(Re)Humanizing Leadership in Risk Management with Holly Ransom

Feb 25, 2025

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Welcome to RIMScast. Your host is Justin Smulison, Business Content Manager at RIMS, the Risk and Insurance Management Society.

Our guest, Holly Ransom, an internationally acclaimed speaker and leadership trailblazer, will be a keynote speaker on May 6th at RISKWORLD 2025 in Chicago. Holly previews her keynote as well as shares nuggets of risk knowledge she has collected throughout her career. Holly gives tips for leadership qualities and skills that are needed more than ever in this uncertain environment. She speaks of resilient leadership and confidence in crises. She tells how to recover a strong brand from a crisis when handled properly. She speaks of the importance of lifelong learning, not as an ideal but as a practice. Listen for Holly's keynote theme and her advice for leaders today in this insightful episode.

Key Takeaways:

[:01] About RIMS and RIMScast.

[:14] Public registration is open for RISKWORLD 2025! RIMS wants you to Engage Today and Embrace Tomorrow in Chicago from May 4th through May 7th. Register at RIMS.org/RISKWORLD and the link in this episode's show notes.

[:29] Register now! The Super Savings Rate ends on February 28th!

[:37] About this episode. We will be joined by Holly Ransom, who is one of the keynote speakers who will be on the main stage at RISKWORLD 2025 on May 6th. We will get a preview of her session, "Humanizing Leadership in a Tech-Enhanced World."

[1:10] RIMS-CRMP Workshops! RIMS will partner with Purima once again on March 5th and 6th to deliver a virtual RIMS-CRMP Prep Course. Links to these courses can be found through the Certification page of RIMS.org and this episode's show notes.

[1:30] Virtual Workshops! "Managing Data for ERM" will be hosted by Pat Saporito. That course starts on March 12th, 2025. On March 26th, Pat will also host "Generative AI for Risk Management."

[1:52] On April 16th and 17th, Chris Hansen will lead "Managing Worker Compensation, Employer's Liability, and Employment Practices in the U.S."

[2:05] A link to the full schedule of virtual workshops can be found on the RIMS.org/education and RIMS.org/education/online-learning pages. A link is also in this episode's show notes.

[2:16] RISKWORLD registration is open. Take advantage of our Super Savings Rate by February 28th. Register at RIMS.org/RISKWORLD. Also, remember there will be lots of pre-conference workshops being held in Chicago just ahead of RISKWORLD.

[2:34] These courses include "Applying and Integrating ERM," "Captives as an Alternate Risk Financing Technique," "Contractual Risk Transfer," "Fundamentals of Insurance," "Fundamentals of Risk Management," RIMS-CRMP Exam Prep, and more! Links are in the show notes.

[2:55] Our guest today is Holly Ransom, and she is one of the keynote speakers who will be on the main stage on May 6th at RISKWORLD. She will lead the session "Humanizing Leadership in a Tech-Enhanced World." We're going to get a preview of her presentation.

[3:08] Holly will also talk about some of the world leaders she has shared the stage with and why she found them impactful.

[3:17] Interview! Holly Ransom, welcome to RIMScast!

[3:24] At RISKWORLD 2025, on May 6th, Holly Ransom will present a TED-style talk, "Humanizing Leadership in a Tech-Enchanced World."

[3:41] Holly can't wait to be there in Chicago. She is excited that so many will be attending! Her keynote goal is to explore how important authenticity, empathy, and purpose in leadership are amid technological change.

[3:59] It's easy to lose sight of authenticity in an industry that's all about metrics and frameworks. We need to maintain that focus on building resilient teams that can navigate uncertainty with confidence and clarity. That's what Holly will share at RISKWORLD.

[4:34] Holly will be diving into the high-performing culture element. A lot of Holly's work with high-performing sports teams and in the corporate landscape is about how to get collective effectiveness.

[4:45] Holly's keynote will pull on those insights to ask what it looks like to influence positively the environment to get the best out of the people around her, maximize creativity, and seize the innovation opportunity. That will be where it comes together in her conversation.

[5:22] Holly discusses the metrics of success. It depends on the organization. There are performance metrics for revenue and reputation that show how effective a business is. She talks about looking beyond traditional KPIs to other ways to measure effectiveness.

[5:51] These other measures may include new products to market, rate of innovation, successful growth of new products versus legacy brands, psychological safety scores, team engagement, and recognition.

[6:12] Holly looks for proactive measures and team collaboration quality. That's a combination of metrics beyond what organizations have traditionally measured. Pick out of the KPI soup the ones that benefit you. Which ones measure the needle moving in your organization?

[7:01] Holly has spoken at events within the risk industry. RISKWORLD will be her largest risk management speaking event.

[7:23] Holly sees the risk profession as having an incredibly important role, making sure that safety is maintained and people safely get to where they want to go, inside their organizations.

[7:39] These are the people laying down strategy and setting the innovation roadmap, and how we get there while maintaining the expectations of our customers, standards for our employees, and the license we have to operate within our community and the broader society.

