Two years into my PMM career, I realized I'd been making the same executive communication mistakes repeatedly—and they were costing me.
I'd present comprehensive analysis and get polite nods. I'd send detailed updates and get no response. I'd offer recommendations and watch them get ignored.
Meanwhile, a peer PMM with less experience was getting promoted, invited to strategy meetings, and consulted by executives on major decisions.
I asked our CMO what I was missing. She said: "You communicate like a PMM presenting to PMM peers. Executive communication is different—different structure, different focus, different expectations. You're making mistakes that signal you're not thinking at their level."
That conversation was uncomfortable but necessary. She walked me through five specific mistakes I was making—mistakes I didn't even realize were problems.
Fixing these mistakes changed everything. Within six months, I went from being excluded from strategic conversations to being asked to present at board meetings.
These weren't small communication tweaks. They were fundamental shifts in how I approached every executive interaction.
Mistake #1: Leading With Context Instead of Conclusion
What I was doing:
I'd start presentations with background and context, working my way toward the conclusion:
"Over the past 6 months, we've been tracking competitive movements in the enterprise segment. We conducted 40 win/loss interviews, analyzed competitor product launches, and assessed market trends. Based on this analysis, we're seeing three patterns emerge. First, competitors are investing in compliance features. Second, buyers are increasingly prioritizing security certifications. Third, our positioning isn't resonating with enterprise buyers. So based on all of this, I recommend we reposition..."
By the time I reached my recommendation (slide 12), I'd lost half the room.
Why this is a mistake:
Executives want the answer first, then the supporting logic. They're deciding whether your recommendation is worth discussing. If they have to sit through 10 minutes of context before understanding what you're recommending, you've wasted their time.
How I fixed it:
I inverted my entire communication structure. Now I lead with the conclusion:
"Recommendation: Reposition away from enterprise segment and focus on mid-market where we win 58% of deals vs. 18% in enterprise. This would sacrifice $8M in enterprise TAM but double down on $40M mid-market opportunity. Here's why I believe this is the right path..."
The impact:
Executives engage immediately because they know what you're recommending. They can decide in the first 30 seconds whether they agree, disagree, or want more detail.
The CEO told me after one presentation: "This is exactly how I need information presented—answer first, then defense of the answer. Saves everyone time."
The rule: If you can't state your main point in the first sentence, restructure.
Mistake #2: Presenting Information Without a Clear Ask
What I was doing:
I'd present analysis and end with: "So that's the competitive landscape. Any questions?"
Or: "Here's what we learned from customer research. Happy to discuss further."
No clear ask. No decision needed. No specific action requested.
Why this is a mistake:
Executives are making dozens of decisions daily. If you don't tell them what decision you need, they'll move on.
Ending presentations with "any questions?" signals you're reporting information, not driving decisions. Executives will nod politely and forget your presentation within 10 minutes.
How I fixed it:
Every executive communication now ends with a specific ask:
"Decision needed: Approve $200K budget for compliance partnership or choose one of the alternative options. We need a decision by December 15th to impact Q1 enterprise quota."
"Asking for: 30 minutes on next exec meeting agenda to present repositioning recommendation and get alignment on strategic direction."
"Request: Weekly CEO update added to my calendar so I can proactively surface competitive intelligence instead of waiting for requests."
The impact:
Executives know exactly what they need to do. They can approve, reject, or modify—but they're making a decision, not just receiving information.
Response rates to my emails went from 30% to 85% after I started ending every message with a clear, specific ask.
The rule: Every executive communication should answer: "What do you need from me?"
Mistake #3: Getting Defensive When Challenged
What I was doing:
When executives challenged my recommendations, I'd get defensive:
CEO: "I'm not sure repositioning away from enterprise is the right move. We've invested 18 months building enterprise capabilities."
Old me: "But the data clearly shows we're losing 82% of enterprise deals. We've interviewed 40 customers. The research is solid. Enterprise buyers need compliance features we don't have. The numbers don't lie..."
I'd argue back, re-stating my evidence, trying to convince them I was right.
Why this is a mistake:
Getting defensive signals you're attached to being right instead of finding the best answer.
Executives challenge recommendations to stress-test them, not to attack you. When you argue defensively, you sound like you can't handle pushback—which undermines executive presence.
How I fixed it:
I learned to acknowledge challenges without defending:
CEO: "I'm not sure repositioning away from enterprise is the right move."
