Power Women: Holly Ransom On The Power Of Asking The Right Questions

Power Women: Holly Ransom On The Power Of Asking The Right Questions

by Melissa Sheddan | Whimn MARCH 26, 20191:18PM

Barack Obama, Richard Branson and three PMs have personally requested her skills. Oh, and she’s 29.

“I hadn’t met a leader who energetically presented the way he did. Others tend to be intense – like they’re trying to convince you of something. There’s a real calmness to Obama and an extraordinary security in how he fills his own skin. He knows what he stands for.”

I’m speaking with Holly Ransom, the Perth born, 29-year-old Australian businesswoman personally requested by Barack Obama to moderate his only Australian talk when the former President visited last year. As we chat, however, I realise that descriptor is just as fitting for Holly herself, a woman who is both incredibly calm and secure in her purpose.

A year shy of her 30th birthday, she’s one of the world’s most respected thought leaders, asking the tough questions to reveal the emerging trends and challenges affecting businesses and professionals today. In short, she’s an extraordinary human.

When I’m researching her for our whimn.com.au Power Women series, I’m struck by the sheer number of her achievements – more in three decades than most of us tick off in a lifetime.

Chair of the G20 Youth Summit (where she was called on by three PMs – Gillard, Abbott and Rudd), co-author of a UN strategy paper, AFL board member, keynote speaker introducing the Dalai Lama, CoffeePods podcast host, Ironwoman, Richard Branson’s dream dinner guest, festival creator and fearless leader of a business whose clients have included Microsoft, the AIS and DFAT. That business is Emergent, of which Holly is CEO, a specialised consulting firm focused on building the capacity of organisations to execute change. If this was the early 2000s, we could call her a “disruptor.”

She’s precise, a clear communicator, an optimist. On the topic of what power is, Holly is eloquent: “I’ll take this in an optimistic view – an ability to successfully influence an outcome for the betterment. That is power, whether individually or collectively.”

The Power Of Asking Questions, Even If You Don’t Have The Answer

It’s this ability to see the ‘we’, alongside the ‘me,’ that’s shaped Holly’s life. “My grandmother is my biggest influence. She’s always told me, ‘Holly, if you walk past it, you show the world it’s okay’,” Holly says, adding, “That was an empowering sentence to be gifted with as a child.”

For Holly that meant bailing up her principal for a school fundraiser where they donated funds to a local homeless shelter after a chance encounter with a homeless man at her local shopping centre. Reflecting the thought leader says, “I could see the problem, and something I could do to equal a better outcome. But ultimately you want something self-generating, so people can help themselves. It started there and has been propelled by continually asking better questions and pursuing a better answer by virtue.”

The Power Of Mentors

One of those questions is as simple as asking someone out to coffee each week – a commitment Holly made at age 16 – and has continued ever since. She credits the practice with supercharging her learning and career.

“I heard a line, from a mentor of mine once, which said, ‘how long does it take to learn a lifetime experience? Coffee’. So every week I seek coffee conversation or learning conversation for one hour,” she says. Remarkably, Holly says her invitation has never been turned down, “I feel lucky to have grown up in WA because WA was a very flat community and I was a very curious kid full of questions”. She’s met with everyone from politicians to CEOs of our nation’s biggest sporting teams.

“People make fun of me because of the number of mentors, advocates and advisors I have in my life. If it takes a village to raise a child, it takes an army of advocates to raise a young woman. They give me multiple points of truth and challenge me,” she says.

The Power Of Collaboration

Her most recent challenge and foray into the unknown is as co-creator of s p a c e, Australia’s first festival-like event to champion peer-to-peer learning and cross-sectoral collaboration happening in Byron Bay next month (23-26 May, get your tickets here).

The idea came out of a wide-sweeping frustration, “from George St, Sydney to regional Australia,” with leadership changes in politics and a general dissolution and apathy, says Holly. Always the one with the questions, she posed this: How do we stop the whinging and make a positive contribution?

The answer, or at least her contribution, is s p a c e, explaining her vision for the festival.

“It will bring together 300 people who care passionately about the future of this country. It’s not a conference model and you won’t be a passenger. There’s not a distinction between speakers and non-speakers. Rather than a think tank, it will be a do tank, driving activity off the back of it, and starting relationships.”

The Unbelievable Power Of Sport

You get the feeling Holly sweats collaboration. In 2016, she became the youngest ever woman appointed to an AFL football club board, joining Port Adelaide. She was 26. Despite being kicked out of footy at age 10 because girls didn’t play, AFL has remained a personal passion of hers – and watching on as the women’s league explodes brings her immeasurable joy.

“Sport is the silent social worker in this country. You can tackle big issues. In two decades time, I believe we’ll marvel at what AFLW did for gender equality,” says Ransom.

And in two decades time, I believe Australia – and indeed the world – will marvel at Holly Ransom, by then, surely, a household name.

When I feel powerful: When I successfully influenced the G20 leaders declaration in 2013 with a policy document and advocacy campaign. It was an extraordinary movement of young people across the world. It’s my proudest moment.

