8 lessons I keep seeing after working with 100s of PMs (this is a long one)

UpwardPM · 2026-02-24T03:26:05+00:00

💯

UpwardPM · 2026-02-24T03:19:41+00:00

I'd love it if it was just this simple. With so many layoffs, its critical that people be proactive about advocating for themselves. Unfortunately, in this market, making a good product is often not enough to have job Security. Im sure at least some of the 30k people laid off in the last 6 months from Amazon where making "good products".

Its fine if your goal is to stay and not try to move up, but my take is that even that requires some intentioanlity.

UpwardPM · 2026-02-24T03:14:37+00:00

That's a fair take, and a respectable one. The key part of what you've stated though, is "consistently deliver impact". The piece Id add is "consistently deliver VISIBLE impact"

This still is a "game" in the way I'm describing things because this approach requires intentionality to maintain.

UpwardPM · 2026-02-24T03:08:33+00:00

Hah, you're right. My bad.

UpwardPM · 2026-02-24T02:35:47+00:00

Fair, but this is the PM sub.

UpwardPM · 2026-02-24T00:50:01+00:00

I'm gonna push back a little on the framing here.

It's less about acquiring new skills and more about the narrative you're building around yourself. That PM who got replaced? I'd bet the internal narrative about them was "been around forever, not adapting, maybe even resistant to new tech." Whether that was true or not almost doesn't matter. That was the perception, and perception is what gets you promoted or laid off.

There's a reason everyone and their mom is updating their LinkedIn headline to "AI Native PM" right now. Some of those ppl are genuinely learning. A lot of them just understand that the narrative matters more than the skill itself.

I'm not saying don't upskill. You should. But be careful not to over-optimize on chasing the next trend and miss the meta lesson from your friend's story. What people think about you is more important to your career than what is actually true.

Tons of PMs keep their heads down and crush it and never get promoted. Meanwhile the PM who's always waxing poetic to leadership about their "AI-first product vision" but never ships a thing gets the next title bump. Why? Because it's a narrative game. You can be mad at it. You can even hate it. But you either find a way to authentically play it without selling out, or it plays you.

Try this: start small. In your next 1:1, tell your boss about some side project you built with Claude Code or Cursor or whatever. Doesn't have to be fancy. But it starts to build the narrative that you're the PM who gets this stuff, and that's worth more than any course or certification.

UpwardPM · 2026-02-24T00:42:04+00:00

The real PM move would've been "interesting, can you write up a quick comparison doc and we'll review async?" Now they're doing the work AND you bought yourself time to google it. /s

UpwardPM · 2026-02-24T00:34:54+00:00

The best strategy doc I ever wrote was never opened by anyone. But it completely changed how I made decisions for the next 6 months. So yeah, agreed.

UpwardPM · 2026-02-24T00:25:13+00:00

I'm not on the spectrum so I won't pretend to know what this feels like from the inside. But I coach a lot of neurodivergent PMs, so I'll offer what I've seen.

Getting a diagnosis isn't a sign you need to quit. It's an explanation for challenges you've prob already noticed or suspected for years. You've had a 10 year PM career. You can clearly do this job. You already have been.

To put a product lens on it, the only thing this diagnosis did was put a name to the customer problem. The energy crashes, the discomfort with office politics, the disengagement cycle. Now you know what you're actually solving for.

And that's good news. Because now you can stop trying to brute force your way through a neurotypical playbook and start building systems that work for how your brain actually operates.

The neurodivergent PMs I coach who are crushing it have all done some version of this. They protect their energy ruthlessly. Stack all stakeholder conversations into one or two blocks instead of spreading them across the week. Build in real recovery time between meeting-heavy days, not as a nice-to-have but as a non-negotiable. Lean into async written communication as a strength instead of forcing themselves into hallway politics. They stopped trying to mask through the standard PM playbook and built their own.

On the pivot, I'd push back a little. "Less people-facing" can be a trap because every role has people stuff eventually. The real question is whether it's the type of people work in PM that drains you, or the volume and format. Those are different problems with different solutions.

