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How Not to Be a Crap Boss!

We’ve all had them. 

The boss that steals your ideas and presents them as their own. Refuses your holiday request without explanation. Micro-manages your every waking moment.

The one who plays favourites, is quick to criticise and slow to praise, who assumes an air of superiority whenever we’re around.

Reducing the frankly devastating impact that working with such people can have on our lives is one of the biggest reasons for moving into entrepreneurship.

We want to be our own boss and live free from oppression, grind culture and the Sunday Evening Pit of Dread.


But you’d be surprised how easy it is to slip into habits and behaviours that would make our previous Bosses From Hell envious.


When the buck stops with us and the full weight of running our business falls on our shoulders, it’s all too easy to let that stress leak out in unkind and unprofessional ways – not only with those we work with, but also with ourselves.

As someone who has recruited, trained and led teams for the best part of 17 years, I’ve seen the good, the bad and the downright ugly when it comes to management.

I’ve worked with some truly courageous and compassionate leaders who still inspire me to this day.

And I’ve worked with some who made the lives of everyone they interacted with miserable.


As a business owner, we have the power to make or marr the days of the people we work with.

The truth is that leading a team is a privilege… and not everyone is cut out to be a manager. It’s a skill few put sufficient time, money and energy into learning.

Remember how that 👆  boss used to make you feel?

Yeah… DON’T be that person.

Here are some pointers for things to avoid… and what to do instead.

how not to be a crap boss

1. Get Organised, Be Transparent

The greatest help you can give your team – whether you’re beginning to work with a single contractor or onboarding a whole team – is to get organised.

For so long, your business has been your baby and you’ve gotten used to doing everything yourself.

It’s exhausting… but for those control freaks amongst us (🙋‍♀️) it is also deeply safe and fulfilling. We don’t have to share information with anyone, or open the inner workings of our business (and our mind) to others.

But if you want to set your team up for success, you need to create organised spaces for:

  • A central hub where you’ll manage everyone’s tasks (Notion, Trello, Asana, ClickUp etc)
  • A shared document storage area with relevant permissions for the team (Google Drive, Dropbox)
  • SOPs (Standard Operating Procedures) for your key business tasks
  • A secure password sharing tool (try 1Password or LastPass)
  • A shared communication channel where the entire team can talk and collaborate (Slack, WhatsApp, comments in your PM tool – try to avoid email)

Organised systems and workflows are the key that unlocks your business’ and team’s true potential. They are the foundation that will support all of you to thrive as you grow together.


2. Share a Cohesive Vision + Clear Goals

One of the commonest things I’ve seen business owners struggle with when they begin to grow and lead a team is learning to communicate a consistent vision to those who work for them.

As entrepreneurs and creatives, most of us have no problem coming up with 1,406 ideas and new directions for the business before breakfast every day…

BUT that doesn’t mean those ideas should be constantly shared with your team.

Giving a clear overview of your vision for the business, plus your long- and short-term goals when onboarding new team members is crucial; shepherding them (and yourself) towards that vision consistently is true leadership.

People thrive when they feel sure about where they’re headed and why. They will produce their best work, solve problems that come up and support you through the hard bits if they feel like they are sharing the vision with you. Let them!

[Sidenote: If you need some help creating your roadmap and getting clear on your vision, let’s give you a Business Glow Up!]

how to celebrate with your team

3. Create a Culture of Safety

It’s cheesy, but it’s true – be the change you want to see.

If you’ve had horrific experiences with irate bosses or toxic work culture before, ask yourself how can you create something different now that you have the power to curate a working environment for yourself and others.

Treating your team as human beings – with flaws, quirks, other responsibilities and outlooks that might differ markedly from your own – is crucial.

Foster an environment of inclusivity and intimacy by encouraging team members to share, laugh, support each other and collaborate.

And don’t be afraid to show your own humanity – when something has happened in your personal life, you’re sick or exhausted, or you’re having a day of doubt, share it.

Part of the beauty of having a team is truly knowing you have people in your corner. Talk it through. Ask for help. Being the boss doesn’t mean being untouchable.


4. Have Realistic Expectations

It’s tempting to imagine – when we’ve been grinding on alone for so long – that hiring a new employee is going to magically solve all our problems.

