I discovered this paradox while working with a scale-up from an edu-tech space, selling AI education programs for Fortune 500s.
The more a piece of content tried to demonstrate expertise, the more likely it was to be dismissed by actual executives.
We created what we thought was the perfect thought leadership piece. It had everything:
- Original research from McKinsey and Gartner
- Quotes from industry leaders
- Professional design with elegant infographics
- A 15-step framework for digital transformation
- Case studies from successful implementations
The response from one CTO at a Fortune 1000 company?
“It’s all theory, no scar tissue.”
That’s when it occurred to me. Executives don’t care about:
- Excessive citations of well-known research (“Yes, I’ve read McKinsey too”)
- Perfect, polished writing with no rough edges
- Comprehensive step-by-step frameworks that make complex decisions seem simple
- Too many best practices, not enough war stories
- The phrase “research shows” (an immediate credibility killer)
They need substance above all.
And I got another proof of it when we decided to test something.
Instead of preparing a beautiful infographic, we shared a simple, not-properly-sized screenshot with a few honest words from the Founder.
The engagement suddenly tripled:
And this trend remained consistent:
- Content pieces that admitted to failures or mistakes saw 3.4x higher executive engagement
- Articles with personal stories outperformed data-heavy pieces by 2.7x
- Posts containing phrases like “I’m not sure” or “I might be wrong” received 89% more comments from other executives
- Content that challenged conventional wisdom got shared 4x more than content that reinforced it
The “Anti-Polish” Effect:
We tested this systematically across 6 campaigns. Content that looked slightly unpolished – with occasional typos, personal annotations, or “thinking out loud” segments – consistently outperformed professionally edited pieces in every metric:
- 2.8x higher response rates
- 3.1x more shares within executive teams
- 4.2x more direct replies
- 5.3x more meeting requests
It showed me true executive-level expertise isn’t demonstrated by knowing all the answers.
It’s shown by asking better questions, acknowledging complexity, and being comfortable with uncertainty.
The moment you try to present yourself as an unassailable expert, you signal to real executives that you’ve never actually sat in their chair.
Want to see how your content scores on the “expertise paradox” scale?
Here’s a quick test: If your piece could be published in Harvard Business Review without any changes, it’s probably too polished to be effective.
“This Actually Made Me Cringe”: Raw Executive Feedback That Changed How We Create Content
Warning: What you’re about to read might hurt if you’ve invested heavily in traditional thought leadership.
These are real, unedited quotes from C-suite executives who participated in our content feedback study. We promised them anonymity in exchange for brutal honesty. They delivered.
On Traditional Thought Leadership:
“The moment I see ‘thought leadership’ in a headline, I assume it’s written by a junior marketer who’s never had P&L responsibility. Real leaders don’t call themselves thought leaders.”
– CEO, $200M Software Company
On Case Studies:
“Another ‘success story’ where everything went perfectly? Please. Show me what went wrong and how you fixed it. That’s what I forward to my team.”
– CTO, Fortune 500 Company
The “Consultant Speak” Problem:
“If your content could appear in any industry publication, it’s worthless to me. I need specific insights that would get you fired if you were wrong.”
– CFO, Manufacturing
Most Devastating Feedback:
“This reads like AI-generated best practices from someone who’s never had to make a real decision with real consequences. I can smell the lack of experience through the screen.”
– COO, Healthcare Technology
Yikes.
We also had the opportunity to ask them what actually stops their scroll. Here’s what they had to say:
1. The “Oh Sh*t” Moments
“I read every word of that email where the founder described how they lost their biggest client. Why? Because I’m terrified of the same thing happening to me.”
– CEO, SaaS Company
2. The Unfinished Thoughts
“I appreciate seeing someone think through a problem in real-time, including their doubts. Perfect answers make me suspicious.”
– CIO, Financial Services
3. The Career-Risking Takes
“If your content couldn’t get you in trouble with someone, why should I spend time reading it?”
– CMO, Retail Chain
Common Phrases That Make Executives Stop Reading:
Based on the conversations I’ve had with the founders, I compiled a list of forbidden phrases that take your content from exciting to “meh”:
- “Best practices show…”
- “Industry leaders agree…”
- “Research indicates…”
- “The key to success is…”
- “Our proven framework…”
Phrases That Actually Engage Them:
Based on the “forbidden phrases”, I’ve prepared a couple of examples where the hook doesn’t have to be templated – it writes itself:
• “I got this completely wrong…”
• “What I still can’t figure out is…”
• “This might be controversial, but…”
• “Here’s what keeps me up at night…”
• “I have no idea if this will work, but…”
Executives aren’t looking for polished wisdom. They’re looking for real insights from people who have faced similar challenges. The more perfectly packaged the content, the less likely they are to trust it.