When I feel powerless: In the same year I was diagnosed with clinical depression. It’s a scary experience and was a challenging 10 months working through it. It puts you on your arse because your body is dictating things. You feel out of control. You feel powerless. I’m fortunate I had support structures and got the right help.

How I’m using my power: I’m passionate about inclusion and the role of tech is where I am focused. In 40 years’ time, I’d like my legacy to be as a leader who is using tech for good, tech for outcomes like shared economic benefits and higher standards of living.

Four big ideas from my most popular podcast guests

Four big ideas from my most popular podcast guests

When I was nineteen years old, my mentor Virgil shared a line that proved to be a lightbulb moment for me: “How long does it take to learn from someone’s lifetime of experience?”

“A coffee!”

In a flash, learning and development became clear for me- I didn’t have to wait for a special invitation to join an esteemed leadership development program or to be recognised for a structured mentoring initiative… Learning was entirely within my grasp and was utterly my own responsibility.

I promised myself there and then I would actively cultivate coffee conversations with people who I admired, respected and aspired to learn from – weekly. Nearly 10 years on, I don’t think I’ve missed a single coffee exchange, and it’s probably been the single greatest habit I’ve built when it comes to my own personal growth (there are worse vices than caffeine and learning!).

Emboldened by the impact these conversations had on my own life, I decided to start a podcast to share the incredible lessons, insights and stories offered by people I’m fortunate to meet, know and call my mentors and friends. Now 65 episodes in, we’ve featured everyone from an 8-time world champion surfer to a 7th generation kung-fu master, a navy commander, ASX 100 and Fortune 500 CEOs, adventurers, Olympic gold-medallists, and a symphony orchestra conductor. We had close to an equal gender split (60/40 female:male), and guests in their late 70s to early 20s. I intentionally did my best to curate an eclectic mix of cultural backgrounds, industries, religions and sexual orientations.

My objectives for the podcast seemed simple enough at the time:

1)   To paint the archetype of the ‘changemaker’ as someone more tangible, closer to you and to me. My hope was listeners would be inspired to take on the idea of ‘being the change’ they want to see in the world.

2)   To crack open the “formula” for change, making it less Colonel’s ’11 secret herbs and spices’ and more ‘open source’ intelligence. My guests had to be pragmatists- deeply reflective, honest and candid in sharing their experience to empower listeners to shift from inspiration to implementation.

3)   To question answers rather than answer questions. We talk a lot about cognitive diversity in the world right now but recording this podcast made me realise how rarely we’re truly exposed to divergent thinking unless we intentionally facilitate it. 

I’ve been humbled by the reactions to the podcast from all around the world, many of which have come from the phenomenal Linkedin network- thank you. You’ve told me how my podcast with Alisa Camplin got you through your first half marathon and how Ros Savage inspired you to go climb a mountain. How you’re a different father to your daughter after listening to my podcast with Liz Broderick (this conversation in Calgary moved me to tears). Or how Mandy Rennehan got you ‘woke’ on diversity and inclusion, how Holly Kramer and Ron Gauci made the communication and engagement side of organisational change ‘understandable and doable’ for the first time. And how Rob Jones’ insights helped you get through a tunnel you were struggling to see a light at the end of.

You told me over and over again how valuable you found guests’ insights for your personal and professional goals. Thanks to all who listened, shared and particularly those who took the time to provide feedback- I had no idea how to produce a podcast when I started but I believed vehemently in the quality of the conversations. Every time I have heard about the effect these have had on someone it lights me up. A big thanks to Sydney Morning Herald for giving the podcast a shout-out in the ‘top business podcasts’ list too!

To wrap up season one, and before I launch the new season, I’d love to share with you a few titbits from our top-rating podcasts:

Dom Price (Coffee Pod #2) – High Performing Teams & Leaders, and What to Expect from the Future of Work with Atlassian’s Dom Price)

Dom is the guru on all things collaboration, team-work, innovation and future-of-work (his official title is Head of R&D and Work Futurist at Atlassian) and listeners loved him for both his incredibly practical advice and his no-BS, entertaining communication style. If you’re dealing with establishing an internal culture of innovation, thinking through what ‘lived’ workplace diversity feels like (as opposed to what ‘talked’ d&I looks like) and how to achieve effective collaboration- Dom’s podcast is for you. One of my favourite quotes comes from Dom’s reflection around intentional learning:

“I have this mental model I do every quarter. It’s my three by three. My three across are time horizon one, time horizon two, and time horizon three, and my three along the side are me, my team, and Atlassian as an organization, and I map out my quarter. What are the activities I’m going to do and where am I investing? So, I’ve always got some things top right. They are for my team, or for Atlassian, and they’re time horizon three, they’re going to pay off in a year. They’re the long term outcome bets. Then there’s the bottom left hand corner. They’re the things for me for today. They’re very transactional. What I do is, notionally, when I’m shifting boxes, I change the way I act. So, for the transactional stuff, it’s scrappy, it’s quick, do it, move on. My main goal with the transactional stuff is how can I prevent it occurring again? How can I automate it and make it go away? Because it’s not massively valuable. The problem with the top right box is it’s highly speculative, but it also means a completely different mindset. When I go to events or function where I’m top right, what I do is say to myself, “I need to give myself equal parts consumption and equal parts reflection.” Now, way too many leaders, in my experience, see that as a waste, because there’s no work being produced, but, if I don’t give my brain and my heart and my intuition time to consume that, then it’s just surface level. It’s not made it inside, and so, if I’m going to invest 24 hours in the event, there’s no harm investing 24 hours in consuming from that event. Makes complete sense.”

