Mentoring relationships

How to discuss sensitive topics in a mentor meeting

Are you finding that your mentoring conversations are getting into some serious waters? Here are 7 tips for sensitive mentoring topics.

Phil Norris

Published on 

June 16, 2022

Updated on 

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Workplace mentoring has become increasingly common in recent years, with research finding that 70% of Fortune 500 companies now have a mentoring program.

It’s not hard to see why.

Mentoring plays a key role in employee retention strategies, with 81% of millennials prepared to stay with their employer for 5+ years when they receive mentoring, according to Deloitte.

And it has a host of other benefits, from supporting employee development to increasing engagement. Nine out of 10 employees in one study say having a career mentor is a source of job satisfaction. But the mentor-mentee relationship isn’t always a perfect fit, especially when there are sensitive topics to discuss.

That doesn't necessarily mean the relationship is set up for failure. Follow these seven tips for dealing with sensitive issues in a one-on-one mentor meeting.

Allow the other person to share their feelings

Human nature can be a real detriment to an effective mentor meeting.

For many of us, our desire to empathize and make people feel better about difficult situations leads us to share our own thoughts on a subject.

Sometimes, we’ll try to put ourselves in the other person’s shoes. How would we feel if the issue they’re describing happened to us?

We might even take things a step further by sharing our own experiences of that issue, or a similar one.

Problem is, that’s not a very helpful response. When we take an issue and run it through our own experiences and biases, our perspective becomes warped. We can never truly understand how anyone else feels about anything because we’re not them — we’re us.

So don’t even try. Rather than responding with an anecdote from your own life — or even worse, trying to play devil’s advocate — simply take the time to listen.

Ameet Mehta, the CEO of SyndicationPro, a Real Estate Syndication Software, leads a top-notch team of sales and marketing professionals. The backbone of their performance is mentorship and Ameet argues that the best way to mentor someone is to not tell them what to do, but be a sounding board:

“A mentor should be someone with whom the mentee can bounce ideas. This includes being a sounding board for both good and bad ideas. It is important to provide honest feedback and help the mentee see different perspectives.”

Give them the space to share how they feel, asking questions at appropriate points (i.e. without interrupting their narrative) to give you a fuller understanding of the issue at hand. 

Only offer your own take on things if they specifically ask for it. And even if they do ask, make it clear that the most important thing is how they feel, not how you would feel in the same situation.

Add structure to your mentor meetings

For many people, half the battle of discussing a sensitive topic lies in figuring out the best way to introduce it.

Should you wait for a lull in conversation? Blurt it right out at the start of a meeting? Leave it until the very end, when you’ve covered everything else on your agenda?

That’s why it can be helpful to build some structure into your mentor meetings. Not so much structure that it stifles the natural flow of conversation, but enough that both parties understand when and how to raise difficult subjects.

Ideally, try to find the time early in the mentor-mentee relationship to set expectations around meeting structure and clarify when one person should speak and the other listens.

Anup Kayastha, founder of, an intuitive tool to compare heights between people or objects, holds that building accountability into your meetings is paramount.

“It is essential that you have some kind of accountability system in place. It's easy to get distracted by work or other commitments, so set up check-in times during which both parties check in on how things are going. This will help keep everyone on track and ensure that everyone feels heard.”

Make it clear that after one party speaks, the other will get their opportunity to respond or ask questions. That way, there’s no risk of interruptions, which makes it easier for the person discussing the sensitive topic to fully explain how they feel.

Also, set parameters around the objectives of your mentoring sessions and what the mentee hopes to achieve from attending them.

Fact is, mentoring isn’t really about giving the mentee specific answers to the problems they’re facing — it’s more about giving them the skills to solve their own problems.

When both parties understand that the other isn’t going to try to “fix” them, it gets a whole lot easier to speak about difficult subjects.

Leave space to build a trusting relationship

What does it take to build a successful mentor relationship?

Clearly, there are lots of elements involved. But one of the most important is about how the relationship begins and develops over time.

Per Olivet Nazarene’s research, the overwhelming majority of mentor-mentee relationships start out and develop naturally, with neither party making the first move.

How did the mentor-mentee relationship start?  A study by Olivet Nazarene University
Image source

When these relationships are given space to develop over time, they are more likely to feel mutually supportive and beneficial. And there’s also likely to be a greater feeling of trust between mentor and mentee.

Think about it. Would you find it easier to discuss a sensitive topic with someone you’ve known for years, attended team-building events with, and who you feel has your best interests at heart? Or someone with whom your relationship is purely formal?

A lot of people would choose the first of those two options.

Of course, there’s nothing intrinsically wrong with a more “artificial” mentor-mentee relationship, in which one of the two parties asked the other to get involved.

But in those cases, it’s arguably even more important that the relationship has time and space to grow.

The stronger the bond between mentor and mentee, the more trusting the relationship will be, and the easier it will become to tackle sensitive or challenging issues.

