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Career Coaching Questions
Table
Motivation 🚀
What do you look forward to most when you come to work? What parts of your role would you like to spend more time doing?
“I really enjoy when I’m able to go deep on a problem uninterrupted and explore the data to uncover potential insights.”
Motivation 🚀
What sucks your energy at work? What part of your job feels most like ‘work’?
“I really find the meetings where we need to check in on meeting progress draining.”
Motivation 🚀
What are you really good at, but never want to do anymore?
“I’m really experienced at Project Management, but it drains me.”
Motivation 🚀
What drives you to succeed?
“I want to make my parents proud.”
Goals 🥅
Imagine yourself in three years. What do you hope will be different about you then compared to now?
“In 3 years, I want to be managing a large team.”
Goals 🥅
What is your progression goal in 6-12 months? How will you measure success for that?
“I’m really hoping to transition into Product Management by the end of the year.”
Goals 🥅
Tell me about your ideal next role. What characteristics does it have from a responsibility, team, and company culture perspective? What characteristics does it not have?
“In my next role, I hope to be owning a product and managing a small but senior team. I hope that the role doesn’t include too much travel.”
Reality 🪞
What are the three most important characteristics of the role you want to get into? How would you stack rank yourself from strongest to least developed among these traits from 1 - 5?
“As a PM, I think I need to develop Project Management, UX, and Product Sense. I would rank myself as 5, 3, and 1 respectively.”
Reality 🪞
What constructive feedback have you gotten in the past that you’re working on? What areas would you like more feedback on?
“I’ve gotten feedback that my follow up emails need to be more concise, but I feel pretty good about that now. I’d love more feedback on my executive presence.”
Reality 🪞
How might you get better feedback about this skill? Who can you ask? How will you ask?
"For example, I could send a feedback request form to my 3 closest colleagues telling them I want to develop XX. Please can you give me 1 - 2 pieces of feedback on how I’m doing and how I can improve?’
Options ⚖️
Let’s brainstorm the options. What are some of the ways you know of to develop that skill?
“I saw a course on project management. There’s this book that I’ve been recommended. I could take our Head of Product to coffee...”
Options ⚖️
How could you apply that skill in your current role? What projects in our team would allow you to explore that skill?
“There’s a project where our product team wants someone from our department to collect feedback. That would help me develop product sense.”
Options ⚖️
What gives you anxiety or stress about these pathways? What might prevent you from being able to achieve this?
“I’m worried I’m not technical enough to take on that project. I’d be afraid of getting in over my head.”
Options ⚖️
Who’s really good at this that you admire? How might you learn from them more?
“I’ve seen Sally in Finance do this really well, maybe I can take her to coffee?”
Work 🏋️♀️
What are the specific actions you’re going to take between now and next time we meet?
“I’m going to send a request for feedback, I’m going to go to coffee with another PM, and I’m going to offer to support on XX project”
Work 🏋️♀️
How will we track progress? How will we know once that skill is developed?
“I’ll have 2 really specific examples of how I’ve used that skill to drive an impact that I can use in an interview for my next role.”
Work 🏋️♀️
Imagine you’re not able to make progress between now and next time we meet. What would be the main reason? How can I help ensure that doesn’t block you?
"I have a lot of projects coming up this month... I might not be able to find time to make this all happen. I could use your help prioritising what needs to be delivered on time and if there are any that could be pushed or delegated?
Work 🏋️♀️
What actions do you want me to take to support you on this?
"You could have a conversation with the Head of Product and see if they have any products launching that I could help test and give feedback on.”
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