334 - Embracing Uncertainty: How to Lead When the Stakes Are High with Rick Williams Leadership's Rick Williams
19 Jun 2025 · 24 min
Rick Williams, a former physicist and author of Create the Future, discusses how leaders make decisions under pressure. He uses Kennedy's Bay of Pigs and Cuban Missile Crisis to show why diverse advisory teams and structured listening beat gut instinct, and outlines a three-level listening model for effective leadership.
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Welcome to Listening with Leaders. I'm Doug Noll, lawyer turned peacemaker. I teach executive leaders how to listen to emotions rather than words so that they can become the leaders everyone wants to follow. And I teach those same leaders how to be authentically present, available, and connected to their families despite being insanely busy. I have learned that we are 98% emotional and only 2% rational. Learning how to listen to emotions is, in my experience, the foundational skill of life. Stick around to the end of the show and I'll reveal how you can be on our next guest in 15 to 20 minutes. So let's get started. Rick Williams, welcome to Listening with Leaders. I looked at your background when I saw you were coming on the show, I just had to shake my head. You've done it all. Started out as a physicist and then consulting and then corporate governance and bestselling author. And wow, what an incredible life. Let's start at the beginning and give us a little bit about your backstory.
Doug, it's great being with you. And I know that you and I shared education here in New England. You went to Dartmouth and I went to Harvard Business School. I'm still, for better or worse, here in New England and suffering through with not having any real springs here. You're back in California. So, we'll start off with a demonstration. Grecia, who's the smarter person?
I don't know about that, but I do have to say I do live in a very beautiful place in the Central Sierra Nevada.
Yeah, yeah. I, again, I started life as a— I went to the University of Pennsylvania in Philadelphia and started life as a physicist working with the aerospace industry here in the Boston area, helping get some very sophisticated stuff into space and helped mess some astronauts and all, lots of good fun. And then I went to business school at Harvard and then after that was a management consultant with Arthur D. Little here, based, headquartered here in Cambridge for 10 years and worked with clients all over the world, mostly here in the US, but some outside the US. And most of that was working with either US federal agencies, helping them develop the very important environmental energy regulations. I can go back to that. And then also with private clients, trying to figure out how they should be more successful in the business they're either doing or trying to get into. And a lot of that led me to, got me to see how leaders make decisions and how difficult it is to make decisions. I don't care whether you're in the private sector or the public sector for all sorts of reasons. And that's why I ended up— I'm not going to belabor this, but I ended up writing the book Create the Future on how to be more creative, make better decisions for your company and yourself. So I'll take that as my little plug of the program. But anyway, that's that experience of working with top leaders as they make really tough decisions. Led me to realize that is the handbook of how you make decisions is— can be a valuable contribution to the leadership literature. And anyway, that's how the book was written.
So I think what really attracted me to your work is that I teach a graduate class at Pepperdine University in decision-making under stress and uncertainty. And I'm teaching— basically, I'm teaching people who are going to be in alternative dispute resolution, whether they're decision makers themselves or their lawyers, LLMs, or people who are based— they're faced with the proposition of helping people make a decision when there are no good choices in front of them. And the risks are high and there's incredible uncertainty and stress because of course the knowledge base is limited. And so that I got really interested in your work because of that, because we share this fascination with how people make decisions. Especially difficult decisions.
Boy, I gotta tell you, you're making me jealous again. I've actually had lunch at the Pepperdine campus looking out over the Pacific Ocean. But anyway, that's another story.
I'll just stop you right there. I was teaching my class in December on a Tuesday. It was a week-long class intensive, and I look out the window and there's the fire at Pacific Palisades exploding right in front of us. So, oh my gosh, it's lovely being down there except when the fires explode.
The difficulty that every one of us has as a leader of any organization, I don't care whether you're the CEO or department chair or a group head or executive director or, I don't know, governor of the state. I mean, everybody, all of us as individuals, is that people expect us, they expect us to know what's going on. They expect us to understand every issue. They expect us to know the right thing to do. And in truth, we don't. The truth is we don't. The truth also is that many of us are afraid of that fact that people are expecting us to be somebody we're not. And so one of the things I think is important for all of us as leaders is to be able to acknowledge that Okay, A, we have an important challenge before us. It could be an enormous opportunity or it could be a great threat. And to say, okay, what is the challenge before us? If we're successful in dealing with this, what is success going to look like? And ask that as a question. And I recommend that if at all possible, you don't try to do this on your own. Get a trusted team of people around you. Maybe it's the senior leadership leaders of your organization, or maybe it's your board of directors, or maybe bring in some outside advisors.
