Spot The HiPPO Trap Before You Say Yes
Most PMs are playing inside a rigged system.
You think you’re interviewing for a leadership role.
You’re actually interviewing to become a high-priced scribe for the HiPPO (Highest Paid Person’s Opinion).
Here’s how to audit the system before it breaks you.
The 3 Buckets That Predict PM Pain
Most red flags are not random. They cluster into three buckets.
1. Decision Rights Risk
This is the big one.
If decisions are centralized (often with a CEO or a single leader), the PM role becomes ceremony:
you gather input
you write docs
you run meetings
you ship what someone else picked
You are accountable, but not empowered. That is a trap.
A quick example of how this shows up in real life:
A PM spends 6 weeks building a pricing model, aligning stakeholders, and setting up the rollout plan.
Then the CEO changes the whole strategy in a 15-minute Slack thread.
No post-mortem. No learning. Just a new direction and a PM left holding the bag.
Signals:
“Every product decision needs approval.”
“We move fast because the founder has strong opinions.”
“You’ll work closely with the CEO on everything.”
People speak carefully instead of clearly.
2. Trust and Culture Risk
This is the “fear org” pattern.
When trust is low, people stop telling the truth. They start protecting themselves. And great talent becomes quiet.
Signals:
Team members warn you about culture, but say someone will “shield” you.
Nobody can name one real problem with how they work (because they’re scared).
Colleagues speak disrespectfully about each other.
You notice you are treated as “not important” from day one.
3. Commercial and Process Risk
This bucket tells you whether the company plays fair and whether the role is real.
Signals:
Offer changes late in the process (even slightly).
Promises that are not in the contract.
Contract clauses that feel one-sided or strange.
Long interview loops and take-home work that looks like free consulting.
“We don’t negotiate” before you even try.
Excessive “we are a family” energy or love-bombing.
The 10-Minute Red Flag Score
Use this before you accept.
Score each statement from 0 to 2:
0 = not present
1 = maybe
2 = clearly present
Use Notes to capture proof, not vibes.
And if you’re actively interviewing, pair this with a cleaner search process like the one in Remote product jobs: stop doomscrolling so you’re not wasting cycles on roles that were never real to begin with.
Decision Making (0–2 each)
Decisions require exec approval for small things ( ___ ) Notes: ______
They can’t explain clearly who decides what ( ___ ) Notes: ______
Priorities change weekly or “CEO is very involved” is framed as a benefit ( ___ ) Notes: ______
Trust/Culture (0–2 each)
People give vague, rehearsed answers ( ___ ) Notes: ______
You sense fear or tension in normal conversations ( ___ ) Notes: ______
People hint at problems but avoid details ( ___ ) Notes: ______
Your instincts feel “off” despite a great offer ( ___ ) Notes: ______
Process (0–2 each)
Offer terms changed late ( ___ ) Notes: ______
Big promises not in writing ( ___ ) Notes: ______
Take-home work is too close to “free consulting” ( ___ ) Notes: ______
Hiring process shows low respect for your time ( ___ ) Notes: ______
Total Score: ____ / 22
Simple rule:
If you score 6+, pause.
If you score 8+, treat it as a no unless you have a strong reason and a clear exit plan.
Paid members get the printable one-page scorecard (PDF) plus the auto-scoring Excel version so you can run this audit fast without rebuilding the table every time.
Yellow Flags vs Red Flags
Not every “bad smell” is a dealbreaker.
Some are just growth pains in a scaling startup.
The difference is simple:
Yellow flag: messy, but honest.
They can name the issue, explain why it exists, and tell you what they’re doing to fix it.
Red flag: messy, but defensive.
They deny it, minimize it, or blame individuals.
Use this quick filter:
If you ask a direct question and they answer with specifics, it might be a yellow flag.
If you ask a direct question and they answer with vibes, it’s usually a red flag.
The Questions That Surface the Truth Fast
These are designed to force concrete answers. No fluff.
Decision making
“Walk me through the last product decision you made end-to-end. Who disagreed, and how was it resolved?”
If they can’t name a real disagreement, they’re hiding something.
“What decisions will I own in my first 30 days without additional approval?”
If the answer is “it depends,” press.
“When was the last time product said no to leadership and it stuck?”
If it never happens, you are not joining a product org.
Trust and culture
“What’s hard to talk about here?”
Healthy teams can answer this calmly.
“Why did the last PM leave?”
If you hear “culture fit” repeatedly with no specifics, watch out.
Role clarity
“Why are you hiring a PM right now?”
Bad answer: “We have too many tasks.”
Good answer: clear outcomes, boundaries, and success metrics.
Work expectations
“What does a normal week look like here?”
If long hours are worn like a badge, that is usually a culture problem, not a growth story.
Hiring integrity
“What would make you say ‘this isn’t working’ in the first 90 days?”
You want honesty and shared expectations, not vague positivity.
How to Validate Without Relying on Interviews
Interviews are staged. So you need one layer of real signal.
Do at least one of these:
Check LinkedIn tenure patterns. Lots of short stays in product is a warning.
Message one person currently there and one person who left.
Ask:
“What surprised you after joining?”
“What would you fix if you could?”
Look at job posting volume and repetition. One open role is normal. The same role reposted again and again is a smell.
You’re not hunting for perfection.
You’re hunting for patterns, which is also why I’m strict about only sharing roles with direct company links and a repeatable filter described in Our job verification process.
If You Already Joined and It Feels Wrong
Sometimes you only see the full picture inside.
Here’s the practical play:
Name the constraint clearly: “Decisions are centralized, outcomes are still on me.”
Try one repair loop: propose a decision rights map and a simple operating cadence.
Set a time limit: 30 to 60 days to see if power actually shifts.
Build your exit plan quietly: keep your story clean, keep your energy, protect your resume.
Need help navigating this?
Paid subscribers get priority support for positioning and interview clarity, including how to exit cleanly without damaging your story. And if your first 30 days already feel chaotic, you’ll recognize the pattern from Bad PM start recovery.
A PM career grows through compounding impact.
A broken system breaks compounding.
The “Green Flags” People Forget to Look For
It’s not enough to avoid red flags. You want signs of a healthy product system.
Green flags:
They can explain decision rights simply.
They can name real tradeoffs they made and what they sacrificed.
They are honest about problems and proud of how they resolve conflict.
They respect your time in hiring.
They define success in outcomes, not hustle.
Final rule
If it feels off early, it’s usually worse later.
Not because you’re anxious.
Because your pattern recognition is working.
Your job is not to talk yourself into the role.
Your job is to choose an environment where good PM work is allowed to exist.
What’s a red flag you ignored that ended up being the reason you left a role? Reply and let me know. I’ll share the best ones (anonymously) in the next issue.
One last thing before you go
If you’re actively interviewing, don’t stop at avoiding bad roles.
The fastest way to land a good one is to run this scorecard on fresh postings, then focus your effort on the few that pass, and if you want to see how I keep the list clean, you can skim Remote product jobs: stop doomscrolling as a quick overview of the approach.
Upgrade now to get:
29 verified remote PM roles (USA, last 7 days)
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