3 Questions to Start an Online Conversation

You’ve just accepted a new LinkedIn Connection request. You’ve checked their profile before accepting because you want to make sure their connection will be beneficial to you and your network. All looks good.

And then . . .

You get it.

A LinkedIn message from them. Great! You open it wondering what it will say. Immediately you feel disappointment.

It’s a big, paragraphs long, mini-essay ALL ABOUT THEM.


There’s no sense in responding. They might not even read what you wrote. You just take your disappointment and move it to the side as you read the next message.

What you were just a part of is exactly like being introduced to someone at a party and they immediately start talking at you all about themselves – what they do, how they do it and how it can help you. All without having asked you a single question.

Then, to finish the “conversation”, they hand you their business card and tell you to call them if you need help. And then they simply walk away.

You shake your head a bit in shock, surprise, maybe even disappointment. You didn’t matter at all in this “exchange”.

When a new connection on LinkedIn sends you a big, long message and hasn’t engaged with you at all, it’s the digital equivalent of this same scenario.

It feels really crappy.

We’ve all had this done to us.

We might even have done this ourselves.


I’ll be the first to admit that digital conversations can be hard. Heck, so are in person conversations. They can be awkward and downright uncomfortable sometimes.

But they’re not impossible.

If you don’t know how to start a conversation with a new connection, try asking a question first. It’s a pretty safe bet.

Start with something like this:

How are you finding LinkedIn for growing your network?


How do you like LinkedIn for finding potential clients?

or even

How do you like LinkedIn?

You might notice from these examples that each of them has “LinkedIn” in it. That’s to find some common ground first. Given you’re connecting on LinkedIn, it’s easy to use the platform as common ground.

I got more than a 25% increase in responses when I started to open my conversations with new connections with a question about their experience with LinkedIn.

After a few weeks, I tried different opening questions to see if I could increase that rate. And, now, every few months, I test out a new question to see if I can increase that rate.


Pick a question that has that common ground element – whether it’s being on LinkedIn, where you live, the industry you’re in – anything that will establish some rapport.

And then ask it.

Try it out for a week or two and then switch it up.

Ask a new question.

See if you get more responses.

Keep trying new questions until you hit the one that people like to answer.

People want to connect. They want to network. They want to get to know new people. They want to grow their businesses.

Make it easy for them and for yourself.

Ask a question. Start a conversation. Then talk about business.

You’ll find people will engage with you more often and openly then when you spam them with your business offerings right from the start.


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