management about creativity in sales.

Let me get straight to the point:

Are we raising our kids better than we’re managing our sales teams?

Think about it. When your daughter wants to quit ballet and try MMA fighting instead, what do you say? “Good for you, honey!” When your son switches from basketball to football every other month, you support it.

Why? Because we instinctively know that:

  • Testing different approaches builds confidence
  • Discovering what works is messy
  • The joy of finding your path is irreplaceable
  • Failure is just feedback

Yet Monday morning rolls around, and what do we tell our sales teams?

“Stick to the script.”
“Follow the MEDDICC questionnaire.”
“Here’s your talk track.”
“This is how we’ve always done it.”

No wonder your top performer is staring at LinkedIn job listings during your Monday morning meeting.

The Creativity Crisis in Sales

There’s nothing worse than a sales rep sitting on their couch Sunday night with that knot in their stomach, dreading another week of robotic sales work. I’ve been there. You’ve probably been there too.

The problem isn’t the quota. It’s the cage we put around how they can achieve it.

When a rep can bring their own creativity to a deal, magic happens:

  • They’re invested in the outcome
  • They tap into their natural strengths
  • They actually ENJOY the challenge
  • They solve problems AI never could

What Leaders Get Wrong

Dear sales leaders who are nodding along but will change nothing:

If you agree that creativity and opportunity are essential for children’s development, why are you blocking it for your teams?

Your playbook isn’t sacred text. Your process isn’t perfect. And your “this is how we’ve always done it” mentality is killing the spirit of your best people.

A Challenge for Sales Teams

Next week:
1. Ask each rep to bring ONE creative approach to a stuck deal
2. Give them permission to try something that isn’t in the playbook
3. Celebrate the attempts, not just the wins
4. Watch what happens to their energy

And for the individual reps reading this:

Find the parts of your job where you can inject creativity. Guard those opportunities fiercely. Work on things you’re passionate about. I promise AI won’t replace a genuinely creative, passionate salesperson who brings humanity to their deals.

Your motivation will thank you. Your results will speak for themselves.

And your Sunday nights might actually become enjoyable again.