Dear CEO —
I could’ve died when I attempted to mingle at a networking happy hour recently.
I’m a 30-ish customer success manager for a sports equipment company, and I feel stuck.
I can’t seem to get promoted, and I think the reason is that I stink at small talk and mingling.
I recently made a lame joke at our happy hour about how you can “pick your nose, but not your family.” I was met with slight smiles and dead silence.
The truth is that I’m a huge introvert, plus I’m just plain awkward.
I think this holds me back from making good connections and relating to my current bosses.
I’ve thought about looking outside the company for other opportunities but, I’m worried that I really don’t have much of a network to rely on and that I would just flounder in the world of anonymous applications.
I’m frustrated, and I’m wondering if you have any advice for me. How do I get unstuck?
— Ray G, New York, NY
Dear Ray —
Your problem is a lot more common than you may realize. The gift of gab wasn’t bestowed upon all of us. And while some people are natural networkers who love meeting new people, it’s a burdensome chore for others.
I can tell you that small talk didn’t come naturally at first to me, either. But the good news is that you can get better at it. And it will make you a better networker, too.
Here are the three things I’ll ask you to do:
Develop a set of conversation starters.
Do more listening —less talking.
Find common ground /interest that allow you to relate to the person as much as you can. (Hint: Your starter conversations can help with this.)
Do those things, and you will improve.
Being introverted doesn’t mean being awkward. Unless you feel it’s time to quit your job, try these on your current bosses to see what happens. (Then try the “20 Questions” interview form with them.) And absolutely use these networking skills on people already in your network and new contacts you hope to have.
Conversation Starters To Riff-Off:
Like with many things, getting started is sometimes the hardest part. So, let’s dig into some good conversation starters for a setting like a networking event, dinner with clients, or a conference.
The straight-forward Introduction: Start with a simple self-introduction, mentioning your name and your role or the organization you’re affiliated with. “Hi, I’m [Name], and I work with [Company/Department]. How about you?”
Give a Compliment: A sincere compliment can be a great icebreaker. “I loved the presentation you gave earlier. Could you tell me more about that project?”
Comment on the Event or Setting: “This is my first time at this conference. Have you been here before?” Or: “These events always have such interesting speakers. Is there anyone in particular you’re looking forward to hearing from?”
Ask About Their Role or Organization: “What do you do at [Company]? I’ve always been curious about the kind of projects you handle.” Or: “How long have you been with your current organization?”
Bring up industry News or Trends: “Have you been following the recent developments in [specific industry topic]? I’d love to hear your take on it.” Or: “There’s been a lot of talk about [recent industry innovation]. How do you see it impacting our field?”
Work-related Experiences: “How’s your experience been so far with this event/conference/workshop?” Or: “Any key takeaways from the sessions you’ve attended today?”
Seek Recommendations: “I’m always looking for good industry-related books or articles. Do you have any recommendations?” Or: “Do you know of any upcoming events or seminars that would be beneficial for someone in my line of work?”
Common Connections: “I noticed you were talking to [Colleague’s Name]. How do you two know each other?” Or: “I see we both know [Mutual Connection]. How did you meet?”
Open-ended Questions: “What’s the most challenging aspect of your job?” Or: “What’s the most rewarding project you’ve worked on recently?”
Personal, Yet Professional: “Are you from [City/Location] or did work bring you here?” Or: “I noticed you’re using the [specific tool or software]. How do you find it compared to other options?”
Travel or Location: “Did you have to travel far to get here?” Or: “I’m new to this city. Do you have any recommendations for places to eat or things to see?”
As the conversation progresses, be mindful of cues indicating whether the other person is engaged or if they may need to move on. Always be ready to adjust the conversation or gracefully wrap it up if needed.
Practice With a Trusted Colleague or Friend
While the idea might seem unconventional at first, practicing conversations through role-play with a friend or colleague can be incredibly beneficial. Role-play is frequently used to train people in a whole range of conversations, like difficult talks with team members, sales calls, and negotiations. Being prepared will increase your confidence and allow the real you to come out without being awkward.
Actively Listen — and Allow Yourself to Relate
This might sound simple, but it’s crucial: truly listen. Direct your full attention to the individual, absorbing every word they say. Instead of preoccupying yourself with your performance or the next question to ask, be present in the moment. By posing thoughtful questions and remaining genuinely engaged, you’ll find that most will resonate with your approach. Before you realize it, you’ve made a meaningful connection.
One Final Tip
Should you struggle to recall your conversation starters, jot them down on a reference card and keep it handy. But, ensure you’re not visibly referencing it during a conversation. 
Use it as a subtle reminder and take the opportunity to genuinely learn about someone.
In our next discussion, we’ll delve further into nurturing and maintaining these freshly established connections. Until then…
Good luck!
Sincerely,
