The Ballad of the Secret Boss

Intentional, transparent, inclusive, and accountable. Or not.

If trust is a cornerstone of good management, then a management dynamic fundamentally built upon duplicity is probably…not good — even when it springs from good intentions. But sometimes it is just so darn expedient!

Gather ‘round now while we sing of well-intentioned chicanery, of wishcasting, of unchallenged assumptions, of feckless inertia. Our song is a tale as old as the professional organization. It’s the thrilling saga of the secret boss.

That’s right: the secret boss. The coworker who is responsible for your assignments, workload, feedback, and performance assessment, yet is not your direct manager. 

Oh, you think your direct manager is responsible for your assignments, workload, feedback, and performance…but for one reason or another, that’s not how it is working out. You’ve got a secret boss!

Dun dun duun.

It’s possible I coined the term “secret boss” (at least in this context). I can’t easily find other references to it in the business literature I’ve surveyed.¹ But I FOR SURE didn’t invent the concept of the secret boss. 

In fact, I’ll bet everyone who’s spent any time in the corporate world is deeply, painfully familiar with it. This particular dynamic forms all the time, and I’ve seen it become pretty toxic. 

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A long, long time ago I found myself in the position of being a secret boss. I didn’t really recognize it at the time, but as I realized later what had happened, it put me on the lookout for this dysfunction.

In my case, I’m pretty sure the situation resulted from generally good intentions, but in perilous combination with lack of domain expertise and a kind of path-of-least-resistance structure.

I was in a non-managerial position but had a little bit of creative leadership responsibility.² I think — though this was never explicitly communicated to me — the general consensus amongst my superiors was that I wasn’t ready to be a people-manager. Probably correct! 

So when a new team member was added to my team, that person was assigned to report to the same individual that I was reporting to. We were peers in the organization. 

Now, I’m sure at some level I chafed at not being put in charge here (I don’t really remember my reaction, but I know me…). Whatever — at that point I’m not sure that I even wanted to be a manager. So, fine. We’ll be peers. 

Over the course of the following weeks and months, however, it became clear that the explicit reporting structure had little to do with the reality on the ground. 

My manager would meet with me for updates on my work, as expected. But these meetings would also involve the performance of this peer; and then my suggestions for their tasks, my thoughts about their career path options, and my expectations for their role on the team. 

What began as “check-ins about the new team member” morphed: now I was prioritizing their work, I was evaluating their work, I was giving them feedback and advice, and I was finding them opportunities — I was managing them! 

But as far as they knew, I was their peer! (And not for nothing, my paycheck also indicated I was their peer.)

This situation led to some deep discomfort. We’d have conversations that, from one point of view, were peer-to-peer, and from the other were report-to-manager. Easy enough to say I was the “lead” on one project or another, and could take the creative reins. But delivering critical performance feedback was fraught. 

And at all times I felt like some kind of spy in my own house. I was a secret boss!

Nonetheless, I was lucky. My “secret report” (which I guess would be the other half of the “secret boss” relationship?) was super easy going. Good at the work, generally affable, not consumed with a need to climb the corporate ladder.

As uncomfortable as I became with the situation, I’m not sure they really ever put all that much thought into it. Or at least they didn’t think it was worth a fight. Still, I wish I had better recognized the situation for what it was at the time. It benefitted neither of us.

For a number of reasons the experience didn’t last more than a few months, but it left enough of a mark that I’ve tried to be particularly vigilant about not letting it unfold again.

And yet, well, vigilance be damned. Sometimes we turn around and some dynamic has formed right under our noses.

I have been a secret boss, as noted. I’m also pretty sure I’ve been a secret report (more than once). I know that I’ve inadvertently created secret bosses. And I’ve watched as other managers have put secret bosses into play.

Basically, any way in which I could have done this wrong, I have done this wrong. I don’t know: maybe if one does something long enough one is bound to make all the mistakes. Or maybe I’m just an idiot.

But in any event, the phenomenon of the secret boss is a vexing team dynamic largely because it really can — and often does — form out of good intentions. Sometimes it can really seem like an obvious and right answer, at least at first.

Imagine you’re trying to get a brand new hire set up for success on your team. You might ask a more seasoned team member to “partner up” with them — help them learn the ropes, understand the peculiarities of the team and its position in the larger organization, and develop opportunities for impact.

All fine and good. But without really careful attention, that’s got secret boss potential written all over it. 

Sure, you’ll meet with the new person regularly, and give them support and feedback. You’ll try to be a good, responsive, supportive manager to them. But…you’ll also meet with the more senior peer.

You’ll ask how it’s going with the new person. You’ll send gentle instructions about how they might help guide them. And then you’ll follow up on how it went. You’ll ask the new person if that other team member has been helpful.

And then, with all this insight the senior person has about the rookie’s performance, you’ll ask for feedback that you can deliver to them. But you’ll try to keep it, um, discreet, because you want the new person to feel like they have a manager and a peer, not two managers. Fair enough, right?