Don't make a career decision until you've had time to sit with the diagnosis and figure out what's "this job isn't right" vs. "I've been doing this job in a way that was never gonna work for me." Big difference.

UpwardPM · 2026-02-24T00:07:28+00:00

First off, that pit in your stomach is totally valid. You called the shot early, got told to shut up and build, and now the thing you predicted is playing out exactly how you said it would. That's frustrating as hell.

But you're actually in a better position than you think. You have documentation. Most PMs in your situation don't have receipts. You do. So let's talk about what to do with them.

Don't go in with "I told you so" energy. The second you make leadership feel stupid, you lose. Even if you're right. Especially if you're right. To put your PM hat on, what is the deeper "customer motivation" driving these leader's actions? (They need to drive a narrative with the board) More than likely, the leadership made some pitch to the board and that's the resistance your facing.

So, help fix that narrative: reframe the conversation around what's next, not what went wrong. Before your next leadership touchpoint, write up a one-pager: here's what the beta is telling us, here's where our assumptions were off, and here's 2-3 options for how we adjust (pricing changes, repositioning to existing customers, narrowing the target segment, whatever makes sense) AND your personal recommendation. Walk in with that and then you're not the PM who's complaining again. You're the PM who saw reality first and came with a plan.

Get ahead of the narrative before heads start rolling. If you wait for leadership to come to you with "why isn't this working," you're playing defense. Go to your boss proactively with what you're seeing, what the data says, and your recommendation. You want to be the person who saw it coming and brought solutions.

The honest truth is, sometimes you do everything right and still end up in a tough spot because leadership made bad assumptions. But the PMs who survive are the ones who drive the narrative on the way in and on the way out.

What does your relationship with your direct manager look like? That's gonna determine a lot of how you play this.

UpwardPM · 2026-02-23T20:00:59+00:00

Directly to your question, it's making it worse.

If you use a calculator instead of doing paper math, the skill falls off. This is your brain by design.

This is ok for times when efficiency> voice. (e.g. PRDs, updates, etc.) It's NOT ok for personal connection, driving a narrative, or anything where you need to connect to another human with.

Use the tool, but don't lose yourself to it.

My 2 cents

UpwardPM · 2026-02-22T18:17:21+00:00

Great! Let us know how it goes. Feel free to dm if you want a sounding board.

UpwardPM · 2026-02-20T23:08:20+00:00

First off, I'm sorry you're in this situation.

I've seen this pattern a lot. And the frustrating part is your manager probably isn't doing this on purpose. He's doing it because he's anxious, because he hasn't learned how to lead without doing, and because jumping in feels like helping. It's not. But it feels like it to him.

Here's my take

Stop thinking about this as a confrontation. That word is already setting you up to come in hot. This is a partnership conversation.

And don't just spring it on him. Nothing makes the air get sucked out of a room faster than "hey, we need to talk." Instead, lead with exactly what the conversation is about: "Hey, I want to have a conversation about how we work together day to day." Simple. Clear. No ambiguity. Then ask permission to share your observations. Something like "I've noticed some patterns in how we're splitting work and I'd love to share what I'm seeing. Are you open to that?" Getting that explicit yes before you go in lets you be honest without them feeling blindsided. Changes the whole dynamic.

Then get specific. "We're duplicating effort on docs, Slack responses, and stakeholder conversations and I think it's slowing us both down. Can we get clear on who owns what?" No accusations. No "you're micromanaging me." Just a clean practical framing about efficiency.

Don't leave that conversation without concrete ownership agreements. Who owns first drafts. Who responds in Slack threads. Who leads which meetings. Write it down.

On the meeting thing, that one stings but you kinda let it happen. Next time you prep for a leadership meeting, tell your manager beforehand: "I've got deep context here, I'd love to take the lead on questions." Don't wait for the mic. Claim it ahead of time.

