Dear Businesslady: How Do I Manage?

Hi Businesslady,

I work at a small tech startup (~30 employees) on a small team of five: my manager, a senior colleague, myself, and two other coworkers at my same level. After a long six months of my manager slipping into more and more toxic and unprofessional behaviors, he is being fired. As a response to his departure, my department is being reorganized: my senior colleague and I are both being promoted. I now am a Director which means I report to a VP and manage my two former peers.

I think (and have been told by my coworkers and my new manager) that I have a lot of the skills needed to guide development of the products we need to deliver to customers, but this is my first time in a management role and I don’t want to fuck it up!  

I have more experience with this specific job than my new direct reports, but I am younger and generally less professionally experienced than both of them. I also used to be their coworker and am now their manager. I know that my relationship with them will change, but I don’t want to either be too distant or too familiar.

Also, my ex-boss was a pretty poor manager — he had a tendency to retaliate in response to feedback and on multiple occasions targeted one of the people I now manage (sometimes reducing her to tears). He left the other one mostly alone, although both experienced inappropriate professional behavior from him that was both personally hurtful and damaged our ability to deliver products. I don’t want to be like him! But I also don’t want to waste time and energy reinventing the wheel if there were some good things he did.

Do you have any advice for a first-time manager? And do you have any advice on how to tackle these weird dynamics?

Thank you in advance,

Violet Newstead (or Finally Got Rid of My Franklin Hart, Jr.)

Dear Violet,

First of all, congratulations! And, thanks for this letter. The world (and my inbox) is chock-full of stories about horrible behavior going unpunished, so it’s incredibly satisfying to read a tale of a bad boss actually getting fired.

Second of all, I’m ashamed I had to google your signature because somehow I have never seen 9 to 5. Even after it was the outro music when I was on TV! This oversight has been weighing on me, and now I’m even more eager to rectify it at the first available opportunity.

Third of all, you are smart to be proceeding thoughtfully into your new position, and you’re already considering all the right things. It’s great — on both ends of the equation — when a friendly rapport can exist between a manager and their employees. As long as everything’s going smoothly, there’s no reason why you can’t chitchat and joke just like any two coworkers at the same level. But you can’t let it go too far and try to be “a cool boss, not like a regular boss.” At some point, you’ll have to put on your Authority Hat and deliver an unpleasant message, so you want to make sure that your dynamic leaves room for that transformation.

We all phase through different roles relative to the people in our lives. Like sometimes your romantic partner suddenly becomes your domestic supervisor, overseeing your job of “not sloshing soup everywhere, which you’re about to do if no one stops you.” And it’s easy to accept an urgent “hey, watch it!” in that context, because you’re on board with the shared goal of “a soup-free floor.” On the other hand, if your partner snaps at you about some random arbitrary nonsense, that’s gonna be less well received. Especially if dictatorial edicts become a trend. The trick (and tricky thing) is to maintain that sense of shared purpose up and down the org chart. This means narrating goals and processes before they can seem random and capricious — and doing the back-end assessment work of ensuring that they aren’t.

When I look back on the times I’ve “gotten in trouble” with my managers, it breaks down into those two basic groups: incidents where I could acknowledge that I’d handled something poorly, versus unexpected reprimands that I would’ve needed telepathy or a time machine to anticipate. There’s some overlap — the occasional “oh wow I had no idea that’d be an issue but now I see why it’s a problem” — but even that has more in common with the first category than the second. And while it’s never fun to confront the fact that you’ve made a bad judgment call or failed to execute a crucial task, it’s easy enough to get past. You do what you can to fix the problem, learn the lesson that prevents a repeat occurrence, and move on.

So your first job as a manager is to figure out what you want from your staff, and your second is providing clear, unambiguous guidance regarding those expectations. That’s not easy of course (that’s why bad bosses are legion), but it’ll be easier for you than for someone who’s stepping in from the outside. You know your organization, which means you know what successful performance looks like, and chances are that’s given you a good intuition for identifying potential problems. From your macro view in the manager’s seat, you can look at your team as a whole — either confirming that everyone’s doing their part, or offering nudges to course-correct as necessary.

Those nudges could be anything from quality control to deadline enforcement, and you should get comfortable with delivering them. The rhythms of friendly conversation can beguile you into using softening language, like “would you mind” and “it’d be great if you could.” While there’s nothing wrong with a rhetorical “request-vs.-command” approach, be careful about letting things sound too optional when they’re unequivocally important. Again, you never want negative feedback to come as a surprise.