As one CTO put it:
“I don’t need another ‘7 Steps to Digital Transformation.’ I need to know what someone else learned from screwing up a digital transformation so I don’t make the same mistakes.”
The $200K Lesson:
We spent thousands trying to sound authoritative, only to learn that authority comes from admitting what you don’t know. The content that executives actually share internally isn’t the polished thought leadership piece – it’s the rough draft that shows real thinking happening on the page.
The Data That Made Us Trash Our Content Calendar (And What Actually Works)
Let me shatter some “best practices” with real data from our analysis of 24 executive-focused campaigns:
The Timing Myth
Remember all that advice about posting on Tuesday at 2 PM? Here’s what we actually found:
Most successful time to reach executives: Sunday between 6-7:30 AM
One CIO told us: “Sunday morning is when I actually have time to think.”
Worst time: Tuesday-Thursday during business hours
As one CEO put it: “Who do you think is reading thought leadership during actual leadership time?”
Content Length: Everything We Knew Was Wrong
We analyzed engagement data across 1,367 pieces of executive-focused content. The results were shocking:
- Articles under 500 words: Almost zero executive engagement
- Articles 2,000-3,000 words: Limited engagement
- Sweet spot: Either very short (sub-200 words) or surprisingly long (5,000+ words)
Our highest-performing piece was a 7,842-word article that looked like an internal memo published accidentally. It’s been generating inbound leads since October 2023, and it’s still working well.
The Format Fallacy
Engagement rates by content type (contrary to every “best practice”):
- Professional videos: 0.7% executive engagement
- Polished infographics: 1.2% engagement
- Webinar recordings: 0.9% engagement
- Raw Zoom recordings: 4.3% engagement
- Unedited email threads: 8.7% engagement
- Personal Google docs with comments enabled: 11.2% engagement
Time Investment Paradox
Here’s the data point that made our content team mutiny:
- Content that took 2+ weeks to create: 1.3% average engagement
- Content created in under 2 hours: 6.8% average engagement
At that point, we felt it’s time to go on a long vacation.
breathing heavily
The Intellectual Discomfort Metric
We developed a new way to predict content performance: measuring how uncomfortable it makes our (or the client’s) marketing team.
The correlation was almost perfect:
- Content that marketing approved immediately: 0.8% executive engagement
- Content that made marketing nervous: 3.2% engagement
- Content that marketing tried to stop: 7.4% engagement
- Content that legal had to review: 12.3% engagement
The Data Behind Disagreement
Posts that strongly disagreed with common industry positions saw:
- 4.2x higher share rates
- 3.7x more direct responses
- 5.1x higher meeting conversion rates
Why? As one CEO explained:
“If you’re saying what everyone else is saying, why should I pay attention to you specifically?”
The Most Surprising Finding
The single strongest predictor of executive engagement wasn’t:
- Word count
- Time of day
- Format
- Design quality
- Source credentials
It was what we call “intellectual tension” – the degree to which the content challenged existing executive assumptions or created cognitive discomfort.
The Anti-Framework That Actually Works (Or: How to Create Content That Executives Actually Forward to Their Teams)
Let me share the exact opposite of everything you’ve been told about executive content creation. This approach emerged from our failures, was refined through testing, and—most importantly—is backed by real engagement data.
The “Intellectual Tension” Template:
1. The Contrarian Opening
Instead of: “5 Best Practices for Digital Transformation”
Use: “Why Most Digital Transformations Are Actually Digital Theater”
Real Example That Worked:
Subject Line: “we’d save $50K if we had this 11 years ago…”
Open Rate: 47%
Meeting Requests: 13 in 24 hours
2. The Strategic Admission of Ignorance
Instead of: “How to Solve Your Cloud Security Challenges”
Use: “Three Cloud Security Problems I Haven’t Solved Yet”
Actual Results:
- Traditional expert piece: 0.8% response rate
- “Thinking out loud” piece: 6.7% response rate
Here’s the template that consistently works:
—
Subject: [Controversial Statement] + [Admission of Uncertainty]
Opening: Direct challenge to conventional wisdom
Body: Personal story of failure/learning
Close: Open question (not a call to action)
—
The “Ugly Email” That Got a 92% Response Rate:
Here’s the exact email that generated more C-suite meetings than our entire Q2 campaign budget:
Subject: this might be a terrible idea (thinking out loud about data security)
[Name],
It’s 3am and I can’t sleep because I think we’ve been approaching enterprise security completely wrong for the past decade.
