How to Start a Conversation: 3 Scenarios to Help get Real, Impactful, and Better Relationships


I recently put out my 38th course on Pluralsight: Becoming a Better Communicator. I was asked an interesting question by one of the people who got early access to this course… I’ll edit the question a little:

What if I don’t know how to start a conversation? Do you have any tips for someone who is shy like me?

This reminds me of someone in one of my audiences who asked, how do you network? What do you say when you first go up to someone?

I know this can be debilitating. How to start a conversation can leave you weak in the knees and anxious to leave early.

figuring out how to start a conversation can be scary

The person who asked for tips for shy people to start conversations then gave me three scenarios:

  1. Talking to strangers
  2. Friends who I haven’t seen for a long time ( I Am pretty shy and cant hold long eye contacts)
  3. People who I just met.

I have two answers for just about any situation… these might sound cheeky but I don’t mean them to. It’s just a lot more simple than people think. After I share these two answers I’ll share specific ideas for each of those scenarios.

My first two general answers are:

First, just say anything. Yes, you might mess this up. Yes, you might sound like a dork. But you’ll never know unless you say something. I’ll give ideas down below but the point here is you won’t start a conversation if you don’t say anything.

Second, practice. If you want to get better at this, get uncomfortable and do step one multiple times. Do it when you are really embarrased, or feeling shy. Nothing super bad is going to happen to you… so you might as well practice. I’ve found people are generally happy to have someone else start a conversation, or say hi. Don’t think they are going to punch you in the face just for saying hi or asking how they are.

So, say something and then practice over time. That’s it. That is my general advice.

Now, to the specific scenarios:

How to Start a Conversation with Strangers

Ah, the ol’ networking question. Whether you are at a networking event or not, I imagine you can find something you might have in common with the other person. If you are at a networking even for, say, project managers, you know you can talk about anything project management. If you are at a networking event with marketers, programmers, etc., you should have an idea of what you might be able to talk about.

Usually you’ll find something you might have in common that you can talk about. If there’s nothing, you can talk about something as mundane and cliche as the weather. Just don’t dwell on that.

I’d recommend simple questions like:

  • “What did you think about the speaker?”
  • “Have you been to this networking event before?”
  • “How long have you been a project manager? What did you do before that?”

These are simple “ice breakers.” They focus on the other person, and their interests and experiences. I definitely recommend How to Win Friends and Influence People… a classic and a must-read to help you with these types of questions. There are a billion questions like this, you can find them from a simple online search.

One thing you might want to do is practice some of these questions before you go. This might sound silly to some of you but if you are nervous about this, practice asking the question. Get some muscle memory on these questions.

How to Start a Conversation with Friends You Haven’t Seen for a While

Great question! I’m thinking about people you went to school with, or people you worked with a few companies ago. You can either try the “catch up” line of questions, like, “what have you done since you left school (or, XYZ company)?”

You can try the “have you heard from” question: “Any idea what ever happened to Jeff?” Or, I’ve heard from Sarah over the last couple of years, she seems to be doing really well!”

These questions are geared towards connecting based on something you both had in common, and perhaps are both interested in. Just realize that sometimes the other person you are talking about might have meant more to you than to them… Or, they had bad memories or not-as-impactful memories from those shared experiences.

Another idea is to simply ask about them: “What have you been up to these last few years?” You can ask about their professional life, like where they have worked, what jobs they have had, etc. You can ask about their personal life… just be tactful and respectful. Watch for cues of not wanting to go into certain areas.

Hey, guess what? I have a book recommendation for you: How to Win Friends and Influence People. Sound familiar? Look a few lines up and you’ll see it there. Dale Carnegie goes into a lot of this in this book. It’s not just a formula for how to start a conversation, it’s way of thinking. It’s a shifting in attitude about you, others, conversations, etc. And, it’s a fun and an interesting read.

How to Start a Conversation with People You Just Met

This third scenario is similar to the first one but I’ll add a change: let’s say this is either deeper into the conversation, or it’s the second+ conversation with someone you may have met at last month’s network meeting. Perhaps the first advice I have on how to start a conversation with this person is to avoid overthinking why they aren’t starting a conversation with you! Don’t worry about it, don’t assume they hate you, or find your horribly boring.

Stop the assumptions. 

Just go up to them and ask them a question. You’ve already done the ice breaker questions… where do you work, how long have you been a project manager, etc. So don’t do that again. Having those same conversations will likely make them think you don’t remember them, you weren’t paying attention last time, you don’t care, etc.

If you are in a heavy networking mode, whatever that means for you, this can get a little tricky remembering who you talked to, when, what you talked about, what you need to follow up on, etc. That’s what JibberJobber helps you keep track of. More than a place to store phone numbers and email addresses, JibberJobber allows you to take notes on what happened, where your relationship is at, and what you need to do next (action items).

So go to the next level. Maybe you say, “Last time we talked you said you were working on a big deadline. Was that for this last month? How did it go?”

This shows you paid attention and cared enough to remember what you talked about last time.

Maybe you say, “Last month we talked about the project management challenges you are going to address in your company this year. I’d love to learn more about what you are thinking, and some of your solutions!”

Notice that so far, in this whole blog post, you are asking about them, their interests, what they are doing, etc. At no point have I suggested you talk about you.

Seem unfair? Don’t even worry about it. There might be a natural point in the conversation where you share what you are doing… but refer back to the book I’ve already recommended twice. Dale talks about the power of making others feel important. You do this by talking about them. If the relationship progresses, the conversation will progress. But if you want to start these conversations, focus on them. The alternative is to say something like:

“Hi, I’m Jason. I work at this place, on these projects. Me, me, me, me. Isn’t that interesting?”

It could be interesting, but I’m not going to suggest that approach.

One more idea on how to start a conversation with anyone:


Sounds obvious. Sounds basic. It is both. But too often we’re more concerned with how we look, or what they will think about us, that we don’t reserve enough space to care about them, and what they have to say. I’m fascinated by people… where they came from, why they are the way they are, where they want to go, what they care about, what they think about, what concerns them, etc.

When you actually care about what they have to say it is much easier, and more natural, to start a real, engaging conversation with others.

Good luck! Go back to my basic answers: try something (anything), and practice!


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