The Management Problem

During lunch on Monday at An Event Apart in Chicago, just after I had presented my talk What’s Your Problem? Putting Purpose Back into Your Projects, I sat with a group of gentlemen who all work on the same team at a large publishing house. They were kindly enthusiastic about my message and said it echoed their private conversations about the way they wish things were done at their company.

“We were all nodding our heads,” one said, “but the people who really need to hear it are our managers. They would never come to a conference like this.”

My immediate response: “Well, maybe you should have their jobs.”

Reflecting on it now, that was really shortsighted of me to say.

We spent the rest of the lunch talking about the frustrations they face as a multi-national corporation with deep hierarchy, siloed teams, fragmented technology platforms and outdated policies. And what did they blame for this failure to evolve? The dissociation of management.

Like any game of telephone, the more links in the chain, the more likely the intended message will be misheard or altered as it travels down the line. This is rarely malice (though that does sometimes occur), and it usually isn’t apathy either. No one wants to be the one responsible for a communication breakdown. But the further away you sit from the initiator, the easier it becomes to do.

I see this as a challenge of empathy. The manager’s hands don’t do the work, so he doesn’t understand how it moves. As new best practices emerge, he’s aware that tides are changing, but he can’t fully comprehend why or how. As a result, he can’t properly communicate it to others. Then he’s put in a position to direct the change within the organization, but he doesn’t have the vocabulary to do it, so he hires a middle manager — someone to explain what his direct reports are doing, who can oversee them better because she has the skills to do so. This is usually someone who was in a senior doer position at her last company and is now trying out how to be a manager. As time passes, she becomes less and less familiar with the materials her team molds on a daily basis, and as tides change again she feels incapable of weathering the storm. So she hires someone else to sit between the craftsmen and her. Someone more familiar with the direction things are moving. And so on, and so on, and so on.

Be honest, you know I’m not oversimplifying it.

The problem with managers is that they’re totally disconnected from the everyday doing getting done. In a pinch, they wouldn’t be able to do it if they tried. They can only talk about doing it, because that’s the role they’ve had to play, for their boss who can’t talk about doing it at all. He can only talk about talking about doing it. The more abstract level. The work around the work around the work. Where the bets are made.

And so it seems that as our careers progress, we get further and further away from the craft. So it shouldn’t surprise you much when your boss knows a shit-ton less than you do. Don’t be bitter. It’s normal. And just as it’s his job to get buy-in to allow you to do your job, so should your job be to teach him what he needs to know to get the buy-in.

The problem with managers is that we expect them to be a better version of ourselves, and that’s just not the purpose they serve — nor want to. Management is the process of dealing with or controlling things or people. Their job is quite literally to be in charge. If you work for them, then it’s your job to make sure they value what you do. If they don’t value you, that’s on you. It’s your job to hone your skills; it’s your job to follow industry trends. And it’s also your job to share that knowledge with your manager in a way they can deeply understand and appreciate it. The whole point of hiring you was to take the doing off their plate, at least to some degree. Don’t expect them to be able to do as good or better than you, and make the time to guide your career, too.

Empathy is a two-way street. If your manager doesn’t get you, chances are you don’t get them. What can you do to make them more successful? Where do they need help? Maybe if you took the time to figure out what problem they’re trying to solve, they might be more inclined to understand your problem, and pave the way for you to solve it yourself.

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  1. says

    Great article. As a Technology Manager in a fortune 100 company, I feel so disconnected from the bits that run the products I am responsible for. I also learned a while back that there is no way I could be as smart as the people I manage across their spectrum of bit-shifting. Once I recognized, acknowledged and was open about this, I became a better manager.

  2. Michael "Spell" Spellacy says

    Great post, Witney! This comes at at time where I am taking on more of a managerial role so I will be sure to carry your message here with me.

  3. says

    This is a really great, Whitney. I think we all need that reminder now and then. It’s so easy to develop bitterness and resentment towards a manager, because you feel like they don’t know what they’re talking about and therefore should not be in a higher position than you. But, they are just doing their job and you should be doing yours by educating them. Managers deal with a lot of things the “doers” would never want to bother with. We forget that, sometimes.

    It’s very true that further we get in our careers, a lot of times, we get further from the “doing”. In fact, I know a lot of managers that mention in passing how much they miss creating the work themselves.


  1. […] I wrote about how it’s our responsibility to ensure our managers value us and truly understand what we do — and how and why we do it. Most managers want to set their […]

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