good boss

What’s a good boss? No, it’s not the nice ones.

“Derek, how do I know if someone is a good boss during an interview?”

A young, eager graduate asked me this question during one of my talks.

“What do you mean by a good boss?”, I replied.

“Well, I want to avoid those horrible bosses I read about where they are always unreasonable and don’t care about their employees. I want a kind boss that can be my mentor.”

I paused for a moment.

This made me think about all the thousands of articles I have read about “leadership”, which paints the ideal boss as a kind, inspiring mentor, that will empower and trust their people. And I imagine this young graduate asking me this question is conflicted between how these articles describe a good boss, with the actual bosses that are out there.

It’s a valid concern because choosing the wrong boss can be damaging to your career, sometimes permanently.

So I started thinking about all my previous bosses that actually made a positive impact on who I am today. To my surprise, none of my previous bosses were one of these “good bosses” that those articles described.

My first boss was horrible but I owe him my career

“Derek, I want a cup of coffee on my desk every morning, black with no sugar.”

Michael drinks too much coffee. I probably make him at least five cups a day. He runs an accounting firm in London, and he decided to hire me to be a junior accountant which was great because I needed some income while I did my professional accounting papers.

He was one of these “horrible bosses” described by these leadership articles today.

“Why is this taking so long Derek? It’s already the second day I don’t see much work done. Were you doing any work yesterday?”, Michael said sarcastically.

“I have been working hard on this. It took five days last year and now you only gave me three days, there’s not enough time”, I complained meekly.

None of my previous bosses were one of these “good bosses” that these articles described

Michael had a bad temper, and even though I felt it was unfair, I tried my best to control my emotions because I really needed this job.

“The client is pressuring us on fees, so you will do the same work in less time. If I don’t see it completed by tomorrow morning, I am going to be very disappointed”, Michael replied.

Michael never bothered to sit down with me to explain how I can work faster and better. No “mentoring” the way these leadership articles say a mentor was supposed to be. He just let me figure it out myself, and at the end of every assignment, he would be sure I would receive the criticism I deserved.

I don’t think I’ve worked so efficiently before this. I was always kind of relaxed during university but the real world felt harsh. Nevertheless, despite what I felt was unfair, I worked really hard and completed the work the next morning.

good boss

Michael looked my work, and as he was going through each page, his ears started to turn red and I knew this was not a good sign. He looked up, and instead of praising me for being so efficient, he started berating me for all the mistakes I made in my work.

“I expected more from you Derek! These mistakes shouldn’t be made by you!”

Doesn’t matter if I had to work tirelessly to complete the work in record time. Michael will never allow me to have a single excuse for producing mediocre work.

This was just one of many similar experiences I had working with Michael.

I believe many people today visualise a mentor as someone that patiently guides them through your work, almost spoon-fed like they’re in a class. But I learned a lot from Michael not because of any “mentoring”, but through all this direct, transparent criticism I get from him every time I made a mistake.

And I got better and better at my work, and always held myself to high standards, because I knew if I didn’t, Michael would not hesitate to remind me of my shortcomings.

The Right Intentions

After many months working for Michael, one day, something unexpected happened.

“Derek, I know you think I’m being horrible to you, but this is the only way you’re going to learn fast. I want you to know that I will always hold you accountable to a high standard even though you are only a junior accountant. This is how my first boss coached me, and this is how I am coaching you.”

He said this in such a calm manner, and it took me by surprise. I felt his sincerity in his words and intention to teach and help me grow. Don’t think it ever crossed my mind that he was trying to coach me.

While I don’t agree with him on his style completely, I feel fortunate that he set such a high bar for me as my first boss.

He was never an “understanding boss” and his uncompromising attitude made me into a professional with high standards and strong work ethics. A attitude that I carry with me today as a business owner.

The “nice boss” will hurt your career

“Does Alex know that he shouldn’t be doing that again?” I asked one of our senior team.

“Yes, I mentioned it to him a few months ago”, said John.

“But why is he still doing it?”

“I wasn’t too direct, I kind of said it my way, in a better way so as to not sound too harsh.”

“It’s clear the message didn’t get through to him because he has not changed. It’s been a few months, and now when this person is not performing, you’re telling me that you sugarcoated the message and haven’t made it clear to him that this a serious problem?”

This is a typical conversation I have with a “nice boss”, who struggle to clearly criticize the work of their team because either:

  1. They misunderstand being a good boss as being an understanding boss
  2. They don’t like conflict
  3. They are vain and care too much about what other people think about them and want to be seen as a “good boss”
  4. They are afraid that their staff will leave them so they are nice, but realise that they are only thinking about themselves and not you

A clip about Jony Ive describing why Steve Jobs is so direct with his criticism

If you report to a nice boss like this, unfortunately you’re never going to grow.

Because you will always think you’re better than you actually are. And when you’re frustrated as to why you’re not growing in your career (the market is never “nice” and will always adjust you to your true value), you’ll be trapped feeling like a victim.

You won’t realise that it was your boss’ unwillingness to clearly and transparently criticize you that made you stuck.

Think about your current boss. Is he or she like this? If they are, I encourage you to have an honest conversation with them and demand for real feedback. Make them feel safe that you can take this feedback.

“Tough” is better than “Nice”

Sometimes I hear people complaining about their bosses not being understanding and have unreasonable expectations of them.

But ultimately, it’s a question of comfort vs growth. If you’re thinking “why can’t growth also be comfortable?” then I would say growth = change and all change is naturally uncomfortable. So if you want a boss that is easy on you, then you’re probably going to to be in your comfort zone and grow slower than those with a tougher boss and higher expectations.

Assuming you’re serious about building a strong foundation for your career, and you had to choose between a nice boss that won’t criticise you and push you out of your comfort zone, and a tough one that can be stressful to work for in the short term, I would ask you to choose this tough boss over the nice boss.

People often don’t reach their full potential without high standards and expectations imposed on them.

Don’t let a nice boss keep you in your comfort zone and hurt your career, with their misguided concept of what a good boss is.

A tough boss is contributing more to your career growth than you realise.

Happiness

Happiness = Reality – Expectation

If reality is worse than your expectation, you’re unhappy. If reality is better than your expectation, you’re happy. And guess what? You can’t control reality but you can control your expectations.

People who are constantly unhappy probably imposed some expectation on themselves or on others that are not aligned with the reality of life.  I always find the easiest way to get through a rough patch is to tell yourself “It’s supposed to be like this, it’s not about easy or hard, it just is like this.”

And you can accept this, find ways to improve and be happy. Or you can constantly fight an emotional battle that you will not win.

Adjusting our expectations changes our emotional state.

It’s not about giving up and not doing anything to make your life better. In fact, it’s the opposite. You can’t improve your life if you’re not seeing clearly and burdened by unhelpful emotions.