10 Questions To Win A Second Meeting
A good question can change the conversation.
A great one can change the relationship.
Here’s the truth: no single question guarantees a second meeting.
But the right one, asked with genuine curiosity, can move things forward.
It can shift the conversation from surface level to meaningful. It can turn a polite chat into a real partnership.
When you ask questions that help clients think, reflect, or see something in a new way, you earn the right to stay in the room.
You become more than a service provider. You become a trusted thought partner.
That’s the power of curiosity.
10 Questions That Win a Second Meeting
Here are ten questions that consistently open doors and deepen relationships.
- What’s your team doing really well right now?
- What’s a challenge you’d love to solve?
- What trend are you watching in your industry?
- What do you wish you had more time to focus on?
- What’s changed in your industry recently?
- What would make this year a big win for you?
- What insight surprised you in a recent project?
- What’s your most demanding client asking for?
- What skill would unlock your next level of growth?
- What’s something you’ve been meaning to explore but haven’t yet?
Think of these as your go-to curiosity builders.
They work especially well when you want to dig deeper after someone mentions a challenge, wrap up a meeting with a meaningful next step, or move a conversation from small talk to something that matters.
They’re also helpful when a discussion stalls. A well-timed question can bring new energy into the room and show that you’re truly listening.
The Real Magic Is in the Follow-Up
The question is only the start.
The follow-up is where the real progress happens.
If someone shares a challenge, offer a helpful introduction to someone who can assist.
If they mention a goal, send an article, tool, or idea that can move them closer to it.
If they talk about a skill gap or opportunity, propose a way you could help fill it.
Those small, thoughtful gestures show that you’re paying attention. They turn curiosity into value.
That’s what builds trust.
And over time, that trust leads to second meetings, deeper partnerships, and long-term results.
Ask with Intention. Follow Up with Generosity.
Business development isn’t about clever pitches or perfect timing. It’s about staying curious.
Every conversation is a chance to learn more about what matters most to your clients. When you lead with curiosity and follow up with generosity, you stand out.
Because people remember the ones who listen.
They remember the ones who ask thoughtful questions.
And they especially remember the ones who show up with help.
So before your next meeting, take a moment to look at these ten questions.
Choose one or two that fit the situation.
Then, when the time comes, ask with genuine curiosity and listen fully to the answer.
Because great relationships don’t grow just when someone buys from you.
They grow from caring enough to ask.
Mo
P.S. Curiosity starts conversations and GrowBIG AI helps you take them deeper, by suggesting smart, tailored questions and follow-ups for every client meeting.