Our CRO and CMO were in a budget battle. CRO wanted $500K for enterprise sales expansion. CMO wanted that same budget for brand awareness campaign.
Both asked me for competitive data to support their position.
I panicked. If I supported CRO, CMO (my boss) would be upset. If I supported CMO, CRO (who controlled sales enablement budget I needed) would stop collaborating.
So I tried to stay neutral: "Both initiatives have merit. The data could support either approach depending on strategic priorities..."
Both executives saw through it immediately. CRO told me I was being evasive. CMO said I wasn't being helpful.
I learned a hard lesson: Trying to avoid executive politics doesn't keep you neutral—it makes you irrelevant.
Our CFO pulled me aside afterward: "You had the best market data to inform that decision, but you wouldn't take a position. When you refuse to make calls because you're worried about politics, you lose credibility with everyone."
That conversation changed how I navigate executive dynamics.
The Mistake I Made (That Most PMMs Make)
What I thought: Stay neutral in executive conflicts. Don't pick sides. Focus on the work and avoid politics.
What I learned: Neutrality isn't possible when executives have competing priorities. Trying to avoid politics just removes you from strategic conversations.
The reality of executive politics:
Executives have different goals, different metrics, and different perspectives. CRO cares about pipeline. CMO cares about brand. VP Product cares about roadmap. These priorities naturally conflict.
When PMM has data that informs resource allocation, staying neutral means:
- You're not helping executives make better decisions
- You're seen as someone who won't take positions
- You lose credibility with all executives (not just one)
- You get excluded from strategic conversations
The shift I needed to make: From "staying above politics" to "navigating politics by making independent recommendations based on data."
The Framework That Changed How I Navigate Executive Politics
After losing credibility by trying to stay neutral, I learned a framework from a former COO on our board:
"Don't pick sides. Pick positions. Back them with data. Be willing to be wrong."
This means:
Don't align yourself with executives—align yourself with what the data says is best for the company.
When CRO and CMO asked for data to support their competing priorities, here's what I should have done:
Step 1: Analyze Both Options Independently
I should have built an independent ROI analysis of both options:
Enterprise Sales Expansion ($500K):
- Expected pipeline: $3.5M over 12 months
- Expected close rate: 18% (our historical enterprise rate)
- Expected revenue: $630K
- ROI: 1.26x (low confidence due to poor enterprise win rate)
Brand Awareness Campaign ($500K):
- Expected impact: Increased brand consideration by 15-20%
- Pipeline impact: Difficult to attribute directly
- Expected revenue: Unknown, 12-18 month lag
- ROI: Uncertain
Alternative I discovered: Mid-Market Sales Expansion ($500K):
- Expected pipeline: $5.2M over 12 months
- Expected close rate: 58% (our historical mid-market rate)
- Expected revenue: $3M
- ROI: 6x
Step 2: Make a Clear Recommendation (Even If It Disagrees With Both Executives)
I should have presented this analysis to both executives:
"I analyzed both proposals. Neither is optimal. Enterprise expansion has uncertain ROI because our 18% win rate makes it high-risk. Brand awareness has unclear attribution.
My recommendation: Invest in mid-market expansion instead. ROI is 6x vs. 1.26x for enterprise. Data shows we win 58% of mid-market deals vs. 18% of enterprise deals.
I know this isn't what either of you proposed, but it's what the data supports."
Step 3: Defend the Position Without Being Defensive
When CRO pushed back: "But we need to crack enterprise—that's where the big deals are."
My response should have been: "I understand the strategic appeal of enterprise. But at 18% win rate, we're burning resources on low-probability deals. If we want to attack enterprise, we need to fix our win rate first—which means addressing compliance gaps. Without that investment, enterprise expansion is throwing money at a segment where we're structurally disadvantaged."
Respectful disagreement backed by data, not evasion.
The Three Types of Executive Politics PMMs Face
After navigating executive dynamics for several years, I've identified three recurring political situations:
Situation 1: Competing Resource Priorities
The dynamic: Two executives want the same budget/resources for different initiatives.
The wrong move: Try to satisfy both by hedging or saying "both are valid."
The right move: Analyze both options independently, recommend the one with better ROI, acknowledge tradeoffs.
Example:
CRO wants sales headcount. VP Marketing wants demand gen budget. Both cost $400K.
My analysis:
- Sales headcount: $400K → $2.4M pipeline → $840K revenue (at 35% close rate) = 2.1x ROI
- Demand gen: $400K → $3.8M pipeline → $1.33M revenue (at 35% close rate) = 3.3x ROI
My recommendation: "Demand gen has higher ROI (3.3x vs. 2.1x). We should invest there. Acknowledge CRO wants sales capacity, but data shows marketing spend generates better return."
