Lead Like a Freak: Unconventional Wisdom for Sales Leadership
Why Do the Same Sales Challenges Persist Despite Our Best Efforts?
Most sales leadership advice sounds impressive but delivers mediocre results. The same recycled concepts about “building accountability” and “driving performance” fill business publications while sales leaders struggle with the same challenges year after year.
What if better sales leadership isn’t about better execution of conventional wisdom, but about fundamentally different thinking?
In “Think Like a Freak,” Steven Levitt and Stephen Dubner present problem-solving approaches that challenge established thinking. While not specifically addressing sales, their framework offers exactly what sales leaders need: intellectual rebellion against stagnant practices.
Here are five principles that can transform how you lead your sales organization.
1. The Power of “I Don’t Know”
Conventional Approach: Sales leaders project certainty even when guessing. They make definitive statements about markets, forecasts, and strategies to appear confident.
Freakish Approach: Exceptional sales leaders embrace uncertainty as the starting point for discovery. They distinguish between what they know and what they assume, creating space for genuine exploration.
In Practice:
Start your next leadership meeting by identifying three critical unknowns affecting your business
Replace “I think” statements with “Let’s find out” questions
Create psychological safety for team members to highlight knowledge gaps
Reward those who identify unknowns rather than those who pretend to have all the answers
2. Root Causes Over Symptoms
Conventional Approach: When deals stall, leaders blame discovery skills. When win rates drop, they mandate more training. When forecasts miss, they implement stricter pipeline reviews.
Freakish Approach: Effective sales leaders look beyond immediate explanations to find underlying causes that cross departmental boundaries, challenge assumptions, and reveal systemic issues.
In Practice:
Before implementing solutions, identify at least three possible root causes for any significant challenge
Analyze lost deals with the same rigor as won opportunities
Form cross-functional teams to investigate sales issues that might have non-sales causes
Track leading indicators that reveal problems before they impact results
3. Strategic Quitting
Conventional Approach: Sales organizations celebrate persistence and “never give up” mantras, often continuing with failing approaches long after evidence suggests they should pivot.
Freakish Approach: The best sales leaders know when to stop investing in strategies, markets, or accounts with diminishing returns. They establish clear abandonment criteria and redirect resources to higher-potential opportunities.
In Practice:
Set explicit milestones for each major initiative with predefined abandonment triggers
Conduct quarterly “stop doing” reviews to eliminate low-value activities
Celebrate strategic withdrawals as examples of good judgment
Create a framework for quickly identifying and abandoning unproductive approaches
4. Incentives That Drive Real Behavior
Conventional Approach: Sales compensation focuses narrowly on closed revenue, inadvertently encouraging behavior that optimizes short-term results at the expense of customer relationships.
Freakish Approach: Effective leaders design incentive systems that align individual rewards with comprehensive business outcomes, recognizing that what you measure shapes behavior more powerfully than what you say.
In Practice:
Test your compensation plan by asking: “How could someone maximize earnings while damaging the company?”
Incorporate customer success metrics into sales compensation (and vice versa)
Experiment with team-based components that reward collaborative success
Balance immediate revenue targets with leading indicators of future growth
5. Unconventional Data as Competitive Advantage
Conventional Approach: Sales organizations track standard metrics—pipeline coverage, win rates, average deal size—generating predictable insights and unremarkable results.
Freakish Approach: Forward-thinking leaders analyze unexpected data combinations and sources to uncover insights their competitors miss, creating strategies others can’t easily replicate.
In Practice:
Analyze communication patterns in successful versus unsuccessful deals
Identify correlations between win rates and factors outside traditional sales metrics
Study customer usage data to refine your ideal customer profile
Map the timing of deal stalls to identify critical momentum points
The Competitive Edge of Thinking Differently
The gap between average and exceptional sales leadership isn’t about working harder within conventional frameworks—it’s about thinking differently about your fundamental challenges.
The principles from “Think Like a Freak” aren’t just interesting thought experiments. They’re practical approaches for sales leaders tired of implementing the same solutions and expecting different results.
While your competitors remain locked in conventional thinking—pursuing the same strategies, measuring the same metrics, and solving the same problems in the same ways—your competitive advantage lies in intellectual courage.
The courage to question assumptions, embrace uncertainty, and explore unconventional solutions—even when they make you uncomfortable.
That’s what it means to lead like a freak.