How Dame Stephanie Shirley broke the rules of work

Leadership lessons from Britain's top tech entrepreneur (that you've never heard of).

by Sarah Ellis
Last Updated: 10 Sep 2019

Dame Stephanie Shirley is one of Britain's top entrepreneurs and philanthropists – and yet few people have heard of her.

She founded the software company Freelance Programmers (now part of the Sopra Steria Group) in the 60s. It grew to employ 8,500 people and was valued at $2.8bn (£2.3bn) when she sold it. Retiring in 1993, she has since given more than £67m away to charitable projects.

Her relatively low profile may soon be a thing of the past. Her book, Let It Go, has been re-published by Penguin, and a film of her life is in development.

Shirley arrived in the UK in 1939, aged five, on the Kindertransport (which saved nearly 10,000 mainly Jewish children from Nazi Europe). She was accompanied only by her sister. On leaving school, she decided not to go to university opting instead for a career in mathematics and technology. Frustrated by slow progression and a male-dominated workplace, she started her own software company from her kitchen table in 1962 with just £6. 

In the early stages of her company, she often signed letters as "Steve", finding this gave her a much higher chance of securing meetings and new business. Her enterprise grew – initially employing nearly exclusively women – and went on to be floated on the stock market. In 2000, she become the third richest woman in The Sunday Times Rich List (after the Queen).  

Shirley's attitude to work was extremely progressive. She introduced job-sharing, shared-ownership and flexible working in the 60s, breaking the the rules of work because she saw a better way. Here are four leadership lessons we can learn from her:

1. Treat everyone like adults  

"Have faith in other people," says Shirley. "No-one is faultless, but nearly everyone has virtues (often hidden) and potential (often unrealised)." Her business put this philosophy into practice, paying people for the work they delivered rather than the time they put in. Her approach, in direct contrast to the traditional command-and-control managerial view, resulted not in anarchy and idleness but instead in unrivalled productivity.  

MP Helen Whately recently suggested in Parliament that flexible working should be offered as a default position by employers rather than something that needs to be requested. Building a culture based on trust and accountability paid off for both Shirley and her employees  at least 70 of whom became millionaires through her shared-ownership scheme.  

2. Invest in building resilience 

Shirley's story is littered with examples of perseverance and dogged determination. In her early years, she applied repeatedly for promotion despite significant resentment at her ambition. Later, it took her 11 years to achieve a shared-ownership structure for her organisation, which she names as one of her career highlights. 

She explains: "If I had to offer a single, simple explanation for my company's survival and ultimate success, it would be just this: hard work. I stuck with the idea and made it work." 

3. Redefine our relationship with success 

Shirley didn’t have designs on being an entrepreneur. Indeed, when a journalist once described her as such she had to look up what it meant. And personal wealth wasn’t her starting point: even when she later amassed significant wealth, she gave much of it away. Instead, she was motivated to solve the problems of inequality that she personally experienced in her own career: "For me, success comes from doing my best to achieve something worthwhile – never if it’s easy or I could have done better." 

4. Work-in-progress 

Shirley is committed to continually learning and improving. She started work straight after school, using her evenings and weekends to earn a degree in mathematics. She used her holiday allowance as an opportunity to gain work experience elsewhere (although this was partly because she couldn’t afford to go on holiday).

In her company charter, written in 1984, she outlined the business's values, which included professional excellence and growth, demonstrating that hers was an organisation with learning embedded into its DNA.

As futurist Alvin Toffler puts it: "The illiterate of the 21st century won’t be those who can’t read or write, but those who can’t learn, unlearn and relearn." Shirley has no economic incentive to continue working yet, at 85, she shows little sign of slowing down.

Sarah Ellis is the co-founder of Amazing If and a speaker at Management Today's Inspiring Women conference on 21 November. 

To find out more about Dame Stephanie Shirley, watch her TED talk: Why do ambitious women have flat heads?, read her book: Let It Go, and listen to her interview with Sarah Ellis on the Squiggly Careers podcast 


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