Executive Job Search

What Goes Into a Walking Deck (And Why Most Executives Get It Wrong)

Bill Heilmann
What Goes Into a Walking Deck (And Why Most Executives Get It Wrong)

The 7 sections—and why the 30-60-90 plan makes or breaks your Walking Deck.

Common mistakes:

Mistake 1: Passive closing
"Thank you for your consideration"
(Too weak for executive positioning)

Mistake 2: Desperate positioning
"I'm available immediately and eager to start"
(Signals no other options)

Mistake 3: No clear next step
Leaving it ambiguous about what happens next
(Make it easy for them to move forward)

The right approach:

Be clear about what you want to discuss next. Show enthusiasm without desperation. Make yourself easy to reach. Position from strength (you're evaluating mutual fit).

The Complete Walking Deck: Slide Count and Flow

Total slides: 15-25

Here's the optimal flow:

Slides 1-3: Introduction (Title + Personal Brand) -Slides 4-7:* Proof (Career Highlights) -Slides 8-15:* Strategy (30-60-90 Day Plan) ← CORE SECTION -Slides 16-18:* Business Case (ROI and Value) -Slides 19-22:* Validation (Testimonials + Proof) -Slide 23:* Call to Action

Notice the structure:

  • You establish credibility first (who you are, what you've done)
  • Then you demonstrate strategic thinking (the 30-60-90 plan)
  • Then you justify the investment (business case)
  • Then you validate with social proof (testimonials)
  • Then you propose next steps (CTA)

This is psychological sequencing—not random order.

The Creation Timeline: How Long It Takes

Don't rush this. A properly researched and developed Walking Deck takes 15-25 hours spread over 2-3 weeks.

Week 1: Research and Analysis (8-10 hours)

  • Deep research on company, market, competitors
  • Talk to customers if possible
  • Analyze financial data if public
  • Identify specific challenges
  • Develop strategic hypotheses

Week 2: Content Development (8-10 hours)

  • Write situation analysis
  • Develop 30-60-90 day plan
  • Create business case and ROI projections
  • Draft other sections
  • Gather testimonials

Week 3: Design and Refinement (4-5 hours)

  • Design slides (clean, professional, not over-designed)
  • Refine messaging and flow
  • Practice presenting
  • Get feedback from trusted advisors
  • Final polish

Total: 20-25 hours over 2-3 weeks

Is this a lot of work? Yes.

Is it worth it? Absolutely.

This is the single most important business development effort of your career—selling yourself into a $300K+ role. Twenty hours is nothing compared to the return.

The Most Important Section: Why 30-60-90 Makes or Breaks It

Let me be completely direct: Your Walking Deck lives or dies based on your 30-60-90 day plan.

Here's why:

The title slide is important. Your brand positioning matters. Career highlights provide proof. The business case justifies the investment.

But the 30-60-90 day plan is where you demonstrate executive-level strategic thinking about their specific situation.

This is where hiring managers can actually see how you think. Not what you've done, but how you analyze and solve.

The difference between winning and losing:

Losing 30-60-90 plan:
"First 30 days: Learn the business and meet the team"
(Generic, obvious, shows no strategic thinking)

Winning 30-60-90 plan:
"First 30 days: Conduct sales process diagnostic focusing on the three deal stages where you're losing 60% of pipeline. Shadow 10 calls, analyze last 50 deals, interview top performers and struggling reps. Deliverable: Diagnostic report identifying top 3 friction points with quantified impact and fix recommendations showing projected 18% conversion lift."

The first approach: Could apply to any role at any company

The second approach: Specific to their sales challenge, shows diagnostic thinking, projects measurable outcomes

That's the difference between getting passed over and getting the offer.

Spend 40-50% of your Walking Deck creation time on the 30-60-90 section. Research their specific situation. Think strategically about their challenges. Develop concrete, measurable approaches.

This is where you prove you can think at the executive level.

Common Walking Deck Mistakes (Summary)

After reviewing hundreds of Walking Decks, here are the most common failures:

1. Making it about you instead of them

  • Too much focus on your credentials
  • Not enough focus on their challenges
  • Generic content that could apply anywhere

2. No company-specific research

  • Template language
  • No mention of their actual situation
  • Generic 30-60-90 plan

3. Unrealistic promises

  • "I'll double revenue in 60 days"
  • Overpromising destroys credibility
  • Conservative estimates are more believable

4. Poor design or over-design

  • Too much text per slide
  • Competing fonts and colors
  • Looks unprofessional

5. Weak or missing 30-60-90 plan

  • Generic goals like "learn the business"
  • No specific outcomes or metrics
  • No demonstration of strategic thinking

6. No business case

  • Avoiding the ROI conversation
  • No financial framing
  • Missing the business justification

7. Too long or too short

  • 40+ slides = too much
  • 8-10 slides = too little
  • Sweet spot: 15-25 slides

The Bottom Line

A Walking Deck has seven specific sections, each serving a distinct purpose:

1. Title Slide: Immediate positioning and value proposition -2. Personal Brand:* Executive identity and specialization -3. Career Highlights:* Quantified proof of value creation -4. 30-60-90 Day Plan:* Strategic thinking demonstration (MOST IMPORTANT) -5. Business Case:* Financial justification and ROI -6. Testimonials:* Third-party validation and proof -7. Contact/CTA:* Clear next steps

The most critical section is the 30-60-90 day plan.

This is where you demonstrate strategic thinking specific to their company and challenges.

Most executives get this wrong by writing generic goals:
"First 30 days: Learn the business and meet the team"
(This is obvious and shows zero strategic thinking)

The right approach is company-specific and strategic:
"First 30 days: Audit current sales process, identify 3 friction points in deal cycle through data analysis and call shadowing, propose fixes with projected 15% conversion lift"
(This demonstrates diagnostic capability and strategic thinking)

The structure matters:

  • Total slides: 15-25
  • Creation time: 20-25 hours over 2-3 weeks
  • 40-50% of time on 30-60-90 section

What Walking Decks do that resumes can't:

  • Demonstrate how you think (not just what you've done)
  • Show company-specific strategic analysis
  • Project future value with concrete plans
  • Provide business case justification
  • Differentiate you from all other candidates

The investment is significant. The return is exponential.

Twenty hours of strategic work to win a $300K+ offer with 10-20% premium compensation and multiple offers to choose from.

That's executive-level ROI.



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Written by

Bill Heilmann