Dane Sanders

Does Dreaming Encourage Leaving?

published9 months ago
5 min read

Hey Squad Leader

Imagine the scene: After just ten months, your most vital talent gives you her two weeks' notice. You're perplexed. Maybe even a bit hurt.

"What went wrong?" you ponder. "Was it something I said?"

To make matters worse, it's also peak season in a brutal labor market. Your hurt turns to frustration… and then irritation. Your pondering pivots too.

"Isn't it a bit unprofessional of her to bail now?"

Then, the final kicker: You find out through the grapevine that she's going to work for your direct competitor… for a title change and a bit more money.

Now, you're gutted. It's feels personal. You can't get your mind off of what feels like a betrayal. So many other fires are vying for your attention, but you can't stop thinking about this mess. Your partner gently suggests you're obsessing. And, they're right.

"But, c'mon!" you protest! "Why did my best employee just up and leave me?"

Previously on TMYD

Last time, I made the case that if you want your employees to help you achieve the company’s dreams, it’s critical that you help your employees achieve theirs.

Paychecks aren’t enough. If you want their heart, they need yours too.

When I suggest to leaders that they ought to encourage employees to dream, most — if they’re honest — get a little bit nervous.

“Won’t dreaming wake them up to the idea that they should leave?”

It’s a completely understandable fear.

As a young entrepreneur, a veteran business leader and I were talking through Michael Gerber’s E-Myth Revisited. In it, the author paints a picture of entrepreneurship with a fictional scene: An upstart baker going to work for a famous bakery.

When she first lands the job, she is thrilled!

But after being there for a minute, she realizes that she’s working hard for someone else’s dream and decides to break out on her own. It’s not surprising. That dynamic is so familiar, it’s cliché.

What surprised me wasn't the scene in the book. It was my colleague's selfish response: “Well, I’m sure not sharing this book with my employees,” he blurted.

The implication was clear: He viewed employees as leased property, not people.

Will Inviting Dreams Wake Them Up?

It’s not that much of a leap to start believing that if you invite dreaming, you’ll encourage leaving too. But, you’d be wrong.

If the data is any indicator, they were thinking of leaving already.

That’s the big misunderstanding in the Great Resignation.

Most employees are considering quitting because they wonder if another job might get them closer to their dreams. So, they see their current job as a stepping stone instead.

This is the moment when fear can enter the conversation. As leaders, we are scared to invite dreams because we’re afraid to lose something we don’t even own.

It’s objectifies our employees. Even our language gives the impression it’s all about us. Are our employees ours?

It turns out they’re not.

New Glasses

The leaders of Great Organizations see things differently.

Said better, they see things through other people's glasses. They look at things like turnover from all sides, including their employees. Then, when they put their glasses back on, they can see everything better. They leverage empathy as a strategy to gain data that is otherwise inaccessible.

Look. I’m not naive to the reality of turnover. Not only is it expensive, but it’s also painful. But if it’s going to happen at some point anyway, wouldn’t it make sense to make the most of it?

Leveraging Trust

Everyone knows that teams run on relational trust. Stephen Covey famously wrote that teams travel at the speed of trust. Your collective capacity gets smaller when you don’t actively build more of it.

You’ll never get the job done without trust.

When someone moves on from your organization, consider it a trust test.

Make no mistake. The employees left behind are watching what you do next.

Want to know the quickest way to build trust in those moments?

Celebrate the exit.

Leverage the moment.

Turn the negative you’re experiencing into the positive that it could be.

The Magic of Positive Turnover

At TMYD, we call employees that leave well “Positive Turnover.” That’s not spin. That’s facts.

Consider the logic:

  1. An employee is thinking about leaving (or is frustrated or just generally disengaged).
  2. You intervene by asking about their dreams (better: you offer to help them achieve them).
  3. They (a) experience and then (b) internalize that even if they don’t have their dream job, they have a job that helps them achieve their dreams.
  4. Their engagement goes up, and retention now has a chance to follow.
  5. The employee doesn’t stick around forever (none do), but they stay longer than they would have.
  6. This saves you money in the short term and builds trust in the long term. Every month of not having to replace a key employee is money in your pocket.
  7. With dreams affirmed, other people in the organization feel safe to talk about their ambitions.
  8. Employees who will leave tend to forecast it, buying you time to prepare.
  9. The goodwill you invest in travels — you become famous as an organization making recruiting easier. Glass Door becomes your friend.
  10. You create a strategic advantage over your competition because you play big (freedom) while they play small (fear).

In short, the fastest way to encourage organic engagement, retention, and recruitment is to actively support employee dream pursuits, whether at your company or beyond.

This isn’t just the human thing to do.

It’s also the strategic thing to do.

Next Time on TMYD

In our next installment, we’re taking a turn back to you.

More specifically, we will talk about why so many leaders fail to lead themselves very well. We talk a big game about the important stuff (big game) but prioritize the urgent (small game) instead. I can’t wait.

Proud of you,


P.S. If you feel like cheering or sneering about the ideas in this newsleader, let me know about it at — I’d love to hear and promise to answer you back personally.

P.P.S. Bonus A brand new season of Converge: The Business of Creativity Podcast officially launches next week (and will continue to publish on the alternate weeks to this publication).

Leaders subscribed to (you) get early access to my interview with Essentialism and Effortless author Greg McKeown. Check it out here!

Dane Sanders is CEO of His team of certified mental health professionals and coaches - trained in TMYD's motivation modality - offer workshops tailored for organizations looking to become great. Tom Rodriguez is TMYD's Chief Mental Health Officer. Comments, questions, and inquiries are always welcome at

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