[8:05] Holly says risk management is one of the most complex jobs inside an organization. Holly worked in large corporations in mining and banking early in her career. She spent a lot of time with CROs. Their risk reports to the board were around 150 pages, before cyber frontier.

[8:44] Holly has empathy for risk managers who must influence other executives to understand the risk agenda and embrace and support it. The skills of risk professionals have probably never mattered more as we navigate the complexity.

[9:30] The 150-page risk reports Holly saw in her corporate career were filled with information, including heatmaps. It was important to call attention to what mattered most and report it realistically while discharging risk duties responsibly. It's an interesting tightrope to walk.

[10:22] Holly mentions the role that smart risk plays in innovation and progress. In high-performing teams, if you keep doing the same thing, you can't maintain your competitive edge. There is always an element of risk in the evolution of strategy and approach.

[10:49] Netflix embraced risk in its strategy of pivoting away from rental to streaming, first with owned content and now into live sports. There were difficulties, but now Netflix is one of the most successful stories of the last 20 years.

[11:52] Netflix was prepared to "cannibalize" itself and jump on what it saw as an emerging technology opportunity to stake out a new business model. Netflix continues to add new subscribers.

[12:40] What can leaders learn from Netflix? Ask yourself what you are doing as a leader to build your peripheral vision. How do you make sure you're not getting caught in the way you do things or the way your industry operates?

[13:02] How do you expand your view so change does not catch you off-guard and the opportunities and threats that come are things that you as a leader are beginning to think about? AI could be an example of something relevant to leaders at the moment.

[13:21] Ask what's the question you need to be reflecting on. What's the strategic question you can take to your leadership team or board that allows you to get into a "meaty" conversation on the topic with ideas on how the board wants to respond to it, proactively versus reactively?

[13:40] How are you keeping your finger on the pulse? Do you have a source outside your deep industry expertise or outside where you operate? Are you having periodic conversations with a leader in another industry sharing observations and data points?

[14:06] How do you turn an observation into a question that sparks the thinking and the conversation that can be the catalyst for transformation? Get into conversations with your colleagues. What does this mean for us and how can we do something significant for us with it?

[14:27] Netflix started very early in strategic conversation and prepared to take strategic bets on what part of its portfolio and what allocation of its resources to give to this new idea.

[14:41] You see this process in a range of businesses, however they structure it. Some businesses have an innovation arm. Other places have a budget allocation per department for new ideas each year.

[15:05] There needs to be a meaningful skin in the game each year, building the muscle of working up an idea and attempting execution. That allows you to get real opportunities, rather than just intellectualizing risk. What will you learn in the process to try better next time?

[15:35] Plug Time! RIMS Webinars! On March 13th, our friends from Global Risk Consultants will return to discuss "How to Make Your Property Insurance Submission AI-Ready".

[15:49] On a unique day and time, March 26th at 2:00 p.m. Eastern Time, members of the RIMS Strategic and Enterprise Risk Management Council will extend the dialog that began in the recent RIMS Executive Report "Understanding Interconnected Risks".

[16:07] More webinars will be announced soon and added to the RIMS.org/webinars page. Go there to register. Registration is complimentary for RIMS members.

[16:19] Nominations are also open for the Donald M. Stuart Award which recognizes excellence in risk management in Canada.

[16:27] The Spencer Educational Foundation's goal to help build a talent pipeline of risk management and insurance professionals is achieved in part by its collaboration with risk management and insurance educators across the U.S. and Canada.

[16:46] Since 2010, Spencer has awarded over $3.3 million in general grants to support over 130 student-centered experiential learning initiatives at universities and RMI non-profits.

[16:59] Spencer's 2026 application process will open on May 1st, 2025, and close on July 30th, 2025. General Grant awardees are typically notified at the end of October. Learn more about Spencer's Grants through the Programs tab of SpencerEd.org.

[17:18] The Conclusion of My Interview with Upcoming RISKWORLD 2025 Keynote, Holly Ransom!

[17:37] Holly has been to Chicago and loves it, but not Chicago winters! This will be Justin's first time in Chicago. He'll do the generic bucket list Chicago stuff when he finds a couple of pockets of time, to enhance the experience.

[18:34] During the pandemic, there were studies done on leadership communication during a crisis. There was a difference between leaders in companies who performed well in the face of adversity, versus others.

[18:58] There was a big piece around leaders who could demonstrate authentic concern. An example of this was New Zealand's former Prime Minister, Jacinda Ardern, after the terrorist attack in Christchurch.

[19:14] She had an incredible ability to show empathy and to see it as a moment of extreme sadness; an opportunity to bring the nation together.

[19:31] Successful leaders in crisis focus on what they can control and communicate with a transparent confidence. Ed Bastian at Delta did a good job managing the 2017 system outage across Delta. He appeared in a video message to customers within hours and took ownership.

[20:12] He offered compensation proactively versus reactively, making it right for his customers, knowing that how he handled the situation would set Delta's reputation and make the comeback stronger.

[20:29] You can build back a stronger brand and reputation by how you handle a crisis. You can have a higher brand score after a crisis you've handled well. Your relationships need to be in hand before the crisis. Be proactive in stakeholder relations so there are credits "in the bank."