But I wanna add something there. I wanna interrupt you cuz it, you're making a critical point. And what I teach is look around the room. If everybody looks like you, you're in deep shit.
Absolutely. No, I agree with you 100%. And that's so the team that, what I call the Create the Futures team, should not be a lot of people look like you.
That's right.
It should not be a lot of people who all went to Harvard Business School or to Dartmouth.
That's right.
And it doesn't mean they have to be— I'm not gonna say what doesn't have to be, but it should be people who have different experience. So you may wanna have the person who's your CFO. You may wanna have somebody who is head of operations or your head of research or marketing or something like that. You may wanna bring somebody in off your board of advisors who's a key advisor on where the heck is all this going anyway. And often think about somebody who, I like to talk about the person who is the sort of naysayer, the person that says that's never gonna work. Okay, I'd actually like to hear why it's not gonna work or why people might think it's not gonna work. I also wanna hear from the person who has the crazy ideas that will never work. Because often the best ideas that we have in our lives are from that person who had the crazy idea. Now, maybe that won't work, but the way they're thinking about it gets us to think along a different track that really might work.
Exactly correct.
So, when we're talking about getting a team together, an advisory team, a trusted advisory team who will collaborate together themselves, then put those questions before them. Do we really understand what the heck's going on here? And once we do, then we create a vision of where we're going to go, where we're going, what would success look like? I tell that when I speak to business groups, and I do speaking as a keynote speaker, I talk to them about President Kennedy's experience with both the Bay of Pigs and then with the Cuban Missile Crisis.
Right. Irving, Irving. Absolutely.
You can just tell this story as well as I can. Absolutely. But for your audience, the Bay of Pigs, he was just presented with a program that I developed during the Eisenhower administration that the CIA wanted to land some Cuban exiles on Cuba and they were going to overthrow Fidel Castro. And Kennedy said, okay, if you think that's the right thing to do, let's do it. This was within like 3 months after he took office. It was a catastrophe. He really didn't question anything. He didn't ask whether this was a really great idea. It was a catastrophe. And then a year later, during the Cuban Missile Crisis, which is when the Soviets put intermediate-range missiles into Cuba, he then wouldn't— he said, look, we're going to do this completely differently. I learned my lesson here. I'm not going to just take the word of every body who is an advocate for invasion or whatever. I'm going to get people in here because I want to hear different points of view. I want to establish real alternatives to the choices I have. He also established some lines of communication with Nikita Khrushchev, who was the Soviet premier. So he had lines of communication, different lines of communication going with the people he was dealing with. And he then sorted through, he took the time to go through, took the time to go through the options, really understand what his choices were, and then make decisions about how to deal with it. And, you know, he ended up doing what he called the naval blockade of Cuba and got the Soviets to back down. So, yeah, all from a Harvard guy, same leader, all from a Harvard guy. Yeah, those, those are two examples when the same leader started by making an enormous mistake. By not doing what you said and getting other people's, getting other points of view involved. And the second time he faced a similar situation, he did that. He got to put his group together. He made some separation between himself and the group. So it wasn't just about himself.
That's right.
Frankly, I think one of the mistakes Trump's making is put himself too much in the center of all of this. That's right. As opposed to putting some separation. Trump is dealing with real issues, but he's making it— a lot of what he's doing is making it about himself as opposed to, gee, I want to step back, I want to get great advice on the right way to go here, and then give himself maneuverability room.
Well, he's making—
I'm not talking about politics. I'm just talking about the decision. No, he's making work as a decision maker, a negotiator.
Exactly. Coming at it not from a political perspective, but looking at it from decision-making theory and practice. He's making another huge mistake, and that is he's trusting his gut. And I don't know about you, but I teach my students that gut instinct is absolutely the worst modality for making a decision. When people are making gut decisions, to me it means they're lazy thinkers and they don't want to engage in the hard work of critical thinking to do everything that you're talking about. And we know from Kahneman's work, for example, that intuitive thinking, system 1 thinking, is all about pattern recognition. And if the pattern's not exactly the same as the 1,000 other examples you've lived with, you are going to make a bad decision, especially when the stakes are really high. So gut instinct is the worst thing to do.
