Riffing Sales Reps

I once worked with a senior sales leader who doubled as the head of our business unit. His position carried significant weight, and his approach to sales left a lasting impression on me—but not in a good way.

During prospect presentations, he would often “riff.” You know, like how rappers freestyle without preparation—purely creative, completely improvised. At first, it sounded impressive, even compelling. But riffing in sales is a dangerous game. Creativity often overshadows reality, and the promises made can stray far from what’s actually possible.

The Risks of Riffing

Here’s the problem: Customers buy into the polished pitch, only to realize later that the “solutions” presented were more imagination than execution.

By then, it’s too late. Decisions have been made. Internal approvals have been secured—often from teammates, management, even the C-suite and the Board. Backtracking after all that? Nearly impossible. For many, it could be career-ending. No backing out. And sales reps who riff know this. They rely on it.

What Happens When Riffing Wins?

When companies fall for the creative pitch instead of hard facts, they end up in long-term agreements with the wrong solution partner. The fallout looks like this:

1. Constant SLA Failures:

Promised service levels are rarely, if ever, met, leaving decision-makers scrambling to mitigate damage.

 2. Contractual Stalemates:

The relationship devolves into an exhausting cycle of threats to terminate the agreement, countered by desperate promises to improve.

 3. Endless Triage and Regret:

Hours wasted in triage meetings, escalating frustration, and a growing sense of regret for choosing the wrong partner.

How to Spot and Avoid Riffing Sales Reps

1.   Trust Your Gut:

Riffing sounds too good to be true—because it usually is. If a pitch feels overly polished but lacks substance, healthy skepticism is warranted.

2.   Demand Specifics:

True solution partners can back up their claims with detailed documentation, case studies, and examples of where they’ve successfully delivered on similar promises. Riffers can’t.

 3.   Skip the Scripted References:

Never let a prospective partner control reference calls. Sales reps often name-drop their customers, but these are usually cherry-picked contacts who will paint a rosy picture. Instead, do your own research:

• Look up executives on LinkedIn in similar roles or functional areas at those companies. (A good Technology Advisor will offer to do this for you.)

  
  

• Reach out to your own network to see who has worked with the company or other executives they know who have worked with the company.

  
  

• Reach out for a private, candid conversation. Confidential discussions often reveal the real story.

Why It Matters

Avoiding a riffing sales rep isn’t just about preventing a bad purchase—it’s about protecting your career. Choosing the wrong partner can lead to wasted resources, damaged reputations, and long-term regret.

Remember: a great pitch without proof is just noise. Be vigilant, ask the hard questions, and do your own digging. It could save you and your organization from years of frustration—and it just might save your career.

Technology Advisors

Technology Advisors can be invaluable in navigating the challenges outlined above. We bring expertise in evaluating vendors and solutions, cutting through the noise of overhyped pitches to identify what’s realistic and deliverable.

By leveraging our deep industry knowledge and firsthand experience with technology partners, we can help you spot red flags like “riffing” sales reps and ensure claims are backed by real-world results.

Additionally, we guide you in conducting due diligence, such as vetting references and analyzing case studies, to ensure you choose a solution that aligns with your organization’s needs—saving you from costly mistakes and potential career risks.