16 Questions to Help You Build a Better Relationship with Your Boss (or anyone else)
These go a little deeper than, "Um...can I have next Friday off?"
Usually, people have a fairly one-way relationship with their boss. It doesn’t have to be that way. Leadership doesn't have to happen from the top-down. In the best companies, leadership lives everywhere.
There’s a couple of key skills that are crucial for leaders to unlock the everyday genius in their teams. One is the ability to build mutually beneficial personal relationships with people and the other is curiosity - the ability to ask great questions.
I’ll talk more about those in future posts, but suffice it to say, that great questions contribute to building great relationships.
Getting to know your boss on a deeper level doesn’t just benefit you. It benefits them. Asking them generative questions helps them surface their own wisdom, redirects their attention and energy from all the problems they face and gets them thinking about new possibilities. And that’s what leadership is all about, regardless of where your box on the org chart happens to fit.
QUESTIONS TO ASK RIGHT NOW
What’s a lesson you’ve learned during your career that stands out as particularly important? How did you learn it?
What’s a professional challenge you’ve faced that’s shaped how you lead today?
What do you love doing most day-to-day?
Imagine I’m exceeding your highest expectations…what are a couple of important things you’d be able to direct more attention to?
What’s a meaningful experience you’ve had with a co-worker and what made you choose that one?
What makes you choose to lead others?
What are doing when you’re at your very best? When do you feel the most energized at work?
How do you bring out the best in people?
When is a time you’ve been really happy for someone else?
What are a few of your biggest aha moments and what did you change as a result?
What’s a belief you’ve changed your mind about and what caused you to change it?
If our team was exceeding your highest expectations, what would be happening?
What are 2-3 things you see working well on our team right now?
Where are you seeing our purpose, mission and values being fully lived?
What’s are the most important personal characteristics or strengths you look for when hiring someone?
What’s something you’d like people to understand about you or job?



This is a useful list. I think that often people are too focused on trying to impress or demonstrate what they know and that can hijack the potential for deeper relationship building if you aren’t careful. Personally, I will make a habit of incorporating these kinds of questions into the conversation. Thanks for sharing...
Number 12 is my favourite.