Who is your best assistant? On coaches, trust, and the friend who wasn't who he seemed
By Zoran Hristov ·
There is a young man in a house full of strangers. His father left for a war twenty years ago and never came back. Suitors have moved into the family home, eating his inheritance one feast at a time, and everyone has an opinion about what he should do. He is polite to all of them. He has no plan.
Then an old friend of his father’s appears at the door and says the thing nobody else will: stop waiting. Go and find out for yourself.
That is how Homer opens The Odyssey. Not with Odysseus, but with his son, Telemachus, stuck. Soon after, another familiar figure steps in: Mentor, the man Odysseus trusted to look after his household. Mentor stands by Telemachus in the assembly, finds him a ship, and sends him across the sea to ask the people who knew his father. Telemachus comes home a different person.
Here is the part most people forget. Neither of them was who he seemed. Both times it was Athena, the goddess of wisdom, wearing the face of someone Telemachus already trusted. She could have appeared as herself, all light and authority. She chose familiar faces instead, because advice only lands when it comes from someone you believe is on your side.
Three thousand years later, we still call that kind of person a mentor. The word reached English in the eighteenth century, by way of a French retelling of the story, and it has meant “wise counsellor” ever since.
So here is a weekend question, and I’d like you to take it a little personally: who is your Mentor? Who is actually helping you shape your career and your working life, and how sure are you that they are who they seem?
Everyone has a stake
Make a quick list of the people you go to with a career question. For most of us it looks something like this:
- Your manager. Often genuinely invested in you. Also has a team to run, a headcount to protect and a quarter to deliver. When you ask whether you should take that other offer, they are not a neutral party.
- Your partner. Loves you, knows you best, and shares every risk you take. That is exactly why “should I quit and start again?” is so hard for them to answer cleanly.
- Your friends and colleagues. Kind, and quick to tell you you’re right. Friendship is built on agreeing more than it’s built on precision.
- Your feed. Tells you what worked for someone else, in someone else’s career, presented at its best angle.
- A chatbot. Available at 2 a.m. and endlessly patient, and often a little too eager to agree with however you framed the question.
None of this is a criticism. These people, and tools, matter. But notice what they have in common: each one has a stake in the answer, or no stake in you at all. The question isn’t who is the smartest person around you. It’s whose only stake is you getting better.
That is a short list for most people. Often it is empty.
Even the best stop improving on their own
In 2017, the surgeon and writer Atul Gawande gave a TED talk with a blunt title: Want to get great at something? Get a coach. He opened with a line worth putting on a wall: “I think it’s not just how good you are now, I think it’s how good you’re going to be that really matters.”
Then he told a story against himself. He had entered practice in 2003, and for years his results improved steadily. “I watched my complication rates drop from one year to the next,” he said. “And after about five years, they leveled out.” He wasn’t getting worse. He just wasn’t getting better, and he couldn’t see why. “Is this as good as I’m going to get?”
So he did something surgeons don’t do. He asked a retired professor of his, Bob Osteen, to come into the operating room and watch him work. The case went beautifully. Gawande didn’t expect much feedback. Osteen came back with “a whole page dense with notes.” The light had drifted out of the wound for half an hour and Gawande hadn’t noticed. His elbow kept rising, a sign he wasn’t in full control.
Small things. Invisible to the person doing the work. Gawande’s summary of what a good coach does is the best I know: “they are your external eyes and ears, providing a more accurate picture of your reality.” After a year of coaching, his complication rate dropped further still.
He was also honest about the cost: “It was painful. I didn’t like being observed.” Remember that sentence. We’ll come back to it.
Careers plateau in exactly the same way. For the first few years, everything is feedback: new skills, new people, steady growth. Then you get good enough. The reviews say “meets expectations” and the feedback stops, not because there’s nothing left to learn but because nobody is close enough to see it. Somewhere around year five, a lot of capable people quietly level out and don’t notice.
Silicon Valley learned this the expensive way. When Eric Schmidt became CEO of Google, the investor John Doerr told him he needed a coach. Schmidt, a very experienced executive, didn’t think so. Doerr’s answer, as Schmidt later retold it, was that even the best tennis players in the world have coaches. The coach was Bill Campbell, a former football coach who went on to advise Steve Jobs, Larry Page and a generation of founders, and whose methods fill a whole book, Trillion Dollar Coach.
The pattern is the same in the operating room and the boardroom: the better you get, the harder it is to see your own blind spots, and the fewer people are willing to point them out.
A small exercise for this weekend
Take five minutes on Saturday morning, before the week gets its hands on you again.
Write down the two or three people you actually go to with career questions. For each one, answer two things:
- What is their stake in my answer?
- When did they last tell me something I didn’t want to hear?
If every name has a big stake, or nobody has told you anything uncomfortable in a year, you’ve found your plateau. That is not a failure. It’s just the moment Gawande reached in the operating room, and the moment Telemachus reached in his father’s house: good enough to keep going, not yet sure how to get better.
The catch
Finding someone whose only stake is you getting better is half of it. The other half is harder: a coach can only help if you let them see you, the way Gawande let someone watch him operate even though he didn’t like being observed. That takes trust, and trust is a more precise thing than it sounds.
That’s part two: So what is trust, exactly? It covers what trust actually is, why it’s built in very small moments, six ways to build it with a coach, and whether you can trust an AI coach at all.
Frequently asked questions
Do I need a career coach if I’m already good at my job? That is exactly when a coach helps most. Atul Gawande’s surgical results had levelled out after about five years of practice. Coaching, from a retired surgeon who watched him operate, improved them further. Skilled people plateau because nobody is close enough to see their blind spots, not because there’s nothing left to learn.
What’s the difference between a mentor and a coach? A mentor usually shares their own experience: “here’s what I did.” A coach mostly asks questions and helps you see your own situation more clearly: “what do you want, and what’s in the way?” Many people benefit from both. The word mentor comes from Homer’s Odyssey, where the goddess Athena, disguised as his father’s friend Mentor, advises the young Telemachus.
Have a good weekend.
— Zoran
Sources: Atul Gawande — “Want to get great at something? Get a coach”, TED 2017; Eric Schmidt, Jonathan Rosenberg and Alan Eagle, Trillion Dollar Coach (2019); Homer, The Odyssey, books 1–4; Mental Floss — the origin of the word “mentor”.