Sam Mostyn (Coffee Pod #25) – Breaking Free From the Binary with Non-Executive Director Extraordinaire Sam Mostyn

Sam is a truly exceptional systems-thinker and has pioneered change across business, civil society and the public sector throughout her career. A name synonymous with diversity and inclusion in Australia, Sams’ comments around the role of cultural institutions and, particularly, sport in driving social progress really hit a chord with listeners. Sam was the first female AFL Commissioner and shared candidly her experiences and lessons influencing change in the ‘boys club’. I spent a lot of time reflecting on the ideas Sam shared, particularly her comments around how being angry, in her experience, limits the effectiveness of your advocacy. I loved her observation that sport is the ‘silent social worker’ and an incredibly powerful lever for change. I cannot recommend this conversation highly enough for leaders of organisation and social change. One of my favourite remarks Sam made was (reflecting on the challenges of driving change):

“I think the one I still struggle with is ensuring that I understand all the multiple stakeholders affected by the change that I want to be part of, really understanding where their perspectives are and how to engage and show respect whilst pushing hard for that change. And it takes an enormous amount of … I think you’ve got to be really quite patient and have good self control and engage respectfully. So for me, that remains … And also, I think the thing I’ve learned on the way, Holly, and I’m learning to this very day, is you make a big mistake if you think you’ve suddenly got the whole thing sorted and you understand it be moving part… active listening as part of change is probably the thing that I come back … And it’s hard for any of us because when you want things to get better, whatever your particular field is, there is a desire to get it done now and speed and maybe not understand the damage you cause on the way through.”

Sifu Singh (Coffee Pod #31) – Mastering, Stress, Performance and Mindfulness with World-leading Martial Arts Master Sifu Singh

I wasn’t at all surprised by the popularity of this episode. Sifu’s voice is like hot chocolate and his insights around mindfulness – how to actually achieve being present in the moment and what it takes to unlock that next level of your performance potential – are truly masterful. Sifu is a high-performance coach of military special forces, secret service, SWAT teams, and over 100 law enforcement agencies across the globe. He’s a 23rd generation Tai Chi master! This podcast got me ‘mind boxing’, catalysed a new morning routine (which has definitely improved my start to the day!) and given me a whole different frame to understand training to perform under pressure. One of my favourite quotes comes from Sifu’s discussion of stress and peak performance:

“There’s a saying that says that when stress hits you, you resort to a diminished state…, you only have 10% of your capabilities actually available. So you fall to that percentage. So instead of training, training bigger, stronger, faster, that idea, and just increasing your ability and only accessing 10%, my question is, how do we access more? And train the less of that idea? When we can start to do that we get a balance. Now I’m not saying don’t train and work out, be strong and healthy, that’s important because the body’s the vehicle. But the mind, the mind is the engine. The mind is the general. We say the mind is the general, and the body and emotions are the battle. The breath is the strategy, and the chi in your energy are your soldiers.”

Rob Jones (Coffee Pod #53) – Using Challenges & Tragedies To Your Advantage With Marine Corps Veteran Rob Jones

This podcast received some of the most powerful and emotional responses of the whole season. Rob was a combat engineer in the US Army when an IED blew up underneath him, taking both his legs. Unwaveringly optimistic and determined to make a difference to the lives of others, Rob has cycled across America, run 31 marathons in 31 days and won an Olympic bronze medal all the while raising funds for veterans’ charities. If you want a conversation you won’t ever forget listening to, you’ve got to listen to Rob. I’ve probably reflected on this podcast 50 times since listening because of the way Rob challenged me to think differently about the way we treat/help/support people who are going through struggle in order to ensure we enable them to be stronger out the other side. Rob frames stress as being akin to a heavy weight on the barbell at the gym and talks about how we have choice as to whether we let that weight come down or we use it to build strength. Acknowledging that sometimes the weight feels overwhelming, Rob talks about support should look like a “spotter”:

“Sometimes, you do need help. Sometimes the weight’s a little bit too much at first, so you need somebody to come in and spot you. You don’t want them to lift the whole weight themselves for you. Let’s say you’re doing a lift and you have a spotter and you’re not quite being able to lift it. What do they do? They don’t just rip it up. They do the finger, right? They do the one finger and they say, “It’s all you. It’s all you. It’s all you.” Maybe sometimes that’s what you need. You might need somebody to point you in the right direction or give you that leg up, but it really is just trying to view your situation from a bird’s eye view and maybe even imagine somebody else is in the situation trying to figure out what you would advise somebody to do in that situation.”