Your Boss Is Leaving for Another Job. Should You Follow?

When your boss leaves for a new company, it can be tempting to try to follow them, especially if you’ve had a strong working relationship and built up trust. But is it a good idea? In this article, the author offers advice from Nancy Rothbard, a professor of management and the deputy dean at the Wharton School of the University of Pennsylvania, and Arika Pierce Williams, a leadership development consultant and the president and founder of Piercing Strategies. They outline five questions to ask yourself before making the leap: 1) Do I know why my boss is choosing to leave? 2) How critical has my boss been to my success? 3) How worried am I about the organization’s future? 4) Do I have the option to leave — and do I really want that? 5) Has my boss explicitly offered me a job?

When your boss leaves for a new job, it can trigger a wave of introspection. You might find yourself thinking about your goals, your sense of loyalty, and whether your own career is headed in the right direction. Perhaps most importantly, the departure raises a question: Should you follow?

It’s natural to feel worried or uneasy about what lies ahead either way, according to Nancy Rothbard, a professor of management and the deputy dean at the Wharton School of the University of Pennsylvania. “The psychological reality that many people experience when their boss leaves is fear,” she says. “They wonder, ‘What’s going to happen to me if I stay or if I go?’” The decision to follow your boss requires careful consideration. You’re not just switching workplaces, after all. You need to reflect on your priorities, principles, and where you see yourself in the future.

In the end, it’s up to you, says Arika Pierce Williams, a leadership development consultant and the president and founder of Piercing Strategies. “You have to own your career,” she says. “Your boss can influence its direction but shouldn’t control it.” Here, according to Rothbard and Williams, are the five questions you need to ask yourself before you follow your boss to a new opportunity.

1. Do I know why my boss is choosing to leave?

People move on from jobs for many reasons, your boss included. It doesn’t necessarily mean that they’re miserable or that they think your current company is doomed. “They might want more money or career advancement or better work-life balance or just the chance to do something new and different,” says Williams.

And while it’s impossible to know exactly what’s driving their decision, it’s worth trying to understand your boss’s motivations when you’re considering following them out the door. Williams recommends asking your boss to have an offline, one-on-one conversation. They’re likely to be more candid in private than they are in public with the team. “Try to learn what they think the new organization or opportunity offers that their current one lacks,” she says. 

Having this information can help you make more informed decisions about your own path, she adds. It might also prompt you to look closely at your role and organization and see if it matches your personal and professional goals.

2. How critical has my boss been to my success? 

Your boss’s departure is likely to have a deeper impact if they’ve been more of a mentor than a manager to you. You might worry about your career growth without their guidance, or your standing at your company without their advocacy on your behalf, says Rothbard.

“The departure could leave a hole in terms of your support network within the organization,” she says.

Rothbard recommends evaluating the breadth of your connections at work, or what she refers to as your personal “ecosystem of sponsorship.” Look at potential avenues for growth and advancement. If you have mentors and sponsors other than your boss, and if you see possible ways to move up in the company without your boss’s direct backing, this departure could be a chance for you to explore new opportunities. It might even be a way to step out from under their shadow.

“But if you don’t have other sponsors and you don’t see a pathway for growth without the support of your boss, that’s when you’re going to be more concerned about remaining,” she says.

3. How worried am I about the organization’s future? 

Your boss’s leaving has an effect on your career trajectory, but it also has implications for the larger organization. “You’re not just thinking, ‘What’s in it for me,’ but also, ‘Where’s this company going and what’s going to happen to it as a result of this departure?’” says Rothbard.

This is especially true if you subscribe to your boss’s vision and leadership style. “If you believe this person is so essential to the organization’s future, you’re going to be more worried about their leaving,” she says.

Rothbard suggests taking a hard look at the potential successors in line for your boss’s position, assuming you’re not among them. Consider whether you trust these prospective leaders to guide the organization in a way that fits with your values, or if you fear they might steer it in a direction that concerns you.

This is also a prime time to have a skip-level conversation with your boss’s boss about your future, adds Williams. True, you might not be ready to move into your boss’s role, but there might be an opportunity to assume some of their responsibilities. “It’s a moment to look at the gaps in your technical and leadership skills,” she says. “Get clear on what you’re working toward and the things you need to accomplish before you’re seen as ready to step into a larger role.”

4. Do I have the option to leave — and do I really want that?

These considerations might be moot, at least in the near term, if you don’t have an explicit offer from your boss or another opportunity lined up, notes Rothbard. “It’s a luxury to quit your job,” she says. “And it’s hard to be idealistic about your career without an available alternative that aligns with your values.”

In this case, you might need to stick it out — and that’s not necessarily a bad thing. Your boss’s announcement might have initially stirred emotions and concerns, but with time, things tend to settle. You might find that your career can progress even without your boss’s cheerleading. And the company can continue functioning without them. 

“We often have a gut reaction to things and sometimes we’re wrong,” she says. “You might need to give others the benefit of the doubt.”

Lacking an immediate escape route is also an opportunity for some soul-searching, says Williams. Change is hard; it’s understandable why you dread having to start from scratch with a new manager. “Getting assigned a new boss can feel like starting your job all over again,” she says. But your inclination to cling to what’s familiar might not be the wisest career move, she says. “Having someone you trust, like a career coach, mentor, or friend, can be helpful in sorting through these feelings and getting unbiased advice.”

5. Has my boss explicitly offered me a job?

For starters, don’t feel slighted if your boss hasn’t asked you to come with. “It might not have occurred to them, and it might not be in their thought process to even ask,” says Rothbard. 

But if you’re close with your boss and you value your professional relationship, it’s worth exploring the possibility. Rothbard points out that it could be mutually beneficial for your boss to consider bringing you along. She cites research that suggests that hiring high-functioning groups of people who already work well together tend to quickly get up to speed in new organizations. Their established relationships and trust allows them to hit the ground running and make an immediate impact. 

No need to be pushy or desperate. Simply ask whether there could be a role for you at the new organization, says Rothbard. “It might not be starting tomorrow; it might be two months from now or even later in the future. But it’s good to keep that dialogue open.”

And yet, don’t get carried away and assume that your boss always knows best, cautions Williams. “Reach out to the people who would be your colleagues so you can understand what the opportunity entails and what the culture of the organization is like,” she says. “Your role might look very different at the new company from your current one.”

Having a boss whom you trust with your career is a beautiful thing. But remember: bosses are humans, too, “and they can operate selfishly,” says Williams. “They might want to bring you along because it makes their life easier.”

Harvard Business Review