Let’s talk about something that can take your inside sales game from meh to amazing!
asking the right questions and then really listening to the answers
These two things can make all the difference between a conversation that fizzles out and one that leads to a deal (or at least a solid next step).
The Art of Asking the Right Questions
Not all questions are created equal. If you just fire off a checklist of generic ones, you’ll sound like every other salesperson out there. But when you ask the right questions? That’s where the magic happens.
Try these:
- Open-ended questions → “Tell me more about the challenges you’re dealing with.” (Gets them talking instead of just saying yes or no.)
- Digging deeper questions → “What’s been the biggest impact of that on your team?” (Uncovers the real pain points.)
- Reflection questions → “Sounds like that’s been a major roadblock—what have you tried so far?” (Shows you’re listening and keeps the convo flowing.)
Why Active Listening Matters
You’ve been on calls where you know the other person isn’t really listening. Maybe they’re waiting for their turn to talk, or worse—half-distracted by emails. Don’t be that person. When you actually listen, prospects can tell.
Here’s why that’s a game-changer:
- People trust people who listen. If they feel heard, they’re way more likely to open up and work with you.
- You get the full story. The more you listen, the better you understand what’s actually keeping them up at night (and no, that’s not a question to ask—it’s a feeling to uncover). Once you know that? You can offer a solution that fits.
- Stronger connections = better sales. There’s an old saying: people buy from people they like. A better way to put it? People buy from people who make them feel heard and understood.
Here’s the Game Plan
- Be present. Close your email, stop checking Slack, put your phone away, and actually focus on the person you’re talking to.
- Talk less, listen more. Let them do most of the talking—you’ll learn so much more that way. That’s also why great questions matter (see #3).
- Ask smart questions. Not just to ask something, but to get deeper into what they really need.
- Repeat back what you hear. Saying, “So it sounds like your biggest challenge is X—did I get that right?” proves you’re paying attention.
- Use what you learn. Now that you actually heard their challenges, connect the dots with follow-up questions. Then, show them how your solution helps.
At the end of the day, inside sales isn’t about talking people into a deal. It’s about understanding them so well that the deal makes sense for both of you.
Next time you’re on a call: ask better questions, slow down and listen.
Watch what happens,
Lynn