How to be the best boss you ever had

We become self-employed because we want control over our lives and choose who we work with, what we charge and how we manage our work/life balance.

If you were to take a step back and ask yourself how that’s working out for you, what would you reply?

Listening is vital to being a good boss – so have a good old chinwag with yourself and listen carefully. Are you overworked? Do you feel appreciated? Do you have the direction and focus you need to get job satisfaction, or are you overwhelmed with miserable, routine tasks?

Your most important responsibility when you’re working for yourself is you. It’s up to you to ensure you’ve got the best working environment to promote your wellbeing. If productivity or profits are down, morale is low, and quality is suffering – it’s up to you to do something about it, before there’s a mutiny in the ranks!

Cast your mind back to the bosses of your past. Who were the great ones, and what was it they did that you loved? Who were the awful ones, and what did you grumble about?

Here’s my self-management checklist for what to do and what to avoid.


To be a good boss, you need to…

Be appreciative

Tell yourself you did well. Honestly, look in the mirror and say it! It’s too easy to stop noticing and appreciating those little things. No-one else will give you the daily encouragement you need, but your motivation will suffer without it. When you reach an important goal, reward yourself with something you enjoy. List your achievements and put them on your noticeboard.

Care about you personally

Do you feel valued as a person when you’re working? Do you cut yourself some slack when you’re ill? Remember, you wouldn’t have a business without you so you deserve to be valued. Plus, people who feel valued are happier, more productive and relaxed.

Care about your personal development

That dream boss who is keen to help you reach your full potential, professionally and personally, can now be yours! What are your aspirations, your life goals, and your vision for the future? As a good boss to yourself, you can take a genuine interest in pursuing these. Whether you need to find a mentor, take some training or attend a personal skills workshop – the choice is now yours!

Give proper focus and guidance

Why are you doing what you’re doing? What defines your daily task list, and what vision are you trying to fulfil? Unproductive, stressful work happens when these questions aren’t being asked. So give yourself clear direction by regularly assessing your personal and professional priorities and organising your work accordingly.


To avoid being a bad boss, avoid being…


We are all our own worst enemy – and when we’re our own boss, self-criticism can reach screaming pitch. If an actual boss spoke to us the way we speak to ourselves – dismissing our successes, picking up on every little mistake and berating our looks, we would have strong grounds for legal action! So go easy, show yourself understanding and let yourself be.

A bully

One of the characteristics of bullying set out by the TUC is ‘setting a person up to fail by overloading them with work or setting impossible deadlines’. That phrase could also be a definition of bad self-management – do you heap work on yourself and set crazy deadlines? Be honest. The out-of-control task list is a good place to start. If you set yourself tasks more quickly than you cross them off, consider setting a more manageable pace.

A slavedriver

What kind of hours are you putting in? How much work do you take on? Do you organise your workload according to your own capacity, or are you constantly trying to fulfil your clients’ slightest whims? The temptation is to promise the earth when you’re trying to win that contract – but you’ll pay for it later. Remember to be true to yourself in everything you do, no matter what the pressures.

A ditherer

There is nothing more frustrating than a boss who can’t make their mind up, or who needs to consult their line manager, their mother and a personal astrologer before deciding on anything. One of the hard truths about being in business for yourself is that every single decision is down to you – and this can feel like quite a weight. Again, all you need is a good vision, business plan and strategy against which you can test every option that comes into your life.


So what kind of boss are you to yourself, and where can you improve? Hopefully this little checklist will give you some pointers on where you can improve. Happy managing!

About the Author:
Catherine Lee is a business blogger and founder of Kaleidoscope Virtual Assistant Services.  She has more than 20 years’ experience in office management and Personal Assistant Services, and is now an indispensable right-hand woman to executives working all over the country. Catherine is also on a mission to inspire women to make careers as self-employed Virtual Assistants, and to encourage Virtual Assistants to remember they are giving essential, professional business services and to know their own worth.

Julie Hall

Business Mentor & founder of Women Unlimited

Julie is the founder of Women Unlimited and a business mentor to women who know they are ready to step into their leadership. She works closely with them to help them remove the blocks that hold them back and achieve their business goals. Clarity, Focus, Strategy, Mindset and Marketing.

Be the change that you want to see. Step into your leadership.