Wheel of Business Development

Stalled deals often have a common cause.

(And it’s easier to fix than you think.)

You didn’t ask the one thing they needed to hear.

Most client-facing professionals mean well.

But in conversations, good intent isn’t enough.

What matters is asking the right questions.

The kind that uncover what actually moves the work forward.

Having coached 50,000+ professionals through this exact challenge, I’ve learned something crucial.

Questions are a business developer’s greatest tool.

They move relationships forward when everything else stalls.

They uncover challenges no deck could reveal.

They open doors that presentations can’t.

They build trust faster than any credential.

Here are 20 smart questions to ask your clients, organized into 4 categories:

Building Trust
✅ What prompted you to take this meeting today?
✅ Who else should I connect with to help you best?
✅ What do you wish outside partners asked more often?
✅ What makes a partnership feel effortless on your side?
✅ What’s a priority for you right now that’s not getting enough attention?

Uncovering Challenges
✅ What feels harder than it should right now?
✅ What’s one risk you’re trying to avoid this time?
✅ What’s a past initiative that didn’t work out, and why?
✅ Which internal hurdles usually slow things down for you?
✅ What might others push back on if we move this forward?

Advancing the Work
✅ What outcome would help you justify moving ahead?
✅ What would make it easy for others to say yes to this?
✅ In your view, when would be the right time to get started?
✅ What does early success look like for you and your team?
✅ What’s your typical process for making a decision like this?

Strengthening the Relationship
✅ How can I stay helpful without being intrusive?
✅ What kind of value feels most helpful to you right now?
✅ What’s changed for you or your team since we last spoke?
✅ What’s something you’re excited about, inside or outside work?
✅ Which relationships or projects are most energizing for you lately?

I always tell my coaching clients:

Don’t rush the pitch.

Slow down.

Ask better questions.

And listen.

I mean, really listen to what they are telling you.

Because real relationships and real results start with a question that makes someone feel seen.

Try one of these in your next client conversation.

Listen for what surprises you.