Whether you’re well on your way career-wise, or you’re just starting out, the right mentor can have a profound affect on your career and life choices.

While you may not always make the same decisions as those who have gone before you, the insight from experienced women, both from inside and outside your current industry, can be invaluable when it comes to navigating the various decisions you’ll have to make along the way. Listening and trusting in the advice from a mentor can help you learn from their successes, and from their mistakes, which can often be just as important.

Login to our member site (or join, if you haven’t already), and browse through our roster of professionals from all industries, and from cities across Canada. When you find someone who you think might be able to share some insight that is useful to you, don’t be shy: reach out through the site and arrange a meeting. With mentor/mentee relationships, we advise in-person meetings, adding a personal touch that can’t be achieved through messaging alone, but you can approach it any way you like. To help you get started, we’ve created a cheat-sheet of questions to ask, that should prompt some enlightening discussion, and almost certainly result in some terrific stories from earlier in their career. Meet over coffee (or drinks, if you prefer) and let the conversation happen naturally. Most of the women you’ll meet will be more than happy to share their thoughts with you.

Here are five questions you can ask your mentor to get you started:

1. How did you decide on your current choice of career?

Rather than get into the nitty-gritty, start with lighter question; one that will provide some background on their career choices. Some variation of “How did you get started?” will provide you with a history of where they are coming from, and give you a better idea of who they are. For example, where did they go to school? What did their parents do for work? Where else have they lived and worked? These follow up questions will help you to understand the breadth of experience that your mentor possesses, and might serve as either a dose of reality or a breath of fresh air when compared to your own path.

2. What was the single best decision you ever made regarding your work or career?

This another light-hearted question, but one that should help your mentor open up and share more detail about their choices. You and your mentor might be at the start of a long and lasting friendship, but a question like this will make great use of the time you spend in this first meeting.

3. What has been the biggest challenge you’ve encountered?

Now we’re getting into the really good stuff. The answers you get to this question could be very eye-opening indeed. Maybe they’ve experienced a difficulty that is similar to something you’ve been through, or maybe they’ll spare you from a hardship that is easily avoided. Either way, this question alone is worth your time, and the cost of coffee or lunch, as the case may be, and then some.

4. If you could do it over again, what would you change?

One the surface, this question might seem similar to the one above, and the answer you get might be connected, but it is entirely different. Your mentor might have had to overcome challenges and hardships, but they might be grateful for the learning opportunity those tough times presented, and have no regrets at all. Asking this specific question, and even clarifying what you mean by it, can open up a whole different set of insights that could prove very useful. For example: would they have chosen a different major in university? Maybe they would pursue a relationship with a mentor sooner (now they’re learning from you!) or choose different jobs in their work history to gain valuable experience. Maybe there’s an embarrassing moment or two in their past that they would like to relive in order to make a different decision? At minimum, this question should prompt a great story, and at best it could save you years of career development by learning from their experience.

5. If you were me, what would you do about (X)?

Even if your mentor is not from your industry, this question could prove valuable. There’s a reason you’ve chosen to pursue a relationship with a mentor, and it’s probably because of a specific goal or challenge you’re facing. Must you follow the advice they give? Absolutely not, but their insight could be extremely helpful when it comes to forging your own path. Having the background and insights from the previous question, you also now have context for the response they give. Whether or not you agree with their advice is besides the point— the real value is in having an outside perspective; another way of looking at your problem, challenge or decision than you might have considered. For this reason, a mentor doesn’t need to be from your exact industry, and over time you might find that insights from people outside your circle with different backgrounds can prove helpful.

While the above questions might seem like they formalize the relationship you have with your mentor, it’s best to make great use of the time you have, so both of you can get value right away. Remember, your fellow members are motivated to help you as well— to give back and share their knowledge. Don’t hesitate to reach out and ask for help, as you might be surprised how many people are willing to share, and be a massive help as you navigate your career.

Want to get started now? Join or login and find a mentor now.

Sign up now for free