Stop Asking Lame Sales Questions (And Start Being Useful)

Most salespeople ask the same predictable, cookie-cutter questions. “What’s your biggest challenge?” “Who makes the final decision?” “What’s your timeline?”

I get it. We’ve all been trained to qualify and these are the questions we need to find answers to if we're going to win deals. Let’s be honest—these questions aren’t exactly sparking deep, insightful conversations. Half the time, the prospect is rolling their eyes before they even answer.

But as buyers continue to evolve - as I've written about here - and as they are bombarded with sales and marketing noise, it's now necessary to up our game.

If you actually want to help your prospects, get them talking and build your own credibility, it’s time to upgrade your questioning strategy.

The Problem With Basic Questions

Basic sales questions make prospects feel like they’re being put through a dull corporate survey. They offer nothing. No insight, no perspective, nothing they couldn’t have just written in an RFP.

Worse, they make you sound like a low-level box-ticker instead of someone who actually understands their world. And guess what? The best buyers - the ones with real budgets, real influence - don’t have time for that. Today, as buyers have more power, they are not looking to work with another sales rep, they are looking for someone who is looking out for them.  

So let’s fix it.

Leveling Up Your Sales Questions

Instead of using basic, transactional questions, start using thoughtful, insight-driven questions that add value. That means asking questions that:

• Make the buyer think - instead of just reciting answers they’ve given a dozen times
• Position you as an expert - because you actually bring something to the conversation
• Reveal deeper insights - that the prospect might not even realize about their own business

Here’s a cheat sheet:

Why This Works

🔹 You sound like a peer, not a vendor. When you show up with insights, prospects treat you differently. You’re not just another rep - they see you as someone worth talking to.

🔹 You uncover better intel. These questions get to the truth behind a deal - the priorities, the juicy politics, and hidden factors that actually drive decisions.

🔹 Your prospects appreciate it. The reality is that most sales conversations suck. When you ask better questions, you actually make the conversation interesting for them, too. And that’s rare.

How to Get Good at This

If you’re still relying on standard sales questions, here’s how to step up your game:

Do some actual research. Read about their industry. Know what’s happening. Drop a stat, a market shift or a relevant client example - something that shows you’re paying attention.

Practice asking the questions out loud. Changing salespeople's behavior is not easy. Use my AI bots that let sales reps practice their pitch and their questioning strategies. Here's a quick example.

Listen. Really listen. The whole point of asking smarter questions is getting better answers. Don’t rush to the next pitch—dig deeper when they say something interesting.

Final Thought: If you’re still asking, “What’s keeping you up at night?” - just stop. You’re better than that.

Ask better questions. Have better conversations. Make prospects glad they talked to you.

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