Sales Leadership Failure: The $1,000,000 Lesson Every Board Eventually Learns.

A story about clarity, courage, and what really drives business performance

Every leader has a handful of stories that stay with them – the kind that resurface years later, usually at exactly the moment you need the reminder.

This one came back to me during a recent leadership interview. One simple question unlocked a memory I hadn’t revisited in years and dropped me straight back into a boardroom where a very expensive truth was about to be revealed.

The lesson is just as relevant today as it was then.

When the chair called

“Chris, I need you to look under the hood.”

The Chair of a mid-sized software business had made a decision no Board ever takes lightly. He had removed the CEO and needed an independent, forensic review of the organisation — its structure, leadership, performance, culture, and, most importantly, its people.

These engagements always tell a story. However, this one came with a twist.

While I can’t share confidential details, the patterns and lessons are universal. In fact, they’re too important not to share.

A $1,000,000 sales team producing nothing

At first glance, the business looked impressive.

They had:

• A Sales Manager who looked and sounded every bit the sales leader
• Five Sales Executives on generous salaries
• Fully expensed vehicles, lunches, and client entertainment
• Memberships in every relevant industry association
• Premium expo booths and conference attendance
• A well-funded marketing engine feeding them leads
• On paper, it looked like a sales powerhouse.

In reality, it was the most expensive mirage I’d ever encountered.

Here’s what we uncovered:

• Zero new business in 18 months
• No defined sales strategy
• Forecasts detached from reality
• No understanding of customer pain points
• No clarity on decision-makers or influencers
• No structure, accountability, or performance discipline

At one point, I joked with the Chair: “Pay me $900,000 to stay home and do nothing – I’ll guarantee the same results and save you $100,000.”

We laughed, but the truth landed heavily.

This wasn’t a sales problem. It was a textbook sales leadership failure – hidden behind confidence, activity, and unchecked assumptions.

How sales leadership failure takes hold

Importantly, this situation hadn’t emerged through arrogance or neglect.

Instead:

• The Chair had been unwell and stepped back from day-to-day oversight
• The CEO lacked the experience to build a scalable, disciplined sales engine
• The Board didn’t have deep sales expertise and accepted reports at face value

As a result, forecasts went unchallenged. Promises replaced evidence. And no one noticed the iceberg directly ahead.

Sales leadership failure rarely announces itself loudly. More often, it creeps in quietly, disguised as optimism.

When HR loses its strategic seat

Next, we looked at HR.

A long-serving, well-liked team member had been promoted into the role. She was warm, caring, and genuinely loved by staff. Every week, she baked cakes, gathered people together, and made sure everyone was “feeling okay.”

The intentions were good. Unfortunately, the outcomes were not.

Because HR was no longer:

• Involved in organisational strategy
• Building workforce or capability plans
• Aligning talent to business needs
• Supporting leaders with selection tools
• Driving culture or accountability

Instead, HR had become a social function – not a strategic partner.

And when HR steps out of strategy, recruitment quickly follows.

There was no structured selection process. Leaders hired based on familiarity, comfort, or gut feel. Predictably, bias crept in, both conscious and unconscious.

Then came the tribes.
Tribes turned into silos.
Silos hardened into factions.

And performance began to fracture.

Fear, mistrust, & a business at risk

With the CEO gone, uncertainty filled the vacuum almost immediately.

Whispers circulated:

• “Are we next?”
• “Will customers leave?”
• “Who’s actually in charge now?”

Managers became defensive. Teams retreated inward. Trust evaporated. I could almost hear CVs being quietly updated.

Businesses rarely collapse because of one dramatic event. Instead, they fail because hundreds of small cracks are ignored.

By now, those cracks were widening fast.

The Turning Point

Every successful turnaround starts with two deceptively simple steps.

1. Absolute Clarity of Strategy

No fog. No wishful thinking. A clear understanding of what the organisation will pursue and what it will no longer tolerate.

2. The Right People in the Right Roles

Capability aligned with responsibility. No assumptions, bias, or “mate’s choice.”

We began the repair using our POP™ Selection Assessments, starting with sales.

Because here’s the universal truth: When revenue is broken, confidence is broken.

Fix the sales engine and hope returns.

And that’s exactly what happened.

As clarity emerged, fear subsided. As capability improved, performance followed. Politics gave way to progress.

The leadership lesson that matters

You don’t need a global consultancy with eye-watering fees to fix these issues.

What you do need is:

• Clarity
• Courage
• The right expertise at the right moment

Sales leadership failure doesn’t just damage revenue. It damages trust, culture, and people.

The good news? You don’t have to navigate this alone.

Companies like Validity Group specialise in restoring structure, rebuilding capability, and helping organisations recover from exactly these situations.

And we always begin the same way.

We listen first.

Because that’s where real change begins.