You’ll convince yourself it will all work. It won’t! No matter how hard you try, the artifice will be exposed. Like building your subdivision on an ancient burial ground, one big rain and those skeletons are bubbling up through the unfinished pool, Poltergeist-style.

Unless the new person is particularly oblivious (in which case, why did you hire them?), they will realize that their “peer” is at best a spy in their own house, or at worst, a secret boss.

And what does it do for the senior team member at performance review time? What are you going to do, review them as a manager even though in the organization, that’s not actually their job? Thanks for taking on all those management tasks, secretly, but alas, you let the work for which you’re actually responsible suffer because you spent so much time secret-bossing. Below target.

It’s not a winning scenario.

Now, sometimes, the problem is just that there isn't any other obvious answer given the circumstances. Even if your gut is tingling that something doesn’t feel right, there does not seem to be a better solution available.

You don’t have a manager available for that new hire, say, so you’ll just have them report to you. You don’t really have time for that, of course, so you’ll gently suggest to one of their peers that they help out. See above.

You know the danger, but you’ll just do it this way for a little while, until you get out from under whatever the current pressure is. Then you’ll fix it! Mmm hmm.

Or maybe the dynamic has already developed slowly and quietly, good intentions and necessary shortcuts building up over time, when somehow it comes to your attention. You think to intervene, but upon observing it…well, actually, it seems to be working okay!

You think, if it ain’t broke, don’t etc. You convince yourself that changes at this point will be more disruptive than productive. On paper, you tell yourself, this seems unhealthy, sure. But look how well it’s actually working!

Maybe! Probably not. But maybe!

Because every toxic relationship works for a while, right? That’s how it becomes a relationship. Once this one blows up, as you know damn well it will, you’ll ask yourself, why didn’t I fix this when it was nascent? Why didn’t I fix this when changing course would have been easy? Why didn’t I fix this before I ended up sitting here in HR’s office getting yelled at?

Let’s be clear that a secret boss is distinctly different from a mentor.

Mentorship does not (well, should not!) problematize reporting relationships. I love it whenever my direct reports also have mentorship relationships with very senior folks.

Presumably — hopefully! — the mentor is helping teach them to think critically about what I say and do. Presumably the mentor is helping them to contextualize my leadership, and giving them another ear to listen to ideas, suggestions, and complaints.

We should hold our managers accountable. I do it, and I expect it to be done to me! It’s not threatening behavior — it’s great! It makes me a better manager, and helps my reports grow in more fulsome ways than I could ever hope to help them with by myself.

That mentor? Not a secret boss. Even if they end up helping the person challenge their actual boss, that’s generally a healthy dynamic.³

For many of the same reasons, other kinds of “executive sponsor” relationships are also not secret boss situations.

As a manager, I want to provide my team members with all the support and visibility they need. But that’s hardly ever possible with a team of any reasonable size. If they've got the gumption to get themselves some highly-placed advocate, good for them! 

That person may be high up in the organization, they may even have more decision-making power than I do. But not a secret boss!

If I were to boil down to four words my management philosophy at this point (at least my aspirational philosophy…), those words might be: intentional, transparent, inclusive, and accountable. 

That first secret boss situation I encountered was none of those things. But importantly, I wasn’t any of those things either. I didn’t necessarily control the situation, but I controlled (or should have controlled) myself. If I had it to do it again, I might approach it differently. 

Because the secret boss dynamic often springs from expedience, or at least opportunity, by nature it lacks intentionality.⁴ And it relies fundamentally on at least a lack of transparency — and more realistically, a lack of honesty. It is, at root, a deception about the very structure of the organization and the individuals’ roles therein. 

Generally, no one involved has the scope to even be considering inclusivity. And accountability is obviously meaningless if nobody is being forthright about who is even leading whom.

Intentional, transparent, inclusive, and accountable? I rather think not.

So, sure, maybe there’s no revolutionary insight here: don’t be a secret boss! Don’t create secret bosses! If you figure out that you have a secret boss, call it out!

The secret boss dynamic is one of those insidious trust-killers that creeps up out of well-meaning, if expedient, decisions, unintended consequences, and the inexorable inertia of a busy team. The important thing is just to be able to recognize it, hopefully earlier rather than later.

The principles of intentionality, transparency, inclusiveness, and accountability will provide some defense to the dynamic developing in the first place, and should provide some helpful tools to fix it if it manages to develop anyway.

1. It’s a phrase in video games, of course, which makes it really annoying to search for in a management context. If anyone knows of it, comment!

2. Earned through a combination of skills, yes, but also frankly, luck, privilege, and opportunity. May as well be forthright about such things.

3. I’m not so naïve as to think this can never go wrong or become unhealthy. Of course it can. Still, I think that’s usually a risk worth taking.

4. Which is not even to say: if it is being done intentionally, that’s a whole other, very serious, problem.