How Not to Suck as a Manager: The Case Packet & the Self-Check That Cannot Fail

A weekend course, a team case study, and a three-part packet. Parts A and B are written from the employee’s chair. Part C turns the chair around, and asks a question that has only one answer no matter what you say.

Almost everyone can describe a manager who made the work worse. Very few people can describe being one. That gap is not modesty — it is a measurement problem, and this assignment walked straight into it.

The setup

The course ran as an active-learning weekend: Friday evening, all day Saturday, Sunday until one. Somewhere inside that, each team had to build and perform a case study.

Your team will create and analyze a realistic workplace scenario featuring one of two problematic manager types from our readings. You’ll demonstrate both the dysfunction and potential solutions through dialogue and analysis.

There were actually three options, not two. Option A, the “Compensating for” (or Selfish) manager. Option B, the “Out of Touch” manager. And Option C: choose your own adventure — invent your own dysfunction. I mention it because it is the only place in the packet where you are not handed a diagnosis in advance.

The timeline was as compressed as it sounds. Friday, thirty minutes to pick a manager type, assign roles and draft an outline. Saturday, sixty minutes to finalize a dialogue script and rehearse. Sunday, eight minutes in front of the room — three minutes performing the dysfunction, five minutes analyzing it.

One line in the brief matters more than it looks:

You do not need to submit any material, but use this as your guide to develop your scenario and presentation.

Nothing was collected. No grade on the artifact, no rubric came back, no annotated version to compare against. That is worth naming up front, because it decides what evidence survives. There is no graded deliverable from this one. What survives is the packet and what I did with it.

Part A: two stories, told from the wrong chair

Two of those options come with a long first-person story attached — and both are narrated by the employee.

Option A, the “Compensating for” (or Selfish) manager, opens with the boss’s words: “That is unacceptable.” The narrator has fifteen years of leadership behind him, in and out of a warzone, and is being told flatly that he is not doing well. He asks for examples and gets other teams’ data points, at a level of abstraction he cannot act on.

What stayed with me is the year in between, because none of it is dramatic.

And then: “The more I asked for clarification, the less clarity I received. I was flabbergasted. Worst off, I started to believe her.”

Option B, and the part I keep rereading

The “Out of Touch” manager opens on a promotion: “Congrats, Terry, you are my new Chief of Staff.” Four were in the running. The narrator did not expect to win, and says why:

I wasn’t the most senior, I didn’t resemble the director’s personality or even was from the same generation. I was shocked I was chosen. Maybe he wanted something different? Maybe this was a vote for change?

That is the sentence the rest of the story is built to break. He reads his selection as a signal that difference was wanted. It was incidental — and everything he was good at, “think out of the box, challenge the status quo,” turned out to be surplus to the role as the boss understood it.

The boss has been in the job over ten years, in a role people were typically promoted out of within five to seven. Nothing has forced him to adapt. What follows is not cruelty; it is a slow narrowing.

The moment that lands hardest is small. He suggests letting the department feed back on an unsettled program. The answer: “we already gave them a chance to talk, we’re going with this way.” Their chance to talk had been the boss announcing it at a team meeting. Consultation had happened, in the sense that words were said in a room.

So he stops. “Over time, I became the COS he wanted me to be — dutiful, and I did what I was told. I did the bare minimum because why would I want to do more if there was no reason to?”

Two different managers, two different failures — and both narrators spend the story interrogating themselves.

The characteristic lists

Each story is followed by a second section, and the packet gives it a heading I did not expect: “Part 2 – Does this define the manager?” Then a numbered list of characteristics — five for Option A, nine for Option B.

That heading is a question, and it is the right one. Does a list of behaviors define a person? The packet asks it two sections before Part C quietly stops asking it. Hold onto that.

The lists themselves are more useful than the stories, because they describe behaviors rather than traits. From Option A:

Me first, everyone else second. Focused on personal goals vs goals of team; even if they say they are for the team’s best interest, typically when the time comes, they will put their interest first.

Desire to use “Hierarchy leadership”. Leading a team of “yes” people… Although the managers say they want different ideas, they typically end up pushing back on those that have a “backbone and disagree” with what they say.

Option B’s nine run longer and land differently. Three of them:

The grass has settled — Been in role a long time, either in the current location, original person in role, or oldest/ most experienced.

Pushes others only in the way they (the manager) want to be pushed — Does not like to be out of comfort zone, so will not challenge unless it is in the area they are comfortable in.

Focus on their goals vs the goals of team — The leaders’ goals are always first, although they can confuse their own goals as the obvious goals for others. (AKA - My goals are the teams goals)

That last parenthetical is the most honest line in the packet. Not I put myself first — that would be easy to spot and easy to refuse. Rather: I sincerely cannot tell my goals apart from the team’s. Nobody catches that in themselves by introspection, because from the inside it does not feel like a preference. It feels like the obvious priority.

One item appears verbatim in both lists: “Lack of understanding of differences. Inability to understand & get best out of team, especially those not doing the same things as the leader.” Two different dysfunctions, opposite causes, and the same output — the people whose work doesn’t look like yours get less from you. That repetition is the single most useful thing in the packet, and I don’t think it’s an accident.

Part B: five ways out, four of which are containment

Part B supplies candidate causes — imposter syndrome, masking insecurity, goal orientation, role identity, plain lack of curiosity — and then a set of “paths to consider” for the employee. Each manager type gets its own list. Five are offered against the Option A manager:

1. Connect to the manager. Learn what drives them, make yourself useful to it.
2. Compartmentalization. Stay for the parts you value, let go of what you can’t control.
3. Leave the role, team, or company.
4. Reduce the engagement. Quiet quitting, quoted through Office Space: “I do just enough not to get fired.”
5. Stay & Fight. With the warning attached: “you could also be seen as a troublemaker, which might make the situation worse.”

