Career Convo Template
Career Conversation
This is a rough outline of how I structure my career convos.
To prepare for our career convo, please read this outline and think about how you’d answer some of these questions. You do not need to answer them in writing ahead of time, though you can if you wish. Most of these questions are better discussed live anyway.
Part 1: Dreaming of the future and setting a goal
Prompt: Five years from now, you and I are catching up over a coffee or beer, and we’re celebrating that you’ve finally been able to hit a specific goal in your career.
Question: What goal did you hit? It’s absolutely not required that [company] is in the picture
Examples:
“I’m the cofounder and CTO of a startup and we just closed our Series A.”
“I’m solving hard problems at [company] and I’ve hit my goal of becoming an E6/E7/E8”
“I’ve moved on from tech, and opened a coffee shop in South America”
“I’ve hit my goal of transitioning to be an EM at [company] or another big tech company”
Part 2: Milestones and Virtues
Now that we’ve looked out 5+ years, let's talk about a few milestones that might help get you to that goal as well as some virtues you might need to develop.
Question: What are the 2-3 milestones you think you need to hit, or the virtues you need to develop to hit your goal?
Examples:
“To hit the goal of becoming a startup cofounder, I need to become super strong at selling my ideas and vision.”
“To hit the goal of becoming an EM, I need to hone my people skills and have a high level of emotional intelligence, compassion, empathy and humility”
“To hit the goal of opening a coffee shop in South America, I need to work on my leadership, creativity and managerial skills.”
Part 3: Shaping your experience @ [Company]
You have a 5-year goal in mind. You’ve identified some milestones or virtues to get you there. Lets talk about shaping your experience at [company] to get you to your goal.
Sample questions I might prompt you with (you don’t need to have answers for all of these.)
Over the next year, what are the 1-3 skills you think are most crucial for you to develop?
What other skills should you focus on gaining, developing or working towards mastering? How would you rate yourself in terms of those skills today?
What are some specific areas you’d like to receive feedback on?
Are there other people you need to connect with (given their strengths) to help you execute successfully or who can help support your growth?
What are 1–3 skills you recognize in yourself? Can you identify your top two?
What are 1–3 strengths you recognize in yourself? Can you identify the top one?
In current or previous roles, what parts of the work have you enjoyed or found most interesting? Why?