The more you listen the more trust you build into your mentoring relationship. As the relationship grows the more sensitive the topics might become. 

For example, your mentee might confess that they are ready for a career change, and it would seem natural to them to seek your advice. Be prepared to tackle these questions openly, including admitting that you feel conflicted if you don’t see a path for them within your current firm.

Ensure mentoring sessions aren’t rushed

Sticking with the issue of time, no one wants to feel hurried when it comes to raising a sensitive topic.

We might prefer to ramble, tell an unrelated anecdote, or build up to it in stages.

Clearly, that becomes a lot more difficult if your mentoring sessions only happen sporadically, or are squeezed into tight time slots between multiple other meetings.

Clearly, this is an issue for a lot of mentees, with two in five saying it’s “fairly” or “very” difficult to get time with their mentor.

How difficult is it to get time with your mentor?  A study by Olivet Nazarene University
Image source

It’s easy to see why.

Between your daily standup meeting, your weekly KPI review, and your monthly one-to-ones, that doesn’t leave you with a whole lot of wiggle room.

But mentoring sessions are precious for mentee and mentor alike, and they should be viewed as such.

To foster an environment in which each party feels comfortable tackling sensitive topics, it’s absolutely vital that mentor meetings aren’t treated as inconvenient or non-essential — something that can be moved or canceled at the last minute because something else came up.

If the mentee doesn’t feel confident that their next mentor meeting will actually happen as planned, there’s little incentive for them to plan out talking points. That means there’s much less chance they’ll feel comfortable raising big, difficult subjects.

Do your homework

As either a mentor or mentee, it’s simply not acceptable to be uneducated on so-called “challenging” issues, such as culture, race, religion, and sexual orientation.

Just as you might learn a new hard or soft skill to further your career, you should also give yourself the time to read up on those issues (and lots more besides).

Sure, you can’t be perfectly prepared for every single conversation that might crop up.

But whatever your role in a mentor meeting — whether you’re the one raising a difficult topic, or the one who needs to respond — you should have the knowledge to discuss it in a sensitive manner.

Simply put: the better informed you are, the easier it becomes to speak about sensitive subjects.

Look out for your own wellbeing

Fact is, it becomes easier to deal with challenging topics if you’re in a positive frame of mind at the start of a mentor meeting.

On the flip side, if you’re carrying a bunch of external baggage into a session, even relatively innocent topics can become tough to talk about.

Obviously, everyone has good days and bad. Sometimes, the way you feel is simply out of your control. But there are positive steps you can take to influence your physical and mental wellbeing, such as: 

  • Signing up for your organization’s wellness program, if available
  • Making time for daily physical activity
  • Maintaining a healthy diet
  • Leading an active social life
  • Giving yourself time to relax during a busy week

None of those factors is a “silver bullet” that will guarantee you always feel completely prepared to discuss sensitive topics in mentor meetings.

But by prioritizing your own wellbeing, you’ll be better placed to support your mentee (or mentor) when they encounter a challenging situation or have something difficult to talk about.

This goes for your mentee as well. Sometimes those we mentor are hyper-ambitious and want to grow fast. This can lead to lots of commitments and a fast track to burnout. In these situations, a mentor can be an anchor to remind their mentee what’s important. 

Arthur Worsley, the Founder of The Art of Living, a website that helps top performers lead happier, more balanced lives, and a former McKinsey Associate shares that his top mentoring strategy is helping mentees focus their energies:

“I once recommended to my mentee that he take a break from learning new skills for a little while, and instead focus on honing the skills he already had. This is something that many of my employees struggle with—they think they have to learn new skills all the time in order to stay competitive in their field. But if you stop learning new things for a while, you'll actually be able to pick up on them faster when you do start again, which is exactly how it turned out for my mentee!”

Remember, the agreement is not the goal

The purpose of a mentor-mentee relationship isn’t to get both parties 100% aligned on every issue they discuss.

After all, you’re both professionals, with your own skills and experiences. There’s no reason to think that you’ll agree on absolutely everything.

Not only that, but simply getting the other person to agree about a sensitive issue doesn’t necessarily do anything to solve that issue.

Imagine you’re a mentee. When you’re bringing a sensitive topic to the table, you want the opportunity to discuss it fully — to understand how you feel about it yourself, and to potentially identify some appropriate courses of action.

As such, it makes little difference if your mentor agrees with your viewpoint on the topic. What matters is that they give you the space to speak and the tools to move past it.

Wrapping up

By their very nature, sensitive topics can be difficult to discuss.

But that doesn’t mean you should shy away from them — far from it.

In reality, the ability to cover difficult ground in mentor meetings is a sign of a successful mentor-mentee relationship. The more you do it, the easier it becomes, and the greater the trust between mentor and mentee.

Far better to tackle the occasional difficult conversation than to only ever talk about superficial subjects that don’t truly benefit either party.

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