Bad bosses don't just make work harder. They distort how you measure your own worth. I've worked under both. after 20 years, I have some pretty good reflections on what good and bad leadership actually looks like.
A client described a meeting with their boss last week. Nothing dramatic. Routine catch-up about workload and upcoming deadlines. Then the boss said something like: the team sometimes needs to put in extra time "on weekends when needed."
Just a phrase. Slipped in. Casual. Not a demand. Not a request. Nothing written down, nothing agreed to.
My client caught it immediately and has been sitting with it ever since. They never agreed to work weekends. It was never part of the conversation when they joined. But now "when needed" is floating in the air between them, and no one has defined what it means. My client doesn't want to push back on something that wasn't technically said. The boss doesn't have to own something they never technically asked for.
That's not communication. That is management through implication. And it's one of the more subtle forms of bad leadership I hear about regularly in sessions.
So we went back to basics. What is he actually doing this job for?
Not to impress the boss. Not to become CEO. Not to prove something. He's been in the industry long enough, worked hard enough, proved himself enough, and sacrificed enough that he has a clear and specific goal: financial freedom. A defined number. A defined point at which he can stop trading his time for someone else's agenda and start living by his own. He went into that role knowing exactly what he needed from it.
That kind of clarity changes everything.
Once you know what you're actually there for, you can run every decision through that filter. Working weekends "when needed" does that get him closer to financial freedom? No. Does it cost him something he won't get back? Yes. Does his boss's implicit expectation have anything to do with the reason he took the job? No.
This is what a values assessment does in practice. Not a theoretical exercise about what matters to you in the abstract. A concrete grounding in what you're actually trading your time for, and whether any given demand on that time serves it or erodes it. When you're clear on your values, someone else's expectations stop having the same grip on you. They become something you can assess against your own standard rather than something you absorb and feel guilty about not meeting.
The boundary becomes obvious once the values are clear. He's not working weekends because working weekends doesn't serve what he's there for. That's not a negotiation. That's alignment.
And that is something bad leadership consistently tries to disrupt or manage: your connection to the reason you showed up in the first place.
I've been thinking about leadership a lot. Not as a management theory. As a psychological one. Because what happens inside you when someone leads you badly is worth examining closely. It doesn't just make work harder. It distorts the way you measure your own competence, your own value, your own read on reality. Bad leadership has you second guessing years of outstanding work. It did for me.
I've had bosses on both ends of it. I've worked across Chicago, Japan, Melbourne, and Hong Kong. I've had people who made me better and people who made me question work I knew was solid. I wrote about what that career taught me in What I've Learned in 20 Years of Corporate Work. This is a different cut on the same material. It's less about the career itself and more about what bad leadership does to the person inside it.
At an analytics and CRM consultancy in Chicago, my boss had one principle: "get it done when it needs to be done, and I don't care when or where you do it." That was the whole framework. No performative presence. No expectation that being seen at your desk was the same as doing your job. He trusted me to manage my own time and deliver. He treated me like an adult. I did deliver. Most people do when they're trusted.
Then an International media agency. I stayed for six years. Over that time I was promoted three times, eventually to Director of Analytics in Melbourne, AUS. That kind of progression doesn't happen in a broken environment. What I remember from those years is fairness. Bosses who were clear about what was expected. An environment where you could make a mistake, learn from it, and not be quietly written off for it. I felt like I was in it alongside the people above me, we were a team, not being managed at from a position above. Six years is a long time to stay anywhere in media. I stayed because the environment made it worth staying.
Those two experiences set a reference point. I knew what good felt like. And I knew what it produced.
I've talked about the psychology of work pressure in more depth in my In The Rooms series. Three complaints show up in almost every job related counselling session, and they all connect to the same root. Worth watching if any of this is familiar.
At some point, that corporate ladder you're climbing stops being ambition and becomes a trap, because you're always looking for the next thing.
William Ferrell, M.Couns.
My first regional APAC agency role in Hong Kong had three different bosses in six months. No KPIs ever set. No strategic direction. No sense of what I was supposed to be building toward. I had the experience to create my own structure, but that's not the point. Leadership is supposed to orient people. What I got instead was a series of transitions and an absence where direction should have been. That didn't last long.
Then a large international FMCG conglomerate. The first year was genuinely good. I got a significant amount done and got recognition for it. Then my manager changed, and things shifted. He moved substantial parts of my work to other people. He never sat with me on strategy. He never shared his vision for what we were building together. He never really even had meetings with me or talked to me throughout the week.
To sum up my experience with him, there was one meeting that crystallized the whole experience.
We built a project brief together. Sat in the same room, agreed on scope, KPIs, deliverables, the full scope of work. Documented. Signed off. I completed the project and presented it back.
He told me it was completely wrong.
I brought up the brief. Specifically. This is what we agreed. This is exactly what I built.
He couldn't tell me what was wrong. He said he'd expected something different, but he could not say what that different thing was. Not once across multiple conversations. He would look at my work and tell me he didn't like it, but he was never able to articulate why, what he wanted instead, or what specifically missed the mark. I even asked for examples of what he expected. Crickets...
