I once received an enthusiastic email from a blog reader that went something like this: “Hi! I love what you do. Can you share any freelance writing tips with me?”
Frustrated, I stared at the screen. I had no idea what parts of my work she liked or why, which mattered because I’ve worked in communications roles across several different industries. I didn’t know what sort of writing she liked to do, nor her range of experience with writing or freelance. Most of all, her question was not only incredibly basic, but something she could easily Google for a quick hit of resources, tips, and information, so what did she even want from me? With no incentive to reply, I hit delete—not because I didn’t want to help her out, but because the ask itself showed a lack of intention and detail, two really important elements of relationship building in the professional world.
Intention and detail are two really important elements of relationship-building in the professional world.
You could certainly chalk this experience up to poor communication skills, and I almost did. But then I remembered, a little sheepishly, that . . . I’ve been in her shoes. Early in my career, I contacted a female leader I admired in my community to “connect over coffee.” I had good intentions—I wanted to learn from this woman’s expertise and follow in her figurative footsteps—and yet, I never received a response. Now, I understood why.
Inviting someone to network through the classic coffee date sounds good in theory but only if done right. Time is precious, and all interactions and efforts need to feel worth prioritizing on our to-do lists. So here are six ways to maximize this kind of meeting and make it beneficial for all involved.
1. Know what you want.
Before you contact someone, make sure you know exactly what you’re trying to accomplish. Do you want to be introduced to someone in a certain role? Are you looking for a “here’s how I did it” story to garner tips? Do you need a job? Do you want feedback on an specific idea or project, or an answer to a direct question? Are you motivated to switch careers and want advice from someone who has gone down a similar path?
If your answer is “I don’t know . . .” then spend more time thinking about what you’re attempting to achieve, as well as why this one individual could assist you in those endeavors. Trust me, that’ll be the first question they will want answered the moment you sit down. Determine your goal, then ask to meet.
Doing digital detective work shows that you value someone’s time and intend to use it well.
2. Do your homework.
You would never show up for a job interview without knowing at least the bare minimum about a company or organization in terms of their mission, values, clients and more. Right? I hope so. The same is true for showing up to meet a professional peer. Chances are high that the person you’re meeting has some sort of digital presence—an online portfolio, a LinkedIn page with work history, an Instagram account—that can provide useful context.
For example, it would be strange for me to meet with an author I admire and ask, “What books have you written?” That information is most likely already at my fingertips, so I should be motivated enough to gather it in advance. Conversely, if I met with a fellow writer who said, “So, who do you write for?” I’d wonder why she chose not to check out my readily available website.
Doing your fair share of digital detective work doesn’t make you a creep; it shows that you value this person’s time and intend to use it well.
3. Make it easy to say yes.
We’re all busy. Most people have no desire to add yet another meeting to her packed schedules. If you want someone to reorganize his or her day in order to meet with you, make it insanely easy for her to do so. Whether you choose to reach out via email, phone, or in person, be sure to include a short introduction to who you are, how you know of him or her, what you want and suggestions for when and where to meet. Additionally, take initiative to provide a time, date, and location. Suggest one to three days that work for you, and keep the meeting under 30 minutes. Note flexibility where possible. Pick a location convenient to the other person and mention you’re happy to pay.
Here’s a loose script as an example:
Hi Jane! I’m Mary, a freelance writer based in the Midwest. I read your recent piece on the upcoming election and loved how you outlined reasons to vote. Would you be willing to meet for coffee in the next two weeks to talk about how I can pitch some political articles to the same publication? I know you’re busy, so I promise to only take up 30 minutes of your time and cover the costs. I’m available weekday mornings between 8 and 10 a.m., and we could go to the Starbucks downtown near your office location. Thanks for considering.
Be present, make eye contact, put your phone away—all the things that polite people do at the bare minimum.
I mean, if I got that email from someone, I would think, “OK, so I know what who she is, what she wants from me, how long it’ll take and, bonus, I get a free latte without going out of my way. Why not?” And even if I didn’t have the bandwidth that particular week, I would probably feel more inclined to figure out a way to help her out in the future.
Basically, make it really, really, really easy for them to say yes and show up.
4. Be a good host.
Imagine you’re hosting a party at your home. You would be there when guests arrived. You would offer them something to drink or eat. You would most likely want them to be as comfortable as possible in your presence. When you ask someone to coffee, you are hosting them in a public space, but the conditions are relatively similar.
Plan on being at the agreed upon meeting spot 20 minutes before the other person arrives, so that you have time to grab a table in a quiet corner spot. Take the stress off of them looking for you in a crowded room, which will put them at ease immediately. Wait for him or her to arrive before ordering anything. I can’t tell you how many times I’ve met someone for coffee, only to arrive on time and see that they were almost finished with their drink as I stood in line by myself. It feels awkward. Don’t forget to offer to pay as a show of good manners; if they decline, let it go, and if they insist on paying for themselves or the both of you, let them. Be present, make eye contact, put your phone away—you know, all the things that polite people do at the bare minimum.
Most critically, if you’re going to be late at all, cancel the meeting. It’s better to give that person their time back, even on short notice, than to waste it completely. Remember that canceling leads to rescheduling, which can be frustrating (like when you reschedule plans with a friend five different times—by the 5th time, both people are kind of over it). If you asked to meet, and you’re the one who can’t fit it into your schedule, the other person will be less likely to prioritize your request to meet going forward.
5. Lead the conversation.
Be prepared to guide the conversation. There’s nothing worse than sitting down with someone at their request, only to have them stare at you blankly, waiting.
Write down a list of all the things you want to learn from this person, every question you’d like to ask. Then, figure out how to make it more specific. “How did you end up in marketing?” becomes “I saw that you used to work at X, and now, you work at Y. What advice do you have for someone looking to make a similar transition?” Rather than, “What publications do you recommend writing for?” Say, “I love writing about X, and have checked out the pitch process for A and B publications. Do you have suggestions for writing opportunities at similar outlets?” From the get-go, dive into the heart of why you’re both there and what you hope to discuss.
Keep in mind that good leaders are good listeners as well. Take notes so you don’t forget anything.
Keep in mind that good leaders are good listeners as well. Take notes while the other person speaks so you don’t forget anything. Look for opportunities to add value wherever possible. Pay attention to the time so you can gracefully note when you’ve worn out your welcome.
6. Follow up with gratitude.
Within two days of the meeting, be sure to thank the other person, ideally via email or handwritten note. It can be quite simple: First and foremost, acknowledge your gratitude for their time, which is a gift as much as a tangible item. Note a memorable detail from the conversation if you can, and then gently remind the other person of any next steps. If you promised to provide additional information, include it in your message through attachments or links and then “close the loop” later on. For example, let’s say he or she introduced you to a new business contact. Down the road, when you’ve spoken with that person, you could reach out to your coffee date to let them know the outcome. This showcases follow through on your part and acknowledges, again, your gratitude for their help.