New me: "That's a fair point. We have invested significantly in enterprise. Here's why I still think repositioning is the right call: The 18-month investment hasn't changed our 18% win rate—enterprise buyers need compliance certifications, not just features. But I could be missing something. What would change your assessment?"
The impact:
Executives appreciate when you acknowledge their challenge and then defend your position calmly. The phrase "I could be missing something" signals you're open to being wrong while still advocating for your recommendation.
The CFO once told me: "I push back hard on recommendations to see how people respond. You defend your position without getting defensive—that tells me you've thought it through."
The rule: When challenged, say "Fair point. Here's why I still believe X, but I could be wrong. What would change your view?"
Mistake #4: Buried the Business Impact in PMM Language
What I was doing:
I'd describe PMM work in PMM terms:
"We built a comprehensive competitive intelligence program with battle cards for each competitor, quarterly positioning updates, and sales enablement materials. We've achieved 82% sales adoption of battle cards and positive feedback from reps."
This sounds like successful execution of PMM activities.
Why this is a mistake:
Executives don't fund activities—they fund business outcomes. Saying "we built battle cards" doesn't communicate business value.
How I fixed it:
I learned to translate every PMM activity into business impact:
"We built a competitive intelligence program that improved our competitive win rate from 34% to 48% over six months. That 14-point improvement generates $4.8M in additional annual revenue. ROI on the program investment: 240x."
Same work. Different framing. The first version describes what I did. The second version describes the business value it created.
The impact:
Our CMO forwarded my business impact summary to the exec team with the note: "This is the kind of ROI we should be tracking for all programs."
I went from having budget scrutinized to having budget increased because I could quantify value in executive terms.
The rule: Every PMM activity should translate to: Revenue impact, cost avoidance, or efficiency gain.
Mistake #5: Presenting at the Wrong Time
What I was doing:
I'd send important recommendations whenever I finished them:
- Sending competitive analysis at 6 PM on Friday
- Proposing major budget allocation in week 2 of the quarter
- Presenting repositioning recommendation during crisis firefighting
- Emailing CEO detailed proposals without context on what they're responding to
Why this is a mistake:
Timing affects whether executives can give your communication the attention it deserves.
Friday evening emails get lost in weekend brain dump. Mid-crisis presentations get tabled. Early-quarter budget requests compete with planning chaos.
How I fixed it:
I became strategic about timing:
For major decisions: I sync with CEO's calendar and request specific meeting slots when I know they have strategic thinking time (usually Monday mornings or mid-week afternoons).
For budget requests: I submit in week 4-5 of previous quarter, before next quarter planning lock-in.
For competitive updates: I send early week (Monday/Tuesday) when executives are planning their week, not Friday when they're wrapping up.
For crisis-related insights: I wait until the immediate fire is out, then present: "Now that we've handled the crisis, here's what it revealed about our competitive position..."
The impact:
My recommendations started getting acted on faster. The CEO once said: "I appreciate that you send things when I can actually think about them, not just when you finish them."
Response time to my proposals dropped from 2-3 weeks to 3-5 days simply by timing them better.
The rule: Consider the executive's context and calendar when communicating, not just your own deadlines.
How These Mistakes Compounded
Here's what was happening when I made all five mistakes simultaneously:
I'd spend two weeks building comprehensive competitive analysis. I'd email it to the CEO at 5 PM on Friday (Mistake #5: Bad timing). The email would start with "I've been analyzing the competitive landscape..." and work toward the conclusion on page 6 (Mistake #1: Buried conclusion). I'd describe all the research I'd done without translating to business impact (Mistake #4: PMM language). I'd end with "Let me know if you have questions" (Mistake #2: No clear ask). When the CEO didn't respond for a week, I'd follow up defensively: "Did you see my analysis? I spent significant time on this..." (Mistake #3: Defensive).
Result: The analysis got ignored. I felt undervalued. The CEO thought I was a good analyst who couldn't think strategically.
Here's the same communication after fixing all five mistakes:
Monday at 9 AM, I send an email:
"Subject: Competitive Recommendation: Reposition Away from Enterprise (Decision Needed)
Recommendation: Focus on mid-market, deprioritize enterprise for 12 months. We're losing 82% of enterprise deals vs. winning 58% of mid-market deals. This repositioning could add $3.2M ARR by redirecting sales capacity to higher-probability opportunities.