What this does: Makes a data-backed recommendation that serves company interest, even if one executive disagrees.
Situation 2: Conflicting Strategic Directions
The dynamic: Executives disagree on strategic direction (should we target enterprise or mid-market? Build or partner? Expand or consolidate?)
The wrong move: Present both options equally and let them fight it out.
The right move: Make a clear recommendation based on market data, acknowledge what we'd sacrifice with that choice.
Example:
CEO wants to expand to new vertical. VP Product wants to deepen existing product for current market.
My analysis:
- New vertical: $80M TAM, unfamiliar buyers, 12-18 month investment, uncertain win rate
- Deepen current product: $120M TAM, known buyers, 6-month investment, 58% current win rate
My recommendation: "Deepen current product. Larger TAM, better win rate, faster payback. New vertical is interesting but higher risk and longer timeline. Recommend revisiting vertical expansion after we've captured more of current $120M TAM."
What this does: Frames the strategic tradeoff clearly, makes a recommendation, shows you've thought through both options.
Situation 3: Cross-Functional Blame for Failures
The dynamic: Launch fails or metrics miss. Sales blames Marketing. Marketing blames Product. Product blames positioning.
The wrong move: Defend your function and blame others.
The right move: Present objective post-mortem identifying all contributing factors, own your part first.
Example:
Launch missed pipeline targets. Sales says "positioning was confusing." Marketing says "sales didn't sell it properly."
My analysis: "Launch missed by 40%. Three contributing factors:
- Positioning was unclear for target buyer (my error—I should have tested more rigorously)
- Sales enablement was rushed (my error—I didn't allow enough time)
- Product launch was delayed 6 weeks, shortening sales window (Product factor)
- Market timing hit year-end budget freezes (market factor, not controllable)
Root cause: I moved too fast on positioning without adequate validation. Fix: 30-day repositioning validation before next launch."
What this does: Takes accountability first, then identifies other factors objectively. Disarms blame game.
The Behaviors That Build Trust Across Executive Politics
After navigating dozens of politically charged situations, I've learned specific behaviors that build trust:
Behavior 1: Take Data-Based Positions, Not People-Based Positions
Don't say: "I agree with CMO on this" or "I support CRO's approach."
Do say: "Based on win/loss data, I recommend X. Here's why I believe that's the right path, and here's what we'd sacrifice with that choice."
Why this works: You're aligning with data and company outcomes, not with specific executives. Even if an executive disagrees with your recommendation, they respect that you analyzed independently.
Behavior 2: Acknowledge Valid Concerns From All Sides
Don't say: "CRO is wrong about enterprise expansion."
Do say: "I understand why CRO wants to invest in enterprise—larger deals, strategic accounts. The data concern is our 18% win rate makes it high-risk. If we addressed compliance gaps first, enterprise investment would make more sense."
Why this works: You show you understand the other executive's perspective while maintaining your position. This is respectful disagreement, not dismissive opposition.
Behavior 3: Present Options With Clear Tradeoffs
Don't say: "We should do X because it's the best approach."
Do say: "Three options: (1) Enterprise expansion (high upside, high risk), (2) Mid-market focus (proven ROI, limited TAM), (3) Split investment (hedged but diluted). I recommend option 2, but if leadership prioritizes enterprise strategic positioning over short-term ROI, option 1 is defensible."
Why this works: You make a recommendation but show you've considered alternatives and understand different executives might weight factors differently.
Behavior 4: Never Throw Other Functions Under The Bus
Don't say: "This failed because Sales didn't execute properly."
Do say: "Launch had execution gaps across PMM, Sales, and Product. Here's what each function (including mine) needs to do differently next time."
Why this works: Cross-functional respect matters more than winning individual arguments. Executives respect people who take accountability.
Behavior 5: Be Willing to Change Your Mind
Don't say: "I stand by my recommendation."
Do say: "Based on feedback from this discussion, I'm updating my recommendation. VP Product raised a valid point about product readiness that I hadn't fully weighted. I now recommend delaying 60 days vs. launching immediately."
Why this works: Demonstrates you're seeking the best answer, not trying to be right. Executives trust people who update their thinking based on new information.
The Conversation That Taught Me How to Handle Executive Conflicts
Six months after my failed attempt at neutrality, I faced another executive conflict.
VP Sales wanted to invest in enterprise enablement. VP Product wanted to delay enterprise features and focus on mid-market product improvements.
Both asked for my perspective.
This time, I took a clear position:
"I've analyzed our enterprise performance. We're losing 82% of enterprise deals due to compliance gaps Product hasn't addressed. Investing in sales enablement without product investment is low ROI—we'd be training sales to sell something buyers won't buy.
