How to start a good conversation with anyone


Have you mastered the art of starting an interesting conversation with anyone, anywhere, anytime? It’s one of the best life skills to have, as it can open doors in your career and help you navigate any social situation with grace.

“Being able to start and maintain a conversation is important in any setting because it gives you the ability to ‘drive’ the conversation in an effective way for all parties involved. If you’re always at the mercy of someone else’s questions or comments you’ll likely feel like networking is a waste of time,” says networking coach and consultant Alyce Blum.

If the thought of approaching a stranger seems intimidating, fear not. There are tips and tricks that can help you overcome your shyness and fight conversation lulls — regardless of whether you’re an introvert or extrovert. “The truth is that those who self-identify or who have been labeled as introverted have many innate skills that when properly utilized can yield a high RON (return on networking),” says Blum. According to her, introverts tend to be great listeners, generally prepare for meetings beforehand and are detail-oriented, so when it comes to following up with contacts they can reference specifics from past interactions.

“When it comes to starting a conversation introverts might shy away from taking the lead but if they can have a few prepared questions and remind themselves that they too ‘belong in the room’, they will excel once the first few awkward seconds pass.”

Here are four ways you can become amazing at starting conversations — and actually enjoy it.

Arm yourself with conversation openers

“Let’s be honest, most people dislike their work so the worst question we can lead with to start a conversation is ‘What do you do?’” says Blum, who suggests the following openers instead:

  • What brought you to the event today/tonight?
  • What drives you to do the work you do?
  • If there was one person I could introduce you to who would it be and why?
  • What was the best thing you did last summer/over the winter holiday?

Don’t be afraid to veer off the professional track, as we are multifaceted beings with vast experiences and interests. “When we lead with a question that enables someone to be human and not just focus on their professional title or role, it sets the foundation for common ground and trust. In doing so you’ll see that starting a conversation isn’t as bad as you think.”

Ditch boring questions

Blume recommends thinking of the most exciting question someone has ever asked you in a professional or personal setting and using it the next time you’re ready to start a meaningful conversation. Chances are, they didn’t ask you what you do or start by talking about the weather.

“You can choose to ask and answer the same questions over and over and wonder why you’re not seeing any results, or you can be courageous and start asking thought-provoking, out-of-the-box questions that encourage others to share parts of their stories, experiences, and lessons learned.”

Find a networking buddy

Having a networking buddy is not about pairing up to go to an event so that you can rely on each other in case things feel awkward and nobody ends up talking to you. To get the most out of a  buddy system, Blum recommends a networking hack from a Fairygodboss article: Promoting each other’s accomplishments in conversations.

If you tend to be humble or nervous, you might not feel comfortable self-promoting and boasting about your skills and services in a fresh conversation. Your buddy can take care of that for you, and vice-versa. And yes, there is comfort in having a familiar face you can trust in a sea of strangers — just don’t use it as an excuse not to break the ice with new people.

Change your mindset

“Strategic networking isn’t about collecting hundreds of business cards and then feeling badly about yourself when you don’t follow up with anyone. It’s about coming into any conversation with the mindset of, ‘How can I help you?’ instead of ‘What am I going to gain from this person/conversation?’” says Blum.

She recommends taking the pressure to perform off yourself and starting to use conversations as opportunities to make introductions on behalf of others or be a sounding board for others. And remember: everyone has a powerful story to share, including yourself.

More From Ladders