When a Stakeholder Says “Quick Question” (Vol. 1, Issue 2)
- D.B Trench
- Dec 29, 2025
- 2 min read
Excerpt:
Stakeholder chaos rarely announces itself. It sneaks in disguised as politeness. Here’s this week’s lesson in decoding surprise asks before they explode your roadmap.
Full Issue
There’s a moment — a very specific moment — when you know a stakeholder is about to move your entire timeline.
The head tilt. The half-smile. The faux-casual tone.
And then the four words every PM fears more than production outages:
“I have a quick question…”
In Deliveria, this phrase is classified as a Category 4 Risk Event.
Welcome back to The PMTales Dispatch, where we examine chaos under a warm lamp and remind ourselves we’re not the only ones living through it.
This Week’s Tale From the Field
A stakeholder once told me:
“Could we just deliver the dashboard two weeks earlier? It shouldn’t change anything.”
Meanwhile, in the background, the Goalpost Mover creature quietly shuffled into the room holding a clipboard, taking notes on how much trouble we were now in.
Stakeholder chaos rarely comes from malice. It comes from:
optimism untethered from physics
promises made to leadership without checking feasibility
forgetfulness wrapped in confidence
fear disguised as urgency
political pressure disguised as “quick questions”
Your job is not to absorb these emotions. Your job is to translate them.
Survival Lesson #2: Decode the Underlying Emotion
Behind every surprise request is a feeling:
Fear → “My VP is pressuring me.”
Visibility → “I need to look proactive.”
Wishful Thinking → “Surely this can’t be that hard.”
Avoidance → “Let’s pretend this is fine.”
Confusion → “I genuinely don’t remember what we agreed on.”
Technical responses fail because the root problem isn’t technical.
Try this instead:
“Before we adjust anything, what outcome are you hoping for?” “Is the priority speed, quality, or optics?” “Do you need this done… or do you need reassurance?”
Once you name the emotion, the chaos calms.
The Trade-Off Table (Your Best Friend)
Here is the simplest, most diplomatic PM tool in existence:
Option A: Deliver earlier → Lose testing / shift Feature X
Option B: Keep plan → Stability + quality
Option C: Split delivery → Early preview + final later
Option D: Add resources → Time or budget shifts
Then ask:
“Which path best meets your needs?”
Stakeholders don’t mind boundaries. They mind surprises.
The Trade-Off Table removes both.
From the PMTales Armory
If stakeholder chaos has been visiting frequently, try:
Goalpost Mover, Expectation Drift, and Scope Creep Creature Cards - Stakeholders relax when the problem feels like a creature, not an accusation.
Stakeholder Field Guide - Quick scripts + patterns to use Monday morning.
Field Note of the Week
Calm PMs aren’t calm because the world is calm.
Calm PMs are calm because they know:
where the real pressure is coming from,
how to surface the truth kindly,
and how to co-create decisions instead of absorbing demands.
That’s real leadership. And it’s the only antidote to “quick questions.”
What to Explore Next
Until Next Week
You’re not difficult. You’re not inflexible. You’re not “blocking progress.”
You’re the only one looking at the whole map.
See you in the trenches,
D.B. Trench
PM, storyteller, veteran survivor of quick questions
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