(Quick non-management-specific sidebar here, because I’ve been trying to train myself away from this kind of wishy-washiness in all my professional communications. When you’re writing an email that’s full of “I think…”s, it’s amazing how many of those can be summarily deleted. No one’s ever gonna read a direct statement — “We should plan to have a draft by Tuesday”  — and wonder, “But wait, does Courtney actually think we ought to do that?” Old habits die hard, but these days I try to save that phrase for actual instances of uncertainty, and I’d encourage everyone else to do the same. I promise you can still be perfectly pleasant and collegial without auto-undercutting yourself.)

By now you may be wondering, “How am I going to do all this direct, forthright communicating?” Good question! In addition to all the usual mediated communication channels (email, chat spaces like Slack or Teams, etc.), may I suggest: meetings. Ideally in-person when feasible, or via phone/Skype for folks who are remote. Yes, meetings can be more than just rituals where you fight for your preferred flavor of donut while listening to coworkers complain about the irrelevant minutia of their daily routines. Done right, they can and should be an opportunity to absorb individual perspectives and weave them together into a shared story.

This would be my recommendation for anyone jumping into a new management role, but it feels especially appropriate in your situation. One-on-one meetings with your direct reports will give them a chance to explain what (if anything) your predecessor did right, flag any issues that you need to be aware of, and outline the type of relationship they’d like to have with you. You’re not obligated to fulfill every single one of their requests or follow all of their recommendations — you’re the boss now, which means you get to make such judgment calls — but it will at least let you know where they’re coming from.

That initial conversation can also establish your routine going forward. It’s still good to check in periodically via voice-to-voice meetings, but you can determine the frequency and format together. And since you’re new to this, you might also plan to re-evaluate the system a few months from now, and adjust anything that’s not working as well as you’d envisioned. Group discussions will likely be valuable too, but not at the expense of focused time with each employee.

As you’re putting all of this into implementation, don’t be shy about using your own boss as a resource. A couple things jump out to me from your letter: one, you got plucked from a group of peers and chosen for this promotion, and two, your organization seems to be doing damage control after letting a toxic manager run amok. That tells me that the higher-ups see potential in you, and if they have any sense, they’re thinking of this as an opportunity for you to stretch and expand your skills. That becomes totally counter-productive if their perspective is “well, you’re management now — good luck with that, and we shall never speak of this again!” Your own boss should be helping you succeed, and that means they should be more than happy to serve as a sounding board as you grapple with the responsibilities of your new position.

Still, even as I hope your manager is willing to mentor and coach you, I also want you to develop your own self-confidence. There’s a reason that bosses make more money than underlings: you’re being paid to think critically about how your organization works and make tough choices about how to help it thrive. That means taking risks, and then accepting the consequences for the results — the triumphs and the disasters. You want to succeed more often than you fail, of course, but you shouldn’t be so afraid of failure that you miss opportunities to innovate. And you shouldn’t be so afraid of failure that you double down on bad decisions.

In every human enterprise that involves collaboration — whether it’s creative, professional, domestic, or some combination of the three — there’s incredible strength to be found in the ability to acknowledge and learn from mistakes. You want your staff to be reflective and honest about their own performance, and the best way to achieve that is by modeling it yourself. Trust your instincts about what’s best for the team and the organization, and if you get it wrong, trust that your instincts will be even better next time. Hold yourself to the same high standards as everyone else, and then lead by example.

You’ve seen firsthand what bad management looks like and witnessed the damage it inflicts on everyone in its orbit. Now’s your chance to find your own particular version of good management — and you have the rest of your career to keep getting better and better at it. Keep asking yourself: What story are you and your coworkers going to tell together? What are the actions and ideologies that will support and develop that shared story? Seize the “author” part of “authority” and craft a professional narrative that only you can create. As long as you’re amenable to on-the-fly revisions, I have faith that the results will be fantastic.

Courtney C.W. Guerra is an editor and writer with a thriving day job who started giving advice as Dear Businesslady on The Toast in 2014. She’s the author of Is This Working?, a funny, friendly career guide that you should probably buy for everyone you know this holiday season. Keep in touch via Twitter, Facebook, her TinyLetter, or her website.

Need advice? I need problems to solve! Email me: dearbusinesslady@gmail.com. My first column for 2019 will be on promotions, so short questions on that topic are especially welcome. But I’ll happily accept full-length letters about any work-related issue.

Photo by Bethany Newman on Unsplash.

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