How Sales Engineers Handle Difficult Prospects Without Losing the Deal
Ryan Krueger and Samir Sahai Gosser discuss strategies for handling 'prickly' prospects and internal colleagues in sales engineering. They categorize difficult people into distinct buckets and offer tactical advice for disarming skeptics, managing difficult calls, and building cross-functional relationships. The episode also covers best practices for following up on unknown questions and documenting commitments around unbuilt product features.
Summary
In episode 36 of Diary of a Sales Engineer, Ryan Krueger and Samir Sahai Gosser explore how sales engineers can handle difficult or 'prickly' characters both externally with prospects and internally with colleagues.
The hosts begin by categorizing prickly external prospects into distinct buckets. The first is the skeptic who has been burned by previous vendors who oversold software that never delivered value — this person is defensive but convertible, and once won over, becomes a fierce champion. The second is someone who has been forced onto a call by management and is simply disengaged or creating roadblocks. The third, rarer bucket is someone who shows up genuinely rude and in a bad mood, unrelated to the product or sales process. Ryan notes that experiencing this third type for the first time can be emotionally draining and bleed into subsequent calls, and he recommends managers conduct dry-run training scenarios to prepare SEs for such encounters.
For handling these difficult characters, the hosts recommend smiling and maintaining positive energy, using audience management to prevent one difficult participant from derailing a broader group demo, and redirecting deep technical questions to a scheduled one-on-one session. They identify InfoSec, architecture, and technically sophisticated RevOps professionals as the most common sources of unexpected, challenging questions. Ryan emphasizes the importance of saying 'I don't know' when appropriate, committing to follow up within 24–36 business hours, and actually delivering on those commitments — even if the answer takes longer due to engineering availability across time zones.
A major highlight of the episode is Ryan's real-world story of saving an end-of-quarter deal by leveraging a personal relationship with a machine learning engineer to produce a same-day concept demonstration for a hesitant partner, ultimately closing the contract. This story illustrates their broader advice that SEs should proactively build genuine friendships with engineering and product contacts — not just transactional relationships — to unlock influence when deals are at risk.
The hosts then shift to internal prickly characters: difficult fellow SEs, sales reps who micromanage demo style, sales leaders who push SEs to sell unbuilt features too aggressively, and engineering contacts who resist being looped into customer calls. Their advice includes finding personal common ground to defuse tension, directly naming tension in a one-on-one setting and letting silence do the work, and presenting evidence-based arguments rather than positional disagreements. On the topic of selling roadmap features, Ryan strongly advises SEs to document all commitments in shared channels, Salesforce, or Confluence pages to protect themselves and ensure post-sales teams are informed before the deal closes.
Key Insights
- Samir argues that prospects who were burned by previous vendors who oversold software are actually the most valuable converts — once you prove honesty and show real product capability, they become the champions who 'run through walls' for you because you addressed the emotional side of their resistance.
- Ryan recounts how a personal relationship with a machine learning engineer allowed him to pull together a same-night concept demo that unblocked a hesitant partner and closed a major end-of-quarter deal — arguing that without that relationship, the deal would have been lost with certainty.
- Ryan argues that when a large group call includes expensive senior stakeholders, the cost of that call to the buyer signals that the deal has more momentum than the prospect has let on — and SEs should recalibrate their urgency accordingly.
- Ryan describes how his internship manager at NetSuite deliberately role-played an aggressive, rude prospect during a checkpoint review, which threw Ryan off completely — but he argues this single training moment gave him a mental framework he has drawn on every time a genuinely difficult prospect has appeared in his career.
- Samir argues that directly naming tension to a colleague — saying 'I sense some tension between us, can we chat about it?' and then sitting in silence — is counterintuitively disarming because people are not psychologically prepared for that level of directness and tend to open up rather than escalate.
Topics
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