Check-In Like a Boss: Six Questions to See Your Leadership Clearly

Once you begin asking for feedback with confidence, the natural next step is to ask yourself the same kind of questions. A check-in keeps you grounded in what’s working and aware of what needs attention. If you missed the first post in this series, you can read it here: Ask Like a Boss: How to Seek and Give Feedback That Builds Trust

A check-in is not a critique. It is clarity. And clarity gives you the freedom to lead with more intent.

Here’s a set of questions that help you see your leadership through clearer eyes.

1. What do you see as my key strengths as a leader?

Start with what’s right. Naming your strengths reminds you where your confidence lives and helps others talk about what they value in you. Leaders who know their strengths lead with more intent.

2. Where have you seen my leadership make a positive difference?

A recent example shows you when your leadership landed well and how it helped. Impact is rarely felt in the moments we expect.

3. Where do I tend to get stuck or get in my own way?

This is not about fault. It’s about pattern. If someone can point to a moment where this shows up, even better. Seeing where you get stuck helps you move with more clarity next time.

4. What have you noticed about how I generally show up?

Every leader has a way they are experienced by others. It might be calm under pressure, quick thinking, or stepping in when someone looks lost. This question invites a view of the traits people widely recognise.

5. If someone new asked what I am like to work with, what would they hear from others?

This is your leadership reputation and impact. The story people tell about you when you’re not in the room. Check whether that story matches the kind of leader you are working to become.

6. What is one shift in my leadership that would make the biggest positive difference?

This question invites honesty paired with hope. It is forward focused. It keeps the conversation on improvement rather than evaluation.

And when you ask these questions, ask more than one person. One person gives you an opinion. Three or more give you themes. Themes are where the real insight lives.

A check-in like this helps you see yourself clearly, lead with more intent, and model the openness you want from others. Because great leadership isn’t about having all the answers. It’s about staying curious enough to keep asking better questions.