Jim Lawless Speaker Focus
Jim Lawless is a world-class C-Suite advisor and record-breaking freediver, and is ranked among the world’s leading business speakers by Global Gurus.
He has delivered DARE Loop and Second Strategy keynotes to well over a million people across five continents and he has tested his frameworks at the extreme edge, becoming the deepest free diver in British history in just eight months with a dive to 101 metres on a single breath; he moved from non-rider to televised jockey in twelve months.
Jim very kindly took some time out to answer some questions for our speaker focus series.
Hi Jim, I hope you are well. It was back in 2008 we first worked together and it was around the time Taming Tigers was first published. How did you first start your speaking work?
Happy memories Matthew! You were an early supporter of my work and I’ve never forgotten that. Thank you.
It was the faith of a very early client of mine, Brian Lawson of BT, that began it all. He invited me to speak at a leadership event he was running. I declined his invitation twice because I did not think I could deliver. I accepted on the third, very persuasive call. I messed up and finished 15 minutes early. But only Brian and I knew that, and he forgave me. Apart from that it was a success. So much so that an audience member invited me to speak at an event for them. I was then, as they say, ‘at the races!’
So, through a total accident on my part, and a belief on Brian’s part, a new chapter was born for me.
I often say to speakers that having a book does not necessarily lead to bookings – it often compliments the speaking work. However, I have had people wanting to book you on the back of reading Taming Tigers. Did you have any idea at the time how successful it would be and the longevity it has had?
I had no idea at all; I think the only writers who are confident of a commercial success are celebrity chefs.
Taming Tigers has been a success beyond my wildest dreams. I get messages of thanks, for the difference it has made in how lives are lived, from around the world most weeks via my website or social media – and that is the point for me, not the royalties.
I self-published it in 2008. Penguin Random House Bought it in 2012. Yet last year, in 2025 it was featured at the Lviv book festival in Ukraine (where it had become a best seller), so I went there and spoke and did a signing with a queue that lasted much of the day.
Then I travelled on to Kyiv to have a number of meetings and to speak there. In my hotel lobby a senior Ukrainian judge recognised me, thanked me for writing it and wanted a photo. That visit was a deeply moving, life changing experience for me.
You have always been evolving with your keynotes rather than trying to re-position yourself as such – sticking to many of the core values you have always had. Would you be able to give me a little overview of your most popular keynotes – The DARE Loop?
Well, that evolution is because speaking has always been my secondary job. For a serious speaker, I think it must be. My speaking has no value to a discerning audience unless I am bringing learnings and experiences from another source. And over twenty-five years, a ‘primary career’ changes.
Initially, having left City law, my primary job was to explore the ‘Tiger’. I did that in consulting and training projects for my clients. I did that at the racecourse and in the ocean. I did that in my studies and my writing. That work gave me the right to speak about the universal fear we experience as ‘The Tiger’.
Twenty-five years on, my primary role is to architect, with the CEO, an organisation that can deliver ambitious strategies at pace and at scale AND respond on a sixpence when necessary to match technological, political and competitive landscape. I created the DARE Loop to serve those CEOs.
The DARE Loop is a potent tool, keynote and book for a leader who must help others, at scale, to change behaviours, adapt fast and deliver a bold strategy. Faced with uncertainty, humans default to hesitation, escalation or congregations. Some, not many, are able to override the powerful emotions that create that default behaviour. Organisations have been designed to reward that behaviour.
The DARE Loop supports a person to notice and override their nature: the learned story, the prediction of danger, the acceptance of the anxiety that says ‘turn back; wait and see’. It requires seeking clarity on the Result I should be aiming for in my area, an assessment of the potential Actions to deliver that Result and then a conscious, unemotional, Decision about how to proceed. That’s the D A R.
It builds autonomy, accountability and first principles thinking: speed and change.
The E and the Loop are where true the high-performance top spin is generated. The E is to Evaluate. Top athletes are hungry for the route to improve. They own their failures and Evaluate their Decisions, Actions and Results in order to excel. In corporate, political and sometimes military spheres, most people avoid this process if they can.
The Loop is to build the expectation to learn, unlearn, adapt accordingly and iterate fast.
You will need a map for the place outside the comfort zone. How to operate when all your emotions from ‘yesterday’s’, story are telling you to quit, blame, escalate, hold another meeting: HESITATE!
So, the DARE Loop keynote, and the upcoming book, both contain the map.
