Dear Businesslady: How Do I Weather a Chaotic Transition?

On grateful goodbyes and important introductions

Dear Businesslady,

There’s a bit of chaos going on at my job. Due to a weird fluke of timing, there are two leadership transitions happening directly above me: a week after my immediate manager retires, we have a new incoming department director (my manager’s manager) starting. So, not only will I (eventually) be dealing with a new boss, I will also be dealing with a new boss’s boss.

I’ve definitely drawn the short straw on managers before. I’ve had both intense micro-managers who critiqued the way I introduced myself (?!) in a meeting, and absentee bosses who I wouldn’t hear from for weeks. My outgoing boss has been an absolute treasure. She is brilliant, laid-back, helpful, and really the perfect temperament for my work style So, I guess my question is two-fold: 1) How do I let my outgoing boss know how much I appreciate her? 2) What is the best way to make a good impression and develop a good working relationship with incoming bosses?

— Facer of Strange Changes

Dear Changeling,

Your letter was almost eerie for me to receive, because while you’ve described a fairly complicated situation, it’s pretty much the exact same scenario I just experienced in my day job. (To anyone I know in real life: I promise you that I did not write this letter.)

I know you said your question was twofold, but I actually think there are three distinct elements in play: how to express gratitude to a beloved mentor; how to adapt to a major change in workplace leadership; and how to establish a rapport with new bosses. With that complexity in mind, I’m going to make this a one-letter column, because I definitely have some thoughts about how to navigate all of this.

Even though there are a few separate things going on here, they’re actually all related. Thanking your most supportive managers is a way to articulate the things you most value in a boss. It also helps you feel a sense of closure about their departure, which in turn helps you feel okay about the end-of-an-era aspect. With that perspective in place, you’re better equipped to approach a new managerial relationship with an open mind and a model for what success looks like.

It’s Called Gratitude, and That’s Right

First of all, “How do I say thanks to someone who was a positive force in my life?” is the very definition of a good problem to have. And second, even though I have suggestions about how to go about telling a boss how grateful you are, I don’t really think it’s possible to botch being thankful. Any sincere expression of appreciation should hit its mark — especially since awful, hypercritical people aren’t likely to be on the receiving end of such messages in the first place.

Nevertheless, it makes some sense to put thought into anything that’s important to you, this included. While you’re doing said thinking, consider your rapport with the manager in question. For some bosses, it makes sense to write up a card or letter (or email, even) that outlines all the ways you’re indebted to them: here’s what you’ve taught me, here’s how you’ve helped me grow, here’s what I’ll always remember about you. As someone who recently wrote one of these notes, I can tell you that if you’re a crier, it’s probably going to make you a bit teary-eyed — so be prepared for that.

Great bosses come in many flavors, though, and a mushy missive isn’t the right fit for everyone. For a manager you’re friendly with, it can be nice to commemorate the transition away from a hierarchical relationship with a social outing of some sort — grabbing a drink, or dinner. The idea is to create an opportunity to enjoy each another’s company and have a conversation about something other than how the such-and-such project is coming along. Ideally this will be separate from any official going-away gathering your office might have, since you’re unlikely to get much one-on-one time with the guest of honor at a big party.

Finally, the “gifts should flow downward” etiquette rule means that you’re by no means obligated to give your departing manager a present — but that’s not to say you can’t if you’re so inclined, especially if you have an idea for something they might like. Just make sure it’s not something so showily expensive that it’ll make them feel uncomfortable. And if your boss has other direct reports who are roughly on the same level as you, it’s a courtesy to check in with them to see what (if anything) they’re planning. There’s no obligation to precisely coordinate your efforts, but you don’t want to blindside your less effusive colleagues: “Oh, you got them a potted plant you knew they love and wrote them a heartfelt note? Cool cool cool, I stuck a post-it on their monitor that said ‘We’ll miss ya’; now I feel like a real asshole.”

Those Days Are Gone

Here’s another nice thing about orchestrating an appropriately warm send-off for your outgoing boss (in addition to ensuring that you both have a nice bit of pleasant closure): it distracts you from the imminent shifts in your office’s dynamic. Now, in a well-run organization, it’s safe to assume that a change in leadership doesn’t signal a cataclysmic disruption to everything you loved about your workplace. [And here’s where I remind myself that I didn’t want to talk about the election, and press on with a heavy sigh.]

