How to Master the Art of the Icebreaker and Make a Great First Impression Every Time
Relationships of all kinds are formed on common ground. Learn how to prepare for meeting your next new colleague, client, or mentor.
Ever find yourself stuck with a calendar that looks something like this week-in and week-out?
You’re not alone: One of the realities of building a startup is the seemingly-endless series of back-to-back-to-back meetings.
Now I’ve already covered two ways to reduce the pressure of back-to-back meetings, but the fact of the matter is you can’t eliminate meetings entirely.
And if that’s true — that meetings really aren’t going anywhere — you may as well make the most of them; because I still believe some of the game-changing opportunities you’ll encounter will come out of meetings.
Here’s the problem: So often, we end up so slammed with meetings that we walk in not entirely certain of who it is we’re meeting with. On a good day, maybe you remember their first name. But their background? If you’re anything like most people, probably not.
As a result, we end up walking into meetings and delivering an average-to-subpar experience where, at best, we kick things off with a, “Hey, great to meet you.” Not exactly memorable, and it certainly doesn’t make a great first impression.
Sound familiar? If so, read on — because this one’s for you.
The (Simple) Secret to a Great First Impression
The first few moments of a meeting — whether you’re meeting with someone for the first time or the 50th — are vital. They set the tone for the rest of the meeting.
The question is, how do you deliver a great experience?
The answer’s easier than you may think: All you’ve got to do is deliver something slightly above what’s expected — something personalized.
So instead of saying …
“Hey, great to meet you, I’m John.”
You might instead say something like,
“Hi Alex, it’s great to meet you. I’m John. Hey, totally random but did I hear right that you recently attended a 10-day mindfulness retreat? That’s one of my bucket-list items, and I’d love to hear about your experience!”
That’s using what I call an icebreaker sentence and preparing something like this only takes a few minutes of your time. Let me explain.
Breaking the Ice
An icebreaker sentence is an intriguing statement you prepare in advance of a meeting to start the interaction off in a strong way. It’s based on just a few short minutes of research done before a meeting, and helps deliver a great impression when you meet somebody new.
Let me give you an example:
Imagine you’re about to meet with Erin Roberts. In your pre-meeting research, you discover she’s been an entrepreneur for the last 15 years and, in addition to that, volunteers her time with Teach for America.
This resonates with you because you’re also an entrepreneur with a heart for volunteerism, so you might craft an Icebreaker Sentence that sounds something like this:
“Did I read correctly that you’ve done some work with Teach for America! I thought that was so cool — I often work with Reach Out & Read to promote literacy. What kind of work have you done with Teach for America?
When you drop that line, Erin lights up and says, “Yes, that’s right! I’ve worked with Teach for America for years, helping underprivileged students see what’s possible when they dream big and work hard.”
She goes on to explain how lucky she feels to be where she is and knows she wouldn’t have gotten here without help from others — so this volunteerism is how she gives back.
And just like that, you’ve got an immediate connection.
So what exactly happened here?
The Foundation of Every New Relationship
What happened is you found common ground, and common ground is the foundation of every new relationship. Common ground are shared interests, passions, and challenges that connect us to other people. And here’s why that’s so powerful:
When you establish common ground with someone, you cause them to think, “I am like you.” But here’s the thing: Studies have shown that our brain translates that thought to “I like you.”
Of course, an example like the one above may only happen only once for every 20 people you meet. But if you didn’t take the time to do that research, you’d have missed a huge opportunity.
The Do’s & Don’ts of Great Icebreaker Sentences
So the next question is, what makes a great Icebreaker Sentence? While some Icebreaker is often better than none, there are a few steps you can take to deliver an even better experience to the person you’reinteraction with.
Do: Your Research in Advance
Don’t rely solely on what limited information you may know about this person. Instead, spend 10–15 minutes (max) researching them.
And keep in mind, this doesn’t need to be heavy-duty research. Simply use publicly-available information by searching their name on Google, then peruse sites like …
- Facebook, Twitter, or Instagram to see what they’re talking about and what’s important to them.
- LinkedIn to better understand their professional background.
- Their blog (if they have one), for a better understanding of what matters most to them.
- Their company site, for information about the organization and their role within it.
And keep in mind: If you work with an assistant, you don’t have to run this process yourself. Simply have your assistant do the research for you, gather the information in an easy-to-reference profile (more on this later), and send it off to you for review.
Don’t: Use Absolutes
Just because you read something only doesn’t mean it’s true, up-to-date, or accurate. This is especially true when it comes to contacts with common, easily-misattributed names; and there’s few things more awkward than something like this …
You: Hey John, I’ve never met anyone with a Ph.D in both Philosophy and Electrical Engineering. How cool is that!? What inspired you to pursue that path?
John Smith: Oh, well, umm … I actually don’t. I’m not sure where you heard that, because I didn’t even go to college.
You: Oh, err, my mistake. Sorry. I must have, uh, heard wrong. But, hey, it’s, um, great to meet you anyway?
For this reason, I recommend you …
Avoid absolutes and always frame your Icebreaker Sentences as questions
For example, here’s a “safer” alternative to that same situation:
“Hey John, did I hear right that you have a Ph.D in both philosophy and electrical engineering?”
Then, if he answers yes, you can follow up with something like, “Wow, how cool is that!? What inspired you to pursue that path?” And because you phrased this as a question, you have a much less awkward “out,” should your research be wrong.
