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Advice / Job Search / Networking

9 Questions You Have About Coffee Meetings But Were Too Afraid to Ask

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“Invite him to coffee.” “Ask her to grab a drink.” “See if they’d like to meet up to talk in person about their career paths.”

The longer you’ve been in the working the world, the higher the odds that someone’s suggested you do this. Not only that, but he or she always makes it sound so simple. However, meeting with other professionals (a.k.a., strangers) for coffee, drinks, or a meal can feel awkward and unnatural. First of all: How do you score that meeting in the first place? Then, what can you do to keep the conversation going? And finally, how can you make sure the connection keeps growing afterward?

Luckily, you’re definitely not the first person to wonder about the art of the coffee meeting. Here are nine questions many people have about networking that they’re usually too afraid to ask.

1. How Do I Just Reach Out to a Stranger Without Making it Weird?

If you think you’re weird for reaching out to someone you don’t know, relax! People email others they don’t know frequently, and no one is going to think any less of you for sending a message.

The biggest hurdle is making sure what you say is clear, concise, and specific. As Muse writer Aja Frost says, it’s important to identify the reason why you’re reaching out and to keep your pitch short (no more than three or four sentences). If you’re struggling to find the right phrasing, check out Frost’s brilliant email template for getting a meeting with anyone.

2. My Former Co-worker Knows This Guy—How Do I Ask for an Introduction?

Having a middleman makes the process easier since you have someone to vouch for you. However, don’t take asking for an introduction lightly. Assess whether or not you know this contact well enough (and are on good enough terms with) so that an ask won’t create problems.

Be straightforward about why you want this meeting. I’ve definitely been in awkward (like, really awkward) situations in which a friend told me one thing and then did something completely different as soon as I made the connection for her. Long story short: The bridge was burnt between the two of us.

Need help crafting the perfect message? Muse co-founder Alex Cavoulacos has got you covered with this “Could you make this introduction?” email.

3. How Do I Follow Up if I Don’t Hear Back?

First, don’t panic if someone doesn’t respond right away to your first email. People are busy, have different schedules than you, and forget things easily. Keep in mind that many professionals receive upwards of 60 to 100 emails per day (or more!), so there’s a good chance yours got caught in typical inbox drudgery.

If you’re looking to follow up, be sure to make your email short (one or two sentences), pleasant (drop the “you forgot to email me back!” stuff), and specific (“I emailed you last week about meeting because…”).

Need help on being politely persistent? The Muse’s very own Director of Brand Strategy and Community, Elliott Bell, has got your back on effective follow-up.

4. When and Where Should We Meet Up?

Your “when” will probably be limited by schedules, but if you have some leeway, try to meet up during off-peak restaurant or cafe hours. Avoid the morning coffee rush like the plague, and try to avoid the lunch rush, too, while you’re at it.

In terms of where, there are a few basic things to keep in mind:

  • Noise level: You don’t want to be yelling to hear the other person.
  • Seating: There should be some. A networking contact once suggested we meet at a hip coffee bar near her work. Emphasis is on the word “bar,” because we stood at a counter for almost an hour (which, for the record, was very uncomfortable). Forgo the trendy cafes and pick somewhere with ample seating.
  • Crowds: Pick somewhere spacious where you’ll be able to talk without other patrons spilling over onto your table.
  • Proximity: If you’re the one asking for a coffee meeting, choose a place nearer to the person you’re meeting with. It’s courteous and it also cuts down on travel issues on their end.

See, that wasn’t so bad, right?

5. What Should I Do Before the Meeting?

Step one: Do your research. Look up the person you’re meeting with (LinkedIn profile, social media pages, and published articles are great places to start). You don’t need to go into full stalker mode, but be aware of who you’re meeting with, their accomplishments, and their general career trajectory.

Two, be sure to get the other person’s phone number if you’re meeting somewhere that requires travel. It’s not uncommon for people to run late or to have something come up last-minute, and trying to communicate via email can get very tricky.

Lastly, formulate your questions for this person and write them down. While you don’t want to sound like a robot during your conversation, questions can help guide discussion—especially in the beginning when you first sit down.

For example, if you’re meeting with someone for an informational interview about her job, questions could include:

  • “I know you’re a [job title], but what does a typical day look like for you?”
  • “What’s one skill you need for this field that most people wouldn’t guess?”
  • “Is there anything you wish you’d know about this particular field before you got into it?”
  • “What energizes you about working for [Company A]?”

An important pro tip: Write these questions out on a piece of paper (you know, the stuff from trees)! Typing out questions on a phone or computer is problematic for two reasons. First, it comes off as rude—even if you’re not surfing Facebook while the other person is talking. Second, your battery could die or your phone could just freak out and shut down, and you don’t want to be left with nothing to ask.

6. What Should I Bring?

Good news: This doesn’t have to be complicated. A couple of items to have on you:

  • Notebook and pen: We live in the digital age, but you don’t want to be typing on a laptop or your phone when someone’s giving you valuable words of wisdom.
  • A handwritten list of questions: Again, it’s rude to look at your phone, and people are always impressed when it looks like you’ve done your homework and aren’t wasting their time.
  • Money: Sounds obvious, but how awkward is it to get to a coffee shop only to realize you can’t treat your guest and need him to pay for you?
  • Business cards: They’re always good to have on hand.

Depending on why you’re meeting, it may also be helpful to have a resume, your portfolio, or other materials with you in case the other person asks for them.

7. Should I Pay for the Coffee, Drinks, or Meal?

General rule of thumb: Try to specify this beforehand in your email (“I want to treat you to coffee!”) to avoid confusion, but if it’s a single beverage and you asked this person to take time out of his or her day to meet, you should be the one paying for it.

If it’s a larger meal for whatever reason, both parties typically pay separately.

8. What Do I Do if It’s Not Going Well?

First off, most meetings aren’t as much of a disaster as we think they are. Second, if the meeting is going downhill because the other person isn’t responsive or seems preoccupied, just know that it’s not you.

If it feels like it’s going poorly, the most important thing is to keep your cool and to continue being enthusiastic without not trying too hard to impress. Keep your spirits up, be polite, and ask what you need to. If he or she seems pressed for time, cut your question list down and keep it to the important stuff. Show gratitude at the end, send your thank-you email quickly, and promise to keep in touch. But also know that it really is OK for your meeting to end earlier than you thought.

9. How Do I Stay in Touch?

First things first, send a thank-you email as soon as you’re done with your meeting (pro tip: Have a draft ready to go before you head out to the meeting!).

Now comes the harder part: Keeping in touch long-term. An easy route to go is to periodically follow up on social media with a tweet or a comment on a LinkedIn post. Send emails if this person experiences any big career milestones (like a promotion or an award), or if you come across an article or story that pertains to this person’s work or areas of interest.

Make your life easier by asking during your meeting if there’s anything the person would recommend you read, watch, or listen to to get ahead in your field (or get hired, or whatever it is you’re trying to do). Then read that book, watch that movie, or listen to that podcast, and send over your thoughts.

Great coffee meetings come down to thorough preparation, enthusiasm, and follow-through. If you keep these three major things in mind, you’ll be building those connections in no time.