Item 4 is worth holding against Option B’s story. Reduce the engagement is offered here as a legitimate strategy — but the Option B narrator arrived at the identical withdrawal without choosing it. It was what the job did to him, over months, by attrition. The same behavior is a strategy on one page and a symptom on another, and the packet never notices.

Four of the five ask the employee to adapt, absorb or exit. One asks the manager to change, and it ships with a caveat. Whether or not the packet means to argue this, that ratio is its actual argument: the realistic advice for dealing with a bad manager is containment.

The Option B list is shorter, and the omission is louder than anything on it. Four paths — be patient, connect, compartmentalize, leave. No reduce the engagement. And no Stay & Fight at all. Against the manager who has been in the chair a decade and rejects any perspective but his own, the packet does not put confrontation on the menu.

Part C, where the chair turns around

Then comes the section titled “What to do if YOU resemble these managers.”

One of the biggest challenges – is being self-aware of your weaknesses. If you can read this section and say that some resembles you – well done. You are open to being vulnerable (at least to yourself) and recognize you want to be a better manager. EVERY MANAGER has something to work on. Why? Because you will resemble them in some way at some point… If you don’t feel you resemble any of these, you may not be as self-aware as you think!

Read that as a test and it has exactly two branches:

• I recognize myself in the list → confirmed, I have work to do.
• I recognize nothing → confirmed, I lack self-awareness — which Part C has already told me is the failure mode.

There is no third branch. Every input returns the same verdict, which means the verdict carries no information about the input. I write acceptance criteria for a living, and a check that cannot fail is the thing you send back at review. It proves the test ran. It proves nothing about the system under test.

What it is missing has a name in testing. An oracle is whatever tells you the right answer independently of the thing being tested — a spec, a known-good result, a second system, someone else’s records. Without one you are not measuring; you are asking the subject to grade itself. Part C has no oracle, and neither do I.

Here is the honest part: I read the lists and matched several items, and I could not talk myself out of it. But an unfalsifiable test predicts exactly that reaction, so feeling caught by it is not evidence that it is right about me. It is evidence that it is well written.

The five things it tells you to do about it

Part C does not stop at the diagnosis. It offers a remedy list: improve communication, trust your team, seek to understand different perspectives, embrace mistakes, validate their concerns. Read as a set, four of them ask you to change a disposition and one asks you to change a behavior.

I don’t think the first four are wrong. I think they have the same missing piece as the self-check above them: no oracle. There is nothing outside my own head to consult about whether I trusted my team this quarter. That is the recurring defect in how leadership advice gets written — the diagnosis is behavioral, the cure is dispositional, and nothing in between leaves a record. “Trust your team” cannot be scheduled, evidenced or reviewed. “When someone raises a concern, acknowledge it and say what happened to it” can be — same instruction, written so it leaves a trace someone else could read.

What the weekend actually graded

There is one more document worth reading against all of this: the evaluation criteria on the assignment brief.

A team could score full marks on all five while performing a manager none of them had ever been, and go home unchanged. That is not a criticism of the rubric — you cannot grade someone’s private recognition in eight minutes, and it would be grotesque to try. It is a description of where the assignment stops. Part C is the only part addressed to me as a manager rather than as a subordinate, and it is the one part with no evidence attached, no submission, and no reader.

So the rubric is not an oracle either — it grades the performance, not the recognition. Which leaves the whole weight on the one instrument in the packet that cannot fail.

What would actually settle it

An oracle has to come from outside the thing being tested, and I am the thing being tested — so it will not come from introspection. It has to come from the records I already generate. That is why the characteristic lists are better instruments than the self-check that follows them: they describe things that leave traces. Turn them into lookups rather than feelings:

• Which 1x1s did I move or shorten in the last two quarters, and whose? The calendar knows.
• Did my feedback on the same piece of work change month to month? The comments know.
• Whose work do I ask about first in a status meeting, and whose only when something breaks?
• When someone disagreed with me, what happened to their idea two weeks later? The tickets know.

None of those require me to be honest with myself. They require me to look something up. That distinction is ordinary in testing and nearly absent in leadership development — and it is the whole difference between an instrument that can fail and one that cannot.

The packet half-knows this. Path 1 in Part B suggests using Schein’s Career Anchors to work out what actually drives your manager — an instrument I took in the same course. It works better than the Part C self-check for exactly this reason: it makes you rank forced trade-offs and then hands you a number you did not choose.

There is one entry on the Option A list I do not need a lookup for, because I recognize the pattern: protecting an outcome and treating another person as the acceptable cost. Me first, everyone else second. I did not feel selfish at the time. I felt like the person holding the date. That is exactly what the parenthetical on the Option B list warns about — “My goals are the teams goals” — and I could not have caught it by asking myself whether I was that kind of manager. I caught it because a different assignment made me write the week down in order, with names in it.

So I’d put the packet’s own question above its answer. Does this define the manager? Not by recognition, and not by failing to recognize. By what the record shows I did, on dates, to people who could tell you their side.

I went into that weekend expecting to build a caricature for eight minutes on a Sunday. I came out with one sentence from a page nobody grades, and a short list of things to go look up about myself. The list is less flattering than the caricature was, and considerably more checkable.

If you manage people: pick one line from those lists, find the record that answers it, and read the record before you decide how you did.