Assumptions Are Deal Killers: Here's How to Eliminate Them and Win More Business

A sign that says 'Land Mines'

Nothing Kills Deals Faster Than Assumptions

Assumptions don’t just clutter your pipeline—they derail deals. In every deal review I conduct, I’m constantly on the lookout for them. Why? Because there’s a big difference between what we know and what we only think we know.

What we don’t know—or fail to validate—often becomes the silent killer of deals. That’s why it’s essential to flag assumptions, coach your reps on uncovering clarity, and equip them to validate every critical detail. The result? A cleaner pipeline, faster opportunities, and better outcomes.

 

Sound the Alarm on Assumptions

If a rep uses any assumptive language during a deal review, alarms should go off immediately. Phrases like these are bright red flags:

  • "I think..."
  • "Probably..."
  • "I guess..."
  • "Maybe..."
  • "Could/Should/Might..."

The moment you hear these, pause. Dive deeper. Encourage your reps to ask their clients the tough questions. Assumptions are often a sign that your team needs more insight into the client’s needs, processes, or decision-making dynamics.

 

Validate Everything

Even when your rep provides firm answers to critical questions, don’t stop there. Ask, “How do you know?”

Reps often confidently deliver answers that turn out to be assumptions. For any key point impacting a deal, ensure it’s validated. Not only does this reinforce clarity, but it also sets an example: good leaders don’t assume—they validate.

 

Triangulate Critical Information

When your rep gets information from a single source, encourage them to triangulate by confirming it with other contacts in the account.

Here’s why:

  • Different stakeholders have access to different insights, processes, and people—especially in large organizations.
  • Validation from multiple contacts strengthens your position.
  • Discrepancies in responses highlight areas needing further investigation.

Remember, clients rarely provide false information intentionally, but they don’t always have the full picture either. Triangulating key details ensures you’re operating with the most accurate and reliable data.

 

The Bottom Line

Assumptions kill deals, muddy the pipeline, and waste your team’s time. A thorough deal review may take more effort upfront, but the revenue gains, stronger pipelines, and coaching opportunities you’ll uncover make it worth every second.

Stop assuming. Start validating.