Questions Every Sales Leader Should be Asking

mmckenzie@claridastrategies.com (Maricela McKenzie) — Tue, 30 Jun 2026 04:21:01 GMT

"We're going to have a great quarter."

I've heard that sentence more times than I can count.

I remember sitting in a conference room during our monthly pipeline review. Opportunity after opportunity was discussed. Everyone knew the deals and everyone sounded optimistic. Then we got to forecasting:

"We'll probably close this one next month."

"This one is waiting on procurement."

"They're still interested..."

As I listened, I realized we weren't really reviewing the pipeline. We were reviewing what happened since the last meeting. Every update sounded reasonable and every opportunity still felt alive. But I found myself asking, "Do I have any more confidence that this deal will close than I did last month?"

The answer was no.

There was plenty of activity, but not enough information to know whether the opportunity was actually progressing. So I changed the way I ran these meetings.

Instead of asking for updates, I started asking questions that uncovered what we didn't know. Was the customer actually committed? Who still needed to say yes? What was the next milestone that would tell us this deal was moving forward? If we lost this opportunity today, why would we lose it?

Those conversations changed everything.

Great pipeline reviews don't just tell you where a deal is. They help you understand whether it's moving.

Here are two questions that consistently led to better conversations:

"Looking at this opportuity, can we clearly articulate the buyer's specific problem and the impact it's having on their business?

If the answer is vague, there's a good chance the opportunity hasn't been qualified deeply enough. Deals like this often linger in the pipeline because the customer doesn't yet see enough urgency to act.

"For our top 5 most important opportunities, what's the single biggest obstacle preventing us from closing this month, and what's our exact plan to remove it?"

This question quickly exposes whether a deal has a realistic path forward or whether it's simply occupying space in the forecast. It also shifts the conversation from reporting activity to creating action.

These are just two of the questions I use during pipeline reviews. Small changes like these can dramatically improve the quality of your meetings, your forecasts, and ultimately your sales results.

Every company sells differently. That's why the questions your team asks should reflect your customers, your sales process, and the decisions your buyers need to make. That's what we build together through the SCALE framework, because great ideas aren't enough.

Clear Steps. Stronger Sales.

Clarida Strategies LLC blog

Questions Every Sales Leader Should be Asking