[21:08] Then, when the crisis comes, you can call in favors and ask people to come in, in support. Those people show up.

[22:04] Holly describes her feelings on giving a keynote. She loves it. She says she's on the strange end of the psych profile, in liking to be in front of an audience and talking. Holly says that for her, there is nothing more precious than people's time.

[22:25] She calls it a privilege to have time to impart a message. Her goal is always to give the audience practical tools and new ideas that leave them feeling empowered and less overwhelmed, with things they can immediately put to work to enhance their effectiveness.

[22:56] Holly wants to practically equip leaders as she feels we are in desperate need of new tools to help us overcome the overwhelm, make sense of the complexity, and find our way through the uncertainty.

[23:23] Justin checked out Holly's highlight reel where she has hosted sessions with major world leaders, including former President Barack Obama. Of everyone she has shared a stage with, who stood out to her as a magnetic personality?

[24:06] Matthew McConaughey comes to mind as someone who has real confidence in himself, doesn't take himself too seriously, is very funny, engaging, extroverted, and is a natural storyteller. He is as delightful offstage as he is on.

[24:25] Without exception, the world leaders Holly has had the privilege of interviewing and hosting, tend to be incredible communicators and have an "X" factor to them.

[24:57] Brené Brown was warm, authentically passionate about the work that she does, and genuine in her desire to connect and converse. Holly said Brené Brown was everything you would hope she would be.

[25:55] Holly's last thoughts for leaders of the risk profession: There is an increasing communication demand on every leader to be a storyteller, to be able to cut through because the world has never been noisier, and to help people make sense of what they're saying.

[26:20] People feel overloaded. Uncertainty leads to a bias of inaction rather than action. Risk professionals need to cultivate the skill of storytelling and influencing to convey the critical information they have to stakeholders who don't have the same depth of understanding.

[26:55] We give a lot of lip service to life-long learning. We need to start practicing what we preach, getting "in the gym" and building that new muscle, whatever you can do to widen your view into topics that may not have been traditionally part of your wheelhouse, like AI.

[27:23] AI is becoming increasingly important to understand opportunities and risks. Have you humbled yourself and been a beginner and gotten on the tools, played with them, and taken a master class, to get your hand around it and think about what it means for your organization?

[27:52] It could be GenZ coming in. Do you have a mentor under the age of 26? Think about that if you haven't. There could be a whole range of factors that are looming as things that are going to reset the table. What are you doing to build your understanding and experience?

[28:36] Holly, it has been such a pleasure to speak with you and meet you, in advance of your presence at RISKWORLD 2025. I can't wait to see you on May 6th! You're going to be fantastic, along with Ryan and Rachel! It's been insightful to speak with you, I appreciate you very much!

[29:02] Special thanks again to Holly Ransom for joining us on RIMScast! You can learn more about her at HollyRansom.com. We look forward to seeing Holly at RISKWORLD 2025 on the main stage on May 6th.

[29:15] Remember to register for RISKWORLD at RIMS.org/RISKWORLD. Recent episodes with the other keynote speakers, Ryan Harris and Rachel DeAlto, are now in this episode's show notes. Remember to lock in that Sweet Super Rate for RISKWORLD 2025 before March 1st!

[29:35] More RIMS Plugs! You can sponsor a RIMScast episode for this, our weekly show, or a dedicated episode. Links to sponsored episodes are in the show notes.

[30:04] RIMScast has a global audience of risk and insurance professionals, legal professionals, students, business leaders, C-Suite executives, and more. Let's collaborate and help you reach them! Contact pd@rims.org for more information.

[30:22] Become a RIMS member and get access to the tools, thought leadership, and network you need to succeed. Visit RIMS.org/membership or email membershipdept@RIMS.org for more information.

[30:40] Risk Knowledge is the RIMS searchable content library that provides relevant information for today's risk professionals. Materials include RIMS executive reports, survey findings, contributed articles, industry research, benchmarking data, and more.

[30:56] For the best reporting on the profession of risk management, read Risk Management Magazine at RMMagazine.com. It is written and published by the best minds in risk management.

[31:10] Justin Smulison is the Business Content Manager at RIMS. You can email Justin at Content@RIMS.org.

[31:17] Thank you all for your continued support and engagement on social media channels! We appreciate all your kind words. Listen every week! Stay safe!

Mentioned in this Episode:

RISKWORLD 2025 — May 4‒7 | Register today! | Super savings rate ends Feb. 28.

RIMS Legislative Summit — March 19‒20, 2025

Nominations for the Donald M. Stuart Award

Spencer Educational Foundation — General Grants 2026 — Application Dates

RIMS-Certified Risk Management Professional (RIMS-CRMP)RISK PAC | RIMS Advocacy

RIMS Texas Regional Conference 2025 | Submit an Educational Session by Feb. 24.

RIMS Risk Management magazine

Hollyransom.com

RIMS Webinars:

RIMS.org/Webinars

"How to Make Your Property Insurance Submission AI-Ready" | Sponsored by Global Risk Consultants, a TÜV SÜD Company | March 13, 2025