Stop Guessing. Start Leading: 10 Questions to Revive Sales Performance Now— Especially When Sales Are Stagnant or Struggling

When revenue is flat or sliding, don’t panic—get curious. The fastest way to revive sales performance? Start asking sharper, smarter questions.

As I talk with leaders across industries—owners, CEOs, GMs—one topic keeps bubbling to the top: sales. Whether it’s geopolitical uncertainty, pricing pressure, or shifting customer behavior, sales performance is under scrutiny.

And yet, many senior leaders hesitate to lean into commercial conversations unless it’s their direct domain. They don’t want to micromanage. They trust their sales leaders. But when revenue is flat or softening, the best thing you can do is ask good questions.

At Catalyst Point, we’re not sales trainers—we’re executive coaches who’ve led commercial teams. We know how to support and challenge sellers without usurping them. A well-timed question from a senior leader can do more than direct—it can inspire, surface blind spots, build accountability, and reignite engagement. Especially when it comes from a place of curiosity and care.

And here’s the truth: sometimes it’s not the strategy that needs fixing—it’s the mindset.

We’ve written before about how sales resiliency is a mindset, the ability to stay focused, adapt, and bounce back in the face of rejection and resistance. These 10 questions aren’t just diagnostic tools—they’re fuel for a more resilient, energized commercial culture.

If sales are off pace or stalled, don’t default to assumptions or pressure—start with these 10 questions to revive sales performance now. They’re designed to support your commercial team, pressure-test strategy, and maintain motivation in a tough market:

1. "What customer segments are delivering the highest margins—and are we spending enough time there?”

   This question brings the focus back to value over volume. Not all customers are created equal, and in a resource-constrained environment, focus is everything.

   
   

2. "Are we backing into our sales targets with realistic funnel math?”

   Hope is not a strategy. Ask to see the math: What’s the required number of qualified leads? Conversion rates at each stage? What’s the average deal size, and how long is the cycle? Are those assumptions grounded in recent data?

   
   

   Example: If your goal is $1 million in new sales this year and your average deal size is $50K, you’ll need 20 wins. At a 20% close rate, that means 100 serious opportunities and likely 300+ prospects at the top of the funnel. That’s a lot of activity to generate.

   
   

   Bonus thought: How can you help sellers become more efficient at each stage of the funnel? For instance, if you invest in training that improves their close rate, you could dramatically reduce the volume of opportunities needed to hit your target. STUDY THE FUNNEL.

3. “What’s changing in the customer’s world that we might be underestimating?”

   This keeps your team externally oriented. Are regulations shifting? Are your customers losing headcount, or adopting new tech? Don’t let internal busyness blind the team to external relevance.

   
   

4. “How are we tailoring our value proposition to different customer types?”

   Generic pitches don’t cut it anymore. Personalization is the norm. Ask how the message shifts for different industries, roles, or relationship stages. If it doesn’t or you’re getting blank stares, there’s work to do.

   
   

5. “Are we doing anything to accelerate the sales cycle?”

   Long sales cycles aren’t always avoidable, but they can often be shortened. Is your team scoring and prioritizing leads effectively? Using automation or nurturing content wisely? Are they following up in ways that add value—not just pressure?

   
   

6. “How are we staying visible and valuable to key prospects between meetings?”

   In long-cycle selling, what you do between meetings matters most. Challenge your team to avoid the dreaded ‘just checking in’ note. Are they sending relevant insights, testimonials, tools, or content that keeps the conversation warm?

   
   

7. “What have we learned from our recent wins and losses?”

   Don’t just ask about the scoreboard—ask about the film review. What are we hearing in post-mortems? What’s working, and what’s not? And don’t just study losses—ask what led to recent wins. Are we sharing success patterns across the team? Can we scale any learnings internally?

   
   

8. “Who are our top 10 most valuable customers—and how are we investing in them?”

   Not all customers deserve equal treatment. Ask your team to define "most valuable"—by margin, growth potential, relationship strength, or cross-sell opportunity—and then push for clear strategies on retention and expansion.

   
   

9. “When’s the last time we innovated with a customer, not just for them?”

   If you’ve been supplying a customer for 20 years and have never helped them innovate, you’re still just a vendor. High-performing teams move toward co-creation—solving problems together, not just selling products.

   
   

10. “What’s motivating the sales team right now—and what’s wearing them down?”

    Sometimes the most powerful question isn’t about pipeline—it’s about people. Sales is hard. Rejection is constant. Check in on team energy. Make space for honesty. Nobody buys from a burned-out or defeated seller.

Coach’s Corner: Bonus Reflections for Senior Leaders

• Segment smarter. Don’t settle for generic segmentation. Group customers by industry, margin, size, buying behavior, cross-sell potential, or relationship strength. The sharper the segmentation, the sharper the strategy.

  
  

• Internal customers matter, too. Your sales team isn’t the only audience. Who are your most critical internal customers—those who impact your team’s ability to succeed? Apply the same strategic focus internally.

  
  

• Celebrate wins, not just numbers. Do your people feel seen when they succeed? Are you sharing the "how" behind a great deal? Recognition fuels repeatable excellence.

  
  

• Sellers get told “no” every day. Don’t take your team’s grit for granted. Yes, they can earn big commissions. But they carry rejection as a daily burden. Empathy, flexibility, and visibility matter.

  
  

• Happy sellers sell better. Enthusiasm is contagious. Buyers can sense when a rep is flat or demoralized. The emotional health of your team is a performance lever.

Bottom line:

You don’t have to be a sales expert to ask great commercial questions. In fact, your perspective may be exactly what the team needs. Start with these 10 questions to revive sales performance now—ask with purpose, listen with intent, and lead with curiosity. You’ll not only support your team—you’ll elevate their game.

Want help sparking smarter commercial conversations or coaching your team to sustained performance? Reach out to us at Catalyst Point.