#My Best Sales Advice, Ryan Willumson

2019 was a breakout year for Ryan Willumson—CRO and Co-Founder of Industry Dive.

The company was:

🏆 A Neal Awards Finalist
🏆 A Washington Post Top Workplace
🏆 Named to Inc. Magazine’s Fastest-Growing Companies list
🏆 A Deloitte Technology Fast 500 Winner
🏆 And secured a deal with Falfurrias Capital Partners to accelerate growth

With momentum like that, I wanted to know what helped drive their success.

So, as we were catching up, I asked Ryan Willumson—CRO and Co-Founder—what was the best sales advice he’s ever received.

Ryan’s Best Sales Advice

💬 "The best sales advice I ever received was to shut up. You’re better off fighting the instinct to fill the air. Learn to be comfortable with an extra beat of silence. Not only does it sound calmer and more professional, but usually, the person on the other end of the phone will fill the silence for you and volunteer information that is helpful to get a deal done."

Why Silence is a Sales Superpower

🔹 Most sellers talk too much.
🔹 Most buyers need space to think.
🔹 Silence creates opportunity.

Why Do Salespeople Struggle with Silence?

📌 Pauses in conversation make people uncomfortable.
📌 Sellers feel pressure to fill the space with more talking.
📌 When sellers talk too much, they lose control of the conversation.

I get it—I struggled with silence early in my sales career. If there was a break in the conversation, I panicked.

💡 What I learned? The problem wasn’t the silence—the problem was my lack of confidence in letting the buyer think.

When I stopped pitching and started collaborating, my conversations changed.
✔️ My questions improved.
✔️ My buyers shared more.
✔️ My sales cycles shortened.

💡 Sales isn’t about filling space. It’s about creating space for the buyer to engage.

The Wrong Questions Kill Deals

Many salespeople rely on generic, surface-level questions like:
❌ What’s your goal?
❌ What’s your budget?
❌ Is pricing an obstacle?
❌ Who is the decision-maker?
❌ What is your pain?
❌ Can I show you all our capabilities?
❌ Who else are you speaking with?
❌ How can I earn your business?

🚨 The problem? These questions lead to generic, unhelpful answers.

👉 “What’s your budget?” → “We don’t have one.”
👉 “What’s your biggest pain point?” → “Too many to count.”
👉 “Can I show you our capabilities?” → “Send over some info.”

💡 Better questions lead to better insights.

Ask Questions That Spark Real Conversations

🔹 Instead of: “Is your goal to drive leads?”
✔️ Ask: “How do you define the different stages of your sales funnel?”

🔹 Instead of: “Who is the decision-maker?”
✔️ Ask: “How have similar buying decisions been made in the past?”

🔹 Instead of: “What’s your pain point?”
✔️ Ask: “If you had unlimited budget, what’s the first thing you’d fix?”

💡 Great questions make the buyer think—and when they think, they engage.

How to Use Silence to Win More Deals

Ryan’s advice isn’t just about stopping yourself from talking—it’s about using silence strategically.

📢 Here’s how:

✅ Ask a great question—then wait.
✅ If the buyer hesitates, don’t jump in—let them think.
✅ If they give a surface-level answer, let silence do the work—they’ll fill the gap.
✅ Resist the urge to over-explain—simple answers build confidence.

🔹 Example:
👎 Bad: “What’s your biggest challenge? Oh, I bet it’s X. That’s common. Here’s how we solve that…”
👍 Better: *“What’s your biggest challenge?” [Pause] Buyer: "Well... honestly, the biggest issue is..."

💡 Silence turns surface-level conversations into deep discussions.

Final Takeaway: Silence Makes You a Better Seller

🚀 Sales isn’t about saying more—it’s about listening more.

✅ Let silence create space for real answers.
✅ Ask better questions—generic ones kill deals.
✅ Learn to embrace the pause—buyers will tell you what they really need.

📢 Bottom line: Next time you feel the urge to fill the silence—don’t. The best insights come when you give the buyer time to speak.

About Ryan Willumson

Ryan Willumson spent years as a C-level Hollywood actor before pursuing his real dream—running sales at Fierce Markets.

After eight years in the role, he left in 2014 to co-found Industry Dive with Sean and Eli.

📢 Industry Dive delivers business journalism for decision-makers in the most competitive industries—helping leaders spark ideas, drive innovation, and make confident decisions.

🔗 Learn more: www.industrydive.com