Do: Leverage Unique Interests
Let me give you a real-life example here.
A client of ours was recently performing their Icebreaker Research prior to a meeting, and noticed the other person consistently live-tweeted every episode of Game of Thrones.
And so, when they walked into the meeting, they said something to the effect of, “Hey Erin, this might be totally out there but … Is it true you never miss an episode of Game of Thrones?”
From the way I heard it, you should have seen the way her eyes lit up at that question. My client clearly hit the mark with this one, and laid a strong foundation for that relationship with a single, simple sentence.
All of that to say, keep an eye out for things that seem to be personally meaningful or passionate about; something about who they are as a person, not just a professional.
Don’t: Let the Conversation Veer Off Course
Icebreakers are a strong way to start any conversation, but they do come with one inherent risk: Derailing the conversation.
If you touch on something truly meaningful to the other person, it can easily turn into a lengthy discussion. And while that discussion is probably great for the relationship, that can come at the expense of business objectives.
If you’re meeting with someone, you probably have a goal you’re trying to accomplish in that meeting — and it’s important for both of you that you leave the meeting feeling accomplished, not just connected.
If you notice the conversation moving in the wrong direction, simply take back control of the conversation with a comment like …
“I really want to hear more about that, but I always want to respect your time. We’ve only got about 20 minutes left, and I know we both wanted to talk about [XYZ]. Let’s hash that out and, if we have time, circle back to this.”
Do: Leverage Their Background
If you can’t find much in terms of unique interests, then spend a little time digging into their background. Try to answer questions like …
- Where have they worked in the past?
- Have they had any interesting or unexpected career changes?
- Where have they lived?
With information like that, you can craft Icebreaker Sentences like …
- “Hey, did I read right that you spent some time in Dallas a few years back? I was actually grew up there! Did you ever make it out to Iron Cactus?”
- “It looks like you spent a lot of time working for various corporations before taking the plunge and founding your own company. Is that right? I’m curious: What inspired the shift?”
- “I noticed it looks like you worked for Snapchat before it became the phenomenon it is today. Is that right? What was it like back then?”
Don’t: Underestimate Common Ground
Whenever possible, base your Icebreaker Sentences in common ground, or shared interests. The reason for this is simple:
When we present common ground to someone, they immediately think, “I am like this person.” But because of the way our brains process language, that thought translates to, “I like this person.” And if you can get the person thinking they like you in the first few moments of a conversation, you’re already off to a strong start.
The most obvious form of common ground are shared interests, such as rooting for the same sports teams, engaging in the same hobbies, traveling to the same locations, or watching the same shows.
But that’s not the only place to find common ground. If nothing else, you can also leverage shared connections, and LikedIn is a great tool to find those connections.
Let’s say you couldn’t find any shared interests with someone, so you visit their LinkedIn profile and notice you’re both connected Amy Black. You could use this information to do one of two things:
Either reach out to Amy and ask her thoughts on the person you’re meeting, in which case you could start the conversation with an Icebreaker like, “Amy’s told me great things about you! She mentioned that you just finished a round of fundraising. Is that right? How’d it go?”
Or, if you’re unable to reach out to the shared connection, you could open with a somewhat weaker Icebreaker like, “Hey, I noticed we’re both connected to Amy Black on LinkedIn. I actually worked with her a few years back at Moogle. I’m curious: How do you know her?”
Supercharge Your First Impression with Icebreaker Profiles
One more quick tip for you before we wrap this up: Templatize this process by creating what I call Icebreaker Profiles. Now, ideally, this is a process you’d delegate to your assistant — as it can take up to 20 minutes per person — but the results can be powerful.
An Icebreaker Profile is simply mini profile that highlights the key information about whoever you’re meeting with.
Let me give you an example of what one might look like:
As you can see, I recommend using Evernote to create Icebreaker Profiles, so you can access and update them in real-time. As for the content itself, you can customize it based on your needs. But a standard Icebreaker Profile usually captures the following information (in this order):
- Company Website | This can usually be found on the LinkedIn page or with a Google search.
- Offering | A short description of the product or service they offer (usually found on the company website).
- Personal Information | The person’s name, location, and role within the organization.
- Icebreaker Recommendation | A strong opening statement you can use to kick off the meeting that shows you are genuinely interested and took the time to learn about the person you’re meeting.
- Photo | A picture of the person you’re meeting with (especially valuable if you’re meeting in public place, such as a café, and need to pick them out of a crowd).
- Social Links | LinkedIn, Twitter, Facebook, or a personal blog.
- Additional Info | 3–5 bullet points outlining interesting or unique information about the other person, both personal and professional.
Note: Don’t have an assistant, but still want these profiles? Check out Detective by Charlie, a powerful app that does the research for you, and creates a simple 1-page dossier, much like an Icebreaker Profile.
My Challenge to You: Break the Ice
Open your calendar, and take a look at the week ahead. Pick 2–3 meetings, and commit to creating Icebreaker Sentences in advance. Then — and this is the important part — actually use those Icebreaker Sentences as you kick off the meetings.
Although not every Icebreaker will lead to an unforgettable experience, I think you’ll see a noticeable difference in the tone of the meeting for those you use Icebreaker Sentences for.
And keep in mind: If you have an assistant, you don’t have to do this yourself! Simply send this blog post to your assistant, then delegate the task to them!