What Theresa May can teach you about leadership (yes, really)

Missing the Maybot? The former PM offers some surprising lessons, says Caroline Whaley, co-founder of Shine for Women.

by Caroline Whaley
Last Updated: 04 Sep 2019

I more than most was willing the UK’s second female Prime Minister to demonstrate leadership – regardless of the policies she professed. I wanted to see Theresa May collaborate and stand for something authentic and real. Sadly, looking back on her premiership, there’s not a great deal to celebrate. Unlike Margaret Thatcher, she failed to leave a mark. 

May is recognisable for two things: her failure to deliver Brexit and a selection of trivial minutiae that she let define her. There’s nothing in there I’d be proud of and, in the end, most people felt sorry for her. 

Her biggest single failure was not standing for anything authentic and memorable. She didn’t want Brexit, so couldn’t truthfully throw herself behind it. Yet Brexit was such a tenure-defining issue for her that she couldn’t be known for anything other than that.

What does a leader – especially a woman leader – need to do if they want to be successful?

Find and use what’s authentic to you

If you can be at ease with who you are, embrace it and make it a defining characteristic. Just look at current PM, Boris Johnson. He’s never hidden from who he is. Florid and sometimes inflammatory views that resonate with the fringes of his party. The ability to laugh and joke at times of seriousness. He’s not afraid of his authenticity and knows it’s his greatest asset. 

Listen to your team

Successful leaders will make decisions, but will also do a lot of listening on the way. Sadly, May didn’t. She had a small clique of advisors and battled with her cabinet. She ran negotiations with the EU rather than letting her Brexit minister do it. She took the same deal to Parliament three times without meaningful compromise. This lack of collaboration is ultimately a massive failure of leadership.

Remember, a leader is still a team member. Just because you’re in charge, it doesn’t mean you’re a lone wolf. You go to immense lengths to build a team of people - use them! Theresa May fought those Brexit negotiations herself, when she had a dedicated Brexit Secretary sitting at home. She should have worked with him to reach a successful deal. Share ideas with your team, celebrate each other’s successes and work together to reach a common goal.

Show emotion - but at the right times

Showing emotion is fine. Emotion means passion and shows we’re human. But it’s important to know what impact your emotions have – especially as a leader. We saw May shed tears on multiple occasions during her premiership, most notably when hearing the General Election results, and when announcing her resignation.

Each display of emotion was not met with empathy from the public, but rather seen as a sign of desperation. Arguably, the tears on these occasions did little more than highlight the lack of tears at tragic events including Grenfell Tower and the London Bridge attacks. Smart leaders learn how to regulate their emotions. Unmanaged emotions can really work against you.

Own your mistakes

Everybody makes mistakes. It’s what makes us human. People will respect you for holding your hands up and admitting your errors. But if you try and cover them up, you’ll be found out and scrutinised.

When May called a snap election in 2017, the Conservative Party had a huge lead in the opinion polls, but the gambit failed miserably as May ended up losing her majority. She never did apologise for what is widely considered an unforced error of epic proportion. People don’t trust perfection, they trust authenticity. They’ll listen to you if they think they can believe you.

Be a mentor, not a preacher

Create a really stretching vision and get people to feel excited about it in the same way you are. May notoriously failed at getting Parliament to believe in her plan. Instead of educating them on why it was the best way forward, she pleaded with them to simply go along with it, even offering her own resignation if they did. Mentoring your team allows them the opportunity to learn and envision your plans in the same way you do. Simply preaching your way of thinking can signify arrogance and hollowness.

To give this story a happy ending, regardless of her policies and politics, Theresa May’s premiership did teach us some valuable lessons about leadership. We should put those lessons to good use and become more authentic, more collaborative and ultimately deliver a greater impact in the world.

Caroline Whaley is the co-founder of Shine for Women, a career coaching organisation. She previously held senior global marketing positions at Nike and the Nike Foundation

Image credit: EU2017EE Estonian Presidency/Flickr (Creative Commons)


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