A CMO I’ve trained for years reached out to me last week with a question:
How do you break into an existing group of friends?
While traveling through Europe with 17 people, they found themselves on the outside looking in.
The challenge wasn't that anyone was unfriendly.
It was that conversations were filled with inside jokes and years of shared history.
Every time an opening appeared, someone else jumped in before they could build on the conversation.
By the end of the trip, they felt they'd missed opportunities to develop relationships.
After our call, they suggested I turn the experience into a newsletter.
So this week's newsletter is about becoming part of the conversation without forcing your way into it.
We will cover:
Impression Management
For most of us, the instinct when we feel left out is to do more: talk more or tell another story.
Ironically, that's often what makes joining a group more difficult.
Psychologists call this impression management: our attempt to shape how other people see us.
The problem is that people often sense when the effort feels forced.
Instead of appearing confident, we can come across as desperate or overly eager.
This week's tips are about doing less so that it creates space for people to become curious about you.
This Week's Tip: Find, Stay, Match
1. Find your ally
When we walk into an established group, it's easy to think we have to win everyone over.
We don't.
The fastest way into a group is usually through one relationship.
It might be the person you're seated next to, the one standing beside you, or simply someone you naturally click with.
On the reality tv show Survivor, you'd call this your alliance ;).
Once you genuinely connect with this person, you're no longer an outsider.
That person starts introducing you and creating opportunities for others to get to know you too.
If it doesn’t happen, try again with someone else! Chemistry can't be manufactured, and that's okay.
How to do this in practice: Don't scan the room for the most important person. Look for the easiest conversation. That's often where your first connection begins.
2. Stay curious longer
Inside jokes and old memories make everyone else feel invisible.
Resist the urge to jump in with your own story.
Rather than trying to redirect the conversation, become curious about it.
People are far more likely to include someone who appreciates their stories than someone who competes with them.
How to do this in practice: Instead of saying, "That reminds me..." ask, "It sounds like more happened. What's the full story?"
If this was forwarded to you and you'd like communication tips (and one bad joke) every week
3. Match their energy
One of the most important lessons I teach all my clients, no matter what communication challenge they bring to me, is the importance of matching energy.
You don't need to have lived the same experience to connect with someone.
But when you match the emotional tone of what they're saying, connection comes much more naturally.
If someone is telling a meaningful story about people you don't know, don't tune out. Stay with it! Laugh if it's funny. Be curious if it's surprising.
How to do this in practice: During your next group conversation, pay attention to how the speaker wants everyone to feel. Then respond to that feeling instead of searching for your own example.
This Week’s Funny
If you're learning from these newsletters, your team will too. Forward this to them!
Interested in working together or sponsoring this newsletter? Email me at [email protected].
Now for your funny:

HR and IT need to work as one. Here's how
Every missed onboarding step, delayed offboard, or broken provisioning handoff has a root cause: HR and IT aren't aligned. This guide gives both teams a shared framework for the full employee lifecycle.




