How do you start up a conversation that is engaging and memorable so that the stranger you just met becomes a promising lead for your business?

For those of us who are introverts and tend to be socially awkward, the prospect of meeting with strangers coupled with the pressure of selling and being judged can seem intimidating. But it’s time to get over that fear and realize that having a conversation with another human being really isn’t the daunting task it seems. F.E.A.R. (False Expectations Appearing Real)

On the other hand, if you’re confident in social situations then you need to guard against dominating the conversation and talking too much. Essentially a fruitful business conversation requires the right balance between talking and listening. Too much of either can be counter-productive.

Don’t be fazed by awkward interactions. Sometimes, luck just won’t go your way and you may find the other party unresponsive. Know when to give up and move on to the next prospect. But don’t stop initiating conversation. That gives you some amount of control over the topic and flow of dialogue.

Here are some tips to break the ice with prospects for a better business conversation.

1. Do the background research

For a first-time meeting with a prospect, make sure you’ve done your homework on the firm and related news so that you can walk into the meeting prepared and with confidence. A prospect is sure to be impressed with your knowledge of his business and his needs.

If you are attending a conference, then have a look at who else has registered for the same and do some quick research in advance. Follow all the news related to the conference. These pieces of information will give you the necessary context to easily start up and carry on a dialogue.

If you remember some related news or information you read on LinkedIn or any other social media platform, this could be a great icebreaker to start a conversation. Or in the case of meeting at an event, talking about the forum itself could spark off an interesting discussion.

Winging it isn’t going to be of much help, so if you come across a person whose business you genuinely know nothing about then don’t pretend. Instead, ask some insightful questions to understand their business better.

2. Show interest and listen

Show interest in the other person by asking a lot of open-ended questions. This usually invites a better response than a mere ‘yes’ or ‘no’ question would. It also allows the prospect to reveal information that lets you know your potential customer better. This is immensely helpful in letting you anticipate needs and providing better customer service down the line.

Asking open-ended questions and then follow-up questions will keep the conversation going without those awkward pauses and enable you to build a rapport with your business prospect. This tactic also enables you to draw out the quieter ones who may need a gentle nudge to open up.

But you shouldn’t have to feign interest. Actively listening to what your prospect has to say gives you great opportunities to learn and use the knowledge gained to enhance your sales.

So don’t try to be the star of the conversation. Let your prospect do the talking while making an impression as a good listener. But that doesn’t mean you stay totally silent. Add brief comments and words of appreciation or assent in response to what the other person is saying as a way of encouraging them to carry on.

3. Share your own views and stories

The conversation is not a one-way street. So while being a good listener is important, you need to share your own views and beliefs and contribute to the conversation otherwise you just run the risk of appearing to not have any opinions!

Do respond occasionally to what the other person is saying with comments, observations and suggestions. Since you are likely to be talking of subjects that are familiar to both, this shouldn’t be hard to do. Just remember to keep your responses brief and to the point so that you don’t monopolize the conversation.

Offer insights and solutions based on your understanding of the prospect’s business. Try not to make an overt sales pitch but focus on case studies and stories that would show your own business solutions in a better light.

4. Keep the conversation focused

Finding some common ground on the personal front may be a great way to break the ice and get the conversation flowing, but always remember that this is a business setting and that there is an agenda.

So while you may find great bonding ground over your common love for dogs or baseball, keep 3-4 agenda points in mind and always get the conversation back on track to those. Keep the interaction as professional as possible while allowing for some off-topic exchanges to strengthen rapport.

You want to be remembered as ‘that person who had some really great insights about the business’ not as ‘that person that supports the Mets over the Yankees’. So stay on point.

Play the Beginner. You can in some cases ask to be educated on a topic the prospect brings up. People naturally like to help others learn and understand. Even more they like to show off their expertise. Allowing a prospect to do this ingratiates you to them.

5. Maintain a positive and respectful attitude

It’s probably easier to bond over misfortune or failure but for a productive business conversation, it is far wiser to share positive stories and stay focused on future possibilities. Keep the tone of the conversation positive. Instead of discussing problems, talk about solutions, innovations, and changes that could improve the prospect’s business.

Also, don’t get drawn into arguments. Respect the other person’s opinion even if you disagree and change the subject for a more fruitful discussion. Interspersing the business conversation with non-business topics is great to keep things interesting but avoid bringing up any controversial subjects.


You don’t have to know everything but at least be knowledgeable about developments in your own field so that you always have something to contribute to the conversation. Stay updated on the latest news and trends in your line of business.

Managing customer relationships requires networking skills. So apply the tips and tricks we’ve outlined for you and initiate productive business conversations with your prospective customers.

Talk about food and/or drink, sports, local new events etc.

Ask about their weekend hobbies, food or drink

Keep your eyes peeled for visual clues but not the obvious or mundane (family photos etc.) Every other sales rep will do that. Be different.

Then move to the pain point questions