Questions All Good Leaders Should Ask Pt. 1

Generally speaking, asking rather than telling makes for a better leader and a better experience when trying to mentor team members. Asking is interactive and exploratory.

What does your success look like? This is a great question—while it is just another version of “where do you see yourself in five years” or asking what someone’s goals are, it might feel a little less cliché. And it can be used either to refer to broader long term goals or specific situation the team is currently facing.

Really it can be used in so many situations. Even if a team member is having what constitutes a small problem asking them, “what does success look like to you?” in that scenario can help them visualize the finish line and what it’ll take to get there.

Albeit is similar, “what outcome do you want?” is another good question that leaders ask. This question is good for when there is more than one successful outcome or solution. While the previous question suggests a single answer and action plan, this question suggests there maybe more than one.

If your team member is having a particularly hard time with a situation this might be the best question to ask to help them see it from multiple perspectives.

Again, while similar, the shades of difference allow for a different discussion when we ask a team member: what do you want to change in five years? It focuses on a long term goal but also suggests that along the way that goal will require change or growth. This is about creative thinking and how the team member wants to grow along with the field they find themselves in.

A great follow up to any of the previous questions is: what obstacles are you facing? This allows the team member a chance to ask you the leader for some insight on overcoming those obstacles. Be aware some team members might not want to share what troubles they are having or might not have really thought them through. Asking outright might be difficult but it allows the leader to explore those challenges with the team member.

Most of us know our weakness but are not comfortable recognizing them for ourselves or speaking about them with others.


A mentor is someone who is a trusted counselor or guide; a tutor or coach. It is often used the context of someone more experienced teaching, helping, or guiding a less experienced protege. If someone is being mentored they are the mentee.

Mentoring becomes a partnership between the two parties where one will impart their skills to the lesser experienced partner.

To become a mentor, you should have want to share your knowledge with others, encourage and motivate them, be willing to invest your time, be readily available to answer questions, and figure out if you are the correct mentee for them.

You can figure out how to meet whether it’s in person or via something like Skype or Facetime. You will need to figure out the frequency of your meetings as well. You may want to limit the time frame of the mentoring relationship as well. Remember to keep your meetings confidential.

When you’ve reached the end of the mentoring relationship, you may want to encourage your mentee to go on and become a mentor him/herself.