Your relationship with your boss was going great, until they had to make a tough call. Now you can’t look them in the eye…

Your boss flat out makes Miranda Priestly look like Judy Garland and you don’t know how long you can keep taking flak…

You’re moving jobs and you think the new boss looks okay, but you’ve been wrong before and now you’ve got the jitters…

There’s a great scene in the film The Proposal, in which the beleaguered employees of a New York publishing house scramble to sort themselves out (DM-ing ‘THE WITCH IS ON HER BROOM’) as Sandra Bullock’s boss lady stalks through the office in her five inch heels. Then there’s the LOOK Meryl Streep’s character gives poor Anne Hathaway when she points out that two identical belts look…identical. In fact, now I think about it, there’s a whole franchise, if not a whole genre, dedicated to horrible bosses. They’re frightening and fascinating, unless of course, you happen to actually work for one. But like their counterparts, the hero bosses, they’re actually pretty rare. And thank god for that. But whether you’re dealing with a hell-raiser, a hero, or just a common-or-garden human boss, it helps to know it. And to know what you, dear reader, can do about it.  

How to use this guide

This guide is very howie (very practical). And there’s a big quiz, too, a la a 1996 edition of Cosmo. So if you’re less into the theory and want to get doing, feel free to zip to the quiz and then bliss out in all the how.

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Contents:

The reality of bosses
The myth of management
Quick quiz: Find out what kind of boss you’ve got 
How to: spot a good boss
How to: reframe your expectations
How to: be a brilliant bossee
Next steps: start bossing it 

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THE REALITY OF BOSSES

Being a boss is not an easy gig. Some people take to it like a duck to water, many find it a struggle. Organisational structures often mean it’s hard to move up the ranks without being a manager, so there’s a lot of people who’ve become managers by career necessity rather than having a particular penchant for it. 

It’s part of a boss’s job to make tough decisions. They may find these uncomfortable, or even agonize over them. Sometimes, they must do what they’ve been instructed to do by their bosses (who were told by their bosses, etc.). They might have to dismiss your best work buddy because, as much as you love working with them, they’re not that good at their job. Maybe they need to restructure the team to meet the changing needs of the business and that impacts on you. Perhaps they need to bring in a new layer of management because their role has expanded too much and now you report to someone new. Maybe they’ve had to stop spending as much time supporting and mentoring you because you’ve made it and there is someone else more in need of their attention.

This stuff happens, it’s the reality of the modern workplace. Some of the things that bosses do that bring some gloom may be exactly what they need to do to fulfil their role. It doesn’t mean they don’t care; it means they’re doing hard things.

THE MYTH OF MANAGEMENT

It’s tempting to believe in a mythical leader who rises beyond the echelons of humanity, always gets it right, and can magically solve your problems. Yet all leaders and managers are mere mortals. Whatever type of boss you have, whether they’re brand new to leadership or someone with significant experience, if they’re an expert in your subject matter or have no idea what you do, by the nature of their role, they will influence your working life. For the sake of simplicity, let’s put bosses into three categories:

Human bosses
Hellish bosses
Hero bosses

QUICK QUIZ: FIND OUT WHAT KIND OF BOSS YOU’VE GOT

I think a little mental gymnastics does us all good from time to time. So here’s what I want you to do: start with the number 10 in your head. Got it? 10. Read the statements below and every time you agree with one, subtract one. 

❌ My boss has no interest in my life beyond work
❌ My boss is focused on my inputs (hours in the office/online)
❌ My boss micromanages my every move
❌ My boss has favourites and enemies
❌ My boss dismisses my ideas
❌ My boss barks orders at me
❌ My boss moves goal posts so I never know where I stand
❌ My boss berates me if I make a mistake
❌ My boss blames me when things go wrong
❌ My boss fails to recognise the things I do well

At this point, the number in your head should be somewhere between 0 and 10. Now read these next statements. For each statement you agree with, add one to your total. 

✅ My boss cares about me as a person
✅ My boss focuses on my outputs (what you deliver and how you do it)
✅ My boss is invested in my success and career
✅ My boss acts with kindness when I need it
✅ My boss pushes me to be better
✅ My boss listens to me without judgement
✅ My boss advises, guides, mentors and coaches me
✅ My boss recognises when I do things well
✅ My boss is clear about expectations and standards
✅ My boss lets me know when I am off course and helps me correct

Now your total should be somewhere between 0 and 20. Time to see what kind of boss you’ve got!

If your total is between 0 and 5, sorry, but you’ve got a hellish boss.
A hellish boss can make everything at work seem gloomy. They fill you with fear and insecurity, and make you dread your working days. Their presence makes you shudder, an email from them gets your anxiety rising and if they say ‘we need to talk’ you consider running for the hills. 

It’s almost impossible to live with this type of boss. It destroys your self-belief; your confidence will collapse, and you’ll likely burn out. Perhaps, you’ll be able to manage the situation, by trying to get in their good books. Then you realise they don’t have good books and regardless of how hard you work, however much you adapt to their whims and whether you’ve given every single last drop of blood, sweat, and tears – you will never make them satisfied. It’s just not possible.

If your total is between 15 and 20, congratulations! You’ve got a hero boss.
A hero boss can make everything at work seem joyful. They inject you with the inspiration, confidence, and permission to make your working world a pleasure rather than a chore. These bosses exist in their wonderful glory, but they are a rarely spotted beast. They exist in only a few natural habitats. You might find them in special places with brilliant development programmes or organizations that care deeply about people. They can also exist in the most barren of workplaces, where they’ve experienced the gloom themselves and have chosen not to pass it on, becoming little havens of happiness.

