A Great Resignation, Management Edition

isotopp image Kristian Köhntopp -
June 22, 2023
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This is not much of a blog post, but just a thread dump from Mastodon as requested by a friend, because my Mastodon posts expire after some time.

Based on my work and the people I know, I have some (remote) view into what happens in a few companies at the C- and Mid-Level management. And from where I sit, it seems the great resignation is not only a thing that affects workers, but also managers. It is almost funny.

These people are often pretty awesome administrative people. Mid-level managers with amazing Jira- and Miro-skills, breaking down large work parcels of well-understood jobs into team-sized packages, describing the requirements and planning the required hours, then mapping them onto calendars. Or budget jugglers that take large unstructured sums of cost, and find a way to parcel them out in a halfway reasonable way into individual cost centers and items.

Digital and other transformations

These companies are also all in a series of transformations, at all levels of the stack simultaneously.

  • Many are moving on-premises workloads to cloud, but the workloads are not cloud-shaped.
  • Two enterprises I happen to know about are also changing their implementation language from something exotic to something less efficient, but a lot easier to hire for.
  • One enterprise is also breaking up a monolithic application into a set of microservices, but the cut lines are unclear and need to be found.
  • One enterprise is modifying the way they do business from a single product to a series of interconnected and interdependent products, some of them in highly regulated markets.
  • Another enterprise is changing the way they make their product from mostly manual labor into something based on sensor input and data science.

These transformations require a different kind of manager: they need less of an administrative person, and more business process designer; they require a different kind of empowerment and delegation, from the top to them, and from them on downwards – much more autonomous on the delegation poker side;

What is also needed is an entirely different kind of understanding of the company itself, less interchangeable business administration skills, and more business-specific skills about how the sausage is made.

On top of that are traditional hierarchies and communication structures that are based on in-person attendance and mostly oral tradition, and a skill-set that is well suited for the Clear and Complicated domains of the Cynefin-Model , but wrong for the Complex and Chaotic domains.

The Enterprise cannot perform the set of transitions it must execute to stay relevant, when the entire Org and the people that carry and build the structure of the Org are incapable of transforming their way of working to match the problem. So they leave.

Which for an organization that is in the Complex and Chaotic realm of a transformation makes the problem worse, because the intimate knowledge of the processes that make this company unique and competitive goes with them. The people coming in have to learn these things, but if the Org does not have written account of what matters and has no way of teaching these things that make this company special, it basically loses its specialty and becomes meaningless, interchangeable and then soon extinct.

What Remote Work does for companies

Funnily, companies that optimize for remote work are also companies that out of necessity optimize for a written instead of an oral culture. They tend to have very well documented ways of specifying and teaching what they do, why and how, and a proper self-service onboarding process complemented by a mentoring system – and that also works for mid- and C-level management.

Companies that optimize for remote are executing transformations easier because they understand their meta better. Many workers understand that. Maybe not in this way or even in words, but they can read the room, and they are reacting to their environment, especially the skilled ones.

A preference for remote work is useful even, or especially, if you come into the office, because a company that can do remote properly understands what it does and how it works better than a company that executes “remote” with a “zoom harder” policy.

Interviewing to find organizations that know their stuff

So when you interview, these are useful and interesting questions:

  • How did your company change their way of working during Covid?
  • How did your management style evolve under Covid and after?
  • How do you detect misalignment, disagreement or conflict or other causes for in-person meetings when working remotely, and what are the ways you handle these situations?
  • How do you evolve agreement from oral consensus to documentation to training material? How do you document and teach processes?
  • How did your way of working as a person and as a member of the Org evolve in the last 5 years? What can you point to that illustrates process maturation and advancement?
  • In what way did your Org execute transformations in the last five years? That certainly was not frictionless. What worked, what didn’t, what did the Org learn?

If that reads a lot like a reverse interview – well, that’s what it is.

But the objective is clear: You want to find out if the org you are about to join has access to its own meta, and if it can change and consciously design its org structure, work, and communications culture.

All companies right now are executing a series of transformations at multiple levels of their business. That is because the world right now is a lot less stable than it used to be in the last 50 years. But only those that do not let these things happen to them, but are actively shaping the process will not be painful to work at.

