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It often is a people problem, and when it is, it's likely to be at the leadership level.

What stumps me however is how to move past those problems -- when the decision makers at an organization themselves are what's dragging the ship down, how will things ever change?

Blog author doesn't cover it, but my uneducated guess is... the consult ends with a technical recommendation, but the people problem remains unresolved.




I am familiar with a particular small business. They have this loop:

1. Product and Engineering cooperatively develop a project, scope milestones, cut tickets, do agile, eng writes the code and iteratively works with product to incorporate feedback and it's a grand ole time

2. They get about 80% done with implementation (so they're about 90% if the way through the entire project, impl is usually about half the time)

3. The owner takes note of the project and examines more closely. They profess their opinions all over it, sowing madness and scope creep, freaking out the junior ICs and new hires, and further exasperating the seniors and old hands

4. They scramble, cut other scope that isn't in the Eye of Sauron, do some late nights and cut a bunch of corners, write some shit code here and there, then push it over the finish line a little late and a lot of stressed

5. They have a retro in which they excoriate the evils of scope creep and extol the virtues of sync meetings and exec reviews and more process layers and stamps.

6. Owner doesn't participate in any of the additional process because they don't have time, naturally.

7. A project nears about 80% completion, the owner takes notice, and...

It's really a beautiful cycle. At various points, sometimes someone will notice all the layers of scar tissue, uh I mean process, aren't actually helping, so they cut a bunch of them out. Much rejoicing. Then the next project gets about 80% done, and...

Yeah. Whatcha gonna do? It's the only thing about the company that isn't going to change.


This is probably most 50-200 people startups.


That's what happens when the owner is alienated from the work and doesn't have immediate goals.

When he is alienated from the work and has immediate goals, the failure is quicker and more spectacular.


Sounds a lot like working with the US Air Force, unfortunately.


>What stumps me however is how to move past those problems -- when the decision makers at an organization themselves are what's dragging the ship down, how will things ever change?

People will start new companies and become leadership there (starting the cycle over).


The majority of managers I have encountered have a superiority complex. Because they are the manager they know better. They have a misguided idea that they were promoted on the basis of some meritocracy instead of being good political operatives or shameless sycophants.

That is why only the advice of very expensive consultants is valued. Many times I have had after work drinks with staff who complain that they have been trying to tell the management what the highly paid consultant did.


> The majority of managers I have encountered have a superiority complex. Because they are the manager they know better. They have a misguided idea that they were promoted on the basis of some meritocracy instead of being good political operatives or shameless sycophants

That is usually true. One fix for that is to play into it. Guide them towards the idea but make them think they came up with it and the praise them for it. I always remember the scene in My Big Fat Greek Wedding where the women get Gus to “decide” and come up with the idea that Toula should go work at the travel agency.


Praising a thirsty horse for drinking, after having to forcibly lead it to the waterhole and show it how to drink just isn't in my wheelhouse. It's beyond a certain very-slightly-autistic line of wrong-ness intrinsic to my very soul. I know this holds me back, but, I ... just ... can't.

I will, however, increasingly simplify the explanation of the concept until the conversation reaches acceptance or frustrated dismissal of the topic altogether. This has had patchy success over the years.

Many years ago, after a number of failed explanations, I demo'd to my boss, the IT Manager, the ability to access work emails from a mobile device and how Managers and Salespeople would love it for their productivity and customer relationships. "Nah, I don't think they'd be interested. That's what their laptops are for".

Surprisingly, that particular horse never died of dehydration. I think that's because the next levels up were also thirsty horses.


> I know this holds me back, but, I ... just ... can't

It is messed up, indeed. Better to find another horse. But some people are stuck with their horse for some reason or another.

> I will, however, increasingly simplify the explanation of the concept until the conversation reaches acceptance or frustrated dismissal of the topic altogether. This has had patchy success over the years.

Yeah, that is a better option.

> Surprisingly, that particular horse never died of dehydration. I think that's because the next levels up were also thirsty horses.

Well put. There are thirsty horses all the way up.


That’s an effectively intractable (and common problem). Even when there is a board involved, a skip-level approach to pointing it out is very likely an end of employment situation.

Machiavelli had advice for this situation, and it wasn’t kind.


You come at the king, you best not miss. If I got to the point of going to the board about my CEO, it’s already a him-or-me situation, and that almost always means it’s me who’ll be leaving.

The CEO currently has the board’s support, at least ostensibly, and I’d be faced with moving them off the status quo; that’s unlikely over a routine leader style topic…


> If an injury must be done to a man, it should be so severe that his vengeance need not be feared.

—- Machiavelli


What advice did Machiavelli have?


He didn't so far as I can tell. He wrote The Prince for an audience of rulers, both new and established, aiming to preserve or reinforce their power.

But to be charitable bc that is basically a nit, he would have advised a calculated approach to wielding political influence or instilling fear. He was partial to creating alliances with the adversaries, circumventing them, or otherwise coercing them into agreeing with your priorities.

He was the “Its better to be feared not loved, if you can’t do both” guy so GP is right when they say his advice here would not be kind. Its because his methods are not really what you want to use to make a better environment at work. Ironically, I think all the problems Machiavelli was concerned with were “people problems”, but he wasn’t concerned with fixing them, just doing whatever it takes to maintain stability for a given ruler.


From the Wikipedia entry:

> After his death Machiavelli's name came to evoke unscrupulous acts of the sort he advised most famously in his work, The Prince. He claimed that his experience and reading of history showed him that politics have always been played with deception, treachery, and crime. He also notably said that a ruler who is establishing a kingdom or a republic, and is criticized for his deeds, including violence, should be excused when the intention and the result are beneficial to him.


Murder them and take their power.


Offer them a different behavioral strategy in the guise of managing those weaklings better?

I wish I could say. I suck at fixing that, too.




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