Your stakeholders aren't crazy.

After 6 years of product management, I've realized: every "difficult" stakeholder behavior has a hidden logic.

A thread on the psychology of product stakeholders 🧠 1/ Sales: The Future-Focused Hunters

What they see:
• Revenue targets looming
• Competitors taking deals
• Prospects making demands
• Commission at risk

What they feel:
• Urgency to close deals
• Fear of losing opportunities
• Frustration with product gaps
• Personal financial pressure

This is why they:
• Push for custom features
• Make promises to customers
• Escalate to leadership
• Sound desperate sometimes

Technical folks transitioning to product often struggle with strategic thinking.

Not because they can't think strategically.

But because they're stuck solving the wrong problems.

After mentoring a few bring PMs, here's what actually works for developing strategic thinking🧵 1/ First, let's destroy a myth:

"Strategic thinking means having a grand vision"

No. Strategic thinking starts with being comfortable in the problem space before jumping to solutions.

I made this mistake for 2 years as a PM, trying to come up with solutions before understanding problems.

My first year as a PM, I burned bridges by saying 'no' wrong:

- Lost eng team trust
- Damaged stakeholder relationships
- Got labeled as 'not a team player'

Until I discovered this counterintuitive approach to saying no (that actually builds stronger relationships)

🧵 1/ The conventional wisdom is broken:
- "Just say no firmly"
- "Stand your ground"
- "Protect the roadmap"

These create adversaries, not allies.

The hard truth: Your 'no' is probably making you look weak, not strong.

You left engineering because you were tired of:

- PMs who don't understand system dependencies
- "Product people" who can't think in flows
- Leaders who demand random features
- Roadmaps built on hope

But what if product management was actually about systems?

"Thinking in Systems" blew my mind: 1/ Most technical people are trained to see the world as a series of cause-and-effect relationships:

- Input → Process → Output
- Problem → Solution
- Bug → Fix

But products are systems, with:

- Multiple feedback loops
- Delays
- Unintended consequences

Stop asking engineers for estimates.

Basecamp eliminated them entirely with Shape Up because estimation is the wrong question.

When you ask "How long?" you should ask "How much time is this worth?" 🧵 You ask: "How long will this take?"

Engineer says: "2 weeks"

3 weeks later: "Just need a few more days"

4 weeks later: "Almost done, ran into some edge cases"

Every PM has lived this nightmare.

Your product leader doesn't care about technical debt.

The business case that changes their mind: 🧵 Most engineers-turned-PMs present technical debt like this:

"We need 3 sprints to refactor the user service. The code is unmaintainable."

CEOs hear: "Engineers want to play with code instead of shipping features."

Ah, a PM joining an established team

Eager to make an impact. Ready to use your PM skills

But then reality slaps you:
🚨 Engineers already own the roadmap
🚨 They have years of context you don’t
🚨 And they don’t seem to need you

How do you earn trust & find your voice? ↓ I made this mistake repeatedly in my first years as a PM.

Joining teams with established dynamics, I'd immediately try to "add value" by:

- Questioning their roadmap
- Pushing for more discovery
- Inserting PM frameworks

The result? Quiet resistance and damaged relationships.

User personas are the astrology of product management.

Teams spend months crafting detailed profiles just to feel like they understand their users.

But like horoscopes, they give the illusion of insight without the substance of real understanding.

Here's the hard truth 🔭 1/ Every month, I watch teams debate fictional personas while ignoring actual user behavior:

"Jessica, 35, urban professional, tech-savvy..."

Meanwhile their real users are screaming about basic problems in support tickets.

i turned this career advice from Marc Andreesen (2025 version) into a series of prompts that can change your life: ↓ 1/ Career OS – persistent system prompt

Objective: Set the LLM as your ruthless, practical career operator.
Use when: Starting a new session.

Prompt (copy/paste):

You are my Career Operator. Optimize for: (1) speed of learning, (2) compound credibility, (3) opportunities at Series C–E companies, (4) deep relationships, (5) curiosity about how things work.

Operating principles:
- Favor action over meetings. Propose artifacts (docs, demos, dashboards).
- Assume high-growth chaos. Make plans robust to ambiguity.
- Bias to helping others to build relationships.
- Challenge me to take measured risks; call out conservatism disguised as prudence.
- Keep outputs concise, structured, and usable immediately.

When I give you a task, return:
1) 3-sentence diagnosis
2) A prioritized plan (checklist)
3) The smallest shippable artifact I can produce in <2 hours
4) Risks + how to test quickly
5) The one introduction I should try to make or value I can offer this week

Confession: Most PMs (myself included) do surface-level analysis and call it strategy.

We miss root causes, ignore power dynamics, skip edge cases.

Not because we're lazy. Because we don't know what good analysis actually looks like.

🧵 Every PM has written this slide:

"Key takeaways from user research:"
• Users want faster performance
• Mobile experience needs improvement
• Navigation is confusing

And called it "deep customer insights."

I've never seen a roadmap survive contact with reality.

Not once. In 15+ years of product work.

Yet we spend weeks building beautiful charts and quarter-by-quarter feature lists like we can predict the future.

🧵 1/16 Watch any PM in December:

Frantically building next year's roadmap like they can predict customer behavior, market shifts, and technical challenges 12 months out.

Same energy as checking your horoscope for investment advice.

Confession: I've never seen a PM framework actually work in real life.

RICE, ICE, Value vs Effort - they're all just ways to make gut decisions look scientific.

But we keep pretending they're magic because it makes us feel less like frauds.

🧵 1/17 Product decisions are fucking terrifying. You're betting the company's future on incomplete information.

Frameworks give us the illusion of control. "I used RICE, so if this fails, it's not my fault - the system failed."

You're not bad at decisions. You're drowning in them.