Quick context: We just lost a $2M deal because our security framework was “too thorough” (their words). Made me realize something disturbing…
[Three messy paragraphs with typos]
Am I crazy? What am I missing here?
-[Name]
PS – This isn’t a pitch. I genuinely don’t know if I’m onto something or losing my mind.
Why It Worked:
- No formatting
- Visible thinking process
- Admission of failure
- Real stakes ($2M loss)
- No attempt to sell
- Request for input
The Anti-Webinar Formula:
Instead of the usual “5 Key Strategies” webinar, we tested what we call “Open Surgery Calls”:
- No slides
- No recording
- No preset agenda
- Just a leader thinking through a real problem in real-time
Results:
- Traditional Webinar: 12 executive attendees
- Open Surgery Call: 46 executive attendees
The Content Quality Inverse Law:
We’ve found that executive engagement increases as traditional “quality signals” decrease:
- Remove perfect formatting
- Leave in select typos
- Show your work
- Include dead ends
- Expose your thinking process
The Permission Paradox:
The more you try to position yourself as an expert, the less likely executives are to view you as one. Instead:
- Share what you’re actively wrestling with
- Show your evolution of thinking
- Admit when conventional wisdom isn’t working
- Ask questions you don’t have answers to
As one CEO told us:
“I don’t need more answers. I need someone who’s thinking about the same problems I am.”
The “Zero Polish” Distribution Strategy That 10X’d Our Executive Engagement
Before we wrap up, let me share the exact distribution strategy that consistently works with C-suite audiences.
Warning: This will feel wrong to every marketing bone in your body.
The Anti-Distribution Playbook:
1. The “Accidental” Send
Instead of mass email blasts, we send what appears to be personal thoughts to small groups (15-20 executives max):
- No header images
- Plain text only
- Often with “Sent from my iPhone” footer
- Including phrases like “Sorry if this isn’t relevant to you”
How it worked:
- Traditional newsletter: 0.9% executive response rate
- “Accidental” thought email: 23% response rate
2. The “Work in Progress” Share
We started sharing Google Docs marked as “Draft – Not For Distribution” with comment access enabled.
Actual Example That Worked:
Subject: [Draft] Thinking through the {industry} talent crisis - input welcome
[Name],
Working on a piece about why we're all failing at tech hiring. This is rough/unfinished, but would value your thoughts, especially on page 3 where I might be completely wrong about compensation strategies.
Doc link: [link]
(Please ignore the typos - will clean those up later)
Results:
- 72% open rate
- 47% comment rate
- 13 spontaneous meeting requests
3. The “Thinking Out Loud” LinkedIn Strategy
Instead of polished company posts, we use personal accounts to share “behind the scenes” thoughts:
What Bombed:
“10 Best Practices for Cloud Security in 2024”
- 1.2% engagement rate
- 0 executive comments
What Worked:
“I think I just realized why our entire cloud security approach is backwards (thread of realizations from tonight’s 3AM panic)”
- 27% engagement rate
- 142 executive comments
- 23 direct message requests
The Counter-Intuitive Rules We Now Follow:
1. The “Make Marketing Cringe” Rule
If your marketing team immediately approves it, it’s probably too polished for executives.
2. The “This Feels Wrong” Test
The more uncomfortable you feel sending it, the better it will likely perform.
3. The “Could Get Me Fired” Metric
Content that feels risky consistently outperforms safe content by 7-11x.
Real Example:
A CTO’s raw notes about why a major vendor’s solution was “fundamentally broken” generated:
- 478 executive responses
- 104 meeting requests
- 3 cease-and-desist letters (and one job offer)
The Follow-Up Strategy That Actually Works:
Instead of traditional nurture sequences, we use what we call “Building In Public” threads:
Day 1: Share initial hypothesis (with admitted flaws)
Day 3: Update with new data that challenges day 1
Day 7: Final update admitting what we got wrong
Results compared to traditional nurture:
- Traditional: 0.7% engagement
- Building In Public: 13.2% engagement
The Credibility Paradox:
The harder you try to establish credibility, the faster you lose it. Real credibility comes from:
- Admitting uncertainties
- Showing your work
- Being wrong publicly
- Learning in real-time
Your “Embarrassingly Direct” Content Assessment: 10 Questions That Will Make You Cringe
Let’s close with the exact assessment we use with clients.