Yeah, no, I agree with you. I wrote a piece that's on my website about Trump's tariffs and how not to do the deal. And I think he's violating all of the, all of the things about how do you actually negotiate and come to, come to a conclusion that works both for you and the other side. Has to work for both sides.
That's right. And that's not the way he sees the world. I, as it turns out, I teach negotiation too, and that's just not how he sees the world. And more likely than not, he is going to lose over the long term, especially where it's not— where there are repeat players. And he does not recognize that he's in a world where he's dealing with repeat players, and he builds up a negotiation reputation that's untrustworthy and he's gonna suffer, he and the country is gonna suffer as a result of that because he does not understand good negotiation theory or practice. No, you're absolutely right.
Yeah, no, I agree that. I think you're right about that.
I'm interested in looking at, earlier before we started recording, we were talking a lot about leadership and you were very insightful about how your role changed as you moved out of doing, making widgets into leading widget makers. I think that's the phrase I used. What did, what was your observation about that, if you don't mind repeating it?
Yeah, I, okay. So what I was saying is that I actually was asked a week or so ago to write a piece on lessons learned that what I wish I, what I wish my dad had told me and that, that contributed to my success. When we're asked questions like that, I'm not sure exactly what my dad told me is valuable to anybody else, but I meld it together in terms of maybe some things my dad told, but also the lessons I've learned over life. And one of them is that there is no magic path to success that is the same throughout your life, that what you need to be successful in your 20s is quite different than what you need to do to be successful in your 30s and 40s and even your 50s. And yes, when I was in my 20s, I was very focused on being a recognized expert on helping to— I was designing very sophisticated photo-optical systems that were used in space applications and this sort of thing. And my whole focus was on me. It was all about me. Can I help? What can I do to be more of an expert? More recognized as an expert, make sure I don't make any mistakes, make sure I'm the one that they want to have in the room when they're dealing with these kinds of issues. It was all about me. Okay. The transition from there to the next step up the ladder in terms of being responsible for a project or a team is a huge barrier for, particularly for people like me to overcome because you can't, it cannot be just about you. You now have to be responsible for— yes, you make some kind of a contribution, but you have to be responsible for creating a vision of success for the organization you're going to lead, assuming it's now a department or a project, or even maybe if you go and found a company. You have to be somebody who says, okay, what— it's not just about me, it has to be about success for the team or my department or my company. I have to be I'm not going to be the expert in everything. I'm not going to know everything. I have to be open to listening and learning from the other people that are also part of the team. And other people who may be my customers or my investors or my financiers. They're also people who are going to have a very different perspective and expertise than I do. I have to be open to understanding what their needs are and learning from them. So that transition from being all about me to now I have to be, it has to not be about me. It has to be about the success of my team or my company. And in order for me as the leader to make sure that the team is going to succeed, I have to step back as the center of my own focus and say, wait a second. The customer, my customer, I have to make them happy. The investors, I have to make them happy. I have to understand what they are. And then I have to be producing something that will make them successful because that is how my team will be successful. Anyway, that transition is really hard for people at that stage of life. And understanding that is what I wish somebody had laid out for me in my late 20s. A better understanding, help me understand that more quickly than I had to by my trial and error and learning over time.
Absolutely. There's one more step in that listening process that I think is completely ignored. And that is that once you learn how to listen yourself, which I call Type 2 listening, which is, or Type 1 listening, where you're gathering information, you're listening to different perspectives, you're trying to understand all this different conflicting information and make sense of it all. The next level of listening, which I call Level 2 listening, is where you are listening to make sure the other person feels heard. And that is missed by just about— that's missed by just about everybody. And that's the focus of leadership empathy, is you're no longer listening for information, you're listening to validate other people, to make sure they feel like they've been listened into existence.
Yeah, I think that's a, that's an excellent point. I would also add to it that there's a, within your team, that there's a leadership role of listening, of validating that you're, you are hearing what they're saying, but also helping other people understand each other.
That's right.
I would say those three dimensions of it are very important.
Absolutely. And there are skills. These are the skills that I teach. How do you do that? And these are not skills that are intuitive. In fact, many of them are counterintuitive. But once you learn the skills, it completely changes the dynamic. And that's the power of it.