If your total is between 5 and 15, yep, you’ve got a human boss (most of us do)
The reality is that most bosses are neither all hell-ish or all hero-ish and they’re unlikely to be at one or other end of the spectrum all the time. It’s unrealistic to expect 100% performance, 24/7, from even the most progressive of bosses.

In real life, human bosses:

• Are vulnerable and struggle too – they did not become immune to work and life-based challenges when they got their boss title
• Experience the challenges of working life and often take on what their teams are challenged with too
• Feel joy and gloom just like everyone else and try to do their best
• Have the good, bad, and ugly days just like the rest of us
• Slip up and say or do the wrong things, even when they’re trying hard to get it right
• Get mad and throw their toys out of the pram, have a strop, or a little cry when it gets too much
• Forget to say thank you sometimes, even though they’re really, truly grateful to have you in their team
• Are trying to balance the needs of many and can’t please everyone all the time
• Often must act as piggy in the middle between their direct reports and their bosses
• Are trying to make it through the day, as well as they possibly can whilst riding a unicycle and juggling fireballs.

HOW TO: SPOT A GOOD BOSS

Always seek out a boss who sits somewhere between human and hero. A person who spends 70–80% of their time right of the centre line. Allow them the space to cross to the dark side occasionally. Don’t judge them for it, support them back into the light. Make sure they’re the kind of person who is self-aware enough to know that they crossed the line and have enough self-esteem to say they got it wrong.

A good boss will:

1. Be open about what their strengths are and where their passions lie
2. Tell you what they’re not good at and feel comfy asking for help
3. Give you clarity on their expectations
4. Share enough of themselves beyond work that you feel connected to them personally as well as professionally
5. Know they’re wonderfully imperfect and embrace this openly
6. Pick up the phone and say, ‘tell me what I can do to help’ (or even better, just do something that is helpful) when you’re in a crisis
7. Muck in to support and help create the fix when it all goes wrong
8. Tell you when you’ve done something brilliantly
9. Give you direct feedback when you need to improve
10. Invest in your personal and professional development

Whenever you’re seeking a new or different role, put as much energy into discovering and assessing who your boss (or bosses) will be as you do into considering and analysing the job content, reward, and growth. A boss can make or break your day – choose wisely!

If you’re working with a great boss, make sure they know it! As people work their way through the leadership ranks, they get less and less feedback on their performance. Be the person who tells them what they’re great at, and what they can do even more of. They will be grateful for your candour.

Here’s a little extract from my conversation helpfully entitled ‘leaders are human too’ with the incredible Jo Smallwood (she’s the Small to my Stall!)

HOW TO: REFRAME YOUR EXPECTATIONS

When you look upwards, are you seeking perfection, wanting your role models to be superheroes? Whether they’re your line manager or the most senior people in your organization, do you want more from them than they can realistically give? If you want to feel more joy when it comes to your bosses, you’ll need to adjust your expectations. You must leave room for their humanity.

REFLECTION QUESTIONS What are your expectations of your boss/es? Are those expectations based in fantasy or reality?

FREE DOWNLOAD If you could use a little help, my ‘Realigning Your Expectations of Your Boss’ template is free for you to print and work through at your own pace. Download it here.

HOW TO: BE A BRILLIANT BOSSEE

Have you ever considered how you’re doing as one of your boss’s team members, as a bossee? The boss/employee relationship is a two-way street, yet it’s easy to focus on how their behaviour impacts on you rather than looking at how you impact them. If you both know how your behaviour contributes to each other’s WorkJoy or WorkGloom and do your best to work with that information, you’ll be set up for a more meaningful relationship. This could range from the micro-moments (like grabbing them a coffee when they’re snowed under) to stepping in to support them with a big work challenge. If you can, develop a relationship where you know each other well enough to spot opportunities to bring a little joy (or ward off some gloom). The investment of your energy here will pay off. Here are some examples:

	Joy	Gloom
Your boss	If their joy comes from observing you doing well, have you told them about your latest successes?	If their gloom comes from back-to-back meetings, have you offered to sub yourself into some of them?
You	If your joy comes from being challenged, have you asked them for their thoughts on what you could do differently?	If your gloom comes from a difficult relationship with a client, have you asked for their advice on how to handle it?

REFLECTION QUESTIONS What are your boss’s expectations of you? What are you doing to help them to help you? (e.g., telling them what you need) How could you bring a little WorkJoy to them today?

NEXT STEPS: START BOSSING IT

If it turns out that your boss is hellish or just plain human, that you need to realign your expectations or become a better bossee, do not fear. Here are some things you can do, big or small, to get yourself (and your boss) unstuck and moving towards better things. 

Follow me on Linkedin for tidbits of interesting worky things.

Dive into the WorkJoy Jam podcast archive for interviews with experts on all aspects of WorkJoy. 

Grab my 21-day GloomBusters audio guide ( a five-minute audio pops into your WhatsApp every day for three weeks) and start working your way out of WorkGloom.

Pick a chapter of my book, WorkJoy: a toolkit for a better working life to read each week.  

Book a 1-1 chat with me for an instant hit of strategy, courage or confidence. 

SPREAD THE WORKJOY

We all have a friend with a hellish boss, don’t we? Sure, the stories can be funny over a glass of wine, but the morning after, why not send them this article. And some paracetamol.