A practical guide to unlocking the power of professional conversations.
As a formerly-aspiring corporate girlie who now fully identifies with that title, I’ve had my fair share of coffee chats. And just recently, have begun to be more on the receiving end, rather than the initiating end, of them. I used to think that it was important to just be yourself and go in with a few questions. That is still true, but I now see having coffee chats as almost an art — that can be learned, honed, and perfected.
I know, you may be thinking that it’s unnecessary or maybe even inauthentic to engineer your social interactions. But I think it’s actually the opposite — Preparation unlocks a better version of yourself and ultimately allows you to connect with someone on a more meaningful level. Asking the generic question of “So, what do you like about your job?” will get you a relatively generic answer, but asking something personal like: “I noticed from your LinkedIn that you’ve changed roles recently from a brand manager to a product marketer — I’m curious to know why you made that jump and what you enjoy in your current role vs. your previous one?” will get you a better answer, I guarantee it.
I’ve navigated my way through many, many coffee chats (some more successful than others) and I’ve pieced together a proven guide so you can successfully navigate them too. The following tips are less of a plug and play (i.e., not necessary to use examples verbaitim) but more of a framework that you can adapt to your own style and approach.
Before the call | Do your Research
- Don’t skip the pre-reading! Look up the person’s LinkedIn, look through their experiences and see if anything jumps out as interesting or relevant to your conversation. Then look at if they have any recent posts, articles or pinned content that you can look through. Take notes and formulate some bullet points/questions. This will help guide the conversation and also help you avoid asking generic questions like “so where did you go to school?”
First 30 seconds | Break the ice
- Yes, small talk can be overrated, but it can sometimes be jarring for the person you’re talking to if you launch straight into questioning. This is usually not an issue if you’re meeting in person, but if you’re calling virtually, I’ve found that it always works best to ask something about where they’re calling from (“Are you based out of NYC?”), how their workday is going, or some classic comment about the weather. The key is to only linger here for ~30 seconds, don’t let it drag on for longer than a minute or two!
1–2 Minutes | Set the stage
- To transition into the actual conversation, I usually just lead with “Thank you so much for taking time to meet with me — “ and then I’ll include context of why I wanted to meet with them, followed by a quick run-of-show of what I want to discuss. This helps the person understand where you’re coming from and what you’re hoping to get out of the conversation.
- In full, this could look something like this: “Thank you so much for taking time out of your busy day to meet with me — I wanted to chat because I’m currently working towards a career transition similar to one you’ve had in the past, and felt like I would really benefit from your insights. So I’d love to give you a quick intro of myself, hear about your career trajectory, and then I have a few specific questions about your current role as well.”
- This may seem a bit long-winded, but after being on the receiving end of things, this kind of set up helps immensely to set the right course for the conversation. Your goals may be completely different of course, so adjust to your “why.”
- Note — sometimes, the other person might want to drive the conversation more. So make sure to ‘read the room’ and go with the flow if that feels more appropriate.
1–2 minutes | Your Elevator Pitch
- Don’t forget to introduce yourself. This seems like conversational etiquette 101, but sometimes I’d simply forget to say anything about myself because I was nervous and go straight into a loaded question like “so what are some key skills for your role?” — For the person on the other end, it feels a little impersonal and it’s hard to tailor the response to what is most helpful for you.
- I usually have a rough bullet point list of things I want to tell them about myself that is relevant for that conversation (i.e., my university/major, how long I’ve been working, and where I’m at with my career.) I always end with a transition sentence that reiterates why I wanted to talk with them. For example: “After the experiences I’ve had in this role, I’ve been curious to learn more about what it’s like working more closely with social media. I know you’ve transitioned into that area recently, so I’d love to hear more about your trajectory how you landed there.”
20–25 Minutes | The Conversation
Personal Context + Thoughtful Question = Winning Combination
Now, the actual meat of the conversation — Here’s a solid framework of how to structure all of your questions:
1. Personal Context: Start with a set-up that includes the personal context of why you’re asking them. This is actually something I learned from having coffee chats with multiple summer interns this summer. The ones who stood out were the ones who made it clear why they were asking their questions with a nice set-up. It also helps to get more meaningful answers.
2. Thoughtful questions: Now pair this personal setup with a prepared question. From the receiving end, talking to someone without any prepared questions makes it feel a little like I’m wasting my time. (If you’re asking someone just to for a casual conversation to get to know them, then that is different, and you should make that clear! But if you’re asking for career advice or looking to expand your network, then definitely prepare personalized questions based on your research.) My litmus test — If you can find the answer in entirety on Google or their LinkedIn, don’t ask it.
Here is how this would come to life:
- “I noticed from your LinkedIn that you started your career as a strategist at a creative agency, which is a role I’ve been interested in moving into — what were some of the key skills you needed in that role and how did you work towards building them?”
- “I listened to a podcast that you were featured on recently and you talked a little bit about your approach to work-life balance that really resonated with me — how has your perception of work-life balanced changed throughout your past few roles?”
- “One thing I’m struggling with in my career currently is not feeling like I fit the mold of a ‘typical leader’ — I’m curious if you ever felt something similar or what advice you’d give to someone who wants to attain a leadership position like the one you currently hold?”
The set up is in italics and the questions are in bold — notice how the first part of the question really helps to contextualize the question to prompt more meaningful responses.
1–2 Minutes | Wrap up
Finally, as the one asking questions, make sure to keep an eye on time and give the person an out if they have a hard stop. It usually works well to lead with: “I know we only have a few more minutes, so just wanted to end with…” Sometimes people offer more of their time which is a plus, but it’s always nice to have a calm wrap-up rather than an “oh-shoot-I’m-late-to-another-meeting-sorry” type of goodbye. Depending on the conversation, you may want to ask if there is anyone else they would recommend talking to or ask if you can follow-up in a few months for another coffee chat (if it’s appropriate!)
All of this is, of course, a framework that you can and should tailor to your own approach and goals. Good luck and happy coffee chatting :)
