Privileged whine and request for advice

I don't talk about work a ton for reasons that should be totally obvious, but here's an area where I'm really struggling...

As part of my role, I'm responsible for a lot of strategy. Some of this is also filling a vacuum created by other people, but that's beside the point. So, since I love words, I write words. A few of the things I've put togetehr this year:

1. 3 year roadmap for the organization. The org has never had one of these.
2. 5 year roadmap for post-quantum cryptography
3. Strategy for addressing long-standing container hygiene problems holistically.

With each, I've shared with my peers, my team, some of the more senior leadership, and the feedback I've gotten is all positive. Great, right? Except no, that's not great. The chances that I have gotten all these things right is vanishingly small. What I fear, and a fear that was confirmed yesterday by a friend, is that people are afraid to provide any criticism because of my title and seniority.

This, even after I present them as "draft", "please provide feedback", "criticism is encouraged", "these are not my children", "I know these are deeply imperfect, but the only way forward is through collaboration". None of that has resulted in more than the most cursory feedback.

And yet I know people have read them, because I get positive feedback and can see where they all are in the document.

But then we come back to that title. "Distinguished". It's dangerous. I'm deeply imperfect, and while I'm good at my job (whatever that is lately), that doesn't mean I don't need other people's feedback to really hone in on the future.

I again, welcome feedback from people on how I can create safe space for others. I've tried to always not just acknowledge the feedback, but credit it in the documents as well because they are (ideally) a result of collaboration. But I'm fresh out of ideas here.

Replying to @petrillic@hachyderm.io

Privileged whine and request for advice

@petrillic

Some ideas come to mind:

Part of the problem might be that we view technical problems as requiring technical solutions, when what they need is some short term solution structure and somewhat longer term governance structure.

A roadmap or a strategy is something that you have a structure for adjusting after the first year (or whatever). It doesn't need to be perfect before the organization to start down the path you suggest.

When adjustments inevitably happen, it's not a reflection on your decisions. It just means y'all learned something.

That said, it may help to frame criticism requests as something like "I'd like you five people to each come up with three ways this might go horribly wrong, and suggest how we might mitigate such risks. This will give us a useful starting point to discuss refinements." Rather than the open ended, "Please provide feedback." (the safe space issue is reduced when folks know they are not alone in having to respond, and you get to incorporate risk mitigation activity into your strategic plans.)

(that's probs too much, but I lived that life and have written books about that kind of thing, so I think about it a lot...)

Jul 6, 2026, 00:14 UTCEdited Jul 6, 2026, 00:28 UTCen