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What I Learned from a Sales Engagement That Went Wrong: A Cautionary Tale for Sales Managers and Consultants

In the world of business development, we often talk about growth, targets, and performance. What we talk about far less is what happens when an engagement goes wrong — not because of poor delivery, but because of a breakdown in structure, support, and accountability.

Earlier this year, I spoke to a business development rep who took on a contract to support a growing organisation with their business development strategy. On paper, it was a solid opportunity: clear deliverables, a fixed term, agreed KPIs, and a chance to drive real impact. What followed was a stark reminder that no matter how capable or motivated you are, success in sales depends not just on what you do — but also on the environment you’re working in.

The Warning Signs

From the start, it was clear that there were internal challenges. Leads were recycled repeatedly, overlapping between team members, creating confusion and competition rather than collaboration. The CRM system was either underutilised or non-existent, with spreadsheets acting as substitutes for automation and proper tracking. There were unclear rules of engagement and inconsistent communication across teams. Senior leaders acknowledged these problems, but little action followed.

Worse still, targets were set without historical context or realistic baselines. Hitting numbers wasn’t just difficult — it was structurally impossible.

From the outset, it became clear that internal misalignment was going to be a significant challenge. Leads were being recycled and reissued, with multiple team members unknowingly working the same opportunities. Instead of collaboration, this created internal competition, confusion, and eventually, disengagement. It’s a classic sign of a team operating without a unified go-to-market strategy.

The CRM system was underutilised — or worse, bypassed entirely. Spreadsheets stood in for structured processes, making it nearly impossible to track lead sources, conversion rates, or sales velocity. In an environment where accountability and insight are critical, this level of disorganisation creates risk at every stage of the funnel.

Rules of engagement were unclear. Team members didn’t have clarity on lead ownership, qualification criteria, or handover protocols. The result? Friction, missed opportunities, and ultimately, a loss of trust in the process itself. Worse, when management acknowledged these problems, no corrective action followed. That’s the riskiest sign of all — leadership inaction in the face of dysfunction.

Finally, targets were set arbitrarily — without reference to historical performance, market benchmarks, or operational capacity. Targets disconnected from reality don’t motivate teams — they demoralise them. And in this case, they created a situation where underperformance was inevitable, regardless of individual effort.

⚠️ The Risks These Problems Create

• Low morale and high turnover among salespeople and external contributors.
• Missed revenue opportunities due to lead mismanagement and unclear ownership.
• Inability to scale because core systems (like CRM) are not being used or trusted.
• Damaged client or partner relationships due to inconsistent follow-up and tracking.
• Breakdown in accountability, where no one knows who is responsible for results — or failure.

✅ How to Overcome These Challenges

1. Build from a strong operational foundation
   Invest in a proper CRM system and insist that all sales activity flows through it. No exceptions. Spreadsheets may feel faster, but they kill visibility and scale.
2. Create and enforce clear rules of engagement
   Define exactly who owns a lead at each stage, what qualifies as a handover, and how team members collaborate — and document it.
3. Ensure transparency across teams
   Sales, marketing, and management must operate from the same data and understand each other’s processes. If people aren’t aligned, your funnel will leak at every level.
4. Set data-informed targets
   Targets should be tied to actual conversion rates, deal cycles, and team capacity — not gut feel or legacy assumptions. Revisit them quarterly and adjust if needed.
5. Hold leadership accountable, too
   When internal issues are raised, there must be a plan to address them. Sales leaders who admit to problems but fail to act create more damage than those who don’t see the issues at all.

When I started writing my book, I genuinely hoped I was closing the chapter on witnessing poor leadership — the kind marked by ego, avoidance, and a lack of accountability. But the more I work with organisations and individuals across industries, the more I realise the problem isn’t going away — it’s evolving, and in many cases, getting worse. Titles are getting fancier, leadership language more polished, but the fundamentals — trust, integrity, structure — are still being neglected. And until we start demanding better, we’ll keep repeating the same cycles dressed in slightly smarter suits.