It is the perfect keynote at events where the strategy needs to move fast, senior leaders have become comfortable waiting for instructions and the organisation needs to build momentum. But it gets really exciting when we have time to extend into a workshop where strategic decisions are taken combining the DARE Loop with the strategy at the heart of the event.
You also deliver a talk on The Second Strategy, how to lead disruption and change. What is The Second Strategy, and what are you seeing from clients in terms of their concerns and worries about the future?
The concerns vary by sector and organisational history. My defence clients are moving to a war footing, as we face into very immediate threats and the loss of key allies, having been largely ignored for three decades. My tech clients are executing a variety of strategies to help their clients seize the enormous opportunities presented by AI.
The common thread is the need to consciously architect decision velocity and organisational courage in their organisations, from pharma to submarine building, to deliver the enterprise strategy.
As uncertainty increases, the need to optimise for courage, iteration, innovation, risk taking and deeply aligned autonomy increases at the same rate. That is my world.
Historically, leaders cascaded the ‘strategy deck’ and ‘strategic goals’ and published the ‘new behaviours’. These elements have their place, but often I am called when this work was done a year ago, and nothing has happened.
The Second Strategy is a structured and proven approach to achieving that optimisation. For example, how many executive teams have defined precisely how the Top 100 must experience them – if they are really asking the Top 100 to operate a DARE Loop at speed, (including, inevitably, making errors as they act decisively in uncertainty)?
I have not ever met one who did this work off their own bat. The Second Strategy demands bespoke answers to that question, and a contracted discipline in then delivering the answer.
As we touched upon earlier, you tested your frameworks at the extreme with your freedive to 101m – an incredible achievement. How did that come about in the first place and do you have any more extreme challenges planned?
As a seven-year-old in South London, the sea was a faraway, romantic idea. It belonged to Cousteau and Bond on my TV. It belonged to Jim Hawkins and Horatio Hornblower by torchlight when I should have been asleep.
My world as a working-class male was: work hard and get a white-collar job to feed your family
On our first holiday, I was about 11 years old. It was Shanklin on the Isle of Wight. There was a storm one afternoon and a boat moored to a buoy in the sea in front of the hotel broke free. We all watched it dance about on the waves, waiting for it to crash into the pier. Except for the hotel barman. He stripped to his Y fronts, swam out to it and re-secured it.
Then came the “The Big Blue”. I still listen to the soundtrack on my yoga mat and watch it annually. Finally, I dived in the blue hole in Dahab on scuba and I saw them diving free, deep below me and come up 2 minutes later.
When my eldest daughter became ill, all my powers were taken away. I could not make it ok for her. So, I decided to raise money for paediatric research – by becoming the deepest freediver in the UK and the first past 100m. And I did.
As for the future, well I am writing this on a plane to the Red Sea. Still diving deep. No announced plans. But you’ll always be the first to know Matthew!
If you go could back to the Jim Lawless that first started speaking – what tips and advice would you offer him from what you have learned on the speaking circuit?
Take more risks.
I’d be able to tell him that it all worked out and the children were fed and housed OK after all. And that there was always more headroom for risk than he thought. And not to try to fit in and do it like they say you have to.
it’s natural to look to those who went before. There’s no Chappell Roan without Madonna, no Tarantino without Scorsese. But the sooner you have the courage to find your own voice; the sooner you can make an impact.
I was brought up to be good and get picked. That delayed things immensely.
And lastly, for those who don’t know, a delegate at an event you spoke at some years ago, bet you £1.00 that you could not become a jockey and ride in a TV race within one year. You went on amazingly to achieve this. Did you ever claim that £1.00? If so is it framed somewhere?
The only framed thing I have from that time is a picture of me riding work at full speed on the Epsom gallops upsides Richard Dunwoody. In my view, Woody was the most stylish jockey in either code until Dettori, and he seemed to make time stand still and calculate at leisure whilst galloping a horse towards a jump at Cheltenham.
When I showed the picture to my coach Gee Armytage, she spent 10 seconds working out which of us was which under the helmets and goggles. That she could not tell immediately from my riding position meant the world to me – and was testament to all her hard work.
It hangs on my office wall to remind me I can truly surprise myself when I use the Ten Rules for Taming Tigers.
The pound is in the top right drawer of my desk, safe and sound. But none of this journey was really about money. I could have stayed a corporate lawyer to harvest that.
For more information on Jims speaking work please visit his webpage or contact us on 020 8854 7247