Your first 1-to-1 is quite possibly the most important meeting with your direct report and will set the tone of your relationship going forward. Take this opportunity to really get to know them and dig into what they are looking for out of their role and career.
My recommendation is you want to aim to be professional and empathetic, while still letting your personality carry through.
Before you get into the questions always introduce yourself and your background! This seems simple and obvious but if you miss this it’ll be harder for them to open up to you when they don’t know anything about you!
For these questions it might help if you give a quick related anecdote or even a quick related personal answer. Don’t take too much time doing this because this meeting is about them not you. In order to get people to show honest vulnerability you need to show it yourself first.
What is currently the current top priority in your life?
What is currently the current top priority in your career?
Imagine your life and career in 2 - 3 years. What do you want it to look like?
How would you describe your personal values?
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Values
Here’s a list of values you can use to prompt with as it is sometimes easier for people to pick from an existing list.
Ask them to select 4 words from this list that resonate with them, but also add that they can come up with their own word(s) if they have them in mind.
integrity, honesty, accountability, compassion, courage, creativity, respect, fairness, excellence, loyalty, patience, wisdom, cooperation, autonomy, balance, determination, empathy, gratitude, humility, inclusivity, innovation, justice, kindness, leadership, mindfulness, openness, perseverance, reliability, resilience, service, transparency, trust, adaptability, ambition, authenticity, connection, curiosity, dependability, discipline, efficiency, flexibility, growth, harmony, independence, learning, optimism, purpose, quality, responsibility, security, simplicity, sustainability, teamwork, tradition, vision
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What is currently your most important career goal?
How can I best support you to achieve your career goals?
What gets you up in the morning?
What do you like to do in your free time?