You must find these early in the interview process.

In any case, the information you want to find when interviewing for a job is again:

“Does this company shape itself and its future consciously? Does it design itself? Or does change happen to the org accidentally? Does it understand what it does, and why? Or are they winging it?”

Most management is winging it, most companies are cheating their way to the next quarterlies.

You do your work, but you do have an understanding of what management is supposed to do. Does management understand their job, tho?

Can you respect your current or future management? Can they express the value they provide in a way that is understandable and meaningful to you?

Can they explain the business, and what specifically the competitive advantage is this org has within its own competitive set? Do they know why this differentiation exists, and how it is protected or extended? Do they understand in what way the structure they are building and upholding helps in doing this? And how it needs to change to be able to continue?

Basically, you want to find out if they know the C-level strategy they exist in. If they know what direction everybody is supposed to march in, and what their local objectives are as a part of the greater whole. You need to find out if they have context that they are making local decisions in.

Incidentally, it is this (and not ping-pong tables) that builds engagement and loyalty.

People love to work for a company that understands how it functions, and can talk sensibly about this – about its business and communication processes, and the why and how of useful interaction.

People love to work for organizations that have an idea of how to change and into what, instead of being shaped by accident.


Another contributing factor is that transformations interrupt the value extraction process of neoliberal shareholder value, and also upsets established hierarchies.

Shifting to the left side of the Cynefin model means you need smaller teams of higher qualified people. Teams that perform work in a way that is much harder to quantify, and create value that is hard to express in right-side organizational structures.

That is, shareholders and their demand for dividend and rising stock value interfere with the investment needs, increased risk and hard to measure gains that transformations require, and thus the owners of the enterprise are an impediment to the change that the company needs to be able to continue to deliver value to them.

That is, some individual owners always understand that problem, but the owners as a group don’t and can’t and are working against their own best interest.

Side Remark: Similar structural pressure is currently visible in German society, at the “Berlin vs. Berlin Outskirts” conflict or at the national mobility and energy transformation.

Side Remarks from the Pandemic Coping Discord

A friend gives an example at the individual level

IC: “The existing code is bad and undocumented. Three weeks for the fix, provided there are no landmines.”

M: “So you commit to 3w?”

IC: “No, because I don’t know if there are landmines. Usually there are.”

M: “But I need a binding commitment to before the end of July!”

That’s lack of tech understanding paired with pressure from the shareholder end.

Another friend talks about Stressors

M: “My personal theory is that we are running into some inherent limits of the current management model during the last decade and are now seeing stress fractures.”

K: “But the question is where the stress is originating.”

M: “Complexity (as observed at each management level).”

K: “Ok, that matches what I think if you accept that it is these transformations that are causing the stress. What you call stress fractures I call transformation overload.”

M (responding to the three-week-commitment example above): “A good example for what I mean by complexity at that management level: The manager can communicate only a scalar detail upwards, but the problem is a complex data object. The manager cannot report what happens nor the risk properly.”

K: “A command and control management is unable to handle situations that require nuance and understanding of detail?”

M: “Yes. Management level A needs to reduce their stress, and forces their lower level B to simplify. That increases pressure and stress at the level of B.”

M: C has called this “driven by financials.” The only universal scalar is Euro, but expressing all things in Euros is becoming increasingly harder and is losing information.

M: A lot of fighting and pressure is actually about “simplify your reporting” vs. “accept my complexity.”

M: “This is also in part why we see a preference for managed services. They are an attempt to encapsulate complexity. Often that fails, and the complexity reappears and attacks the PO consuming that service.”

C: “A way to solve the conflict is to ask more ‘Why’ questions downstack, and to create more tasks that allow for interpretation.” That is basically a move to the left-hand side of Cynefin.

M: “That requires a trust that is larger than Euro-Scalars. And ultimately that breaks at the shareholder-level, latest.”

H2: “And non-technical management also believes these things are simple. Click here, and ChatGPT will develop the software autonomously. It’s those pesky IT people making all these things that complicated.”