The miserable two bosses problem

Two Bosses

The ‘two bosses problem’ is an off-shoot of what’s happened with generalized organizational structure in the last decade or more. Most executives could still give two craps about how their company is organized so long as it’s making money, but … organizational structure has grown in importance a little bit as ideas like “disruption” have sprung up. Simply put: you start to care more about org structure when you’re getting hit in the wallet. Usually — almost always — bad org structure means decision-making is slower, and that means rivals can get at weak spots in your rollouts and customer interactions.

As more people started to vaguely care about how people and teams are organized, we had all these experiments in org structure. You’ve got holacracy, which is mostly a flop. You’ve got self-management (similar), which can never be taken to scale. The most common approach, though, is typically “dashed lines” (you work under a person but that manager doesn’t do your performance reviews) and “solid lines” (your actual boss).

Here’s a dirty little secret about most white-collar work: no one really wants to collaborate, but we create all these “cross-functional teams” because some consultant told us it will drive “innovation” forward. In reality, cross-functional teams are normally abject train wrecks. No one is ever sure on who “owns” what, who was invited for real reasons vs. political reasons, and who can assign more to whom. (Now, sometimes this goes well. Oftentimes it doesn’t.)

This is where you arrive at the two bosses problem.

My story with the two bosses problem

My last full-time job was at a B2B consortium company. I had one primary boss (a woman), who sat 15 feet from me. However, her main focus was on print publications — and my role was digital. I worked there 17 months and then got fired. I would say me and her never had a real conversation about my job until about Month No. 13, and you know how it goes: those convos were mostly designed to get my ass out the door.

I had another guy in Seattle who wasn’t my boss, but his “metrics” were closer to what I did. I’d try to get more work from him and collaborate with him on things, and often it worked. But he had a separate boss, was in a different city, and had different ways he was evaluated by his superiors. Overall, it mostly didn’t work.

In the web of all this happening, I had different people in Seattle, Texas, and even New York assigning me work. I’m not putting myself on the cross here, because most of the work was pretty basic, but at times I had three bosses, at times I had five bosses, and sometimes I had two bosses. I think this is the “new reality” of our focus on collaboration and cross-functional teams. We often have two bosses instead of one, and one was the model for about 40 years.

Why is having two bosses (or more) a problem?

On the surface, it isn’t. Work has long been about juggling different things, and two bosses is no different. But here’s the catch: what if those bosses come from different silos? And what if those bosses are both big “sense of urgency” people and “hair-trigger” people?

Here’s what happens then:

  • You’ve got 11 projects across your two bosses
  • Each boss assumes your stuff for him is more important
  • There’s a lot of e-mails flying (“Update plz? Thx”) and awkward cubicle visits
  • Everyone’s hoisting themselves onto the cross at minute-by-minute intervals
  • Priority is falling at the feet of “get it out the door”

Now, sometimes this doesn’t happen — but silos are a powerful thing in business, and it often does.

How do you handle the two bosses problem?

Here’s a good article on the topic from Wharton. Peter Cappelli, who works at Wharton, says the money quote: “It’s not about structure, it’s about execution.” (That summarizes work as a whole.) “As a result, it’s not about looking at a chart.” (More on that in a second.)


From the same article:

Some practical advice would be things as simple as creating one master priority list of everything on your plate and making sure all your bosses have a copy, so when a boss says you need to do this tomorrow, the boss will have an understanding of how this fits in with the other things on your list. Related to that is people being able to get good at self confidence to a degree – to ask your boss, ‘If you want me to so this, what is it you want me to take off the list, because I also have three other deliverables due in the next few days.

That could work. Many managers might screech “But I need my thing noooowwwwww!” but again, this idea has merit. People at jobs tend to love spreadsheets. You toss something on a spreadsheet, you instantly get rid of three layers of anger that might have been there.

The psychology of the two bosses problem

There are a couple of things to understand first:

Pause. Still with me? You’ve got a lot of people whose jobs could potentially be replaced by a CRM running around with no sense of priority. Now add these two elements:

Alright, here’s where we stand: potentially-unnecessary employees who want to be seen as relevant and competent are allowed to assign work to someone who doesn’t directly report to them? Shazaaam! The motherlode, baby! Now I’m relevant, competent, and I’m managing more people. The brass wouldn’t heap more stuff on my plate unless they knew I could handle it, right?

(Probably wrong, but let’s jump over that for now.)

The flip side of all this is when the original manager (the actual one) tells people “I’ll protect you from that other manager and you’ll focus on my own work.” In reality, they won’t do shit. It’s all chest-pounding and “I have some authority here, lemme get after this…” They’ll have one convo with someone and another person up the chain will say “That rank-and-file is working for whoever needs targets hit.” Done and done.

The org chart and the two bosses problem

Just wanted to shove this in here quick. In general, “org charts” only matter as a way to solve a problem or showcase someone’s power. In reality, they break down massively every day — which is what the two bosses problem shows. It’s the same with “job descriptions.” Most people come into orgs and are doing something totally different three weeks later, but no one cares. Then, if there’s a political blow-up or someone from one team is doing work better than another team, everyone is rushing around talking about “job descriptions.” It’s a weapon, plain and simple. Another one? “Best practices.” People only say “best practices” to mean “This is what I do and you should.” I could write a whole book about “phrases that should mean something but are only used as weapons.” Oh, another one? “Professionalism.”

Anyway. Got anything else on the two bosses problem?

Ted Bauer


  1. Great post Ted. Yes love those MBA phrases. Results oriented. Best practices. Job descriptions. Just more and more BS.

  2. Ted, you.re killing me with that spreadsheet suggestion. In my last position I had bosses who wouldn’t ever bother to read emails, let alone tables.

    The problem with management today is that companies are treated and run by people who don’t know how to manage. They are instead built by product engineers or salespeople, and every problem looks like just another product to fix or target to capture, etc. But, that’s just my $0.02.

  3. I read something the other day that suggested a new way to promote into management — choose completely at random, because complete randomness will be more effective than what we’re doing now.

    I think the main problem here is ego and pride. Humans don’t do well with power. I like your suggestion of replacing middle management with a CRM. Let the robots do the management work so the creative humans can get back to the business of creating.

    • Hopefully that’s starting to happen more and more, as it keeps costs down — but somehow, most big companies are becoming more middle-laden.

  4. The bigger the company, the more dense and overly-complex the layers of middle management becomes. Most of this is “overseeing” work done by the regular workers, dragged into meeting after meeting, about how they need to be getting their work done.

    As you can see, there’s a lot of cognitive dissonance from reality here.

    Oftentimes the left hand has no idea what the right hand is doing, and the people who suffer are the actual workers.

    Never again, my friend. Never again.

    • It’s all a complex game. If you’re good at it, you move work off your plate and onto others — and you make a bunch of money in the process. If you’re bad at it, you want to plunge your head in the toilet at 9:44am every day. It’s hard to be in the former category and relatively easy to be in the latter.

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