You’re sitting in a cafe minding your own business, when suddenly you notice that the person you’ve wanted to have as a mentor or boss is sitting at a nearby table. This could be your big moment to make a good impression, or you could totally fall flat on your face in awkwardness. So what do you do?

This scenario was a question that a reader in New York emailed me. And if you’ve had moments like this, too, you have three options. Two of them are ones that you’re probably already weighing. The third is a bit unexpected—but could put you much closer to a seat at that table in the future.


1. Do Nothing

Let’s get this out of the way now. Yes, doing nothing is an option. But if you’re really serious about your career, it’s a terrible option. Don’t waste chances.

Of course, if you’re not feeling up to it (because of nerves, not feeling that you’re dressed appropriately, or some other reason), that’s understandable. It might not be the right time for your target, either, especially if there are any cues in the person’s demeanor that show intense focus or discomfort.

But don’t let the opportunity pass you by. Also don’t send an email saying “I saw you earlier and didn’t say anything,” because that’s creepy. Just proceed to option #3.


2. Approach

If the person is not engaged in a conversation or looking visibly upset, wait for an idle moment, then step up and try this script:

Hi [use the formal Mr./Ms. and the person’s last name]. Do you have a moment? [If the answer is “no,” say “thank you” and move on. If the answer is “yes,” continue.]

I just wanted to come over and introduce myself. My name is [your name] and I’ve really enjoyed your work, especially [something recently in the news]. I’m [a bit about you and your background], and if you ever have some time, I’d love to hear more about your work and career path.

What I’m recommending here is an approach grounded in flattery, brevity, and respect for others’ time. You don’t want to immediately go into “pitch” mode and risk sounding like you’re selling used cars. An informational interview is low-intensity for both parties and, as long as you’re prepared, can get you started on developing a meaningful connection.

Of course, this person can respond to your approach by rejecting you (hopefully politely like, “No, thank you” or “I’m not interested”). You could also get the green light that you’re looking for and walk away with another opportunity! Take the chance.


3. “The Pretzel”

No, this is not some seductive dance step. It’s a tactic I learned at my company, Bureau Blank, about taking a “roundabout” path with networking. Rather than engaging the target person directly, hop over to LinkedIn and see if one or more people in your network are more closely connected to him or her. If so? Reach out and ask for an introduction or endorsement.

I received a pretzel (if I can put it that way) recently when a grad school colleague contacted me on behalf of a person who is interested in learning more about Bureau Blank. He spoke highly of her background and said these key words: “I think you’ll be impressed by her.” Who in your network can say that about you? Identify them and ask for the favor because you’ll get much closer to the opportunity. Think of it this way: You could write a letter to President Obama yourself, but if you could get someone in the Cabinet to endorse you, why wouldn’t you?



The key to all of these options is thinking first, then acting with judgment. Think about what will make connecting with you a meaningful effort for the person you want to meet. Once you know, be bold and step up. Chances don’t come around twice, so have a plan and be ready for whatever comes. Like my parents have told me for years, if you don’t ask, the answer is always “no.”


Photo of man waving courtesy of Shutterstock.