Reflections from the Mentoring Matters podcast
Our own Mentor Relationship Advisor, Carolene Thompson, was recently featured on the Mentoring Matters podcast, where she joined host Dave Sharpe to explore one of the most important and often least visible aspects of any mentoring programme: the matching process.
Their conversation went beyond the mechanics of how mentors and mentees are paired, offering a thoughtful insight into the judgement, care and human understanding that underpin successful mentoring relationships.
We often talk about matching as if it’s a logistical step. Something that happens at the beginning of a programme and then fades into the background. But listening to Carolene, it became clear that matching is less of a moment and more of an ongoing act of judgement.
She described three main routes used on programmes like Help to Grow: self-match, assisted match and brokered match. On the surface, these are straightforward. Participants either choose their own mentor, receive a curated shortlist, or are matched for them if time or engagement has been limited.
But what stood out was not the structure itself. It was what sits behind it.
As Carolene put it, when participants feel overwhelmed by choice, “they will come back and say … there’s too many people. Can you please help us to pick?” That moment of hesitation is telling. It’s not a lack of motivation, but a recognition that the decision matters.
Assisted matching, in that sense, becomes a conversation rather than a selection exercise. It requires someone to ask the right questions, to listen carefully, and to interpret what a business owner really needs, not just what they initially say they are looking for.
There is, of course, a platform and an algorithm. Participants are presented with suggested mentors when they first log in, often based on industry or location. But as Carolene acknowledged, that can only ever go so far. The more complex judgement – the ones that lead to genuinely strong matches, still sit with people.
One of the more interesting parts of the conversation was around what happens when things don’t go to plan. Rematches are rare, but they do happen. Not, as we might assume, because the mentor wasn’t capable, but because something shifted in the relationship or in the participant’s circumstances.
Carolene was very clear on this point. When mentors raise concerns about disengagement, her instinct is not to assume disinterest, but something deeper. “If someone cancels two or three mentoring sessions … something’s wrong” she said. “Whether work-wise or personally, something’s wrong.”
It’s a simple observation, but an important one. Particularly for newer mentors, who may experience this kind of disruption as rejection or failure. Part of the support team’s role is to reframe it, normalise it, and keep the door open.
That idea of an “open door” came up more than once. It speaks to a broader truth about mentoring relationships: they are not linear and not entirely within anyone’s control.
And yet, when they do work, the impact can be significant. Carolene shared examples of businesses experiencing substantial growth, but also acknowledged that much of the feedback they receive is less tangible. Participants often describe their mentors as “fantastic” or say they have helped them “see clearly” or “move forward with confidence.”
These are not always measurable outcomes, but they are meaningful ones.
Another assumption the conversation challenged was the idea that in-person mentoring is inherently more effective. Carolene’s experience suggests otherwise. Having worked across both face-to-face and virtual formats over many years, her view was that the environment matters far less than the quality of the interaction.
“It’s not about the environment that you’re in,” she said. “It’s the nature of the conversation… the rapport that you build … the empathy, the listening skills.”
That aligns with what many experienced mentors recognise over time. Trust is not built through proximity, but through attention. Through how well someone listens, and how thoughtfully they respond.
Perhaps the most grounded insight came right at the end of the conversation, when Carolene was asked what she values most about her role. Her answer was simple: “the people… the desire to be successful… and the ability to be even a small part of that.”
It’s a reminder that while systems and processes are necessary, they are not what ultimately make mentoring work.
Matching matters. But it is not the mechanism that creates impact.
That comes later, in the relationship itself.
Author: Carolene Thompson