The Secret to Spotting a Great Remote Manager


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Let’s explore an underutilized indicator of a great remote manager—valuable for both companies looking to hire and applicants seeking a great leader. Retention rates are typically the go-to metric to use, but I think an even better measure is whether they've experienced boomerang employees: former employees who return to work for a previous manager.

The term "boomerang employee" is often discussed in terms of companies (employees leaving an organization only to return later). On the company level, boomerang employees don’t carry the same weight. The employee was familiar with the environment and the people. They knew what to expect with their return.

I think the more interesting measure is at the manager level. Here's why:

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Imagine this scenario: An employee leaves an organization, seeking a new challenge or a fresh opportunity. Sometime later, their manager moves to a different company and is hiring for a role perfectly suited for the former employee. The manager reaches out, and the employee enthusiastically accepts.

In this case, the employee had no clue about the type of environment they were entering. But they trusted the manager enough to dive in headfirst.

It’s not the company that drew the employee back, it’s the manager.

To me, this says so much more about the person as a leader than references ever could. References are talk, while examples of boomerang employees are action.

It’s often said that people don’t leave jobs; they leave managers. Boomerang employees force managers to reflect on the critical question:

Would people choose to work with you again?

It’s one thing to say “yes” in an interview or provide references, but boomerang employees are tangible proof of a manager’s ability to foster meaningful, lasting professional relationships.

This scenario typically tells me that the manager:

  • Saves the company time and money in hiring
  • Attracts talent that might not have been openly available
  • Is a leader that people want to work with again

Boomerang employees represent more than loyalty. They reflect respect, trust, and the positive impact a manager has had on their careers. If employees are willing to work with a manager again, even after leaving for personal or professional reasons, it speaks volumes about that leader’s ability to inspire and develop talent.

Managers who cultivate these relationships don’t just retain respect. They also build a talent pool that follows them. This pool saves companies time and money in hiring and onboarding.

Leaning on boomerang talent shouldn’t be used for every role. It’s important to strike a balance because over-relying on former employees can limit fresh perspectives and innovation. However, boomerang employees can be invaluable when you need someone reliable to start quickly or when specific, niche skills are required and hard to source publicly.

Why Retention Alone Isn’t Enough

So why not just use retention as the main metric? If they were such a great manager, why would the employee leave in the first place?

Retention tells only part of the story. People leave jobs for all kinds of reasons, many of which have nothing to do with dissatisfaction:

  • They want to go back to school
  • They're seeking a transition to a new industry
  • Their current projects no longer challenge them
  • They’re looking for advancement opportunities
  • They’re taking a sabbatical to recharge or explore personal goals

While managers should absolutely do their best to find solutions that retain talent, there are certain scenarios where the timing just doesn't work. In these cases, a manager who supports employees through these transitions can be more valuable than one who pressures a team member to stay, potentially creating complacency.

True Leadership

I always say, "Be careful of the byproducts of the metrics you are rewarding." By forcing 100% retention at all costs, managers risk creating stagnation and disengagement. Employees who feel pressured to stay may become complacent or resentful, leading to reduced productivity and innovation.

This approach ultimately harms both the company’s growth and the manager’s credibility. You want a leader who actively supports and celebrates growth, even when it leads an employee in a direction outside the company. You want a leader who says goodbye in a way that leaves the door open for future collaborations.

To foster boomerang relationships, managers should:

  • Cultivate relationships through a people-first approach to leadership
  • Assist team members with references and referrals when it's time to move on
  • Build trust by supporting employees’ growth, even if it means leaving the team
  • Instead of shaming departures, offer a proper send-off that celebrates contributions

The Value of Boomerang Employees

For managers, boomerang employees are a badge of honor, proof of their impact and ability to lead effectively. For companies, these employees save time, reduce hiring friction, and bring unique knowledge and experience to their organization. For applicants, they provide a clear preview of the type of leader they’re signing up to work with.

At the end of the day, good remote managers have references. Great remote managers have had boomerang employees.

So, ask them: Are you the kind of manager employees would return to?

TLDR

Boomerang employees (those who leave a manager and later choose to work for the same manager) are a powerful and underutilized measure of leadership.

They reflect trust, respect, and the lasting impact a manager has on their team members.

This indicator helps you get an inside look into the question: "Would people choose to work with this manager again?"

Quote of the Week

A leader’s success is best measured by the people who choose to follow them, even when they don’t have to.

In Other News

Introduce yourself to your remote team
"Some teams just call them “intro pages”, again at GitHub we call them “Human User Guides”, but I like the term “Talk to Me pages” to encourage actual chatter. I love being able to see that someone on my team also likes certain board games of mine, or even learning what not to bring up with someone."

What we can all learn from a 4-hour workweek
"When you do multiple things at once, you finish all of them later. Worst case everything gets completed close to the very end. When you work only on one item at a time, you deliver most of the items earlier. Every item takes less time from start to finish. And this is priceless, especially when you need to bring value early and often."

In Case You Missed It

The Truth About Ghost Employees
The latest attack on remote work is centered on "ghost employees" or workers who disappear from their responsibilities while still collecting a paycheck. Recently, I shared the real truth behind what's going on.

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Marissa
​Founder, Remote Work Prep

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