Repetition can be a beautiful thing. Hopefully, your boss is asking you questions regularly. If your boss has the heart of a teacher and the wiring of a coach, he or she is asking you questions about your approach, your performance, your dreams, and more. For you to grow in your capacity as a leader, questions cannot be a one-way street. I have come to realize there are a few things I need to repeatedly ask if I hope to grow in my organization and continue to add value to our teams.
When it comes to coaching the people I lead, I have a few “on hand” questions I ask regularly that serve as a conversation starter in one on one meetings. More often than not, I only make it through a few of them before we are off to the races, but a set list is helpful to provide a framework for development.
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It also helps to bring predictability to our meetings. For those who have noticed the pattern, they know a few things I am always going to ask, and can come prepared. If you’re looking for a primer on coaching people you lead, here’s a great resource.
One of the things I’m trying to work on is doing a better job of asking questions of my boss. In one of my recent one on one’s with him, I realized I don’t have a set list of questions I bring to him. These meetings are still incredibly productive, but I want to be better at my job, a more valuable part of our team, and constantly aware of what he is seeing from his perspective.
So, I’ve been working on a list of questions I want to rotate through. I may not ask these every meeting with him, but here is the list of questions to ask your boss to grow as a leader.
Here are the five questions I’m going to ask my boss regularly (and a few alternates, as well).
Where are we going?
This question applies in the immediate context as well as the big-picture perspective. Where are we going as an organization? What is the end goal? What does success look like?
If your boss would say, “We’re going to have the most donut shops in the tri-city area,” but you thought you were aiming to be the best gourmet destination donut shop, those are vastly different trajectories.
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Hopefully, your boss is constantly reminding you of the vision, but that may not be your situation. Find out where your boss sees your organization going, and think through how that should influence your approach to your job.
What do you see as the biggest threat _______?
This question has a few different layers, and all of them may serve to be important.
What does your boss see as the biggest threat to your performance? What is encroaching on your time that you don’t even see?
To our team?
Assuming you work in a team context, what is the biggest threat to the dynamic and growth of your team? What does your boss see as being something that could be detrimental if not addressed? It may be something tactical, relational, or strategic.
To our company?
You may be less able to see the potential threats to the organization, but that does not mean you’re less able to address them and help position your company in a way to be ready to take on something lurking on the horizon. What are the things happening either internally or externally that could pose a threat to the company as a whole?
To our industry?
This takes a step further from practical and more into theory. What are the things that are current or future threats in your industry overall? Are there things happening at a systemic level that, if unchanged, could totally alter the way your industry functions? Are there new players coming into the fold that are going to force adaptations? What can you do in your company to be ahead of the curve?
Where do you see me going?
Where do you think I will be in ten years, and the natural follow up processing of figuring out what it is going to take to be ready. Does your boss think you’re on the right path in your company? Do they think you’re at or approaching your leadership ceiling as things stand? From their perspective, what does the proverbial writing on the wall say about what’s to come?
What do you see me missing?
It’s easy to get tunnel vision on what I am supposed to be doing, and not have a big-picture perspective on what I could be doing. I need my boss to bring some vision into my blind spots, or some light into the shadows of my leadership.
Nothing good grows in the dark. Let your boss bring some illumination.
Where are my blind spots? What are the things that I do that I shouldn’t do? What are some things I think I’m good at that I need to work on? What are some things you’d like to see me delegate? Over the next year, what competency do I need to improve on to grow? Have I dropped the ball lately? Am I missing expectations?
What can I take from you?
My boss has wisdom, strengths, and connections that can greatly benefit me in my leadership development.
What competency can you help me improve? Who could you introduce me to that would help me improve? What piece of our vision do you see me missing? Were you in my shoes, what would you do differently, and do I have the freedom to disagree? What’s one book we could read together over the next month?
Here’s a summary. Feel free to copy & paste this list into Evernote, expand on it, and make it more helpful in your relationship with your boss. My hope is that your boss’s desire is to see you grow. If that’s the case, asking these questions with a little frequency will help you stand out as a leader looking for ways to grow, and deserving of more development.
Five Questions to Ask Your Boss
1. Where are we going?
2. What do you see as the biggest threat?
3. Where do you see me going?
4. What do you see me missing?
5. What can I take from you?