Most important relationship you didn’t choose
You can probably name your best boss and your worst without a second’s thought. Someone on your team will remember you just as instantly.
‘Tell me about the best boss you ever had.’
‘Now, tell me about the worst.’
I have asked this question for the best part of thirty years, in executive leadership programmes in glass towers in London, to nurses at the end of exhausting night shifts in Sydney, and of farmhands leaning on gates in New Zealand.
In all that time, nobody has ever needed a moment to think. Both names arrive instantly, sometimes from thirty years and three careers ago. The speed still surprises me. But what’s even more telling is watching what happens to their bodies while they answer.
Describing the best boss, they physically change. They sit up and something behind the eyes switches on and they remember specifics. Not “she was supportive,” but the exact words she said in the corridor after a high-stakes meeting went badly, or the specific Tuesday evening he stayed late to help sort out a complex mess.
I have my own. Years ago, a boss offered me a promotion I was convinced I wasn’t ready for. I tried to talk him out of it: “I’m not the right person for this job.” He said, “I believe in you.” Four words. They were all I needed, and they have stayed with me ever since. He probably doesn’t even remember saying them.
Then, I ask about the worst, and I watch the air go right out of them. I’ve seen shoulders drop and voices flatten. This is an adult with a mortgage and a full, independent life, visibly deflating at the memory of someone they haven’t worked for since 2010.
We remember little from our working lives with that kind of clarity. Ask that same person about their employer’s corporate strategy that year, and you will get a vague answer or a blank shrug. The restructure, the new operating model, the transformation programme with the town halls and the slick launch video, it is all gone, composted into a distant memory of having been stupidly busy.
But the boss? The boss is filed in the body.
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People are often surprised at their own answers when I ask what the best boss did. It is almost never softness. The word that keeps coming up is tough. “Tough but fair.” “He pushed me harder than anyone before or since, and I can see now it brought out the best in me.” “She had standards that frightened me. But when I really needed her, she was kind.”
Listen to enough of these stories and the pattern is unmistakable: nobody’s best boss made their life comfortable. What they did was take the person seriously enough to expect more of them than they expected of themselves. Being believed in, I’ve learnt, feels like being challenged. The tough-but-fair boss and the kind-when-it-counted boss are not two different people.
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This relationship doesn’t just stay at work, it comes home.
Ask anyone who has had a truly bad boss where the impact first showed up for them and it’s not usually in the office. It’s snapping at the kids over nothing. It’s in the Sunday afternoon that starts to feel tense around four o’clock. ‘Work-life balance’ suggests a neat separation, but we know that the impact of having a difficult relationship with your boss doesn’t stop when you clock off.
It also alters your relationship with yourself. A boss is a mirror that you look into forty-plus hours a week. Over time, you start to believe what the mirror reflects.
The good ones reflect a slightly shinier version than you knew yourself to be. You leave their team more confident, more capable.
The bad ones do the reverse, and their verdict can last longer than we realise. I have met exceptionally talented executives, years into successful careers, who still won’t apply for the roles they secretly want because in their twenties a manager led them to believe that they would never be quite ready. They are still, on some subconscious level, reporting to someone they haven’t seen since 2015.
Whole career paths can be shaped by this single relationship. I’ve known plenty of people who have stayed too long in roles they have outgrown because leaving a good boss feels like a betrayal. And I’ve seen people walk away from work they love because of the emotional climate their boss created.
Ask someone what has shaped the way they choose to lead and the honest answer is often one of two sentences: I swore I would never make anyone feel the way he made me feel or I wanted to help people grow into their talent, the way she did for me.
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Consider what other relationship gets this kind of unmonitored access to a human life. Your partner, your parents, your closest friends. Most of these you chose, or the emotional bond grew before the power structure did. The relationship with your boss is assigned. There is power imbalance built into it that would alarm us in any other context. One party holds meaningful power over someone else’s income, prospects, and experience of work life.
The manager relationship, which has the power to impact your confidence, your career, and your Sunday evening, if you’re lucky, gets a fortnightly one-to-one that gets cancelled the moment something more “urgent” comes up.
If you recognise yourself in the Sunday dread or the impactful-for-the-wrong-reasons boss, maybe some of what they reflected to you was fair. Maybe some of it was theirs, not yours. The trouble is that we filed it away in our bodies the same way.
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If everyone has an instant answer to my question, and we do the simple maths, then if you have ever managed a single human being, there’s a chance that you are someone’s answer.
Maybe someone is describing you right now. The question is, what happens to their body when they say it?
I’d love to tell you I know which answer I have been throughout my career. I have better information than most because several times, someone was brave enough to tell me the truth.
Early on in my career, the first time it arrived disguised as concern: “Are you okay?” asked carefully by a brave team member who saw the impact I was having.
The second time it came entirely undisguised: “You intimidate people.”
I still remember the silence after that sentence and my immediate instinct was to defend. To detail the immense pressure that I was under from the deadlines, the unfeasible hours and everything being coming at me from above that I thought I was successfully containing.
Except I wasn’t containing it. It was leaking out of me onto people who had no idea what I was dealing with and no reason to care. From the inside, it was just me struggling to cope. From the outside, which is the only vantage point that matters, it was, simply, bad management. My team were experiencing me.
Consider what it took for those truths to reach me at all. The corporate power gradient runs one way: your team can see exactly who you are, in high definition, all day long, but not all that data travels back up. Especially if you are perceived as intimidating. Maybe they laugh at your jokes either way. They tell you your feedback is helpful either way. The worse your leadership gets, the safer your people play it. And the safer they play it, the better you think things are going.