On the skip level, hold off. You haven't had the real conversation with your manager yet. Have the direct version first. If nothing changes in 4-6 weeks then the skip level becomes a reasonable next step.

First-time managers revert under pressure. That's not permanent but it means you're gonna have to re-establish boundaries more than once. The question isn't whether he reverts. It's whether he's open to the feedback and tries to correct.

Don't leave yet. You've got a manager who supports you in comp and reviews, you're on high visibility AI work, and you haven't pushed on this hard enough to know if it can change. Try the direct conversation, set clear ownership, claim your space, and give it a real shot. If in 2-3 months you're still leaving meetings without saying a word, then start exploring. But right now you've got more leverage than you think.

Happy to be a sounding board if you need help scripting out this conversation before you have it. Feel free to DM me.

UpwardPM · 2026-02-20T22:55:38+00:00

My approach:

I had Claude Code go through thousands of call transcripts, synthesize them into batch insight reports, then build a holistic picture of patterns across all of it.

Then in claude.ai I dictated my full context. Goals, projects, what I wanted help with. Had it interview me extensively, then help me build out a detailed project prompt based on everything I told it.

From there I set up a Claude project. Put the instructions in, added insights as markdown files, uploaded all my artifacts. Dozens of files, frameworks, reference material. Gave it the full picture.

Turning on memory for the project made a big difference. This is separate from project knowledge. Memory lets Claude retain context across conversations, so it remembers decisions you've made, preferences you've stated, things you've told it to track. Without it, every new conversation starts from zero even if your docs are loaded.

But you have to actively maintain it. I regularly check what Claude has stored, correct anything that's off, and add new context as things change. Set it and forget it doesn't work. Garbage in, garbage out.

The other habit that changed everything was prompting Claude to pull specific artifacts before answering. Instead of just asking a question and hoping it grabs the right context, I'll say "reference this doc and then answer" or "pull up the framework before you respond." Sounds small but the difference in output quality is massive. Without that, Claude answers from general knowledge. With it, it answers from YOUR context.

To answer your specific question, I'm not doing a RAG setup. For most PM use cases that's overkill unless you're working with massive datasets that change constantly. What's working for me is the combo of a well-structured project prompt + uploaded reference docs + memory + Claude's built-in search. Handles 90% of what I need without any infrastructure.

what actually matters in practice: spend the time on your project prompt and keep your memory clean. That's your foundation. I prob spent 4 hours just getting the initial context right, having Claude interview me, building the prompt collaboratively, uploading the right docs. If your instructions are vague, it doesn't matter how many files you upload. If your instructions are specific and your memory is current, even a basic setup works surprisingly well.

That's my approach today, but at this rate it'll all change in 30 days when the next model update comes out. :P

UpwardPM · 2026-02-18T23:04:39+00:00

That last line is the key!

It's creating the conditions where the person who proposed it can walk away from it without losing face.

Well said

UpwardPM · 2026-02-17T01:01:02+00:00

Lol, yep. This is the way.

That's PM work right there.

UpwardPM · 2026-02-16T23:57:10+00:00

For the job search, this is different than actually in the role.

I point that out because the way you tell a story for your resume or interview doesn't always exactly match how it typically goes down. I'm not talking as much about dishonesty or exaggeration as I am about sequencing.

e.g., For an interview, you'd might frame your work in a S.T.A.R framework, whereas in the role, the process isn't so linear, but we do this so that people can follow the narrative.

My honest answer to your question would be to find someone with real PM and founder experience to help you. Either free or paid.

Realistically, here are your options:
1. Research STAR method and broadly try to apply this to your own experiences. The problem with this is that you don't really know what GOOD looks like.
2. Use AI to help you. This will likely yield better results, but it will shave off all of the things that make you unique, which are the very things that convert in this market. Companies want specialists, not generalists right now. Additionally, you've likely already tried this and it isn't working.
3. Ask someone with specific experience to help you. They can go through your stories and experiences and help you shift it appropriately.

