This year alone, I’ve spent over 600 hours training sales professionals and recruiters. Across all those sessions, one thing has stood out as the biggest opportunity for improvement: asking better questions.
Think about it—during COVID, much of our communication shifted to “talking at” people. It worked for a while. Emails, voicemails, and LinkedIn messages all got results. But those approaches aren’t real conversations. They’re one-way streets.
Back then, the market was ripe, and many of us succeeded without having to fine-tune our interpersonal skills. But now? The game has changed. Market conditions are tougher, and those neglected conversational muscles need a serious workout.
To thrive today, we need to shift back to talking with people, not at them. And the fastest way to make that shift is by learning how to ask great questions. When you ask the right questions, you connect better, build trust faster, and open doors to opportunities you didn’t even know existed.
Here are three practical ways to sharpen your questioning skills and get your conversations back in top form:
1. Prepare Like a Pro
Walking into a conversation without prepared questions is like showing up to a client meeting without a plan—it’s risky and rarely works. Good questions don’t just happen; they’re created ahead of time.
You are defined by the quality of questions you ask.
Take a moment before your next call to think about what you really need to learn. Are you trying to uncover pain points, goals, or decision-making processes? Write down a few thoughtful questions that can help you dig deeper. When someone feels you’ve taken the time to understand them, they’re more likely to open up and share valuable information.
2. Practice Makes Confident
Writing down great questions is a good start, but you need to practice delivering them too. Why? Because the way you ask a question—and how you respond to the answers—matters just as much as the question itself.
Try this: run your questions by a colleague or even plug them into a tool like ChatGPT. See how different people or systems respond. This helps you anticipate potential answers and refine your follow-up. It’s about being ready for wherever the conversation might go.
3. Get Comfortable Going Off-Script
Let’s be honest: sticking to a script feels safe, but real conversations rarely follow a script. When someone gives you an answer, don’t just move on to your next pre-planned question. Stay in the moment. Ask follow-ups. Show you’re genuinely interested in what they’re saying.
Yes, it can be a little intimidating. Freestyle conversations can lead to unexpected twists and turns. But that’s where the magic happens. Those follow-up questions often uncover the deeper challenges, motivations, or desires that help you truly connect with a customer or candidate. And that’s when trust starts to grow.
When people trust you, they’re more willing to explore your ideas, solutions, or job opportunities. But trust isn’t automatic—it’s earned through thoughtful, meaningful exchanges.
The Bottom Line
Asking better questions doesn’t have to be complicated. Prep a few thought-provoking ones, practice them until they feel natural, and then be ready to follow wherever the conversation leads.
Your ability to ask—and listen—is what sets you apart. So, take the time to hone these skills. You’ll not only have better conversations, but you’ll also build stronger, more lasting relationships with the people who matter most to your success.
Butler Street’s Sales Effectiveness and Recruiting Effectiveness programs strengthen these skills (and so much more) - and provide the tools, repeatable processes, and hands-on-exercises to excel. Whether through digital learning, virtual leader-led sessions, or AI coaches, you’ll form habits for success. You’ve got this. Now go out there and start asking the kinds of questions that make people stop, think, and want to tell you more.
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