Answer extracted from the The Best of the Brutal Truth about B2B Sales & Selling podcast — listen to the full episode below.
How to Coach Senior Sales Reps on Complex Deals Without Imposing Your Method
Think like a chess player, not a directive manager. Rather than telling senior reps how to handle enterprise deals, use brainstorming sessions that ask questions about what the buyer is feeling, how the deal advances their career, and where it ranks among their other priorities—this collaborative sounding board builds trust and lets reps own the strategy.
The chess player mentality is about anticipating. Instead of imposing a checklist or playbook, Guillaume works through scenarios by asking: if we make this move with the buyer, what are the potential outcomes? What could go wrong? What could the buyer be thinking at each stage? This kind of dialogue respects the rep's expertise while bringing your vantage point as a manager—you've seen dozens of similar deals, they've seen a handful.
The power of this approach lies in collaborative strategy rather than prescription. When you ask a senior rep "What do you think the buyer is really after here?" or "How does closing this deal change their position internally?" you're not telling them what to do. You're creating space for them to think out loud with someone who has pattern visibility they may lack. Reps take ideas if they feel they're right, not because you told them to follow a process.
As Guillaume explains in the episode, this approach works especially well with senior performers who already know how to sell. They don't need someone micromanaging their activity; they need someone who understands the broader landscape and can help them see angles they might miss. A manager with 10 reps gains visibility into 10 times the deals a single rep handles—that's the advantage you're leveraging, not your authority.
"I stop lying, be honest, ask questions, really understand what they're after, and I work for a Fortune 500 company so I'm trying to be the advocate of FIS when I'm at the client and be the client advocate when I'm working with my internal stakeholder."
Guillaume — Sales Manager at FIS, with nearly two decades in the fintech space selling capital market solutions, trading systems, and treasury solutions across Europe and North America. He brings pattern recognition from hundreds of enterprise deals to his coaching conversations.
One detail worth hearing in full: Guillaume also discusses how to distinguish between deals worth nurturing and those destined to become time sinks—a practical framework buried in the full conversation that applies directly to rep prioritization coaching.
Key takeaways
- Ask your senior reps what the buyer is feeling and how the deal impacts their career—this surfaces real priorities that aren't always visible in the pipeline.
- Use your manager's vantage point (10x deal visibility) to help reps spot patterns they haven't seen yet, without telling them how to execute.
- Trust that capable reps will take ideas if they feel they're strategically sound, making collaborative sounding board sessions more effective than checklists.
- Think through multiple scenarios and outcomes for each move in a deal, shifting your coaching from directive to exploratory.
See also
Why did a successful fintech sales professional transition from individual contributor to sales management?
Guillaume shifted to leadership because he enjoys working with people and helping others add value. In his sales quadrant—prospecting, building relationships, negotiating, and closing—he found that he could multiply his impact by developing his team rather than carrying the full load himself.
What is the impact of wasting time on low-probability deals instead of focusing on opportunities more likely to close?
Most sales professionals spend less than half their calendar time on deals that either close or have a high likelihood of closing, meaning roughly 50 percent of working time goes to deals that do not advance revenue. This is an enormous opportunity cost that could be redirected to nurturing high-probability deals.
How should sales leaders leverage their vantage point of seeing multiple deals across their entire team to improve overall performance?
A great sales leader with 10 reps sees 10 times the deals an individual rep sees, allowing them to spot patterns that individual reps may not see for months or years. By sharing these patterns and insights with the team—what kinds of companies succeed, which ones become time sinks—leaders amplify collective performance without dictating how anyone should sell.