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What did you learn from your worst boss?

Negative thoughts flood the mind as we consider that question. When consultant Scott Eblin thought about it, he decided to act in opposite ways to his worst boss.

Yet it’s not necessarily as simple as “bad boss equals bad actions.” Steve Jobs was described as a horrible boss yet he was also an admirable leader of his company. I remember reading Walter Isaacson’s magnificent biography and wincing on almost every page about something wretched Mr. Jobs had done. It was stunning how awful he could act. But I learned from his good points as well.

Charles Duhigg’s recent behind-the-scenes look at Elon Musk for Wired is similarly horrific at points – the title, Dr. Elon and Mr. Musk, brilliantly sums up the two-sided leadership coin. It describes “rage firings” but also how some associates have been inspired by his dedication to perfection and exceptional mind.

So, good and bad.

The bad behaviour of awful leaders usually stems from ego. It’s all about them. It’s also about the numbers – production, awards, bottom-line results and the like. Nothing else really matters. They are unbalanced; sometimes unhinged.

Mr. Eblin, in his blog post, says common complaints about terrible managers are that they micromanage, are unpredictable, don’t have their subordinate’s back, freak out over the smallest thing, and ultimately don’t care about the person managed. “I hope you’re not seeing yourself in any of these worst-boss behaviors but if you are, why not pick one and be intentional about doing the opposite of that this coming week?” he says. "You probably won’t reach 100 per cent perfection in a week or two, but if you’re sincere in your intent you’ll probably improve in ways your team will notice.”

That’s good advice, and a reminder we aren’t perfect managers ourselves.

How much of being a good boss comes down to caring? Without caring for something – success, goals, and other people – we would probably be ineffective managers. But care for the wrong thing – ourselves only – and it can backfire. Micromanaging means caring for the results more than the individuals we are guiding – and also egotistically believing we can provide the best results. There’s ego again.

The caring has to be directed toward others and balanced. We need to care for our own superiors and their goals, but also for the people we manage. Yet care too much about your team and subordinates and that can lead to questions about your managerial ability. So balance and nuance is best.

The issue of balance comes up in the common complaints Mr. Eblin notes of bad bosses: Being unpredictable or freaking out over the smallest thing. That’s why the anecdotes about Mr. Jobs and Mr. Musk sometimes make us shudder – unreasonably tearing strips off people or firing them.

Except sometimes the small things are big things. Isn’t that part of excellence – sweating the details? Do we need a Jekyll and Hyde split personality to be successful as leaders?

Consultant Wally Bock offered a simple perspective in a recent blog post: Leaders need to treat people right. He taught a supervisory skills class and many of his students thought their job was to motivate team members. But when he asked whether they needed to be motivated, the response was, “No, I just want to be treated right.”

Treating people right does not guarantee success. But without it – without caring for others – everything can fall apart. He suggests what people need to be treated right is:

  • To know what you expect from them, and that those expectations are reasonable.
  • To be offered meaningful work – work of importance to someone.
  • To work in a safe place with people they like.
  • To grow – make a little progress every day.

He also stresses autonomy. We all want some control over our lives. That’s where micromanaging gets managers in trouble. Our autonomy as leaders – wanting control – can interfere with the autonomy our subordinates crave. “Your job isn’t to distribute power, it’s to unleash it,” Mr. Bock suggests.

It’s complicated, but that’s an essential truth of managing. Take some time to ponder the actions of your worst boss – bad, but also good – and your own actions so you don’t become somebody else’s worst boss.


  • There are many reasons for the current high disapproval rates of Donald Trump and Justin Trudeau but one worth mentioning is hyperbole – extravagant statements, over time, can take their toll. Arguably, President Trump’s have made him seem more authentic to supporters while Prime Minister Trudeau’s have undermined his authenticity with the general public. Are you prone to hyperbole to motivate? Is it working?
  • Entrepreneur and former Navy SEAL Alden Mill says that when people care for us, we are wired as humans to reciprocate with care. He calls it the Care Boomerang, critical to the success of teams, since teams are a collection of relationships.
  • Management guru Tom Peters says in his newsletter that the greatest strength an organization can have is not a solid strategic plan but a commitment to listening by each member of the organization.

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