Mark Caswell: Why it’s time to rethink ‘mic drop’ career transitions

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I think we’ve been given bad advice on how to handle job transitions.

When people decide to quit a job, they typically resign out of the blue. Two weeks later, they leave and go do something else. Mic drop. The end. But in my experience, a “mic drop ending” is almost never the best approach—for the person or the organization.

I’ve been on both sides: the leader helping someone transition, and most recently, the person going through one. I’m grateful to have experienced what thoughtful career transitions are capable of being: collaborative, organization-building endeavors rather than solitary, relationship-ending ones.

So, I think we need some new advice on these transitions. They should be a conversation. Something leaders and employees navigate together. A collaborative effort to discover the best possible outcome for everyone involved.

Make it a conversation

Conversations about job transitions take guts and maturity—from both sides of the table. It takes vulnerability and a laying aside of the ego from everyone.

Individuals: Before initiating a transition conversation, it’s really important to get clear on the “why.” There are many correct reasons for leaving but also many that might not be. Has there been a change that’s causing new stress? Is that resolvable? Do you feel “trapped”? Why and how? Is the role not aligned with your skills and passions? What are those? Are you working with an organization that you like but with people you don’t? The opposite?

Answering those questions will help tremendously. Some problems might be resolvable. Some might not be. But having that knowledge will A) give you information on what to do next and B) give the organization constructive feedback it can use. This clarity will also help you avoid making a decision in the heat of battle.

Once you’re confident in your “why,” it’s time to thoughtfully involve your boss. Even in the most psychologically safe organizations, these conversations can be nerve-wracking. But approaching them from a place of empathy for the organization can be game-changing. After all, if you’re no longer a good fit, the best thing for the company is to find someone who is.

Just be sure to go into this conversation with an open mind. Be open to advice or considerations you hadn’t thought of. Be open to changes that might make your situation more tenable. It’s important to be open to being wrong, even as you also ensure you are strong.

Leaders: When an employee approaches you about leaving, it doesn’t feel good. It can feel like a personal indictment and failure. It also adds more work to your plate. However, you have to put ego, fear and frustration in the back seat. Simply hear the employee out. Approach the situation from a place of curiosity rather than judgment.

Once you have clarity on the “why” and the emotions have calmed, I find one question to be crucial: “If I were this person’s mentor or friend rather than boss, would I advise him or her to leave?” You would be surprised at how often the answer is “no.” And if you would not advise leaving, convince the employee to stay. Often, small adjustments or steps in a different direction are all it takes to solve a “fit” issue—especially for younger folks who don’t yet have a lot of context in their careers. I’ve written about the benefits of allowing and encouraging people to transition to other roles if the current one isn’t quite right.

Of course, sometimes the answer is “yes.” This person is no longer a fit for the organization, and, as a mentor or friend, you agree that he or she should leave. That has to be OK, too. Don’t try to save someone you shouldn’t save. And don’t get mad or defensive. It’s normal for organizations to grow out of people and for people to grow out of organizations. We need to start accepting and embracing that as wholeheartedly as we accept and embrace someone who decides to stay.

Thoughtful transition plans

Whichever way the conversation goes, the next step is to collaborate on a thoughtful transition plan. If the employee decides to stay, fulfill the promises you made about the transition—be it moving to another role, connecting the employee with training and development opportunities, or changing your behavior as a leader. Avoid vague commitments and put a real, time-bound plan together.

If the employee decides to leave, work together to design a transition that ensures a good ending and works for everyone. For senior leaders in transition, it might be worth considering a period where the departing employee coaches the next person up. It’s also worth encouraging the person to think about possibly taking a few weeks after leaving to decompress.

It’s amazing how many paths and possibilities can arise when these decisions are a collaborative effort. So let’s make potential transitions a conversation. Let’s make our organizations such that individuals can partner with their leaders to arrive at the best decisions about their careers—in a way that’s thoughtful, open-minded and empathetic above all else.•


Caswell is an adviser and board member at Resultant, an independent technology, data analytics and management consulting firm based in Indianapolis.

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2 thoughts on “Mark Caswell: Why it’s time to rethink ‘mic drop’ career transitions

  1. You’re joking, or wildly out of touch. Maybe this works in executive roles where everyone lives with funny money and hasn’t physically worked a day in years.
    But for the rest of us, no!
    Your employees should be expected to quit without any regard for your enterprise, until worker protections exist that prevent being laid off on the spot with zero notice and no compensation.
    They’ll ghost you until the boss openly discusses pay, benefits, and career opportunities – instead of using the confusion to manipulate or even threaten employees into worse conditions than they can handle.
    Workers will walk out and curse you loudly until you respect their situation and side of the table.

    If you don’t want Mic Drop moments, stop being the kind of people who deserve it.

    1. Wow Charles M! I’m sorry you appear to have worked in environments that don’t value people. I also take issue with your assertion that all businesses are out to screw employees. You may be right in some limited cases, but I submit that in the vast majority of cases, you are wrong – completely wrong! I have worked for 35 years in professional positions where my employers DID value people, they had the conversations suggested in the article at all levels in the organization, and people stayed – for decades. To suggest that the author is out of touch is just, well, wrong. Perhaps you need to evaluate where you work and make a change. If you stay and tolerate things you don’t like, then I would suggest you purchase a mirror.