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How to master icebreaker conversation starters for sales outreach

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Author photo: Katrina Oko-Odoi

Katrina Oko-Odoi

Content Marketing Manager

Coming up with creative sales outreach strategies is one thing — but knowing how to break the ice with potential prospects is a whole other beast.

Because doing sales outreach isn’t about rushing to your pitch. Effective outreach is all about trying to build a genuine connection where a prospect feels comfortable enough to engage and hear what you have to say.

Which means, that first call, email or conversation shouldn’t start with, “Hey! Do you want to buy my product?” Instead, a successful prospecting chat usually starts with some open-ended conversation starters to help people feel more comfortable and connected with you.

When used strategically, business conversation starters “break the ice” and encourage the conversation to continue.

It may sound pretty easy, but coming up with icebreaker conversation starters that aren’t awkward isn’t always as straightforward as you’d think. As with many other things in life, getting started is the hardest part.

Here are 9 business conversation starters for in-person events, phone calls and emails — so you know exactly what to say next time you need to get people talking.

3 conversation starters for work events

Networking and work events are terrific places to build connections and expand your contacts. The thing is, it involves being comfortable walking up to someone and starting a conversation out of the blue.

But with some go-to conversation starters up for your sleeve, work events will be much more manageable.

1. Venue-specific conversation starters

Events generally take place in a venue, and those venues present tons of excellent ice breaking opportunities, like:

  • “Does it feel cold (or hot) in here to you? I’m freezing!”
  • “Have you tried the [food or drink item]? I can’t stop eating them!”
  • “Can you get a wi-fi signal in here? I’m struggling to connect.”
  • “This venue is gorgeous, isn’t it? Have you been here before?”

When in doubt, look around for something in the immediate vicinity to talk about. It doesn’t have to be anything complicated; keep it simple when getting the conversation started.

2. Share a genuine compliment

A sincere compliment can go a long way in quickly building rapport. Make sure you mean it, though, because if it feels phony, it won’t land well. Then, follow up the compliment with a question, for example:

  • “I love your bag! Where’d you get it?”
  • “Your speech was incredible. How in the world did you memorize it?”
  • “I love that shirt. What do you call that pattern again?”

Be ready to keep the conversation moving with follow-up questions or stories, too.

3. Information about what they’re doing at the event

Asking simple questions about why someone is at an event is an easy way to get some chatter going. Try go-to icebreakers like,

  • “What brings you here?”
  • “Do you know anyone else at the conference?”
  • “So, what do you do?”

Sure, these are pretty standard icebreakers for events, but they’re popular for a reason. They can easily take you from talking about why someone’s at the conference to what they do when they aren’t networking.

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3 icebreakers to start a conversation on a phone call

Doing a bit of research before reaching out to a prospect over the phone goes a long way. You’ll not only be more prepared for the call, but you’ll gain insight and fodder for potential icebreaker conversation topics.

1. Location-based conversation starters

Since you’ve already done your research, you likely know where your prospect lives, giving you tons of ideas for conversations starters, like:

  • “What’s the weather like there?”
  • “I see you live in [Location]. I’ve always wanted to visit there. Is it as amazing as it seems?”
  • “I see you live in [Location]. I’ve never even heard of that town! How close is it to [Recognizable Location]?”
  • “Okay, so the only thing I know about [Location] is [fact]. Is that true?”

This line of conversation is a low-stress way to get people talking and usually opens up many other avenues of discussion.

2. Trending topics

When you don’t know what to say, you can always turn to trending pop culture topics or (lighthearted) news. Of course, steer away from politics (unless it’s appropriate). Some examples include:

  • “Have you heard the song Lizzo released this morning? I can’t stop singing it!”
  • “Did you see the heatwave happening back East? It’s pretty crazy weather for November.”
  • “Did you watch the football game last night?”

There are countless ways to use trending topics as conversation starters. Bring up things that are likely relevant to your prospect, and be sure to stay appropriate and steer away from anything too serious or controversial.

3. Questions about work

If you want to stay super professional, stick with icebreakers related to your prospect’s job and role, including things like,

  • “So, what do you do at [company name]?”
  • “How long have you worked in your current role?”
  • “How’d you get into the industry?”

Let the person talk, and ask follow-up questions to keep the conversation going.

3 open-ended conversation starters for emails

Getting a conversation started through email is a little trickier than doing so in-person or on the phone; while you can’t ignore a person in front of you, you can trash an email without any social awkwardness. Here are a few ways to break the ice in emails:

1. Include a funny joke

When it feels appropriate, consider including a funny joke in your email. There’s a couple of ways to use a joke as a conversation starter. For example, you can include a question/answer joke and wait until they respond.

  • “What’s a marketer’s favorite type of cake? Hit reply and let me know your answer!” (wait until they respond to let them know it’s “Funnel”)

You can also share a visual joke that garners a response, like this one from Jonny Sun on Twitter:

Then say something like, “I can’t wait to see which greeting type fits you in your response!”

You can also tell a joke and ask for feedback on it. For example,

  • “[Joke]. Okay, be honest. Was that joke funny, or should I trash it — because I’m getting some mixed feedback over here?”

When you use jokes, it’s all about making the conversation a little less stiff. But they aren’t appropriate for every environment; use your discretion when incorporating funny or witty conversation starters. And, we shouldn’t even have to say it but … no dirty jokes and no mom jokes. In fact, just nix those from your personal convos too while you’re at it.

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2. Ask an unrelated question

Instead of keeping your email buttoned-up, you can also ask for requests or unrelated questions to spark conversation, like:

  • “I’m trying to settle a debate; is your team a Mac or PC shop?”
  • “Do you know my colleague [name]? I think you might have gone to school with them.”
  • “As a web data expert, I’d love your opinion on Google Analytics 4. Have you switched over yet?”

You can get creative with these. As with other types of email conversation starters, the goal is prompting them to reply or getting them interested enough to continue engaging with you.

3. End the email with a question

Okay, this isn’t quite a conversation starter, but it’s a good tactic for eliciting a reply from a prospect. Ask a question related to the email or future follow-up, for example:

  • “Is this something you’re interested in?”
  • “Are you open to chatting about this?”
  • “What time could we video chat so I can demo this solution for you?”
  • “Am I barking up the wrong tree here?”

This approach is also a quick way to gauge interest. If you get a response, you’ll immediately know that a lead is interested in engaging — giving you more opportunities to build rapport.

Get comfortable being the icebreaker to build connections

Inside or outside the office, in-person or online, starting a conversation can feel uncomfortable. But if you want to improve your sales outreach and build genuine connections with your prospects, it’s well worth mastering the art of open-ended conversation starters and getting comfortable with being the icebreaker.

At Copper, we’re passionate about helping our customers build lasting relationships with their prospects, so you can go from breaking the ice to building brand champions for life. Try us free for 14 days.

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