The Executive Coach that dared ask ‘What if?’

Episode #1001: Celebrating the life and contribution of Richard Bosworth, Founder of What if? Forums (UK). Follow the journey that took Richard Bosworth from an agricultural scientist to an admirable, successful, and unconventional Executive Coach in Episode #1001 of the Arete Coach Podcast. Continue to watch the interview, download the transcript, and read the recap.



About Richard Bosworth

Richard Bosworth was the founder and CEO of What it? Forums, an executive coaching practice that started in 1967, and operated from London, England. He was a self-styled “Chief Tormentor” for his clients, and they loved his candor, insightfulness, and questions. His executive coaching practice was global and he worked with national and international businesses, large and small, helping them grow. He started as an agricultural scientist but quit to be a marketer, specializing in business turnaround. In this podcast interview, Richard shares his journey into coaching, his early meet up with Thomas Leonard (the founder of the modern coaching industry), and his foray into tele-coaching, and later Zoom-based executive and peer group coaching. Richard passed away in August 2020, and this interview was recorded with Severin Sorensen, the curator and host of the Arete Coach Podcast on April 27, 2020.


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Key highlights


An unconventional journey and approach to coaching

Timestamp: 1:22


Richard fell into coaching way before it was popular, and at that time, he didn’t know that what he was doing would be classed as coaching. He thought of himself as an unconventional coach because his "Why" and drive came from challenging the status quo.


“I like to get people to look at things through fresh eyes and with fresh thoughts and try out new things and do them differently. And that is what drives me all the time.

He believed that, in the future, people should be more interested in the “What if?” and he would be the one promoting new ideas and asking them, “What about this new idea?” because that was an important part for him—to try and do things differently. Quoting Roselinde Torres, Richard points to the challenges for all coaches, facilitators, and ideation people:

"There are three challenges for the 21st-century leader. One, how do you broaden your sources of information and ideas? Two, how do you expand and diversify your network? And three, how willing are you to let go of the past and step out into the unknown?"

Over the years of coaching, he learned that he doesn't want to be what he called a business doctor or a business blood donor because some people only want to take ideas and knowledge from you without paying for it. So, with time, he realized that the vital thing is to look for the right audience.


The start of his telecoaching practice

Timestamp: 08:12


In 1995, after reading one of Thomas Leonard’s articles about coaching, Richard knew that he had to talk to him. So, he booked himself into the first international coach federation meeting in Houston, where he found himself surrounded by people who were all searching for the same thing.


After attending it, he knew that the telecoaching was the way ahead. He was already doing it for his business development and his social-political change clients, which he had in South Africa, where he moved to in mid-seventies. Not having an opportunity to move his business from Durban to Johannesburg, telecoaching was a way to still help his clients. So, telecoaching is actually something he fell into by accident, not by design.


Becoming a better coach

Timestamp 12:30


The biggest learn for Richard came when, after 20 years in consulting, he realized that he needed to drop that hard wiring for consulting. He needed to get rid of the toolkit he carried around, looking for patients who needed it. Becoming a coach, or an ideation, self-discovery coach, meant to stop looking for a problem that needs to be fixed and to turn towards the "Why." Why does somebody think the way they do?


One of the reasons he had a change in perspective was a program he attended in San Diego, called the 6th Level, taught by Jim Davis. There, he was confronted with a simple but in a way frightening proposition—what are you most proud of or what is your biggest disappointment?

He later realized that when someone says that something is their proudest moment if you ask the right questions and ask them carefully, people start unloading and revealing themselves.


The wisdom he wishes he had when he started coaching

Timestamp 18:04


When asked what his wisdom is today that he wishes he had when he started coaching, Richard emphasized the wisdom to quickly discern the people who really value what you do as a coach because many are only looking for praise and reassurance. Many want to hide away from what is confronting them. There are only a few people that have enough courage to admit they need to change.


When he later realized that, he took it as a lesson and applied it to his business. Right at the start, they look at people and ask themselves: Do they get what we do? Do they want what we do? And are they prepared to graft for it?That, he believes, is one of the reasons his team creates such successful leaders.


The why and the purpose

Timestamp 21:59


Richard's "Why" comes from the passionate belief in challenging the status quo. He is driven by helping people see things through fresh eyes and look at different ways of doing things.

