Career Conversations

This document is based on my experience in different companies and the templates I used there

Life Story

(this will help me know you better and understand the type of challenges you like, your motivations).

Tell me in 10 minutes about your career so far. 

• What jobs did you enjoy the most?.

• Where did you learn more and why?.

• How and when did you know it was the moment to change career? (if applicable)

• Tell me a challenge you are proud of.

What do you seek in your career?

(This will help me understand your motivations, for example. If you tell me that you want to be a Tech lead or a manager, that's useful information but it's more important to understand why, what motivates you. In this way I can guide you, I can give you opportunities and help you because becoming a manager or tech lead is the final outcome of a long process).

• Desire to influence

• Desire for authority

• Desire for prestige / acknowledgement / appreciation / status

• Desire for growth & mastery

• Desire for autonomy

• Desire to do something meaningful

• Compensation

Short-term

• What is it about working at Company  that still appeals to you? What challenges do you continue to face?

• What excites you most about your role? What would you like more /less of?

• How does your role today link to your future goals?

• What new skills would you like to develop?

• What opportunities are you aware of?

• How do you enjoy working with this team? (Address any issues that may come up.)

• Are you still learning and growing in this role?

• How can I make this current role more interesting/challenging for you? 

• How can I best help you in your current role?

Long term 

• What type of opportunities are you looking for?

• What task or project type would you like to do more frequently in the future?

• What does ultimate success look like for you in the next year? What about three years from now?

• What do you see yourself doing 3-5 years from now? 

• How do you plan to get from here to there?

• Do you see yourself staying at Company? If not, how can I help you ?

• If money or your current skills weren't an issue, what would be your dream role?.

If you had to choose one thing, what would it be?

(Using grow)

Goal: What do you want?

Establish what the team member really wants to achieve with their career.

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Sample questions to ask:

• "Where do you see yourself in one, five, and ten years?"

• "What are your interests, values, and motivations?"

Reality: What's happening now? 

Establish the team member's understanding of their current role and skills.

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Sample questions to ask:

• "What are the most rewarding or frustrating aspects of your current role?"

• "Do you feel challenged or stretched in your current role? What would make it more challenging? What isn't challenging you?"

• "What feedback have you received from other people on your strengths and weaknesses?"

Options: What could you do? 

Generate multiple options for closing the gap from goal to reality.

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Sample questions to ask:

• "What can you do right now to further develop skills that would be useful in reaching that goal we talked about earlier?"

• "What stretch assignments, big projects, or experiences could you pursue?"

• "What networking or mentorship options are there?"

Will: What will you do?

Identify achievable steps to move from reality to goal.

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Sample questions to ask: 

• "What will you do? By when?"

• "What resources would be useful? What skills will help you get there?"