🦾 The $100K Deal I Lost (And Why I Deserved To)

Hey Insider, I just watched a $100K deal evaporate. In 90 days. With the owner's referral.

I broke every sales rule I teach, and the market delivered an expensive lesson.

The Perfect Setup That Wasn't

On paper, I was untouchable the clear choice for this client:

→ 4 unicorn successes

→ Dozens of turnarounds

→ 4 years of company insight

→ Private equity owner referral

Three Fatal Mistakes

1. Rushed the Proposal

• They needed budget numbers fast

• I jumped at their urgency

• Became the pricing anchor

• Let competitors learn from my mistakes

I sold a deal to Uber for a client and made them wait more than 6 weeks before providing a proposal because we hadn’t establish their pain and urgency. Being intentional wins deals.

2. Assumed I Had Control

• Trusted the CEO's mandate

• Ignored the team's influence

• Failed to build consensus

• Missed hidden decision makers

I missed that the CEO who normally makes the decisions in spite of his team’s preferences was under pressure from the board to appear more collaborative.

3. Lost the Timing Game

• Presented first (rookie move)

• Let three weeks pass

• Handed competitors the last word

• Forgot the power of recency

Ultimately, I let myself believe the CEO was selling us internally. I failed to remain skeptical and instead was optimistic. FATAL mistake.

The Real Reason Buyers Buy

Your expertise matters less than:

→ How recently they've seen you

→ Who feels heard in the process

→ Whether the team trusts you

→ If they believe you'll collaborate

The CEO later admitted: "You were the most qualified, but the team felt more comfortable with someone else."

Think You're Different?

I hear these excuses daily:

"But they needed it quickly!"

"The CEO said he was deciding!"

“I have the decision makers ear. Mary is the decision maker.”

"I had the best credentials!"

Sound familiar?

These are the lies we tell ourselves when we're breaking our own rules.

Your Deal Rescue Plan

Do this today for your pending deals:

1. Map Your Stakeholders

• List every influencer

• Note their personal wins

• Mark who you haven't met

2. Check Your Timeline

• Review presentation dates

• Compare competitor timing

• Plan your recency advantage

3. Fix Your Process

• List your broken rules

• Schedule missing steps

• Build team consensus

[Swipe This Template] "Before finalizing our proposal, I'd like to understand how the team will be evaluating this decision. Could we schedule 30 minutes with key stakeholders to ensure we're aligned?"

Your Sales Fit Challenge

This week:

1. Review your active deals

2. Mark which ones you're rushing

3. Map all stakeholder priorities

4. Plan your consensus-building steps

Reality Check

The fastest way to lose a deal is to assume you've won it.

Moment of Truth

Which of your "sure thing" deals are you risking right now by breaking your own rules?

Win the Day! Ken Lundin

P.S. The firm that won? They spent three weeks building relationships with every stakeholder. Sometimes the tortoise really does win the race.