Questions to Ask A New Mentee

Building mentoring relationships can take time but if you’re looking to get a good start on that process then the best thing you can do is ask the right questions up front. By learning more about your Mentee and their goals, you can not only make better plans about the work you’ll do together, but you can also use that information to motivate and inspire them forwards.

With that said, let’s take a closer look at some of the best questions you can ask in your first Mentor meeting and how those questions can make a big difference.

Establishing Expectations 

As a Mentor, first impressions are important. When your Mentee comes to you, they’ll probably have an idea in mind about what they’re expecting to get out of mentoring. Even if it’s just a vague idea, it’s good to learn that up-front so you can ensure that the time you spend together will really help them get where they want to go.

On the other hand, they may start out with expectations you simply can’t meet. Perhaps they think that you’ll be able to use your contacts to get them a job straight away with little to no work on their end. These cases are rare but it’s nonetheless important to recognise them as soon as possible, giving you the chance to gently let them down and give them a clearer and more realistic idea of the real road to success.

Understanding Aspirations

When building mentoring relationships, it’s hard to underestimate the value of really getting to know one another. That’s not to say you and your Mentee will become lifelong friends, but that it always helps to know about their long-term aspirations.

For example, they may have come to you so that you can help them secure the same job role you’re currently working in, but is that the job they really dream of? Perhaps they see this role as a stepping stone to some further ambition? Knowing that further ambition will help you offer honest and clear advice about how they can best tailor their career progression to a long-term approach.

Analysis of Current Career

If you want to know where you’re going it’s important to look at where you’ve come from. Asking about a Mentee’s current career history can tell you so much about who they are and how they work. After all, there’s a reason that previous roles are one of the most important parts of a CV.

That being said, it’s important to come to their career history from a non-judgemental mindset while still providing realistic advice.

What does that mean in practice?

If you’re a CEO/former CEO and your Mentee comes to you hoping to one day occupy that role, then that’s a great aspiration on their part. All the same, it’s also quite an ambitious task for anyone to start out on, even with advice from an expert.

If they’ve got years of experience in various managerial/executive roles then they might reasonably be on a path to achieve that with some well-targeted guidance. If they’re twenty-one and their only work experience is flipping burgers then it’s going to take some more work. That’s not to say they can’t become a CEO – only that it’s going to be a longer and more challenging road for them.

When building mentor relationships, it’s important that you’re both on the same page about these things so that together you can set reasonable, achievable goals. 

Assessing Drawbacks

With all the good will in the world, it’s worth noting that there may be times when your Mentee has serious drawbacks that could get between them and their chosen career role. A Mentee seeking to become an accountant, for example, is going to really struggle if they’re the kind of person who’s afraid to do difficult maths.

Once again, this isn’t an insurmountable problem, but it is a real and meaningful issue that your Mentee will have to work through sooner rather than later. Understanding these drawbacks helps Mentors to bring structure, aligning goals in a meaningful order. Put simply, if your Mentee doesn’t have the skills to do the job yet then all the networking in the world won’t help them.

Aligning Visions For the Best Results

It’s no bad thing to have a roadmap, even if you ultimately decide to change it later on. With shared, united goals, you and your Mentee will be in the perfect position to really achieve something special. Without those aligned visions, you may even find yourselves working across purposes, your Mentee tugging in one direction while you try to pull them in another.

As in all relationships, communication is the true key to success and the sooner you start communicating, the sooner you’ll see real, incredible results.

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