The mentor who remembered

I mentored a young finance professional during my corporate career. They were struggling to get the promotions they felt they deserved. Capable, committed, doing the right things technically. But not progressing.

I recognised the situation immediately because I’d lived it myself.

That recognition changed the quality of everything that followed. The conversations weren’t me advising from a distance. They were me remembering, specifically and honestly, what it actually felt like to be capable and overlooked in a large corporate environment. To do good work and watch others progress while you stood still. To not yet understand that technical performance and political navigation are two entirely different games, and that nobody tells you the second one exists until you’ve already lost a few rounds of it.

That shared experience was the foundation. Not my seniority. Not my expertise. The fact that I’d been exactly where they were and could remember what it felt like from the inside.

Most mentoring relationships don’t work like that.

The default mode is advice from above. The mentor has reached a destination the mentee is heading towards, and they point the way. It’s well-intentioned and often genuinely useful. But it operates at the wrong altitude. It tells the mentee what the view looks like from the top without helping them navigate the specific terrain they’re currently standing in.

What most mentoring relationships are missing is situational awareness. The ability to read where the mentee actually is right now, in this conversation, at this point in their journey, and adapt accordingly. Sometimes that means directing. Sometimes it means stepping back and coaching. Most mentors default to one mode throughout and call it mentoring. The ones who produce the strongest results move between modes depending on what the person in front of them actually needs.

That requires something most people underestimate: the willingness to remember accurately. Not the edited, wisdom-inflected version of your past that makes you sound like you always knew what you were doing. The honest version, including the confusion, the frustration, the things you got wrong before you got them right.

I know a business owner of a manufacturing company who struggled with this differently.

His difficulty wasn’t specifically with mentoring. It was with developing his people at all. He avoided giving meaningful responsibility to the people around him. Not because he doubted their capability, but because handing over real authority felt like handing over something he wasn’t ready to lose. His identity as the owner and leader of the business was bound up in being the one who knew most, decided most, and carried most.

The consequence was predictable, even if he didn’t see it coming. The people he wouldn’t develop left. One by one, they calculated that their growth wasn’t going to happen there, and they found somewhere it would. He protected his sense of himself and lost his team in the process.

This is more common than most leadership conversations acknowledge. When your identity is tied to being indispensable, developing others feels like self-erasure rather than leadership. The question worth asking is: what does it say about you as a leader if the business can only function with you at its centre?

There’s a related mistake I see in how businesses bring in high-potential people in the first place.

The hiring decision defaults to skill because skill is measurable. You can evidence it, point to it in a CV, or test for it in an interview. Cultural fit requires judgment, and judgment is harder to defend in a room full of people who want certainty. So fit becomes a secondary consideration, something noted but rarely weighted properly.

The consequence is a capable person in the wrong environment. And even the best mentoring relationship can’t fully compensate for that, because mentoring helps someone grow within their environment. If the environment itself isn’t set up for them to succeed, the development investment keeps running into the same wall.

The mistake businesses make isn’t hiring for skill. It’s treating fit as optional when, in fact, it’s what determines whether the skill ever gets expressed.

Who in your business is waiting for a mentor who remembers what it felt like to be where they are right now?

And are you willing to remember accurately enough to be that person for them?

Have a brilliant week!

Dave Rogers, The Business Explorer

If this struck a chord, my Substack goes further on the same questions. Want help applying any of it to your business? Book a call.

Need a speaker who’ll bring a fresh perspective? Reach me at info@fuelledfitandfiredup.com.

For 30 years, I’ve worked with business owners and leaders who are stuck on the wrong question. My job is to find the right one.