The Manager’s Crisis

Not long ago, I met with a designer I previously managed at Etsy to catch up and talk about her new role (she stepped into a management position shortly after I left). We were talking about some of the challenges she’s facing currently, and inevitably starting talking about some of the decisions I’d made while we worked together.

You know, she said, I really didn’t get why you were making those decisions at the time. In fact, I was pretty against them. Now that I’m a manager, though, I can totally see why you did what you did.

After managing folks for a little while, there are two major crises I’ve identified as not only common, but a consistent source of stress and uncertainty for managers:

Imperfect Decisions

I think most of the people I manage would tell you that I strive to be as transparent as possible at all times. Even when the truth is difficult, I believe leveling with people is better than trying to couch unideal decisions in positivity. But even when you’re shooting straight (and explaining why you’re making the choices you have to make), it can be difficult for individuals to understand or even accept. You, as a manager, understand that the holistic decision, while not perfect, is as close as you can get based on all the factors (both human and organizational). For the person impacted by the change, however, it’s understandably a challenge to step back and see the whole.

One of the most complex problems managers face is delivering unpopular, yet necessary decisions. Acknowledging the imperfections and giving as much context as you can will help people work through those imperfections. Additionally, you should be thinking beyond that particular situation and planning for a future where you can remedy some of its downsides. Share the possibilities with the people you manage, ask what they think, let them know you understand things could be better and that you’re committed to working toward that with them.

Am I Doing a Good Job?

I meet with a lot of first-time managers and one of the consistent threads with each of them is: Am I doing a good job? How will I know? When you’re a designer, you can see your work get better. You know when you learn a new skill or add something to your process that wasn’t there before. Knowing you’ve done great work or improved the product is incredibly rewarding and positive reinforcement that propels you to do even more.

Bad news, managers: you’ll never truly know if you’re doing a great job or not. Even when you do get that adrenaline rush from seeing someone you manage overcome an obstacle or up their skills, it will quickly be overridden by a nagging voice wondering if you actually helped at all. Hell, maybe you didn’t. Maybe you just happened to be their manager at the time. They probably would have kicked ass no matter who their manager was. Does your job even matter? What are you adding?

Yes, it’s like that a lot of the time.

I will say, though, that the best managers I’ve encountered all have that nagging voice. They all worry about whether or not they’re being as supportive as they could be, whether or not the people they manage are happy and freed up to do their best work. These managers default to openness, honesty and trust, because they realize they need the same thing from their teams. These managers are the fastest to adapt when things go sideways, recognize their own shortcomings and evolve their approach.

So yeah, you may never know if (or feel like) you’re doing a great job. But that’s probably a good thing. Embrace the uncertainty.

All You Can Do

Like I said, there’s no silver bullet for these challenges. They’ll never go away. You signed up for them when you said, “Sure, I’d like to try managing people.” Just like designers will never stop solving digital UX problems, so too will you be continuously working on real life UX problems. And while the actual actions you take will inevitably vary by the scenario, here are a few quick principles that should help:

There’s a lot more to it, but those feel like a pretty good start. Management is challenging and filled with uncertainty, but it can also be incredibly edifying and rewarding and one of the best professional experiences you’ll have.

Good luck. :)

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