I ran two sessions on the same afternoon at the halfway point of the UNBOUND mentorship programme. An hour with the mentees, then forty-five minutes with the mentors.
I walked into the second one with my cheeks aching from smiling, because the impact these mentors are having after one or two conversations is genuinely remarkable. I asked the mentees what could be better. One person raised one thing, and it was about diary management. That is an extraordinary halfway report.
So, this is not a piece about fixing anything. It is about the specific moment a mentoring relationship reaches around now, and what a good mentor does differently when it arrives.
That moment is the tipping point between affirming somebody and moving them.
The mentee is being filled up. Now they need to move
Here is what the mentees described to me: confidence returning, a mirror being held up, permission to believe they are good at their jobs.
A product manager back from maternity leave, told plainly by her mentor that her instincts were right. A mentee mid-career pivot, reassured by someone who had zigzagged herself and still got there. A change manager rebuilding her motivation through the menopause, who said the confidence is coming back.
That is you. That is what you have done in one or two sessions, and it is not a small thing.
But there is a tipping point in the middle of any of these relationships, and we are at it. The mentee has been affirmed. If nothing changes, they will finish the programme feeling considerably better and behaving exactly the same.
Everything below is about how you move them across that line without doing it for them.
Know which hat you are wearing
The sharpest exchange of the mentor session was about the difference between mentoring and coaching, and I want to reproduce it because both positions were right.
One mentor, a software engineering leader with forty-two years behind him, put it like this: “Mentoring is telling, here’s the answer, take it away and do it. Whereas coaching is asking questions for them to find the answer themselves. I like to take a more coaching approach, but when they’re a bit stuck, providing I know the answer, steer them back on course.”
Another pushed back immediately. He would never want somebody to tell him what to do.
If you put “what is a mentor” into a search engine, you will get the textbook version: a mentor tells you, a coach guides you. I think the modern mentor is much less telling and much more asking. In practice I switch consciously, and I say it out loud. I am putting my mentor hat on now, because we are getting stuck. Right, I am back into coaching mode.
The honest bit is why we default to telling, and the group named it: the deadline. As one mentor put it, senior engineers give answers to less senior engineers rather than letting them discover, particularly in a lead role where “they don’t feel like they’ve got the luxury of allowing that person to discover for themselves and make too many mistakes”.
I see the same thing in my own business. If I tell someone, it takes three seconds. If I coach them, it might take an hour. The problem is that the three seconds comes back over and over again until you stop being their manager, whereas the hour, invested once, eventually stops needing you.
Which is the point of all of this. You do not want to be their mentor for the rest of their lives. You do it for a period, and then you let them fly.
A quick self-check for your next session: count the number of questions you ask against the number of answers you give. If answers are winning by a distance, you have probably drifted into telling without deciding to.
Watch for the parent and child dynamic
This is the trap I would most want every mentor to have in their peripheral vision.
When a mentoring relationship slips out of adult to adult and into parent and child, you end up carrying accountability that belongs to them. It feels like generosity. It is actually the thing that stops them growing.
It shows up in small ways. You book all the sessions. You set the agenda every time. You chase the piece of work they said they would do. You find yourself slightly relieved when they do not push back.
The mentor who has, to my mind, most cleanly avoided this took a very simple approach. He and his mentee agreed early to meet for an hour every fortnight and have already had five sessions. Rather than mapping her onto his own path, he took a publicly published engineering competency framework from a well known fintech, worked out roughly where she would sit in it, and handed it to her.
“Let’s go through this and decide what applies to you, what you think applies to you, what doesn’t. And then we can work out how far you think you are from achieving this level.”
They keep a shared document that they both comment on and resolve between sessions.
The temptation, when you know the trodden path, is to say follow me, I have walked this. What he is doing instead is putting a structure in front of her and asking her to place herself in it. The framework does the telling. He does the asking.
When the homework has not been done, ask a better question
The same mentor was completely candid that the shared document is empty. He can see the modified date.
His plan is not to chase her. It is to ask what she is finding challenging about doing it.
That is the whole craft in one line, and I said so in the session. “Why haven’t you done this” produces an apology. “What are you finding challenging about this” produces information you can actually use. Nine times out of ten the answer is not laziness. It is that the task was too big, or too vague, or it touched something they are avoiding.
Three questions worth having ready when something has not happened:
- What did you find hard about starting this?
