This artifact was given to me by the David Vinca, who was CEO of the startup I worked for when I was Director of Product. He wanted to get to know my future plans and aspirations. I really valued that he took the time to sit down with me and mentor me in this way.

I then used this at various times with my direct reports / mentees. In one case, I had a direct report who was burning out at work. We had a good enough relationship where he came to me and told me, "I don't know if it's time for me to leave the company."

And then we did this exercise and it help both of us realize he was just working on the wrong team and projects. There was another team that was doing work that really aligned to the kind of work he wanted to be doing and the people he wanted to work with.

So we switched his team and he has actually out-lasted me at the company...he's still there 5 years after that conversation.

I suggest blocking a full day between the direct report and manager, ideally offsite somewhere with a whiteboard. The direct report should fill out this pre-work in advance and the manager should have some time to digest and synthesize the pre-work. Then the retreat time can be used to dig into the answers deeper and discuss the paths forward. If necessary you can do some of the questions live but it is better to give the direct report some silent time to reflect on it alone.

If you need to you can break it up into two half days, but I wouldn't do less than that. People get very personal, talking about what's working and not, how that's affecting their personal life. You don't want to cut that off.

Sometimes when managers suggest direct reports fill out a personal development plan process feels very "blank sheet" like go away and come back with what you want do in three months, six months, nine months. That's really hard for people to do especially if they are early in their career. The good thing about this process is it has very specific questions that help lead you to figure out the bigger vision.

As a manager or some one who knows them well, like a mentor, you probably have information to add.

You go through their answers and say things like, "You said that you really like working with these people, but you didn't mention this person. Do you also like working with that person?" or "Have you thought about this kind of profile of a job?"

Make sure you do this exercise! When you review this with someone and look at what they marked green and red for their actual calendar, the themes of people and projects they like working with and do not like become very clear.

Often people end up with two or even three profiles of the "perfect job." And that isn't necessarily bad. To give an example for myself, at one point when I was going through this, I had two profiles. One was a group product manager director role, and the other was an individual contributor role, a principal product manager role at a bigger company. I had previously been in leadership roles but I was starting to think I might be more happy in a later stage company in a very senior IC role. In the end I interviewed for both roles, and ultimately decided to like pursue the Principal PM path with Gopuff and I'm really glad I did.

After you do this exercise, go talk to people that are in those profiles. That will help you figure out which one is really the right path for you right now.

You definitely have to have like a foundation of a good relationship to do this. If I was an employee and I didn't have a good relationship with my manager, I actually wouldn't ask my manager to do it. I'd ask a mentor or someone who I really had a close relationship or respected.

Priya Mathew Badger

This document is something to help people who are feeling stuck in their careers or roles figure out what's next. I've found this can help re-energize employees and align manager-employees on their career path.

 is your career goal (totally fine if unsure!)

What are you really good at professionally?

What are you not good at or not interested in doing professionally?

Look at what you’ve done thus far in your career

What accomplishment are you most proud of?

What was the biggest low point in that time?

What did you dislike about this phase/role?

Print out your calendar for the last 3 months

Highlight the days/meetings/activities where you were most happy/engaged

Highlight the day's/meetings/activities where you were most unhappy/unengaged

Of all the people you’ve worked with, list the people you’d most want to work with more and why

List the people you’d like to get some distance from if possible and why

Imagine we’re at your retirement party. What do you want people to say about you? Write a paragraph

Pretend your profession is like a company and write down your professional mission and core values.

How many people do you know well or to what degree do you know what it’s like to be one of these roles outside of [your company].

Identify 2-3 roles / profiles of roles you think you would like and list below

Rate each of these role rate them twice. 1 = strong no 4 = strong yes

The first rating is how much in depth knowledge of these roles/careers OUTSIDE [your company] you have. To what degree do you know what a career in this direction looks/feels like and what skills it demands?

The second rating - rate each 1 to 4 on how much you could see yourself in that role.

(knowledge rating =__ , interest rating = __)

Near term, what are the key buckets of work in the next 2 months? Rate each for impact and happiness. 

Career Retreat - Prework

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