Three options with trade-offs:
- Continue competing in enterprise (current path, expected $800K annual losses)
- Reposition to mid-market (recommended, $3.2M upside)
- Invest $600K in enterprise capabilities (uncertain ROI, 18-month payback)
Full analysis attached. Need 20 minutes on Thursday's exec meeting to discuss and get decision. Can we add this to the agenda?"
Result: CEO responds within 2 hours: "Added to Thursday agenda. Like the framing. See you then."
That's the difference these five fixes make.
The Patterns Executives Notice
After fixing these mistakes, I started getting different feedback from executives:
Before fixes:
- "Interesting analysis, thanks for sharing"
- "Let's circle back on this later"
- "I'll take a look when I have time"
After fixes:
- "This is exactly the kind of strategic thinking we need"
- "Can you present this to the board?"
- "I want your take on [strategic decision]"
The difference wasn't that my analysis got better—it's that my communication signaled I was thinking at their level.
The specific behaviors executives notice:
Leading with conclusions → Signals you think strategically, not just analytically
Clear asks → Signals you understand decision-making process
Non-defensive response to challenges → Signals executive presence and confidence
Business impact framing → Signals you understand what drives business value
Strategic timing → Signals you respect their context and priorities
These behaviors compound: Each one builds credibility. Together, they completely change how executives perceive you.
The Conversation That Changed Everything
Six months after fixing these mistakes, our CEO pulled me aside after a board presentation:
"Two years ago, you presented solid analysis but I wasn't sure you could think strategically. Now you're one of the first people I consult on major decisions. What changed?"
I explained the five mistakes I'd fixed.
He said: "That tracks. The shift from 'here's my analysis' to 'here's my recommendation and why' changed how I saw you. You went from executing PMM work to driving strategy."
That's when I realized: These weren't communication style preferences—they were signals executives use to assess strategic thinking capability.
Every time I led with context instead of conclusion, I signaled I couldn't think strategically.
Every time I presented without a clear ask, I signaled I didn't understand decision-making.
Every time I got defensive, I signaled I couldn't handle executive-level discourse.
Every time I used PMM language instead of business impact, I signaled I didn't understand what executives care about.
Every time I sent things at the wrong time, I signaled I wasn't thinking about their context.
Fixing these mistakes didn't just improve my communication—it changed how executives assessed my strategic capability.
How to Fix These Mistakes (Starting This Week)
This week:
Take your next executive communication and run it through these five checks:
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Does it lead with conclusion? If not, move your main point to sentence 1.
-
Does it have a clear ask? Add specific decision/action requested with timeline.
-
If challenged, can I respond without defensiveness? Practice: "Fair point. Here's why I still believe X, but I could be wrong."
-
Have I translated PMM work to business impact? Every activity should connect to revenue, cost avoidance, or efficiency.
-
Is the timing strategic? Consider executive's calendar and context before sending.
Next month:
Record yourself presenting to executives (or practice with a colleague). Watch for:
- How long before you state your main point?
- Do you end with a clear ask or "any questions?"
- How do you respond to pushback—defensive or open?
- Do you describe activities or business outcomes?
Next quarter:
Track executive response patterns:
- Response rate to your communications
- Time to decision on your recommendations
- Whether you're being invited to strategic conversations
If these aren't improving, you're likely still making some of these mistakes.
The Uncomfortable Truth
Most PMMs think these mistakes are style preferences: "Some people like context first, some like conclusions first."
They're actually strategic thinking signals: Executives use communication patterns to assess whether someone thinks strategically or tactically.
The PMMs who get promoted and invited to strategy conversations:
- Lead with conclusions
- Make clear asks
- Handle challenges without defensiveness
- Frame work in business impact terms
- Time communications strategically
The PMMs who stay stuck at tactical levels:
- Bury conclusions in comprehensive analysis
- Present information without asking for decisions
- Get defensive when challenged
- Describe PMM activities instead of business outcomes
- Send things whenever they finish them
The difference in career trajectory is dramatic.
I spent two years making these mistakes before someone pointed them out. Fixing them changed everything—not just how executives responded to me, but how they perceived my strategic capability.
These aren't communication tactics—they're strategic thinking habits.
Master them, and you'll go from presenting PMM work to influencing company strategy.
That's when your career accelerates.