Thankfully someone decided I was worth the risk, asked about my wellbeing, and hoped I wouldn’t shoot the messenger. It was an absolute gift that not many managers get. The nature of hierarchies makes sure that the people most in need of feedback are usually the last to receive it, if at all.
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The worst-boss stories I hear cover the full range. Half are exactly what you would picture – the volatile ego, the micromanager, the perfectionist who is never satisfied, or the angry executive who eviscerates people in public meetings and calls it “passion.”
You would be surprised at the precision of the memories; the exact words, even the exact room, ten, twenty, thirty years on. Sometimes it’s joked about but underneath it the impact is real. How often poor leadership behaviour was justified with “it’s just robust debate,” as “being passionate” or dismissed as “they are too sensitive”.
Which is exactly why the tough-but-fair boss matters as a comparison. The best bosses made people uncomfortable in service of their growth. The worst did it in service of themselves. Perhaps it was anxiety they couldn’t manage, or a baseline need for control. Or simply childhood wounds yet to be tended to.
But the other half of the answers are nobody’s idea of a monster. They are someone perfectly fine, even well-intentioned. Someone who dodged the hard conversation for months because the moment never felt right, while the person on the other end sweated in the ambiguity. Feedback so carefully managed that it contained zero usable information. The boss who said, “my door is always open,” but was never fully present with anything challenging. Someone who acted warm and helpful in one-to-ones but would subtly throw their people under the bus in team meetings, and who would be genuinely wounded, wounded, to hear it described that way.
Their teams definitely wouldn’t say ‘bullied’, but they might say ‘unseen’. That still produces a deflation of the shoulders, even years later. I’ve spent time with close friends revisiting the stories of bosses from 30 years ago with the clarity of distance and experience. The details from years ago are crystal clear, and the body language is still the same.
Too tough and too nice look like opposites. They aren’t, but they do have something in common: neither is genuinely for you. The ones who are for you will make you uncomfortable in service of it.
I know the defences forming, because I have used them all: I have high standards. I’m responsible for the commercial outcomes. You have no idea the pressure I was under. I care deeply about my people.
And it’s not always the case that the boss doesn’t care. Most people care. But the person going home to snap at their kids after another week of postponed feedback or a barking boss isn’t experiencing anyone’s noble intentions. They are experiencing the person. The real, Tuesday-afternoon-under-pressure-because-I-just -found-out-the-budget’s-been-cut boss, not the aspirational one in their head.
Our good intention is what we like to measure ourselves on, but it’s our impact that gets filed in their body.
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We know that this relationship shapes career paths and follows people home. And it was assigned, not chosen.
And how it gets assigned is worth thinking about.
Typically, we give it to people as a prize for being good at something else. The best technical performers get promoted and congratulated. Come Monday morning they are responsible for themselves, the performance of the team and the daily working experience of other human beings.
Do we do enough due diligence as to whether they truly want that job, let alone whether they are ready for it? You get handed a team the same week you are handed a new laptop, and only one of those two things comes with a setup guide.
Then, I wonder, how often do we check how it’s going? Many organisations measure absolutely everything. Engagement, attrition, even the click-through rate on the wellbeing newsletter. But the significant, high-impact relationship underneath all of it, whether people truly trust the person they report to, mostly goes unexamined.
And the numbers we do collect arrive too late to matter. Engagement scores tell you it’s already broken and exit interviews are sanitised, giving us skewed data. After all, it’s much easier for a bruised leaver to tell you: ‘It’s about career progression’ or that they’ve ‘had a better offer elsewhere’ than to say, ‘I don’t trust my boss’.
We spend fortunes on the things around this relationship: strategy, systems, surveys, speakers flown in to talk about culture. But the relationship itself, the thing holding the whole structure up, is left to whatever the manager happened to pick up along the way: maybe a course from a couple of years ago, a half-remembered framework or the flawed example of their own previous bosses who didn’t get any training. How does that compare to the robustness of other strategies in the organisation?
The most important job in most people’s working lives, the one their confidence, their Sundays, and their futures builds on, is, almost everywhere, under-resourced, under-developed, under-supported, and under-loved. Now there is a word you will never see in a board pack.
I don’t have three quick tips for you. Anyone offering to fix this relationship in a quick listicle is describing a different relationship.
What I have is thirty years of asking one question, and the conviction it’s left me with: some people will find a way to thrive regardless of the quality of their boss, but mostly, this is the single relationship at work through which everything else either flows or completely chokes. And we often leave it to luck, hope and some not-fit-for-purpose training.
None of this makes anyone a villain. Most bad-boss stories aren’t written by bad people. Pressure makes good people do dumb stuff. How those stories get written and what is being poured into managers from above and from their own unexamined corporate histories, is a subject I will come back to.
For now, just consider this. Somewhere right now, someone could be answering my question with your name. You don’t get to choose whether you are a character in their story, but you do get to choose what you do about it.
When I left corporate life, the messages that undid me weren’t about the work itself. They were from people recalling small things I’d said or done years earlier, things they still use today. Alot of it I’d said in passing; moments that barely registered with me had been filed away in them for years. If anyone has ever said to you, “you told me something once and I’ve never forgotten it,” you know this already. Your impact is real, and it is mostly invisible to you.
And it cuts both ways. People don’t write to tell you about the other moments, from the time that the pressure you were under overrode your good intentions, but those were kept somewhere too.
Most managers never get told which answer they are. The brave ones ask.
So go on, your turn. Best boss you ever had. And the worst.
What did they do?