If there’s one thing that never gets easier as a leader, it’s saying goodbye to a valuable team member. Employees leave for all kinds of reasons, but as a CEO, it’s easy to feel like you’ve failed somehow.

So, how should you feel when they come back? The corporate world is dealing with a new phenomenon right now—boomerang employees. About 4.5 million U.S. employees quit in November 2021 alone, and people who made big decisions in that sweeping resignation wave have had time to reconsider. According to a study from the Society of Human Resource Management, about one quarter of workers who have quit say they’re open to returning to their previous employer.

As the novelty of the Great Resignation wears off, many employees are asking: How do I go back? Meanwhile, employers are wondering how to do things better this time around? Fortunately, I have discovered these difficult questions have legitimate answers.


In this new era of boomerang employees, it’s more important than ever for both sides to avoid burning bridges.

Not long ago, we lost a talented member of our UX team. He was seen as a rising star, but there’d been a shakeup in his department and he began feeling disconnected from his new managers. This disconnection planted a seed of doubt within him, and when he eventually received an attractive offer from another company, he went for it.

But what happened after he made this decision is what is most revealing. First off, he left on good terms. He gave his two weeks’ notice and, to quote Sheryl Sandberg, “[He] didn’t leave before [he] left.” In other words, he remained engaged, driven, and committed up until his last day.

And it’s not just on employees to depart in a proper manner. Importantly, as a boss, you must refrain from reacting with ego when someone makes the choice to leave. It can be tempting to be offended when someone quits, but your employee has already grappled with the pros and cons, and it’s unlikely their decision is a personal reflection on you.

Furthermore, as a boss, don’t let an employee leave without telling you the things they want to tell you. At my company, we conduct exit interviews with everyone who leaves. It’s a big part of how we understand our employees’ experience and reconcile it against our daily operations.

If there’s something you instilled across the company that didn’t work, it’s your responsibility as the leader to accept the feedback and fix it. In fact, data shows 32% of workers quit because of a lack of opportunities for career advancement. For an employee, this is an understandable issue and, as an employer, it’s also an easy fix.

And another way to think about resignation is framing your employee’s departure as less of a “goodbye” and more as a potential “see you later.” In fact, it may be a better frame of mind (and logical part of a hiring process) to understand that employees’ decision to leave can change later. Your favorite employee could come back.


To illustrate this final tip, let’s revisit our UX worker who had moved on. After four months at his new job, our former UX worker realized the grass wasn’t so green in other pastures. The best part was he felt comfortable getting in touch with his former department managers about potentially coming back.

When the leaders at my company got wind of a possibility of re-hiring him, we knew we needed to get his reentry right. Indeed, his refreshed perspective could be a real benefit for us if we handled the reentry process well.

As an employee, there shouldn’t be shame or hard feelings in choosing to go back to a former employer. If there is, it’s a good sign that returning may not be the right move.

It’s also fortunate that, in the tech industry, we’re used to this. People often leave only to later return. Through those experiences, we’ve learned that they bring some valuable insights with them.

That’s why we do reentry interviews, too. However, it’s critical to do these types of interviews fast. In other words, the first days a worker is back at their desk are the most fruitful in terms of implementing change. This crucial slice of time imparts a halo effect.

A returning employee realizes what it was that wasn’t working beforehand and now has the clarity to re-imagine how their workflow could be better. As employers, it’s on us to let our boomerang employees know we care about their feedback. In fact, it’s that sense of being wanted that brings 16% of workers back to former bosses.


Returning employees are typically more satisfied and show greater commitment than external hires. Our boomerang UX worker came back with a refreshed sense of purpose, in part because he knew he could make a difference. Right away, he had ideas about how we could improve our training processes, because he’d had exposure to something new. He’d also had an opportunity to reflect on how we could improve the way we present our work to clients.

Just a handful of days back on the job, and the rehired employee was already seeing real impact from contributing his insights. Over time, this boomerang employee saw further benefits. He was able to leverage his other opportunity for more seniority and a better salary. The research backs this up: Returning workers have been shown to outperform new hires and are able to leverage that excellence for better compensation and work conditions for themselves.

As a leader and employer, I think it’s a win-win. I see now our rehire has a better understanding of what makes our workplace special and we certainly appreciate having workers who understand our business, our clients, and our team.


Ben Crudo is CEO of Diff Agency, as well as a technologist and e-commerce expert. More

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