Ask These Questions in Your First Conversation to Really Get to Know Someone

As a business leader, one of the highest-leverage ways to accelerate your growth, knowledge, and meet new potential business connections is through networking. Meeting others offers up the chance to learn about new topics, gain unique perspectives — and can even lead to future business partners.

This growth can materialize by meeting people through intros, at events, or even by sending cold emails and LinkedIn messages. Scoring that first call or meeting with someone is just the first step, though. Building strong relationships with new people is a skill that takes serious thought and practice.

Without being able to drive a productive conversation your efforts will be severely hindered. It can actually do you more harm than good if you have a poor or boring conversation skill set. Therefore, it’s key to develop your interpersonal skills. Fortunately, this is something you can get better at through practice and preparation.

To really get to know someone and establish meaningful business connections, ask these questions the first time you meet:

“What are your interests and passions?”

When you ask about another’s interests — conversations will flow easily. People love talking about their passions, and they tend to appreciate anyone who will listen. Don’t just ask the baseline “what are you passionate about?” Dive deeper by asking the “why’s, the how’s,” and following up on specific details.

You can gain significant knowledge about someone through their interests, and more easily relate to them. I look for shared interests — which helps accelerate how fast you get to know and understand one another.

More importantly, by learning about someone’s interests and passions — you have an immediate route to add value to them and deepen your relationship moving forward. If they love cars, for example, you can send them articles or podcasts about cars. You can also connect them with others in your network that share the same interests.

You will know you’ve made a true connection when you ask something and they respond back to you. Let your conversations move forward naturally.

“What’s the biggest roadblock you’re facing over the next 6 months?”

Understanding someone’s biggest challenge in the coming months shows you what they’re going to be focused on. This information may reveal a useful way you can help them.

If someone says their biggest challenge is raising money for their business, for example, you could connect them to investors you know.

Asking about their biggest challenge gets them to open up and reflect. Some people do not have an immediate answer to questions. Bringing up questions that make another person think is an effective way to get to know them and have a deeper, meaningful conversation.

“What are your most proud accomplishments and experiences?”

Although LinkedIn and people’s online personal brands touch on their past experiences, these tend to just offer brief glimpses.

Diving deeper into someone’s past experiences will shed new light into various aspects about each person. Exchanges will help you understand what they have worked on in the past and where their skills lie. Having this knowledge will teach you when they might be able to help you or you can help them.

Conversations give you a chance to hear about who they have worked with and about any particularly noteworthy experiences/stories. There tends to be valuable knowledge in other’s past formative experiences.

For example, I was recently chatting with someone who was young and listed as a “partner” in his company on LinkedIn. I assumed he was a mid-level employee. After talking, and inquiring into his projects — I realized he had worked closely with the CEO of their company and had worked with a variety of exciting companies in partnerships.

This taught me much more about him — and helped create more meaningful conversation as we talked about projects he put significant energy into.

“How do you spend the majority of your time?”

Figuring out how someone has been spending their time and what they have been thinking about gives you a deep glimpse into what their current priorities are. Ask these questions again in a few months time to see what progress they’ve made and what they learned.

Be thoughtful and curious.

Overall, when you meet new people and expect to ask these questions, go into conversations being thoughtful and curious. Pay attention to what they seem excited about. Ask questions — like those mentioned above — and you’ll find that you have made a connection. If this person is one of the lucky ones —  someone you’ve really gotten to know — this person may even have become — a friend.