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Been the boss

I.M. Wright The common thought that “If I were the boss, I’d do things differently” takes on new meaning when you’ve been the boss. Many of us get that chance when our manager is away (or leaves), and we’re chosen to take over for a time. I’ve covered becoming a manager, or even a manager of managers, but I haven’t discussed the weirdness of returning to your old role after being the boss.

When you do your boss’s job, especially for an extended period, you gain respect for how difficult it can be. There’s complexity and nuance to the role that you aren’t aware of without doing it. Some puzzling policies your boss follows prove to be invaluable, while other practices may be superfluous or even counterproductive. Regardless, being the boss is an eye-opening experience that lets you see your world from a new perspective.

When you return to your old role, after being the boss, it feels strange. You may find yourself defending your boss when your peers are upset and criticizing your boss when your peers are indifferent. What the heck happened to you? How are you supposed to engage with your manager and teammates, especially when your boss is struggling? Should you return to being the boss? Glad you asked.

That’s a problem

Let’s start with engaging your peers after being the boss. When they are upset at your boss, it’s important to empathize and remain a trusted member of the team, even though you also understand the tradeoffs your boss is making. Just because you can see things now from your manager’s perspective doesn’t mean you’ve forgotten what it’s like as an underling. Start by reflecting your teammates’ familiar perspective (“That’s so messed up!”), but then perhaps add, “Though, I can kind of see why our boss did that.” That way, you can provide context while remaining close to your peers. Now you can see things from both sides.

As for engaging your boss, the most important thing to remember is that you no longer have that job. When you’re working with someone, you don’t do their work for them. Even if they are newbies, it’s important to let them do things their way, make mistakes, and learn. The same applies to bosses—even new ones. You can provide guidance if they are open to it, but you don’t do other people’s jobs unless they ask for help (or your manager transfers the job to you). You must let your boss do things their way, make mistakes, and learn. Only provide guidance if they are open to it and help if they request it.

Eric Aside

For more on delegating work, read Effective delegation: Assign ownership.

You can do better

But what if you can do the job better? Great managers are, unfortunately, rare. Perhaps you see opportunities for improvement in policies and practices (communications, decision-making, prioritization, and all the rest). Now that you’ve been the boss, these improvements may be more apparent and seem more actionable to you. That’s great. You could make a difference. However, if your boss doesn’t support these changes, they will almost certainly fail. Sure, some teammates will follow you, but others will hesitate if the boss isn’t on board, and everyone will reconsider if the changes impact their rewards and promotions.

Thus, you must first take your proposed improvements to your manager. Talk about shared goals. Talk objectively about the problems you’re seeing without passing any judgments. If your boss is open to considering changes, propose your solutions. I recommend suggesting no more than one or two at a time. If your boss supports your ideas, fantastic! Work together to improve your team and products. If not, that’s okay. You can always suggest other improvements later. Regardless, it’s not your job anymore to be the boss. There are plenty of other problems to solve.

Eric Aside

For more on proposing changes to your boss, read Controlling your boss for fun and profit. For more on driving cultural changes, read Culture clash.

Déjà vu all over again

If you can’t stop thinking you’d be better at being the boss, perhaps you should pursue becoming one. Before taking that step, reflect on all aspects of your experience as the boss. What did you like? What did you dislike? Is there anything fundamental about your boss’s role that doesn’t fit you?

If you don’t like or trust people, being a manager is problematic. If you need to regularly contribute directly to products, managing more than four people is problematic. If you want to feel connected to the day-to-day operations of a team, being a director (or higher) is problematic. Consider what’s important to you and what you enjoy. If you decide becoming the boss fits, go for it! Tell your boss you’re interested in a role like theirs, take on management tasks whenever possible, and join growing teams that need new leadership.

Eric Aside

For more on moving up as an individual contributor, read Individual leadership. For more on becoming a partner or VP, read Making the big time.

You’ve improved a great deal

It can feel weird when you’re no longer the boss, but everyone has their job to do. Reconnect with your peers and their attitudes toward management, even if your empathy for management has grown. Share the context you’ve learned when it’s helpful; otherwise, enjoy no longer having your boss’s responsibilities. If your boss is open to suggestions and feedback, provide them; otherwise, let your boss do their job and you do yours. If being the boss resonated with you, reflect on what you liked and disliked about the role, and pursue it if it suits you.

Regardless, your experience being the boss has made you a better employee. You now understand how decisions are made, priorities are set, and problems are resolved. (Managers should be transparent and inclusive about those things, but often they aren’t.) You are more likely to see both sides of a conflict and probably better appreciate your peers and your manager, even if their faults are no less apparent. When you take problems or solutions to management, you can frame them better for that audience. Getting boss experience is like gaining a superpower. Use it wisely.

Eric Aside

Special thanks to Bob Zasio for reviewing the first draft of this month’s column.

Want personalized coaching on this topic or any other challenge? Schedule a free, confidential call. I provide one-on-one career coaching with an emphasis on underrepresented, midcareer software professionals. Find out more at Ally for Onlys in Tech.

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