Initial Deep Dive Meeting

I typically will send this document out a few days prior to my second meeting with my directs - our 60 minute deep dive. This normally happens in our second week working together. It's an opportunity beyond the initial "hello" to really understand each individual's role, contributions, goals, and challenges. It provides a chance to understand and aggregate team-wide areas that are working well, as well as areas that may need improvement.

I make this a shared document with my direct, with the expectation that they take some time prior to the meeting to reflect & fill in their thoughts.

Much of this is inspired by Google re:Work's GROW document.

Introduction

This document is intended to be a quick summary and overview of your current roles and responsibilities within our team. It will serve as an agenda for our initial 60 minute deep-dive meeting - please use it as an opportunity to think through the key items you’d like to discuss as well as our first chance to really discuss what the team is doing really well and potential areas for improvement.

This document takes the form of a series of Q&As - please feel free to respond however you’d like (bullet points, sentences, GIFs, etc). It’s okay if you don’t have answers to everything - just write down that you’re not sure.

Getting to Know Your Role

1. If you were to describe your role in 30 seconds to someone, what would you say?
2. What major functional areas of our organization would you say you “own”?
3. For the each functional area you own, what are the responsibilities you have?
4. What would people describe as your biggest achievements in the past six months?
5. Who are your biggest partners within your team, and how do you collaborate with them? What’s working best in those relationships?
6. Who are your biggest partners on other teams, and how do you work with them? What’s working best in those relationships?
7. What systems, tools, and services do you access on a regular basis?
8. Are there elements of your role and of the team dynamics that you feel are working exceptionally well and shouldn’t change?
9. Are there elements of your role and of the team dynamics that you feel are not working well and need to be revised?

Goals: What do you want?

1. What do you want to achieve with your career in the next six months?
2. Where do you see yourself in 2-5 years?
3. What would your dream role be? What motivates you to want that role?
4. What goals have you set that you didn’t meet in the past six months, and why?

Reality: What’s happening now?

1. What are the most rewarding aspects of your current role and team?
2. What are the most frustrating aspects of your current role and team?
3. What most frequently gets in the way of you being able to do your job?
4. Do you feel challenged in your role? What would make it more challenging? What isn’t challenging?
5. What feedback have you received from others on your strengths and weaknesses?

Options: What could you do?

1. What are two things you could do right now to develop skills that would be useful in reaching the goals you identified earlier?
2. What big projects on our team would you want to pursue?
3. What mentorship options might exist for you? Are the people in the organization that you admire and feel you could learn from?
4. Is there something Sean or other leaders can do to help you realize your goals?

Will: What will you do?

1. What are three things you can do in the next six months to make progress to your goals?
2. What resources will you need to make that happen?
3. What support or advocacy from Sean or other leaders would help?