My recommendation: VP Product is right. We should delay enterprise push, fix mid-market product gaps where we win 58% of deals, then revisit enterprise in 12 months when we have compliance capabilities."
VP Sales was frustrated: "So you're saying we shouldn't even try to compete in enterprise?"
I responded: "I'm saying at 18% win rate, we're structurally disadvantaged. If we want to compete in enterprise, we need to address compliance gaps first. Otherwise we're burning sales capacity on deals we're unlikely to win. That's not good for you or the company."
VP Sales appreciated the directness: "I don't love the answer, but I respect that you analyzed it objectively. Let's discuss what it would take to make enterprise viable."
That conversation shifted from political battle to strategic problem-solving—because I took a data-based position instead of trying to please everyone.
The Red Lines: What Never Works in Executive Politics
After watching dozens of PMMs navigate (or fail to navigate) executive politics, here are moves that never work:
Red Line 1: Telling Executives What They Want to Hear
This destroys credibility faster than anything else.
If CRO asks for data to support enterprise expansion and your data says enterprise is a bad bet, telling CRO what they want to hear might make them happy short-term—but when the investment fails, you'll be seen as the PMM who gave bad advice.
Executives respect directness over agreeableness.
Red Line 2: Playing Executives Against Each Other
Never say to CRO: "CMO doesn't understand GTM strategy."
Never say to CMO: "CRO is being unreasonable about budget."
Word gets back. Always. You'll lose trust with both executives.
Red Line 3: Refusing to Take Positions
The move I made initially: "Both approaches have merit, data could support either..."
This signals you're conflict-averse and won't make tough calls. Executives will stop consulting you on strategic questions.
Red Line 4: Being Defensive When Challenged
Wrong response: "My analysis is solid. If you disagree, you're not reading the data correctly."
Right response: "That's a fair challenge. Here's my thinking, but I could be missing something. What would change your assessment?"
Defensiveness signals weak thinking. Openness to being wrong signals confidence.
Red Line 5: Aligning Yourself Permanently With One Executive
Some PMMs become "the CRO's PMM" or "the CMO's person."
This works until that executive leaves or loses a political battle. Then you're seen as part of the losing faction.
Align with data and company outcomes, not with individual executives.
How to Recover When You've Made a Political Mistake
I made every political mistake possible early in my career. Here's how I recovered:
Mistake 1: I Stayed Neutral When I Should Have Taken a Position
How I recovered:
I went back to both executives: "I should have made a clearer recommendation last week. I've completed additional analysis. Here's what I believe is the right path and why."
Being late to a recommendation is better than never making one.
Mistake 2: I Told an Executive What They Wanted to Hear (Instead of What the Data Said)
How I recovered:
When the initiative predictably failed, I owned it: "I gave you data that supported your preferred approach instead of the most objective analysis. That was my error. Here's what I should have recommended originally."
Taking accountability rebuilds credibility faster than anything else.
Mistake 3: I Threw Another Function Under the Bus
How I recovered:
I apologized to that function directly: "I blamed Sales in yesterday's meeting. That was wrong—we all contributed to the miss. Here's what PMM should have done differently."
Then I presented a joint cross-functional post-mortem that distributed accountability fairly.
The pattern: Own mistakes fast, correct them explicitly, demonstrate you learned from them.
Executives respect people who recover from political mistakes more than people who never make them.
The Uncomfortable Truth About Executive Politics
Most PMMs think: Good work speaks for itself. If I do great PMM work and avoid politics, I'll build credibility.
The reality: Executive decision-making is inherently political—competing priorities, limited resources, different perspectives. PMMs who "avoid politics" get excluded from strategic conversations.
The PMMs who successfully navigate executive politics:
- Take data-based positions on strategic questions
- Make clear recommendations even when executives disagree
- Acknowledge valid concerns from all sides
- Own their mistakes and update their thinking
- Align with company outcomes, not individual executives
The PMMs who fail at executive politics:
- Try to stay neutral and please everyone
- Tell executives what they want to hear
- Refuse to make recommendations on controversial questions
- Align themselves permanently with one executive
- Get defensive when challenged
The difference in career trajectory is dramatic.
PMMs who navigate politics effectively become trusted strategic advisors executives consult before major decisions. PMMs who avoid politics get excluded from strategic conversations and stay at tactical execution levels.
The executive politics navigation framework:
- Analyze strategic questions independently
- Make data-backed recommendations
- Acknowledge tradeoffs and alternative views
- Be willing to disagree respectfully
- Own mistakes and update thinking
- Never align permanently with one executive
Follow this framework, and you'll go from trying to avoid executive politics to confidently navigating them as a trusted strategic advisor.
That's when your influence grows beyond PMM execution.
That's when your career accelerates.