The 3pm panic when every choice feels equally critical signals decision fatigue, not poor judgment.

Confident PMs don't make better decisions. They make fewer decisions.

This validation framework reduces decision load: ↓ 🔴 LEVEL 1: Irreversible (product direction, team structure)
🟡 LEVEL 2: Expensive to reverse (major features, partnerships)
🟢 LEVEL 3: Cheap to reverse (copy changes, small experiments)
⚪ LEVEL 4: No decision needed (delegate or automate)

Most PMs who naturally sort decisions by reversibility already operate at a senior level.

After studying high-performing PMs for years, I noticed something strange:

The most impactful product managers often do LESS than their peers.

They write shorter docs. Hold fewer meetings. Create simpler processes.

They've mastered making impact look effortless.

Here's how: I spent my first 3 years as a PM writing 30-page PRDs no one read and creating complex processes no one followed.

I thought "good product work = hard product work."

But what if the opposite is true? What if making it harder actually reduces your impact?

99% of PMs complain about their managers.

1% of PMs turn their manager into a career accelerator.

The 1% stopped "managing up" and started creating mutual leverage.

Here's the exact playbook ↓ Your manager spends 2-3 hours/week thinking about your work.
You spend 40+ hours executing it.

This 20:1 asymmetry creates most PM-manager tensions.

The solution isn't more meetings or better updates.
It's creating *mutual leverage*.

78% of organizations now use AI in at least one business function (McKinsey 2024).

But most product leaders are still using it for basic tasks like writing PRDs.

Here's how to leverage AI for strategic advantage (with actual prompts that work): 🧵 McKinsey found only 1% of companies believe they're at AI maturity.

Meanwhile, 43% of professionals use AI tools without telling their bosses (2024 survey).

The gap? Most PMs don't know HOW to prompt AI for strategic work vs. documentation.

The real impact of AI on PM work:

PRDs: 8 hours → 45 minutes
Interview analysis: Full day → 30 minutes
Strategy decks: 2 days → 3 hours
Requirements docs: 5 meetings → 1 async session

Here's exactly how the workflow changes 🧵 BEFORE AI:
- Monday: Gather scattered inputs (2 hrs)
- Tuesday: Blank page to first draft (3 hrs)
- Wednesday: Stakeholder feedback rounds (2 hrs)
- Thursday: Endless revisions (1+ hr)
- Friday: "Actually, can we add..." (∞)

WITH AI:
- Dump all context into structured prompt (5 min)
- Review generated draft (20 min)
- Customize for specific needs (20 min)
- Ship

The "simple 2-week integration" that becomes a 6-month death march.

Every PM knows this nightmare.

Here's why it happens—and how to prevent it before writing a single line of code 🧵 It always starts the same:

Week 1: "Just need to add SSO login"
Week 3: "Actually, we need custom roles"
Week 5: "Oh, and multi-tenancy"
Week 8: "Can we also sync with their legacy system?"

Classic scope creep in action.

ai isn't replacing product managers. ai is revealing what product management actually is.

here's what's happening inside companies right now.

junior pms panic when chatgpt writes better user stories than they do. they watch ai generate product requirements in minutes while they take hours. they see executives asking "why do we need pms if ai can do their work?"

but ai automates the artifacts of pm work, not the thinking that creates them.

every great pm knows this feeling: you spend 20% of your time creating documents & 80% understanding the context that makes those documents meaningful. ai flips this equation & makes the 80% visible.

the three layers of pm work

1. artifacts (ai dominates here)
- user stories
- prds
- roadmaps
- competitive analysis
- status reports

2. synthesis (ai augments here)
- research analysis
- data interpretation
- technical feasibility
- market insights

3. judgment (humans essential)
- strategic tradeoffs under uncertainty
- stakeholder alignment in ambiguous situations
- reading between the lines of user feedback
- building trust across teams

most junior pms spend 70% of their time on layer 1. ai forces you to spend 50% of your time on layer 3.

i guess some people might be uncomfortable with that. i think it actually opens up many more doors.

immediate actions you can take today

30-minute ai audit:

copy this prompt into chatgpt: "analyze my typical pm workweek: [paste your last week's calendar & task list]. categorize each activity as: artifacts (ai can do), synthesis (ai can help), or judgment (human essential). show me where to focus my learning."

reverse engineer ai output:

take any ai-generated prd. identify what's missing: user context, technical constraints, business priorities. these gaps reveal your value.

become an ai amplifier:

use this prompt: "challenge my product decision: [describe your last major product choice]. what assumptions might be wrong? what alternatives should i consider? what data would change my mind?" collections like ai prompts for product work help you skip the trial & error phase of learning effective prompts for product scenarios. ()prodmgmt.world/products/ai-pr…

PMs: When a customer says “I want CSV export,” and you just write it down, you’re wasting the interview.

Here’s how to flip lazy feature requests into goldmine insights.

It took me 5 years of painful interviews to learn this. You’ll get it in 1 minute. 1/ The proper response is to probe the underlying need:

"What would CSV export allow you to do?"
"How are you handling this today?"
"Talk me through the last time this came up"

I've added prompts to AI Prompts for Product Work to help PMs dig deeper: 👉 ($15) 🛍️prodmgmt.world/products/ai-pr…

PMs: 60-hour weeks ≠ impact.

I wasted 2 years on work that looked productive but stalled my career. Elite PMs do the opposite.

Avoid these 6 fake productivity traps. Took me 2 years to spot, you’ll get them in 2 mins. 🧵 1/ Writing detailed PRDs that nobody reads

I spent weeks crafting 20-page documents with perfect formatting.

Reality: Engineers skipped to the acceptance criteria. Stakeholders never opened them.

What to do instead: Start with a 1-page problem statement. Add details only when someone asks specific questions.