Are You Smarter Than Your Boss? Good!

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We’ve all had bosses we were smarter than. And all too often, we’ve been in situations where there was nothing we could do about it.

Before becoming my own boss, I spent a fair chunk of my career trying to escape situations like this. It’s why I try so hard to make Old Street Solutions the best place anyone has ever worked.

However, while researching for this article, I googled “How to handle being smarter than your boss” because I was interested to see the advice out there for employees.

And I came upon this utterly dreadful article from a leadership coach called Lolly Daskal. I don’t mean in how it’s written but in its message to employees.

This article says that if you have a boss who’s unable to do their job, and you find yourself constantly covering their tracks and doing what they can’t, then you should:

  • Be positive, not resentful, and try to find the silver lining
  • Don’t complain or badmouth or gossip about your boss to colleagues
  • Don’t complain about your boss to higher-ups either
  • Don’t use language that could come across as smug or superior and, even if you feel that way, keep your feelings to yourself
  • Never disagree with your boss publicly
  • Be a passive, groveling slave with no identity who runs after their employer’s every whim and kisses their entitled butt repeatedly at every opportunity

Alright, so that last one wasn’t in the article, but the sentiment certainly was.

Daskal’s basically saying put up and shut up. And this is coming from a leadership coach inspiring people to be better leaders.

Well, I’m sorry but fuck that for a laugh.

This is the absolute polar opposite of the advice I would give, and here’s why.

Bosses who want obedience shouldn’t be bosses (and you shouldn’t be working for them)

I don’t expect anyone to just obey me. I want people to challenge me, and I’m actually quite pleased when employees disagree with me. I know my strengths and I know my weaknesses. If someone I employ is better at something I used to do myself, I will step back and let them have at it. I do what Lee Iacocca does:

“I hire people brighter than me and get out of their way.”

The sorts of leaders that Daskal is asking you to pander to in her article are very likely middle managers who know that middle management is as far as they’ll ever go and resent anyone brighter than them on the way up. The tragedy is, that while they’re scared of maintaining their position, their smarter underlings are destined for better things.

But Daskal’s advice seems to be for people who work for old-fashioned, top-down, hierarchical organizations. These types have been going out of fashion for a while now, and the post-2020 surge in remote and flexible working is expediting their extinction. Remote workers have to work independently and autonomously because you can’t be there breathing down their necks anymore.

And that’s only the shittest reason for empowering your employees. A much more obvious one is that employees generally know more than their bosses about their own areas of specialization, so they should be free to make decisions within those areas. Big evil empires always collapse, and it’s because the people at the top don’t listen to the people lower down the chain.

Another good one is that we’re living in the age of the “knowledge worker”. The people whose main capital is to think for a living, whose ideas fuel their organization’s means of producing, developing, and innovating. The smart people who threaten the middle managers’ fragile egos. And the man who coined the term, Peter Drucker, asserted before his death in 2005 that increasing knowledge workers’ productivity was going to be the most important contribution managers needed to make in the 21st century.

My version of Daskal’s advice

If you’d rather enjoy than endure what you do each day, but you have a useless boss standing in the way of your happiness, here’s what I think you should do.

  • Bollocks to being positive. Of course, you’re going to be resentful of a bad boss who you keep feeling like you have to cover for. You’re human. So start by facing the fact that you’re not happy and something needs to be done.
  • You’re obviously going to complain to others about your boss being shit. That’s fine. Do it. We all need to vent sometimes. You might find that your colleague agrees with you and you can discuss what to do. Or they might disagree with you, which is cool too because you might learn something about what your boss is doing and how you’re responding to it.
  • Do complain about your boss to higher-ups. Fuck what Daskal says about “your reputation”. It won’t hurt your reputation if you’re right, and the higher-ups should respect you for pointing out a weak leader in their midst. If they don’t, then they don’t deserve to be the higher-ups.
  • Bollocks to keeping your feelings to yourself. If your boss has done something wrong, tell them. Sure, you don’t have to be rude about it, but if your boss is being a dick, you don’t have to just stand there and take it.
  • Absolutely disagree with your boss publicly. An environment where everyone is allowed to speak freely, share their ideas, and challenge the ideas of others, is the only work environment that will survive today’s climate. As I said before, big evil empires always die.

But what if I lose my job!”

If something can be destroyed by the truth, then it should be.

And if your organization doesn’t foster an environment where all of the above actions are okay, start looking for a new job.

Better yet, come work with me :wink:.

How We Work

Work/life balance is everything, and life comes first. The only notifications I have on my phone are for messages from new joiners onboarding. Everything else can wait. Any questions they have, I will try and respond to them immediately. But when I’m with my wife and my baby son, my focus is them. I expect all my teammates to do the same: To down tools when they’ve finished what they’re doing, forget about work, and get on with the things they love.

Talking of the things we love, we ask all new joiners to write a blog about themselves, intentionally avoiding work as a topic, but rather likes/dislikes, hobbies, and funny stories. That’s because the best way of building a team with a strong sense of community is to invest time in understanding one another.

We have a very flexible working policy. As long as we do the work we’ve committed ourselves to, we should be free to work whatever hours suit us. It takes some juggling and communication with a fully distributed team. But people have kids, pets, hobbies, fitness regimes, whatever matters to them. Everyone’s very good at respecting other people’s time and commitments, and it’s amazing how much quicker work gets done when no one is distracted.

Ultimately, I want our company to be successful, but not because I want fame and fortune for myself, because I want us all to be living our best lives. Trust me, I could be a lot richer if I wasn’t continuously reinvesting our revenue into making our team feel more valued and motivated.

I once had a CEO who told the team, “I’d do anything for money; if it were profitable to have you outside cleaning cars, I’d do it.” This same company used one of my spelling mistakes in a LinkedIn post as an excuse not to give me a pay rise.

Those are the sorts of leaders Daskal is preparing you to work for. Don’t do it. Choose to be happy instead.

Chris Cooke CEO Old Street Solutions

Chris founded three successful startups in Thailand: one was a Scuba Diving School/ Eco-Tourism company dedicated to saving turtles. Once he’d saved enough turtles, he moved back to the UK to pursue his dreams in software.

It was while working for the Atlassian Platinum Solution Partner Clearvision that Chris met Jacek. The two decided there was a gap in the market for easier-to-use Atlassian tools for Jira and Confluence users who don’t have a clue how to code (of which there are many).

“If we’re not making mistakes, we’re not trying hard enough.”