We start with what we want to build, then work backwards to justify the timeline.
"This should take 2 months" becomes "This will take 2 months" in the slide deck.
6/16 Roadmaps fail because they assume static context:
Market stays the same (it doesn't)
Competition stays the same (it doesn't)
Team stays the same (it doesn't)
Company priorities stay the same (they don't)
Yet we plan like none of this will change.
7/16 We roadmap the known unknowns but ignore the unknown unknowns:
Known: "This integration might be complex"
Unknown: "The vendor will change their API twice"
Unknown: "Our biggest customer will threaten to leave"
Unknown: "Legal will block the launch"
8/16 Roadmaps assume perfect execution:
No one gets sick
No one quits
No technical debt blocks progress
No urgent bugs derail the team
No scope creep happens
Have you met humans?
9/16 My favorite roadmap lie: "accurate" time estimates.
"This will take 6 weeks"
(Based on what? The last time we built something completely different?)
We estimate like we have historical data for novel work.
10/16 Stakeholders treat roadmaps like contracts:
"You said Q3, it's now Q4"
"The roadmap shows mobile first"
"This wasn't on the original plan"
But they were built on assumptions that expired months ago.
11/16 What works better than detailed roadmaps:
Clear principles for decision-making
Outcome goals instead of feature lists
Quarterly themes, not monthly commitments
Options, not promises
12/16 The best "roadmaps" I've seen:
3 months: Specific commitments
6 months: General direction
12 months: Strategic themes
The further out, the vaguer it gets. That's honest planning.
13/16 Instead of defending the roadmap, constantly question it:
What changed since we made this plan?
What did we learn that invalidates our assumptions?
What would we do differently if we started today?
Plans should evolve, not persist.
14/16 Stop saying: "Here's what we're building next year"
Start saying: "Here's how we'll decide what to build"
Stop promising features.
Start promising good judgment.
15/16 Many PMs struggle with roadmap pressure due to lacking systems to convey uncertainty while maintaining credibility.
I've built 120+ prompts for these exact situations - stakeholder communication, planning under uncertainty, priority frameworks.
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.
Level 1 decisions:
- Maximum 1 per day
- Fresh morning brain only
- Written analysis required
- Sleep on it rule (24hr minimum)
- Stakeholder alignment needed
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.
From my AI prompt collection - Transform competitive analysis:
"Analyze the spreadsheet thoroughly. Pay attention to:
- Features unique to your company
- Areas where you outperform competitors
- Gaps in market not addressed by competitors"
Real PMs report 40% productivity gains with strategic prompting.
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 old way:
- 10 interviews = 10 hours recording
- Manual transcription = 3+ hours
- Finding patterns = 4 hours staring at notes
- Writing insights = 2 hours
- Total: 19 hours across 2 weeks
The AI way:
- Recording time unchanged (10 hrs)
- Auto-transcription (instant)
- Pattern extraction (30 min)
- Insights with supporting quotes (automated)
- Total: 10.5 hours in a few days