The Paradox of Experienced Leadership
The more experienced you become as a leader, the more your team expects you to "know" things. They look to you for quick decisions, confident direction, and intuitive insights about complex problems.
This creates a dangerous trap: the pressure to appear decisive can prevent you from acknowledging uncertainty, asking for help, or admitting when your gut instinct might be wrong.
Result? Experienced leaders often make worse decisions than they did earlier in their careers, despite having more knowledge and resources available.
Here's how to break this pattern and build decision-making processes that work even when your instincts fail you.
Why Leadership Intuition Fails
The Success Trap
The problem: Past success makes leaders overconfident in their decision-making abilities.
You've made dozens of good calls. Your track record speaks for itself. This creates cognitive momentum—each successful decision increases confidence in your "gut instinct."
But business contexts change faster than intuition adapts. The market conditions, team dynamics, and competitive landscape that shaped your successful pattern recognition may no longer exist.
Case study: A retail CEO who built her reputation on physical store expansion continued opening locations through 2019-2020, despite clear signals about shifting consumer behaviour. Her intuition, honed over 15 years of successful retail growth, couldn't adapt quickly enough to pandemic-accelerated digital transformation.
The Information Filter Problem
The reality: The higher you rise, the more filtered your information becomes.
Your team naturally filters bad news, presents information in ways they think you want to hear it, and avoids challenging your stated priorities. This isn't malicious—it's human nature combined with organisational hierarchy.
Example: A tech company CEO spent 18 months believing their new product was gaining traction because his team presented monthly active users growth. What they didn't emphasise: user engagement was dropping, customer lifetime value was declining, and support ticket volume was exploding. His "gut feeling" that the product was successful was based on incomplete information.
The Speed vs. Accuracy Trade-off
Modern leadership pressure: Make decisions faster with less information than ever before.
Market conditions change rapidly. Competitive pressures demand quick responses. Teams need direction to move forward.
But human intuition evolved for different contexts. Your gut instincts are calibrated for small-group dynamics, immediate physical threats, and social hierarchies—not global supply chains, digital marketing attribution, or complex financial instruments.
The Three Leadership Reality Check Questions (Applied)
Our Reality Check methodology becomes especially powerful for leaders because it systematically counters the most dangerous leadership biases.
Question 1: "What evidence do we have that someone wants this?"
For leaders, this becomes: "What evidence do I have that this decision is right?"
Why leaders struggle with this:
- Pressure to appear confident
- Teams expect decisive action
- Information filtering creates false evidence
- Success history breeds overconfidence
Leadership application process:
Before any major decision:
- List the evidence that supports your preferred option
- Rate each piece of evidence: Strong/Moderate/Weak
- Identify sources of each evidence point
- Ask: "What would someone arguing against this decision say about each piece of evidence?"
Example in action:
A manufacturing CEO wanted to expand into a new geographic market. Her initial evidence:
- "Strong demand in the region" (based on 3 customer inquiries)
- "Competitors are succeeding there" (based on press releases)
- "Our product fits the market" (based on demographic analysis)
Reality check revealed:
- The 3 inquiries came through the same channel (weak evidence)
- Competitor press releases didn't include profitability data (moderate evidence)
- Demographics were promising, but regulatory environment was complex (missed information)
Decision: Run a £50k market test before committing to £2M expansion. The test revealed regulatory barriers that would have cost £800k to navigate. Major disaster avoided.
Question 2: "What surprised us this week?"
For leaders: "What information am I getting that challenges my assumptions?"
The leadership version of this question combats information filtering and confirmation bias.
Implementation:
- Weekly one-on-ones with direct reports focused on surprises
- Monthly "What's not working?" meetings
- Quarterly external perspective sessions with advisors/mentors
Red flags for leaders:
- Nothing has surprised you in weeks
- Your team rarely brings you problems
- Good news significantly outweighs bad news
- All metrics are trending in expected directions
Case study: A SaaS CEO implemented weekly "surprise reports" where each department head had to share one thing that didn't match expectations. In the first month, this revealed:
- Customer support volume was increasing faster than user growth (hidden scalability problem)
- Top-performing sales rep was using pricing strategies that hurt long-term retention (process issue)
- Engineering team was spending 40% of time on technical debt, not new features (resource allocation problem)
None of these issues appeared in standard reports, but each represented significant business risks.
Question 3: "What are we pretending not to know?"
For leaders: "What uncomfortable truths is my team not telling me?"
This is often the most valuable question for leaders because hierarchical dynamics suppress negative information.