Yeah. What I find is that each of us has our own way of speaking, and often we're speaking in our language and our style and our shorthand. I'm sure I do that. I'm sure you do that. And so what I find is that if I'm in a group and somebody is in their own way quickly presenting their case or argument or what the point they're trying to make, that in a way, I'm not doing this all the time, but occasionally I find that I have to in a way translate what they're saying in their language to help other people understand what that person is really saying in the terms of what the conversation is all about.
Exactly. And of course, as a mediator, I do that all the time. Because one person says something that triggers somebody else because they're hearing something different than what was really said because their filters are set in a different way. And you have to help people listen to each other. And leaders have to do that too. As a mediator, that's stock and trade for dealing with conflict. But you're absolutely right. So you wrote, you've written the book Create the Future on decision-making, and it's on Amazon. It is, you're blessed that it's selling and you've gotten recognized for that. That's always fun to get those royalty checks. Who is the publisher?
The publisher is Amplify in Washington, DC. They're a hybrid publisher. I could get into all my stories about publishing a book at this point in life, but anyway.
I know, I'm, like I said, I'm working on number 5. I got the manuscript just about done. I'm under contract with Simon Schuster, so I'll be sending it off to them in a couple of weeks. It's a project to do that. Rick, I got one more question for you before I let you go. What's one thing about yourself that we would never know about unless you revealed it to us?
I am a sailboat racer and I will admit that I sometimes say that everything I learned about leadership, I learned on my sailboat.
Oh yeah.
I threatened to write, I threatened to write a book about that. And so I actually get asked to talk about my sailboat racing, not as much as I do about this, but, right. So last year we did the Newport to Bermuda race and we done the Marblehead to Halifax race. I have a J130. And so if you have 8 or 10 people on your crew who you're not paying, they're there because they want to be with a successful sailing program, a successful leader. Boy, you really quickly have to learn that it can't just be about you. It's got to be about the team.
It's funny you should mention that. I used to race Santana 22s. And I've got a racing— my racing cat's right out here. So we'll be moving up into the mountains to our sailing lake, Huntington Lake, which gets a consistent 17 to 22 knot wind every day. We'll be moving it up there in another month and spend the summer.
Oh, that's great.
On the water that we skied on 2 months ago. What's a J130? How big is the boat?
43 feet.
43 feet. And you got 10 people on the crew?
We usually race with, if we're doing a Bermuda race, we'll have 8 people on the boat, which is mainly a limitation by how many people fit in the life raft.
But, okay. Yeah. Wow. That's how long does it take to race from Newport down to Bermuda? Couple, 3 days?
Think 4 to 5 days.
4 to 5 days. Okay.
4 to 5 days, depending on whether you have wind. So there was a lot of wind. It was a big wind day, a big wind race last, last summer, last June. So we got there actually a whole day sooner than we had expected to be there. So we didn't actually have any accommodations on shore, but we, so was that mostly a broad— we dealt with it, but is that mostly a broad reach down?
'Cause the way the prevailing winds go, or the winds are coming across from the east.
It depends a lot. So that race, that race, actually 2 boats sank going over and another boat sank coming back. Wasn't big. Because of a big storm, but because there was 20-25 knot winds coming from the southwest. So we were actually very close reaching over, up and down the waves, and dealing with that over 3 or 4 days, it's going to be exhausting. Toll on everybody.
Yeah, it's exhausting. Wow, good for you, Rick. I've really enjoyed our time today. Thank you so much for joining me, and I'm sure my audience really appreciates it too.
Great. Thank you, Doug. It was great being here, and hope we'll meet again. Absolutely.
Doug Noll here. Thank you so much for listening to Listening with Leaders. If you are a successful executive leader who would like to be on this program, please visit podcast.dougnull.com/podcast. If you got something out of this interview, would you please share this episode on social media? Just do a quick screenshot with your phone and text it to a friend or post it on the socials. If you know someone that would be a great guest, tag them on the social media to let them know about the show and include the hashtag #ListeningWithLeaders. I love seeing your posts and guest suggestions. We are regularly putting out new episodes and content. To make sure you don't miss any episodes, go ahead and subscribe. Your thumbs up ratings and reviews go a long way to help promote the show and mean a lot to me and my team. Want to know more? Go to my website, DougNoll.com, or follow me on LinkedIn, Facebook, and Instagram. That's @DouglasEnoll. Thanks for listening, and we'll see you on the next show.
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