Most reps ask, “Was that good?”
Top reps ask, “What did I miss?”

There’s a subtle difference between validation and insight—but the impact on your growth is anything but subtle. The truth is, most sales professionals unintentionally handicap their development by asking the wrong kind of questions. Questions that feel safe. Questions that make them feel good. Not better.

Please, Let’s fix that today!

Validation is comfortable. But comfort doesn't close deals.

After a big call, a rep might ask their manager, “Did I handle that objection okay?”

The manager says, “Yeah, you did fine.”
End of story. No discomfort. No real learning.

But here’s the thing: great salespeople aren’t looking for pats on the back—they’re looking for blind spots. They don’t want to hear what went right. They want to know where the deal could have slipped. Or worse, where it still might.

Ask like you're trying to level up, not level out

If you're serious about improving your craft, the way you ask questions—of your manager, of your AI assistant, even of yourself—has to change.

Instead of asking:

“Was my pitch clear?”

Ask:

“Which part of my pitch would’ve confused a buyer who's hearing this for the first time?”

Instead of:

“Did I do a good job handling objections?”

Try:

“Where in that call did I miss the shift in the buyer’s tone or intent?”

Instead of:

“How can I get better?”

Ask:

“What patterns in my questioning style are predictable or ineffective—and how are they costing me trust or control?”

These aren’t just smarter questions. They’re growth-oriented questions. They assume you’ve missed something—and they’re designed to find what that is.

Use your manager for feedback, not affirmation

If you're asking for feedback and it doesn’t sting a little, you’re probably not digging deep enough.

Great managers want to help—but they’re not mind-readers. The more specific and vulnerable your question, the better their answer will be. A few examples:

• “If you were in my shoes, what would you have asked differently when the buyer hesitated on pricing?”
• “Was there a moment in the call where I lost the buyer’s trust? What sign did I miss?”
• “What’s one habit I’ve developed that I probably can’t see—but you can?”

And when they give you something hard to hear? Don’t flinch. That’s the gold. That’s the stuff your competitors aren’t hearing—because they were too busy chasing praise.

Let AI challenge your thinking, not just assist it

Smart reps are also using AI—not just as notetakers or script generators—but as strategic thought partners.

Instead of prompting Tenali AI with:

“Summarize my last call.”

They ask:

“What objections did I leave unaddressed?”
“What did the buyer imply, but not say outright?”
“Where did I rely too heavily on product features instead of solving business problems?”

Use AI to test your hypotheses, challenge your assumptions, and run mental simulations of better conversations. Treat it like a sparring partner, not a secretary.

Discomfort = Progress

Here’s the mindset shift: Good reps want to be right. Great reps want to be better.

The first mindset seeks safety. The second seeks stretch. And yes, the second one is often uncomfortable—because it pokes at your ego, your habits, your blind spots. But that’s where the magic is.

Next time you wrap up a sales call, instead of walking away wondering if you did “well,” ask a sharper question.

Not because it feels good.
Because it works.

Real growth starts with better questions. If you're scared to ask your boss, here’s one to even ask Tenali AI, ChatGPT, Claude, Gemini:

What are the 5 ways I can ask better questions compared to the top 1% users on this platform? Help me identify the gaps.

Go ask it.

Book a demo today: https://calendly.com/aniket-tenali/30min?month=2025-05