- What would have to be true for this to get done before we next meet?
- Is this still the right thing for you to be doing, or has it stopped being useful?
That third one gives them permission to renegotiate, which is a much healthier relationship than one where they quietly disappear.
Give them space, then give them structure
Several mentors described a first session that ran well over time because the mentee had a great deal to say.
One delivery director had a thirty-minute meeting turn into an hour and a half. The conversation flowed, and she still came away unable to work out what her mentee actually wanted. So she sent her away with a structure: come back with this laid out, and we will build objectives from it together. The mentee’s first reaction was that she was not sure she could. “Well, have a try.”
What came back was a clearly structured email, bullets under headings, from somebody whose stated development area is confidence and how she presents things. “I was quite pleased just with that tiny thing.”
I want to defend the messy first conversation before I defend the structure, because both matter.
So many one to ones are transactional. This is what you need to do in this sprint, this is when you need to deliver it. How rare is it that somebody asks about the human? When you give a person that space, they will often use it to say everything they have been holding in, and it will not be tidy. That is not a failure of the session. That is the session.
But the caution from the room was exactly right. A UX researcher with a psychology background, who has mentored for years, put it plainly: there is a danger they stay in the problem space, focus too much on the problem, and never move on to possible solutions.
So: space, then structure. In that order, and do not skip either.
She also made an observation that I think every mentor should expect. Most of the questions she gets are not about the profession at all. They are about navigating office politics and about the person themselves. If your mentee is not asking you technical questions, that is not a sign the pairing is wrong.
The same delivery director gave the best summary of the relationship I heard all day. “The only thing that you can give in this relationship is a promise. I promise to help you. You promise to let me help you.”
What moving into action actually looks like
The specifics from this cohort are more useful than any theory I could offer, so here are four.
A conversation that changed a job. A cloud network engineer had a mentee who was not getting the cloud infrastructure exposure she wanted. She was being handed whatever was available, because she had never said out loud what she was after. He encouraged her to raise it with her manager, or look elsewhere if that went nowhere. She had the conversation. She has since been moved to a different client.
Finding out what you do not want. A mentor working in large scale transformation has been sending his mentee out to talk to people, on the basis that you cannot know whether you like something until you find out what it involves. She now knows what she does not want to do. That is not a dead end, it is a narrowed field.
Pointing at sources, not summaries. Rather than forwarding articles or repeating other people’s thinking, one mentor gave his mentee a list of people to follow. “They’re saying what I would say to you. So you can just follow them.”
Building a brand rather than waiting for a manager. Another has been telling his mentee to stop relying on her management line to get her where she needs to be, and to work out what her brand is and who she wants to be inspired by, whether that is people internally, LinkedIn creators or podcasts. “She’s got to go and find it.”
Notice what all four have in common. In every case the mentor made the mentee do the thing.
Three things to do in your next session
- Ask what they want from the remaining sessions, not from the programme. The goal they applied with has usually moved by now, so ask them what it is today rather than assuming it is what they wrote on the form.
- Convert one piece of talk into one action with a date on it. Not five. One, with a deadline that falls before you next meet, chosen by them.
- Offer one introduction. Most mentees are nervous about asking for one. If you go first, you save them the ask and you show them it is a normal thing to want.
One last thought
I want to leave you with the thing I noticed most across both sessions, because it is not a technique and you will not find it on any mentoring checklist.
Almost every story of real progress started with somebody doing something that frightened them slightly. Raising the awkward thing with their manager. Sending the message. Saying I led this rather than we delivered this. Asking to be introduced to someone.
There is a bravery that arrives eventually, with age or experience or some combination of the two, where you simply mind less about the answer being no. What is the worst that happens if you reach out to somebody? They ignore you. Fine. You go and find somebody else.
Your mentee does not have that yet. What you are doing, whether or not you would describe it this way, is lending them yours until they grow their own.
I believe people have their own answers and just do not know it yet. Drawing those answers out is slower than handing them over, and sometimes it will feel like nothing much is happening, because you have to build the foundation before you can build the house. That is not the relationship failing. That is the relationship working.
One more thing. I caught myself in the session looking forward to us reaching the end of the programme, and then correcting myself, because I do not especially want you to reach the end with these people. You do the structured part for a defined period and then you let them fly. But the best of these relationships should outlast the programme by years, and the ones that do tend to be the ones where somebody was pushed, kindly, before they felt ready.