But, as Richard mentions—the why—is not the only important aspect. It is also about—the how. And his “How” was bringing together a diverse group of business leaders and engaging them in thought-provoking conversations that lead them to take decisively different action in the open. It is about having thought-provoking conversations with ideas planted in there that they haven't thought about.


The best day as an Executive Coach

Timestamp 25:08


For Richard, every day as an executive coach was a wonderful day because he was waking up knowing that somebody somewhere will do something different and that he had a part in it.

“That's the beauty of this job. Almost every day, I wake up knowing that somewhere, somehow, I've made a difference in somebody's life, maybe not directly, but indirectly. But it's the stories that I get back that make every day so rewarding…it's just the joy of knowing that we've helped somebody see things differently, do it differently, and be successful.

The most powerful question

Timestamp 26:56


When asked about the most powerful question he asked as an executive coach, Richard gave an unexpected answer. It is a question one doesn't hear being asked very often, which was exactly why he would ask it. This question opens up a whole new avenue of discovery, and almost nobody thought of asking it before.

“What does your family think?”

As he explains, so many people do the things they do for their families. But they never think to ask if that is what their family really wants.


The most important tools

Timestamp 30:10


Richard used a myriad of tools in his coaching practice. As a consultant, he never stopped looking for questions he could ask. But there are three tools that he found to be most useful. The first is what he called—an aspiration guide. Others might know it as a Be-Do-Have chart. He found it fascinating because it asks you what you want to be, do, and have both in your private life and your professional life.


And once he got that information, it allowed him to ask people if what they've answered in terms of their business is going to deliver what they want in terms of their personal life, which then leads to a whole discussion about family, business, etc.


The other tool is listening to your intuition when you are thinking about what questions to ask.

And the third tool, which he believes a lot of the coaches tend to forget about, is the silence.


“Silence is when the heavy lifting is done.”

The most significant failure as a coach

Timestamp 35:32


One of Richard’s biggest failures happened in the early 90s when socio-political changes were happening in South Africa. He recognized there was a lack of management development training and took it upon himself to set up a management learning center. However, it was the wrong time and place for it, and it brought him to the brink of financial ruin.


That later helped shape his coaching practice because he has known failure and what it can do. He made mistakes, and he is not all about success. He was able to empathize with his clients, and that is something they would recognize. And if some of his clients wanted to take risks, he was always able to tell them to stop, think first, and think about a plan B and C.


Changes in Executive Coaching practice

Timestamp 39:30


Over time, Richard's executive coaching practice changed in two ways. One is the already mentioned shift toward looking for the right type of person to work with. The second one is about focusing on tomorrow and what a person needs to be where they want to be tomorrow.

“What are you going to need in the way of core competencies that you haven't got? What capabilities do you need? And where's your replacement?

Adapting during the Covid-19 pandemic

Timestamp 45:24


While battling serious illness, Richard was considering an idea about going digital with his business. However, back in 2015, when he first tried using Zoom with a pilot group, he realized it was still too early for something like that. When Covid-19 started, it was the perfect time for it, and it started practically overnight. Focusing on the digital is also why the second division of the What if? group is called What if? Business Accelerator.


There are a lot of changes happening, and managers and leaders are faced with new challenges. People no longer want to be led. They want to be engaged and consulted. People have also discovered different advantages of working from home, and the days of working 9-to-5 are slowly starting to fade. For leaders, it is now coming down to how do they add value.


Guiding mantra

Timestamp 1:00:11


“No matter who you are, president of a country, president of a company, president of the local Rotary Club, we all want to talk about what's inside you and inside your head."

"…Get inside people's heads. And ask them—if you've done it that way before, can we do it differently?"

The legacy left behind

Timestamp 1:03:00


The first time Richard measured his life, as he said, was when he was battling cancer and was on an experimental treatment that worked well but resulted in some complications that left him having a cardiac arrhythmia.


One afternoon, he talked to his daughters, and he was feeling disappointed about the legacy he is leaving behind. But then, when one of his daughters expressed concern about where will they hold a funeral and a wake because there were so many people he touched, who will want to come and say something, he was stunned. What he realized then was:

“I'm not leaving behind a building, an institution, or even a business. I'm leaving behind the legacy that's walking around there that will tell the stories of the time they had with me. You can't ask for more than that.



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