My point is, new bigwigs are hired for reasons, and you can trust that they’re up to the task of running whatever it is they’re in charge of. But they’re not actual clones of their predecessors. They will do things differently, and ambiguity is always a little worrisome. I mean, we have a whole expression built around the idea that a familiar bad thing is preferable to a complete unknown. And with bigger, multilayered managerial shake-ups, the impact is correspondingly greater as well. So until you get accustomed to all of the coming changes — enough to quell the nagging worry that somehow everything’s about to be ruined, even though intellectually you know that’s not the case — you might be a little on edge.

Whenever I’m irrationally fixated on something, telling myself that I’m being silly only works about 50 percent of the time, so when that’s not effective, I try to just acknowledge it: I’m kinda freakin’ out right now. Thinking something to yourself like “this is a weird time” can serve as a mantra that shuts down your internal worst-case-scenario generator. Accept that things are strange in the transitional period between the old and the new normal, and try to keep an open mind until you’re reasonably acclimated to the latter.

The Beginning of a Beautiful Working Relationship

There’s always a learning curve when someone is just starting out in a new position, no matter how well qualified, talented, and perceptive they may be. Even a person who’s promoted up from a closely related role will have some learning to do, because every job contains secrets that aren’t revealed until you’re actually doing the work.

As a manag-ee to a newly installed manager, this puts you in a slightly awkward position, because the fact that you’ve been around longer means there will be instances when you’re more knowledgeable than the person who’s suddenly the boss of you. On the one hand, you don’t want to be holding back information that might be beneficial, but on the other hand you don’t want to come across as though you’re trying to tell them how to do their job.

The best way to navigate this early getting-to-know-you period is to trust that your good intentions will be perceptible and follow the lead of the new leadership team. Keep in mind that it’s unlikely that every single thing your former boss(es) did was beyond reproach — no matter how great they may have been — and that there may be net positives ahead that will pleasantly surprise you.

Be generous with your time and institutional knowledge, and be vocal about your willingness to take direction and adjust your habits as necessary. Sure, it’s possible that you’ll end up stuck with a manager who will demand things you find counterproductive and irritating. But you can wait until that actually happens before you start stressing out about it as a possibility. And even though you don’t want to be constantly bringing up “Well My Old Manager did things this way,” you can occasionally bust out a polite version of it in response to any suggested process tweaks that you disagree with. If you’re trying to make a point, the fact that the office was humming along just fine under the previous system can be a powerful counterargument to shaking things up. That said, it’s ultimately the boss’s call, and you want to make sure you’re not suggesting you think otherwise.

By continually asking for feedback, you’re demonstrating that you respect the chain of command while simultaneously opening up valuable conversations about workflow and communication styles. New bosses are busy, and if you’re someone who doesn’t need a lot of hands-on supervision, they’ll probably be happy that you’re not one more thing vying for a major chunk of their tightly-structured attention. If you explain the historical status quo from a position of “but of course, we can switch that up if you think there’s opportunity for improvement there,” you’ll set the right groundwork for working well together.

A Whole New World

I’ll close with a reminder that all of this will unfold in time — the slow geological time at which individual professional humans become familiar with one another and figure out new jobs. Certain miscommunications, minor frustrations, and confusions are inevitable, and not cause for alarm.

If (and only if) a distressing pattern starts to emerge, that’s where you push back a bit. “Hey, new boss, as someone’s who’s been around here a while, I’m a bit troubled by the direction we seem to be heading” — and then follow up with job-specific facts that go beyond your intuitions: “I’ve had a lot of clients complain about the website redesign, and getting rid of the biweekly group meeting has made me feel really distant from other departments.” Unless your concerns are dismissed, you should be able to nudge your office back on track — and if your leadership conclusively demonstrates “I’m not terribly interested in your thoughtful and tactfully delivered suggestions,” that’s when you start updating your resume with a clear conscience.

Hopefully you’ll never reach that last hypothetical step. But even if you do, it’ll take a while to get there. In the interim, you can use the murkiness of the In-Between times to develop your own particular notion of an ideal workplace. Then you either help create it in your old job — to whatever extent your temperament and position allows — or (if that proves futile), you head out to find it somewhere else.

Got a workplace conundrum? Email me! dearbusinesslady@gmail.com

Businesslady is in her early 30s and a successful professional despite her allegedly useless degree in the humanities. She currently does writing and editing for a nonprofit, and devotes the rest of her life to playing video games, patronizing bars, and spending way too much time on the internet. Her career guide, Is This Working?, will be available from Adams Media on April 1st, 2017 — preorder it today!

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