Creating psychological safety for truth-telling:
The process:
- Acknowledge that bad news exists
- Make it safe to deliver bad news
- Reward people who bring problems early
- Never punish messengers (even if the message is wrong)
Practical techniques:
Monthly "Problems Anonymous"
- Team members submit concerns anonymously
- Discuss patterns without identifying sources
- Public appreciation for useful problem identification
"Red Flag Fridays"
- Last Friday of every month dedicated to surfacing concerns
- No solutions required, just problem identification
- Leader goes first by sharing their own concerns
"Pre-Mortem" sessions
- Before major initiatives, imagine they've failed
- Team identifies what could go wrong
- Plan preventive measures
Real example: A consultancy CEO noticed her monthly partners meeting always ended with consensus and optimism. She implemented "What could kill us?" as a standing agenda item. First session revealed:
- 60% of revenue came from one client (concentration risk)
- Two senior partners were considering leaving (talent retention crisis)
- New competitor was poaching clients with 30% lower pricing (competitive threat)
All three issues were "known" by various people but hadn't been surfaced to leadership. Addressing them early prevented what could have been a company-ending crisis.
Leadership-Specific Decision Traps
The Decisive Leader Trap
The problem: Mistaking quick decisions for good decisions.
Teams often interpret decisiveness as competence. This creates pressure to decide quickly, even when more information would improve outcomes.
Reality check approach: Distinguish between reversible and irreversible decisions.
- Reversible decisions: Decide quickly, adjust based on results
- Irreversible decisions: Slow down, gather more information, stress-test assumptions
Framework:
- Hiring senior people: Irreversible (expensive to fix)
- Pricing changes: Reversible (can be adjusted)
- Office lease: Irreversible (multi-year commitment)
- Marketing campaign budget: Reversible (can be adjusted monthly)
The Visionary Leader Trap
The problem: Confusing vision with prediction.
Visionary leaders are celebrated for painting compelling futures. But visions can become so compelling that leaders stop testing them against reality.
Case study: Theranos. Elizabeth Holmes had a compelling vision of revolutionising blood testing. The vision was so powerful that it prevented reality checks about whether the technology actually worked.
Reality check approach: Separate vision (desired future) from prediction (likely future).
- Vision: What we're working toward
- Prediction: What we think will happen
- Plan: How we'll adapt if predictions are wrong
The Experienced Leader Trap
The problem: Overrelying on pattern recognition in changed contexts.
Experience creates mental models that work in familiar situations. But when contexts change, those same models can lead to systematic errors.
Example: Retail leaders who succeeded in high-growth markets often struggle in mature markets because the success patterns are different.
Reality check approach: Regularly question whether your experience applies to current context.
- What's different about this situation?
- When was the last time your standard approach failed?
- What would someone with no history in this industry do?
Building Reality Check Systems for Leaders
Personal Reality Check Process
Weekly leadership reality check:
- Monday: Review last week's decisions—what surprised you?
- Wednesday: Check in with team—what problems are emerging?
- Friday: Reflect on assumptions—what might you be wrong about?
Team Reality Check Process
Monthly team reality check meeting:
- 30 minutes maximum
- Three questions applied to current major initiatives
- No action items (unless someone says "stop everything")
- Focus on surfacing truth, not solving problems
Organisational Reality Check Culture
Systems that support truth-telling:
1. Information Architecture
- Dashboards that show leading indicators, not just results
- Regular surveys that capture team sentiment
- Customer feedback systems that bypass internal filters
2. Reward Systems
- Public recognition for people who identify problems early
- Compensation tied to team honesty, not just results
- Career advancement paths for "reality checkers"
3. Process Design
- Devil's advocate roles in major decisions
- External perspectives required for big bets
- Regular strategy reviews that challenge assumptions
When Your Gut Is Right vs. When It's Wrong
Your intuition is often right about:
- People and their motivations
- Whether something feels "off" about a situation
- Team dynamics and morale
- Customer emotional responses
Your intuition is often wrong about:
- Complex systems with delayed feedback
- Probability and statistics
- Market timing
- Technology adoption curves
The key: Use intuition as a signal to investigate, not as a decision-maker.
If your gut says something's wrong, ask: "What evidence would confirm or deny this feeling?"
If your gut says something's right, ask: "What could I be missing that would change this assessment?"
The Courage to Lead with Uncertainty
The paradox of modern leadership: Teams need decisive direction, but leaders need to acknowledge uncertainty.
The solution: Be decisive about process, uncertain about outcomes.
Instead of: "This strategy will definitely work."
Try: "This is our best current understanding. Here's how we'll know if we need to adjust."
Instead of: "I know what customers want."
Try: "Here's what customers have told us. Here's how we'll test whether it's true."
Instead of: "Trust me on this."
Try: "Here's my reasoning. Help me identify what I might be missing."
The Bottom Line for Leaders
Great leadership isn't about always being right. It's about building systems that help you be less wrong, recover quickly from mistakes, and create environments where truth can emerge.
Your experience and intuition are valuable assets. But they become dangerous when they prevent you from seeing new information or hearing uncomfortable truths.
The Reality Check methodology doesn't make you a worse leader—it makes you a more effective one by ensuring your decisions are based on reality, not wishful thinking.
Remember: Your team doesn't need you to be perfect. They need you to be honest about uncertainty and committed to finding truth.