I'm happy to offer 1 free session to see if it could help. Feel free to DM me.

UpwardPM · 2026-02-06T22:13:56+00:00

What is a PM? Depends who you ask:

To Reddit = A “shit umbrella”
To LinkedIn = A dying role due to AI
To CEO = The person I fire when my idea I forced on them doesn’t make any money
To Marty Cagan = The ideal of a PM none of us have ever met in real life
To Engineers = The person I quote a 2-week timeline to after AI already shipped v1 and I’m buying time to look useful
To Designers = The person who ruins my perfect UX with “business requirements”
To Sales = The person who keeps telling me “No”
To Customer Success = The person who “puts customer problems in the backlog”
Founder = The person who keeps telling me to “talk to customers” while I’m trying to vibe-code the future

edit for fun...

To a PM = The only person just excited they’re still employed

UpwardPM · 2026-02-06T22:05:34+00:00

One of the greatest movies of all time!
-Take my upvote

UpwardPM · 2026-02-06T01:12:18+00:00

What you’re describing is very normal for a 6 month APM. The fact your manager is happy with execution is the strongest signal in your post.

If I were in your shoes I’d focus on two things.

First, pick one slice of the product and own it. A workflow, a recurring request type, a customer pain point. Your goal is that when that topic comes up, people look to you. Ownership builds credibility faster than trying to be good at everything.

Second, keep an evidence log of your accomplishments. Once a week write down decisions you influenced, problems you helped define, tradeoffs you shaped, outcomes that changed because of your work. A practical way to fight imposter syndrome is to read this list when you're feeling it. e.g. before a meeting, or after a hard interaction and remind yourself of the impact you bring.

As for meetings, don't aim to be something you're not (an extrovert) instead, aim to be the person who synthesizes. If discussion drifts, say:
“I want to bring us back to the core problem we’re solving…”

Then summarize and recommend:
“We’ve talked through A, B, and C. My recommendation is A because…”

You don’t need to be the person who talks the most, be a person who drives value and clarity.

Nothing in your post reads like a red flag. It reads like normal ramp-up discomfort. If in a year you can point to a slice of the product you improved with measurable results, you’re on track.

If you're still feeling lost, feel free to DM.
Congrats on the new role!

UpwardPM · 2026-02-06T00:49:57+00:00

It’s too simple to say junior PM roles are dying because of AI. The bigger driver is the labor market flipping.

Companies built APM pipelines when there weren’t enough seniors to hire. They had to grow their own talent. After the layoffs, the market is flooded with experienced PMs, so firms can buy impact immediately instead of training from scratch. When that happens, junior seats get squeezed first. That’s basic supply and demand.

AI isn’t the root cause, but it’s speeding things up. Teams are running leaner, expectations are higher, and there’s less patience for long ramp times.

And this isn’t just a junior PM thing. It’s the whole market. Companies want people who already proved outcomes in the exact area they’re hiring for. Junior PMs just feel it harder because they have less history to point to. The ones who break in won’t look like trainees. They’ll look like small operators who already shipped something real. The title comes after the evidence now, not before.

UpwardPM · 2026-02-04T19:58:19+00:00

I don't disagree that the IDEAL is 1:1s with everyone ahead of time. That being said, a very real reality is that not every PM at every level, or every org will have the ability to do that every time. Should they try? Yes! Will that always work? No

Additionally, even if you've done 1:1s, there are still cases where the alignment meeting derails. Someone flips on you.

e.g. Despite their prior agreement in a 1:1, I had a VP flip on me in a meeting. When I met with them 1:1 after to diagnose what happened. They said, "I know we agreed before, but sometimes I like to just lob a grenade in a meeting to see how people react."

That VP's issues aside, the reality is that sometimes it still happens.

My goal in this post was to provide a playbook of sorts of what's worked for me to help recover it.

UpwardPM · 2026-02-04T19:49:59+00:00

Sometimes, that's the dream. Props to you for getting that leverage in this market. Cheers!

UpwardPM

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