What you've got is in fact a people problem

He credits a man named Sherbie for the three rules. That man was my grandfather.

The best advice Gerry gave me was when I was in a tough spot in college. “Expectations are fickle things that we work ourselves up over. Reevaluate them regularly, they have expiration dates long before they begin to smell funny.”

This is only partly true. It is true that management sometimes faces budget pressure. But the real skill lies in what they do next. They could - easily - come up with a strategy of feature delivery, and communicate it clearly. Ask engineers to pause red tape, be scrappy for the next few quarters, talk to dependent teams to make certain flows easier. Explicitly use their authority to set the rules aligned with leadership.

But this is not what they do. The average management simply pushes indirectly, via 1:1s or individual blaming.

> After the manager declines to invest in engineering quality a few times, they have sent a clear message that quality and reliability are secondary to the desire to get things our the door. Then they blame the staff for their mistake.

Truth.

Anecdata follows but I’m certain this has been getting better in recent years. It’s more common today for management to be swayed by data - my recollections of the 2000s were interactions more along the lines of

“I’ve been doing this for 20 years son, whatever your little spreadsheet contains, I’ve already accounted for just by feeling the air in the room through my superb gut”. - management at that time had gone from playing with Sinclair spectrums in their bedrooms to leading huge multimillion dollar teams, partly because software development had exploded and someone needed to lead those teams. So several managers I ran across seemed to see their position as a result of their greatness and not really anything at all to do with growth in the industry leading to bigger roles needing filled. This is a long way to say it used to be very hard to penetrate a charismatic self-aggrandising tech leader’s thought bubble.

Today I definitely see it as different. E.g. if you rock up with a download of CI job runtimes and a couple of off the cuff quotes from team members about what they do when waiting for CI builds (I.e. not much of value), I’d expect you to pretty easily succeed in establish a case for investing in speeding up that feedback loop and the outcome / measured results chart of that work would likely make its way through at least a couple of senior management slide decks over the next few weeks.

That is the behavior of a pathological leader in a pathological organization. It is all too common.

What’s presented as a technical solution is actually a process solution to address a people problem.

Essentially the rant goes: So all of these people who were not particularly good at people skills in high school go into a career where they think people skills won't matter as much, and check out for 4 years while their fellow classmates are honing their interpersonal skills in one of the most intense personal growth periods of a young adult's life.

Then they graduate, get out into the world and realize that it is all people problems, and now they're even further behind their peers than when they went into college.

In many cases the solution comes in the form of "go away or I will replace you with a very small shell script."

For example, suppose that you have regulator captured by construction companies who want construction to be labor-intensive because they're the ones who get the money. The problem here is not that we need technology to reduce construction costs, it's that construction costs are being artificially inflated by regulators.

But now you come up with a technology that allows construction to be performed in a factory and the local part is limited to taking the thing off the truck and putting it in the building, which takes ten seconds and can be done by the truck driver. Can this solve the problem?

Maybe. It depends on whether the incumbents have enough political power to have it banned or made prohibitively expensive. If they do then it won't work. But if they don't, the technology solves the people problem, by removing the problematic people from the operation. Or forcing them to improve their own efficiency so they can remain competitive with the new technology.

It's especially relevant in B2B work - you have to know what the actual personal goals of the decision makers at your customer business are, because your job is to address that; you're not there to bring them in more revenue or satisfy their customers, your actual goal is to help the manager signing your checks to meet his quarterly KPIs/OKRs/whatever, so you'd better know and prioritize the exact things on that list.

Don't ask me how I know until I'v finished processing it in therapy in a couple years.

There are bosses who get violently angry and fire people. Nobody will trust that boss with honest feedback... ever.

There are the bosses who are simply dismissive of what their staff is already telling them. In that case, the boss is having this meeting to tell his staff "I ignored and forgot everything you told me previously, but this time will be different. I'm prepared to listen this time." That boss may be able to make good on the strategy in the article.

My experience has generally been that, even if a leadership level person is being sincere when they say they want honest feedback and it is safe to offer it, the junior level person they are meeting with doesn't believe it. (An economist would call this an example of the "market for lemons" problem.) That is a big reason why outside consultants can break the ice on something like this, as the article describes, where internal conversations can't: the consultant can credibly promise that honest feedback won't adversely affect the speaker (the obvious way to do that is to not attribute anything to any particular person when the consultant reports to leadership), so they have a shot at actually getting the honest feedback that is needed to get to a solution to the problem.

Then I sold the startup and worked at Google for 6 years.

1 out of 4 managers hit the bar that I figured would be a floor, you could have a constructive conversation with them and they'd help you if something was up.

It's certainly possible to have it on a personal relationship basis - with coworkers or a boss, but broadly? Impossible. If someone wants to take you down, then your "honesty" is going to be used against you.

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

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

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

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.

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.

I have had a lot of success with knowing this, saying “Great! Let’s go” and loudly complaining about things that are fucked up to anyone who will listen.

This has opened a lot of doors and gotten me into a lot of meetings that I otherwise wouldn’t have access to. Sometimes it has enabled me to change things for the better. Other times it has helped me understand why things are fucked up and appreciate the constraints at play. Then I can drive the best improvements possible within those constraints so things are at least a little better.

Yes it takes years of building trust and a track record of successes before you can do this. Worth the investment.

Just because your company is fucked up doesn’t mean all of them are. Part of the briefing to new managers at my company is how to take critical feedback.