My best bosses were women

There’s research going back decades that shows that women make better managers than men.

On nearly all of the relevant qualities that relate to leadership effectiveness, women simply outperform their male counterparts.

And yet, here we are in 2020, and still there are more men in top positions, more male CEOs, more male board members, more male heads of state, more male managers.

Worse, all through workplaces women are underpaid as compared to men (for the same work), as well as being underrepresented towards the top of the tree.

I won’t go into the all the reasons why, be it unconscious (or blatant) bias, the feeling that if we lift women up we pull men down (we don’t) or out and out sexism.

What I will say, is that across my now 34 year career in the UK, Singapore and Australia, I have seen the truth that women make better managers than men.

This is not to say there weren’t some great male managers along the way – there were – but overall, the women were better, more effective, more productive, easier to work with, more flexible, more engaged, listened better, spoke better and quite simply, they had an edge.

I can also say that I have had various people manage me (as my boss) over those three and a bit decades – some great, some dreadful, some mediocre, some OK – and I’d have to say that the two best were both women…


For seven years, I was teaching in a large expat school in Singapore. It was an amazing experience. The school had 2,500 students drawn from more than 60 countries.

Their parents were either usually high performing business people or diplomats, and most of them were heading to top universities around the world. The school’s IB results placed it in the top 10 schools in the world.

The teachers were mainly men, mainly British, and they were colourful characters. Did not suffer fools gladly.

After a few years, the (male) Headmaster left for another international school, and the deputy head (another male) got the job. A New Zealand lady was in the final short list but was not awarded the top job. Instead, she was offered a senior management position, Deputy Head and Head of the Senior School. As such, she was my new boss, as I had just been promoted to Head of Year in the Senior School.

She made an instant impression. At the first school teachers meeting, before term started, she gave a short speech introducing herself. At the back, sat a few alpha male cynical male teachers, who were quietly awaiting this new exec to fall flat on her face.

Sizing up the situation perfectly, she ended her talk by saying “… and in closing, I note that although the men here make up about 75% of the total staff of the school, they are 100% of those sitting in the back row.”

Game on!

She was not someone for taking a backwards step. She was tough, but also open to suggestions. She gave praise where it was due, and spoke to you one on one if you needed help.

I came to admire her greatly, and she and her husband became good friends. She had to navigate some tough times, adolescents can be strong willed, and Singapore had its own rules that had to be respected. The students had to be counselled, cajouled, understood, reasoned with, helped… and in some cases a firm hand was required, in others a shoulder to cry on.

She imparted wisdom in a straight line, so you always knew where you were with her. I learnt a great deal about management, leadership, being effective. Quite simply, an exceptional human being.


A few years later, I was in Perth, running a tech startup through all the trials and tribulations that early stage businesses go through. We were an online real estate business, set up a few years before came to town, and well before Domain or got their act together.

In our early years, we had approached the Real Estate Institute of WA (REIWA) to see if we could work together. What we did (web design for agents, CRMs and such) was not done by them, and perhaps a deal could be done? For 5 years, we received nothing but the cold shoulder. Until a new CEO, a lady, was brought in. Suddenly, the door was open.

On first meeting the new CEO, I was struck by a sharp intelligence and grasp of fact. No beating about the bush, here was clearly someone who could get things done, and would shake up REIWA a bit (which, by then, it required, as it had run foul of the ACCC among other things.)

With no particular end goal in sight, besides what we could do for each other for mutual benefit, we forged a partnership whereby we would send our properties to, and they would allow us to develop off the REIWA platform for our/their clients. This lasted 5 years, until in 2010, we met for a coffee, floated an idea, and within 6 weeks the company had been acquired 100% by REIWA.

Being a 100 year old not for profit members’ organisation, REIWA does not go along buying companies. I think we were the only one they ever bought. But the deal was done, quickly – as it was just so natural a fit – and they took on all our staff, on at least the salaries they had been on before, and I got to run for the next few years.

Was she perfect? No, she would be the first to admit that. But she was strong, you knew where you were with her, and you knew the direction we were all heading in. That’s what you want from a leader.

Two years later, she retired from the CEO position. I witnessed her wisdom, analytical skills and sense of humour up close. She reminded me of my Kiwi boss in Singapore. Not dissuaded from acting, she had a sharp intellect, was charming and much admired.

For both of them, there were some tough days, but I never saw them ‘down’. They exuded confidence. They consulted, argued, listened, and – crucially – acted. Unlike most males in similar roles, there was no ego getting in the way.


Men – this is not an attack on you. We can all have better outcomes if we assist women to reach their rightful positions in management, calling out the artificial blockages and resistance along the way. Our organisations and world will be better because of it. Research has shown that the GDP of the world would be better by $24T if gender equality was reached. So, it’s not only the moral and right thing to do, it makes good economic sense.

Imagine if the planet were run by women. Hell, it’s been run by men for centuries. Let’s give it a try.

Also – have a look at ‘CEOs for Gender Equity‘ and ‘Male Champions for Change‘. Men. Join today.

About the author

Charlie has spent more than 20 years in Perth’s tech and startup sector, firstly as a founder himself, through to exit, and more recently as a writer, advisor and investor. Originally from the UK, Charlie worked in Singapore before arriving in Perth in 1997 to do an MBA at UWA. Graduating as top student in 1999 he set up online real estate business, running it for 10 years before selling to REIWA, whereupon Charlie ran In 2013, he moved to Business News to lead their digital transformation as CEO, and then worked for the federal government’s Accelerating Commercialisation program, funding pre-revenue startups and innovative businesses. He now works in an advisory capacity for multiple tech and other businesses, is managing editor of Startup News and co-host of the Startup West podcast. He also writes a column for Business News on startups. Charlie sits on the advisory boards of WA Leaders, TEDxPerth, WAITTA, the Perth Symphony Orchestra, and the full board of Rise Network.

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