thelighthouse Playbook for a Coffee Chat

thelighthouse.us
7 min readMay 7, 2020

This playbook includes a process and question guide to leverage for your informational coffee chats.

The process:

  1. Reach out over LinkedIn and/or email
  2. Send them a calendar invite with the location (make it easy for them)
  3. Have the conversation (see below for question guides based on the topic)
  4. Send a thank you note and act on any discussed follow ups

Step #1: Reaching Out

Some tips:

  • Try reaching out to people who you are connected to in some way — those will have the highest response rates. Some example might be professionals who work at your current company, alums from your current or past companies, or alums from your college or high school. If you don’t know anyone, be clear on what type of person you’re looking to talk to and ask your friends if they know anyone. If they do, draft an email that they can easily forward to the person to make it as easy and seamless as possible.
  • Be specific in your ask — don’t just ask for 30 minutes of their time or to “pick their brain.”
  • Do your homework before you reach out to show that you know why they are the right person to connect with. Familiarizing yourself with their background will inform smarter questions and show you’re prepared.
  • Make sure your LinkedIn profile is up to date so they can see who you are and what you do

Here are some real examples for reference:

“Hi Jack, hope you are well! We previously worked as colleagues at [company name] a few years ago. I currently work as an [current role] in [current company]. I saw on LinkedIn that you now work in Product Management. I’m exploring making the switch as well and would really appreciate if I could ask you a few specific questions about the transition over email or a 30 minute phone call if you’re open to it?”

“Hi Alex! Long time no see — hope all is well with you. Seems like you have been up to some great things. I just checked out your company’s website and think what you’re doing is awesome. From a personal standpoint, I actually left my job in April — same company I was at since we graduated (crazy). I have been traveling for a bit, and am now at a crossroads trying to figure out my next move. I’d love to catch up and learn more about the work you’re doing. Let me know if you have time in the coming weeks to grab coffee and chat. PS — pretty sure you’re still in my phone as “Alex — Floor 2” from college days…”

“Hey James, The event we met at really encouraged me to look at my career aspirations closer and be more critical of my current role. I briefly mentioned that I had an idea similar to your company’s and really think that there is a big demand for this kind of network. I was wondering if you would have 15–30 minutes in the coming 2/3 weeks to talk a bit more about your experience quitting corporate to start your own business.”

Step #2: Schedule the meeting

Some tips:

  • Make it super easy for them in terms of time and location
  • Send 2–3 available times blocks on your end that are a few days out — switch it up in terms of morning and afternoon options and block off your calendar during those times so that you don’t get double booked
  • If the person is in a different time zone, convert your time blocks so it shows up in their time zone
  • Offer to send through additional times if needed
  • Once you’ve aligned on a date and time, send a calendar invitation so both your calendars are blocked
  • If you’re meeting in person, offer to meet by their office or host at yours (if that’s an option), you can also offer to find a specific coffee shop by their office
  • If you’re meeting virtually, include a Zoom or Google Hangouts link in the invitation or, ask for their phone number before the meeting and say you’ll call them at the time (include that note in the meeting location “I’ll call you at 888–888–8888”)

Step #3: Having the conversation

Some tips:

  • We recommend a 30 minute chat and if it goes over great but be respectful of their time and offer them an out at 30 minutes
  • Before the call, prepare a list of at least 5 questions
  • Before the call, try to think
  • Before the call, review their LinkedIn so you’re prepared, you can also use this to see if you have any shared connections which you can bring up when you kick off the call
  • If you meet in person, offer to pay for their drink/meal
  • Take notes
  • Drive the meeting — see below for a sample structure

Sample Structure:

  1. Kick off: Thank them again for taking the time and catch-up on a personal level (ask them about their day/weekend)
  2. Set the objective: Explain why you reached out and what you’re hoping to cover during the meeting, for example: “As I mentioned over email, I’m currently doing X, and really curious to learn more about Y. Given your background in Z, I thought you’d be a great person to speak with. I have a few questions prepared, do you mind if we go through them?”
  3. Go through your questions: See below for a list of some of our favorite questions depending on the topic of conversation.
  4. Thank them and offer to help: End the meeting by thanking them for their time, mentioning 1–2 takeaways, and then offering to help them. It can be as simple as “Please let me know if there’s any way I can be a resource to you too — whether it’s introductions to anyone I’m connected to on LinkedIn or being a thought partner, I’m always happy to help. Is there anything that comes to mind right now?”

Questions if you’re looking to learn more about a specific industry or role:

  • I’m trying to better understand this specific industry/role, I’ve read a lot about it but would love if you could provide a breakdown of what being in your role entails.
  • What does a typical day look like for you? What are the top 3 things you spend your day doing?
  • What is a typical project? Can you tell me more about a project that you’re most proud of or a project you’re working on right now?
  • How does the role differ based on company size, region, industry, other factors?
  • Why was this role interesting to you?
  • What is the biggest misconception about this role/industry?
  • What do you like most about your job? What’s the best part of the day?
  • Every job has parts that aren’t as glamorous or interesting — what is that for your role? What is the worst/most dreaded part of your day?
  • Where did your colleagues come from? What are they’re backgrounds?
  • What skills are needed to be successful in your role/industry? How did you develop those skills?
  • What are the most helpful career resources (newsletters, blogs, podcasts, courses, books, industry leaders to follow, tools) specific to your industry/role that you would recommend?
  • What does career trajectory look like for someone in your role/industry? Where do you personally see your career going next?

Questions if you’re looking to learn more about career transition:

  • You started your career in [X], can you tell me more about: how you decided you decided to go into [Y]? What sparked the decision? What was your thought process?
  • Once you made that decision, how did you decide where you wanted to focus within [Y]?
  • How did you transition into [Y]? How long did the process take and what did it look like?
  • What were the major differences between working in [X] compared to [Y]? In terms of: day to day / type of work, colleagues / culture, work life balance, compensation / benefits, career path, fulfillment, other factors?
  • How did you position or pitch your experience in [X] to get your first opportunity in [Y]?
  • What were the most helpful resources when it came to making this transition? E.g. newsletters, blogs, podcasts, courses, books, industry leaders to follow, tools.

Step #4: Send a thank you note

Some tips:

  • Send the thank you note — ideally the same day or the next
  • Make it personal and pull out an insight you drew from the conversation
  • Offer to help them again
  • Add them on LinkedIn if you haven’t already

Here is a real example for reference:

“Subject: Thank you!

Hi Jody,

Thank you again for your time yesterday. It was so helpful to learn more about your background and how you made the switch from consulting to tech. I especially loved your suggestion on trying to get onto tech consulting projects to start to build up my experience in the space. Also, I subscribed to Gary’s Guide and the event lineup looks great — thanks again for that recommendation!

I’ll definitely keep you posted as I make the transition and look forward to keeping in touch. Again, please don’t hesitate to reach out if I can be of help in any way.

Thank you again, Jody!

Nancy”

Photo by Kyle Glenn on Unsplash

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