These questions will likely make you uncomfortable. They should.
The Raw Assessment:
Score each piece of your executive-focused content on these criteria:
The “Oh God, No” Test
Ask yourself: “Would I be embarrassed if my competitors saw this?”
- If you answered “no” – Delete it and start over
- If you answered “Oh God, yes” – You’re on the right track
The Litigation Risk Scale (1-10)
- 1-3: Too safe to be interesting
- 4-7: Getting warmer
- 8-10: Now we’re talking
Real example: Our highest-performing piece scored a 9.2 and required three legal reviews 👀
The “Send Without Approval” Question
Could this content have been created and sent without multiple approval layers?
- If no: It’s probably too polished
- If yes: You might have something valuable
The Personal Reputation Risk
Would you be willing to post this under your personal LinkedIn profile?
- If no: Why not? What are you afraid of?
- If yes: But does it still feel safe? Then push harder
The Competitive Advantage
Test If your competitors copied this exact content, would it hurt you?
- No: Start over
- Yes: You’re revealing real insights
- “We’d get sued”: Perfect
Quick Self-Assessment Checklist:
❌ Does your content:
- Use the phrase “thought leadership”?
- Reference well-known research?
- Include stock photos?
- Follow a clear template?
- End with a call to action?
✅ Instead, does it:
- Challenge industry assumptions?
- Share specific failures?
- Include messy data?
- Show unfinished thinking?
- Ask difficult questions?
The “Real Talk” Final Questions:
- Could this content get you:
- Fired?
- Sued?
- Criticized publicly?
If you answered “no” to all three, you’re playing it too safe.
- Would your competitors be:
- Angry?
- Uncomfortable?
- Forced to respond?
If you answered “no” to these, you’re not sharing real insights.
Your Immediate Next Steps:
- Look at your current content calendar
- Find your “safest” planned piece
- Delete it
- Write about why that piece was wrong instead
When (And When Not) To Use The Anti-Polish Approach: Finding The Right Balance
Let’s address some critical questions that might be making you nervous about this approach.
“Won’t This Make Us Look Unprofessional?”
There’s a crucial difference between “unpolished” and “unprofessional.” Here’s how we navigate it:
✅ Strategically Unpolished:
- Showing real thinking process
- Admitting uncertainties
- Including relevant typos in quick-response formats
- Sharing messy but valuable data
❌ Actually Unprofessional:
- Basic grammar errors
- Factual inaccuracies
- Disorganized arguments
- Sloppy research
When This Approach Doesn’t Work
Not every situation calls for the anti-polish approach. Here’s when to stick to traditional polished content:
- Regulatory/Compliance Communications
- Crisis Management
- Public Financial Statements
- Basic Product Documentation
How to Convince Your Team
Here’s how we helped our clients get organizational buy-in:
1. Start Small
- Test the approach with a small executive segment
- Document engagement metrics rigorously
- Use the data to make your case
2. Create a “Safe Space” for Testing
- Designate certain channels for “experimental” content
- Keep traditional polished channels running in parallel
- Let the results speak for themselves
Real Example:
We ran an A/B test with a client’s executive newsletter:
- Version A: Traditional polished format
- Version B: “Thinking out loud” format
Response rates:
- Version A: 2.3%
- Version B: 7.8%
The data ended the debate.
Finding Your Sweet Spot
The goal isn’t to completely abandon professionalism – it’s to find the right balance between polished and authentic. Here’s our framework:
The 70/30 Rule:
- 70% raw insight
- 30% basic professional standards
Signs you’ve found the right balance:
- Marketing is nervous but not panicked
- Executives are engaging but not confused
- Legal is concerned but not blocking
- Your competitors are irritated but can’t quite explain why
Final Thought:
The most valuable email I ever sent started with: “I think I just realized why everything I’ve been saying about enterprise sales is completely wrong…”
It generated:
- 347 executive responses
- 104 meeting requests
- 1 speaking invitation
- And yes, 2 angry phone calls
But here’s what matters: A year later, executives still reference that email.
Because at the end of the day, executives don’t want your polished thoughts.
They want to see how you think.
