Mentoring remains a powerful catalyst for leadership growth, but its success depends on commitment, communication and trust. From setting expectations to listening attentively to offer honest perspectives, mentors create an environment for reflection and contemplation rather than trying to provide straight answers.
In Criticaleye’s most recent CEO Research, an overwhelming 92 percent of respondents said that mentoring had a positive impact on their own capabilities as a leader.
However, it is something that requires openness and a degree of mutual respect and understanding on both sides. Across the following conversations, we discuss the importance of leaving ego behind, preparing with purpose and approaching the relationship with humility and generosity.
I've worked with my mentor for four or five years. I'd give a different answer every year about the benefits and I think that’s sort of the point. If it was akin to training, you'd go on a course, or have a coach, and there would be a set goal. At the end, you would shake hands and either you’ve achieved the goal or not, whereas mentoring – by its nature – has to be flexible.
It has supported me through significant changes in my career. For example, two-and-a-half years ago, when I was promoted into this role, I made the naive assumption of thinking an MD role was the same as being a regional MD, which is absolutely bonkers. I laugh now thinking about it, but I was able to bounce things off my mentor, sharing anxieties and worries.
A really good mentor should at no point tell you what to do; they’ll mentor through questions. It's not a transaction or a one-way conversation. The mentor also needs to put themselves back in the mindset of the person in front of them, and I think my mentor has done a really good job of that. It's easy to forget how insecure you were and what you didn't know; I think it's important that a mentor remembers [that] the person in front of them is carrying a lot of insecurities and will be looking up to them.
It's the best thing I've ever done career-wise. Genuinely, I'd say that to anybody who asked. I certainly don't think I'd be in the role I am now without it.
Set Clear Expectations and Listen Attentively
Ana Dutra, Independent Board Director, Pembina Pipeline Corporation and Board Mentor, Criticaleye
Mentors don’t make assumptions, they ask good questions ... born from the desire to understand where our mentees are coming from and with a genuine intention to help. Questions that blend compassion and – occasionally – tough love. Then we invite our mentees to contemplate options. We provide examples, insights and foresight.
When I was a young mentor, I was more eager to ‘provide answers’ and prove my ability to solve problems. That not only impacted my ability to listen but also didn’t acknowledge the fact that sometimes mentees are not looking for answers, they just want a safe space where they can feel heard, supported and appreciated. I now ask upfront what a successful mentor-mentee [relationship] will look like, what the mentee expects to get out of the programme and what he or she is willing to commit to. Once we are aligned on our mutual expectations, the likelihood that we will achieve agreed goals is much higher.
More than anything else, I am looking for a leader who is committed to the relationship, is open to feedback, [and] energised towards their own growth and the development of others around them. Add to that a dose of self-awareness, humility, compassion and the ability to contemplate situations from multiple perspectives—you have the perfect mentee.
The key thing I have learned as a mentor is to listen and ask open questions. It's a different approach to telling or instructing. It’s also about enabling an individual to understand that you’re there not because you are right, but because you’ve probably had more experience being wrong.
It's important that a mentee reflects about what they want to achieve and, before a session, they say to themselves: ‘I’ve got this opportunity, which is a limited window, to be able to converse with someone who is unbiased, who hasn’t got any baggage, who’s going to be supportive of me and is going to lift me up.’
What I do find is that the people who get the most from mentoring are those who send in thoughts beforehand on the areas they want to cover. The other thing is that in any form of leadership, at any moment in time, something can come at you which you don’t expect—a good mentor will understand this too.
Both sides have to demonstrate a commitment to the relationship because you are both investing that time to think and reflect about things. It’s a two-way relationship based on respect and humanity.
Ultimately, it's these qualities that I think make for good leadership.
A Mixture of Authenticity and Humility
Rachel Osborne, Non-executive Director, Ocado Group and Board Mentor, Criticaleye
An effective mentor doesn’t bring their ego into the room. It's very much about the mentee and where they are. The mentor brings in context and knowledge. For example, one of the things they can do is explore with the mentee some of the unwritten rules that exist in companies, because they’ve been through it all, to allow the mentee to accelerate their understanding of more complicated situations.
When I first started mentoring, I was curious about what things the mentee felt they needed to work on and the things that their boss felt they needed to work on. Over time – as you get to know them – I’m more interested in exploring their aspirations, goals and what success looks like for them, irrespective of the company that they’re working for, so that I can give more holistic mentoring support.
You can often act as a mirror, giving feedback and development growth. While every individual is unique, some of the challenges aren’t unique. As a mentor, you’re not their boss, so it’s a different dynamic, and you can give them feedback on what you see in how they’re thinking about problems and point out what might be blind spots or things that they … haven’t thought about.
I want people who are authentic and have humility as well as the strength, conviction and smarts. I think the best leaders are those that are confident enough to be humble and bring their real selves to work and thrive on the success of their teams, rather than it all being just about their own success.
A Sense of Perspective
Tea Colaianni, Senior Independent Director, Watches of Switzerland Group and Board Mentor, Criticaleye
A mentor [should] bring three things: perspective, honesty and generosity. Perspective comes from experience, sharing the successes as well as the mistakes, the difficult Boardroom conversations, the moments where judgment mattered more than technical expertise. A mentor helps someone see beyond the immediacy of a problem and understand the broader landscape.
Honesty is equally important. A mentor should be able to say the things others might not say. Sometimes that means challenging assumptions; sometimes it means holding up a mirror. The relationship only works if there is trust and transparency.
And finally, generosity. Mentoring is about giving your time, your network, your insights without expecting anything in return. At its best, mentoring accelerates someone else’s journey while reminding you how much we all continue to learn.
Earlier in my career, I mentored by giving advice and sharing solutions. Now, I blend that style with a more questioning approach. ... Today, my mentoring is less about technical capability and much more about judgment, influence and leadership identity, helping people understand how they show up, how they find and use their voice and how they navigate complexity.
The best mentees are curious and open to being challenged. They look for growth and see every conversation as an opportunity to develop. I also value preparation. Mentoring works best when the mentee arrives having reflected on what they want to explore, rather than expecting the conversation to do the thinking for them.
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