Five things to never do in a coffee chat
From someone who has accepted a lot of cold inbound requests for coffee chats
For the past few newsletters, I’ve written about open-ended, big life topics. Today, I’m switching gears to something very tactical: coffee chat faux pas. (In case you were curious, I looked up the plural of “faux pas” in English. Turns out it’s still “faux pas,” but just pronounced differently when you say it out loud.)
I have always been a firm believer in paying it forward, because I’ve only gotten to where I am today with the generosity of many, many others. Over the years, there have been countless coffee chats and phone calls in which I heard words of advice, pearls of wisdom, and even stone cold harsh truths. In most instances, the other person had no real incentive to take the time to chat with me. Now that I’m at a stage of my career where there are people who actually think I’ve got wisdom to impart, I’m excited to be able to do that. In fact, I started this newsletter in large part because I felt that it would enable me to share the things I’ve learned with a bigger audience more effectively.
Anyway, over the past few months, my LinkedIn profile has somehow garnered more inbound interest than ever before. My theory is that I hit a certain number of months in my current role and thus have been plopped at the top of search results for certain search terms. (If anyone can confirm this, I’d love to know!) I’ve taken over ten calls with people since January, which really isn’t that many… It’s only ten episodes of Gilmore Girls, if you think about it.
As I’ve done these calls, I’ve reflected on what makes the coffee chat style conversation meaningful. As such, I’ve compiled a list of five things to never do, along with some good questions for coffee chats below that might be a helpful reference.
Never open the conversation by asking me to tell you more about “my journey” or “my career.”
First off, you have already stalked my LinkedIn. I know you’ve seen it, and in fact, I find it boring to regurgitate my resume to you.
When you ask me to talk about my career (broadly) in a coffee chat, you will inevitably get a five-minute deep dive into some random part of my career. It will be whatever catches my fancy that day. Maybe I was feeling particularly nostalgic about my startup days – you’ll get the TEDTalk on why everyone should do a stint at a startup. Maybe I was feeling particularly like a former consultant – you’ll hear all about the consulting toolkit and how that prepares you for any career. I cannot imagine that this is particularly helpful or valuable to you.
Ask me about specific transitions or roles:
Of the things you learned in consulting, what was most useful in your startup role? Or your role today?
Why did you decide to go to a startup when you left consulting?
How did you choose your current role? What else did you consider?
Do not presume I know your profile or background.
I do my best to remember, but I don’t always have a chance to review your LinkedIn profile before we jump on the phone. I love it when the other person takes the lead and offers to give more context about their background and specific area of interest. This gives me a sense of what I can presume is shared knowledge versus where I might need to slow down and provide more context and explanation.
Do not bury the lede on your goals for the call.
It’s fine if your goal is to get a job working at the company where I’m employed. It’s fine if you’ve already applied for a role. It’s also fine if your goal is truly to just learn more about my job. Be straightforward with whatever your goal is, even if there’s a chance I might not be open to it. It’s a lot less efficient for both of us if you bury the lede and we have to tiptoe around the topic for 20 minutes.
I’ve had calls where I knew the other person wanted a referral to a specific job opening and I had already decided that my answer was going to be a polite but firm no. I’ve also had calls where I read between the lines and figured out that the other person had already applied to a role at my company, and I knew very little about that role. In both scenarios, I felt that I was not providing helpful information for the majority of the call and we were just playing out a script to get to an eventual ask.
If you can lay out your goal in a message to me after I’ve replied to your initial outreach, that’s even better. It can be as simple as:
Thanks for the reply, Isabella! I’d love to chat more – I just applied to XYZ role at ABC company, and I’m curious to learn more about the role and culture.
Or…
Thanks for the reply, Isabella! I’m interested in learning more about working at ABC company though not imminently applying for any roles. Would it be possible to chat just to learn more about the company overall?
My answer to the two scenarios will be quite different, but having that extra clarity ensures that I’ve actually got something useful to offer to you if we hop on the phone. In the former scenario, I might write back and say I have no insight into that role and it might not make sense to chat. In the latter scenario, I’d be more than happy to chat overall.
Never come into the conversation without any questions for me.
Speaking to someone aimlessly for half an hour might be easy for some people, but it is exhausting for me. (And probably some decent percentage of other people as well.) Always have a list of questions ready to go – at best, the other person might be super chatty and just spew wisdom at you, but at worst, you’re catching them between a bunch of meetings and they’re looking for guidance on what you want to hear.
I actually don’t mind when someone has a laundry list of questions and just goes through them with me one by one – it means I don’t have to do any thinking and I can just experience share methodically.
Of course, the questions should be sensible and I should be able to see how they connect back to your situation. More on questions below.
Do not hesitate to end the call early if you’ve gotten everything you need.
Sometimes, we both hit a stride and cover all of your questions really quickly. Maybe I’m just having a particularly pithy day and I’m not rambling as I usually do. Maybe I just so happened to cover all of your questions early on in the call. Maybe you realized that I’m not actually the right fit for your questions.
Whatever it is, it’s okay to end the call early if you’ve gotten everything you need. I’m usually going to give you the full 20 or 30 minutes I’ve allocated for the call as long as you have questions, but if you feel done, you have all the right in the world to say “Thanks for the time, that’s all I’ve got today.” If that feels weird, you can always frame it as, “I don’t want to take up more of your time – I know you’re busy!”
I very, very rarely have a poor impression of someone else because they ended a call early. I tend to appreciate the time I’m getting back and the efficiency on the other person’s part. In particular, there are times when you might realize you’ve hit diminishing returns of hearing similar advice that isn’t yielding net new insights. I love it when someone else has figured that out for themselves.
Appendix: Good questions to ask
A huge shoutout to @A for sharing her list with me, which provided some of the inspiration here!
Based on what I’ve described, where do you see gaps in my experiences or learnings?
My goal is to reach role X or work at company Y because of A, B and C reasons. Based on that, what would you recommend I consider or look into?
What surprised you the most when moving from role A to role B? Anything you had to un-learn? What were the biggest gaps and how did you bridge them?
I’ve seen at ABC company, there is Team X and Team Y. What is the difference between them in terms of roles and responsibilities? How are the two teams structured differently? Is it similar in the industry more broadly, or is this specific to ABC company?
How does Team X set priorities and goals for each year? How are different projects prioritized?
From what I have read (or heard), ABC company emphasizes a certain value or a certain way of working. Have you felt this in your experience and if so, what are some examples?
What is something about the culture at ABC company that is often misunderstood by people looking in from the outside?
What are common career paths that you’ve seen after role X or role Y? Can you provide examples of peers who’ve gone on to do different things?
If you were in my position, what would you think about/prioritize?
Looking back, is there anything you would have done differently with your career?