If we hand over our client work, invoicing, marketing, sales and admin, we’ll have nothing left to do except sip margheritas by the pool, right?!


The honest truth is that bringing on, training and bonding a great team takes more work and more time than you’d think (or want) it to.

It’s not an instant fix (what in business really is?).

But trust me when I tell you that pouring your time and attention into building a great team can become one of your proudest (and most powerful) achievements in life.

For each new team member you bring on, you’ll need to factor in adequate time to get them up to speed.

Remember: when they first arrive – they are NOT you.

They don’t know your clients yet, they don’t understand the inner workings of your brain and they certainly have no idea where you scribbled that genius soundbite that came to you in the middle of the night.

But in time, they can be and do all of these, and so much more.

Treat your team with respect. They are not your minions. You are not the only sun in their solar system.

They are professionals and experts in their own arenas, here to support you with key aspects of your business. Maintaining realistic expectations sets them – and you – up for success.


how to be a great small business boss

5. Communicate + Maintain Clear Boundaries

So much friction within teams can be avoided by setting clear boundaries up front.

Things like role responsibilities, deadlines, invoicing procedure, contact channels, working hours, holidays, escalation procedures, time reporting and job targets should all be communicated (in writing) when you begin work with a new team member.

The easiest way to do this is by putting together a Welcome Pack which is sent to new hires before they start, and maintaining an up-to-date Team Info Area in your task management tool.

Anything that is super important to you should also then be communicated verbally, so you’re confident it’s been fully received.

Then practice what you preach – if you state your working hours are 10am-6pm, don’t respond to that Slack message that comes in at 10:15pm.

If you want your team’s hours to be reported by a certain day of the month in a consistent format, create a template and add a repeating task in your team’s to-do list to submit it on time.

And if you want an employee who’s comfortable owning the relationship with the client whilst delivering their social media strategy, call this out specifically in the job description you advertise their role with.

Managing boundaries in a clean way creates space for more time and energy to be spent on the good stuff – collaboration, great work and delivering an exceptional experience to your clients!


6. Make Time to Celebrate, Praise + Enjoy…

There is a tendency in all of us to rush forward to the next thing, the second we’re done with this thing.

In business, this is especially common as we hanker after the bigger goal / more famous coach / more profitable launch.

But getting present and acknowledging and celebrating your wins – both large and small – is a key piece to building a cohesive, happy team.

This doesn’t have to be hard – why not create a #wins channel in your team Slack, give everyone a paid day off when they’ve worked their socks off on a big launch or take a few minutes to handwrite a thank you note for a piece of work well-delivered.

And don’t forget to extend this love to yourself – celebrate each step you conquer and enjoy the journey of building the business of your dreams.


stepping into being the ceo boss in a small business

7. …And When it Comes to the Hard Stuff, Be Firm But Kind

With great power comes great responsibility.

And sometimes that means letting a team member go, highlighting poor performance or communicating a line that’s been crossed.

These conversations are without doubt, sweaty-palm stuff… but they’re also part-and-parcel of being a leader.

In these situations, the worst thing you can do it (a) procrastinate / avoid the discussion, (b) chicken out and do it by text message, or (c) try to soften the blow by fluffing around the point.

Instead, hold the mantra of ‘firm but kind’, and bite the bullet. Book a brief call first thing tomorrow, so you won’t have all day to get yourself worked up.

And if you tend to get flustered in the moment, take some time beforehand to write out your main points and key phrases. Pop these on a post-it note and stick it near your laptop camera so you have them close to hand during the call.

Some conversations are never going to be easy – but they can still be professional, fair and compassionate.


The bottom line is – developing as a leader takes time.

But it’s all part of the fun of this crazy, challenging, fulfilling, hugely rewarding adventure that is building a business!

If you feel worried, out of your depth or unprepared, I’m here to help.

Being a great boss is a skill anyone can learn. And remember – the kindness and support you extend to your team must first be extended to yourself.

To Your Success, 

           Chelley x

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Hi, I’m Chelley

Let’s make like Marie Kondo and streamline your business so it feels peaceful, profitable and totally on-purpose.

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