That is not feedback. That is someone in a leadership position who either doesn't have the language to say what they want, doesn't know what they want, or isn't willing to own what they're actually saying. The damage it does is specific: you start to doubt work you know is good. You start to wonder if you're missing something obvious that everyone else can see. You start to second guess everything you do. You start to try to reverse-engineer the feedback, which means you start working from someone else's vague dissatisfaction rather than from your own competence. You weren't missing anything. But the doubt is real, and it sticks.
At another consultancy in Hong Kong, there was a biannual anonymous engagement morale survey from HR. If you work corporate, you know these. Feedback came in. Some of it about me was not kind. Instead of handling that as a private management matter, my boss sent the full survey, including the anonymous feedback about me, out to the entire company. The reason given was transparency.
What it actually did was put me in a defensive position I hadn't earned, in front of people who had no context for what they were reading. One person's anonymous view, broadcast company-wide, became the lens through which I was seen from that point until I left. It cut my legs out from under me. Not because the feedback was accurate. Some of the feedback was fair. But because something usually handled between leadership was made public before I had any ability to address it. I suddenly found myself walking into a hostile toxic environment.
That is not transparency. That is abdication. A leader who can't contain a personnel matter and instead externalizes it to the group is managing by consensus and calling it a principle.
At the same company, people didn't feel safe enough to say what they actually thought through the formal channels. Consultants came to me privately to voice frustrations because raising them officially felt too risky. Problems that should have been addressed peer to peer were regularly escalated above people's heads to my boss without first being raised with the person directly involved. What that produces is a culture of surveillance and positioning, not one of honest communication. Not one of emotional safety. People manage up instead of solving the actual problem.
Then there was my Christmas holiday (asked for and approved months in advance).
I went away. Before I left, I briefed my team, handed everything to my manager, and told people to reach out if something came up. I monitored our Teams chat while I was gone and saw nothing that read as a fire or red flag.
For context, I was on a boat in the middle of the ocean with my 75-year-old father. The internet was what it was.
The day I returned to work, I was reprimanded and yelled at for being offline. My boss had already spoken to my colleagues and my team about it while I was gone. He had shared his frustrations about my absence with people who reported to me. "He was reallllllly pissed about that", a few of them told me.
Setting your team up to function without you is not a failure. It's the fucking point. A leader who can hand off, step back, and trust the systems they've built is demonstrating exactly what good leadership looks like. Being reachable at all times is not the measure of whether you've done your job. Outcome is. I had set everything up. Nothing fell over. The reprimand was for his perception of being unavailable. What it communicated was that presence was the expectation, not result.
The pattern across all of it is the same, even if the specific situations are different.
Bad leadership is not just difficult to work under. It distorts your internal reference point. The manager who can't articulate what's wrong with your work trains you to second-guess years of success. The boss who broadcasts your anonymous feedback trains you to stop expecting that personnel matters will be handled as such. The leader who reprimands you for being on holiday with your father trains you to feel guilty for having a life outside of work.
Over time, if you're not careful, their standard becomes your standard. Their judgment becomes the measure you use to assess your own work. That's when it gets genuinely costly. It's also the thing I find most often underneath why high-performing men in Hong Kong don't ask for help. Because admitting something is wrong feels like it disproves the whole story. That pattern is worth reading about separately.
I left my last job having met every KPI I set out to meet when I joined. I accomplished what I went there to accomplish, in an environment that wasn't always working in my favor. I kept to my own standards. I knew what I had done and what it was worth.
These experiences taught me things I come back to regularly in sessions. You are not your job title. You are not your performance review. You are not the feedback of someone who couldn't tell you what was actually wrong. Your own values matter more than any employer's expectations of what you should give them.
The question worth sitting with at the end of any role, in any environment, is straightforward: Did you do what you set out to do? Did you act in line with your own values? Did you give it what you intended to give?
If the answer is yes, that stands, regardless of how the environment chose to respond.
My client isn't in his job to be its most devoted employee. He's not there to climb to a title that impresses people at dinner parties. He's there to hit a number that gives him the freedom to live on his own terms. That's his value system, and it's a completely legitimate one. The boss's implication that weekends are part of the deal is only a problem if my client has lost track of why he's there. When he's clear on that, "when needed" is information about the boss's expectations, not an instruction he's obligated to absorb.
That's what being true to yourself actually looks like in a work context. Not being seen. Not a statement. Just a clear internal map that tells you which demands are worth meeting and which ones belong to someone else's agenda.
The boundary isn't the end of the story. It's the result of the clarity that came before it.
That's not the answer that resolves the anger or confusion that comes from being undermined by someone with authority over you. It doesn't fix the harm. But it gives you something to stand on that nobody can pull out from under you.
Your value was never theirs to give. And it was never theirs to take.
If you're sitting with something from a work environment that's affected how you see yourself, or you've lost track of what you're actually doing the job for, that's worth looking at. Book a session.
William Ferrell is a counsellor and psychotherapist based in Central, Hong Kong. He works with expats, professionals, individuals, and couples. 15+ years of clinical experience. Accepting new clients.
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