The Wisdom Wall

43 quotable lessons, heuristics and mental models. Every one is playable at the moment it was said. No fortune cookies allowed.

Everyone Ted Seides (135)Annie Duke (87)Michael Mauboussin (67)Morgan Housel (60)Randall Stutman (43)Ashby Monk (40)Ana Marshall (40)Sanjay Ayer (35)Chris Douvos (34)Chris Dixon (32)Tim Sullivan (31)Sarah Samuels (31)Mike Maples, Jr. (31)Ali Hamed (31) Best Newest Oldest

“They've learned to create relational closeness without empathy. They've learned to create it without being warm and fuzzy and giving people a lot of couch time. What they've done is they've invest deeply in those people and understanding them.”

Randall Stutman, Apr 13, 2026

“The biggest issues for hedge fund managers, as far as I'm concerned, is a couple things. Number one, many of them like themselves way too much, and so they really need somebody that's willing to be honest with them. They're very powerful people, both financially and personally, and so the ability to speak truth to…”

Randall Stutman, Jul 27, 2020

“profile is your enemy. It makes you a target for litigation. It makes you a target for media scrutiny. It makes you a target for pure jealousy. Profile for all great leaders, unless they can't avoid it, Is your enemy, and your job is not to covet profile.”

Randall Stutman, Jul 27, 2020

“We normally don't learn all that much when we interview leaders. Just like a great ball player, they don't know what they do.”

Randall Stutman, Apr 13, 2026

“Most leaders aren't mature enough to do that because they can't stop from them saying and finishing what the observation means.”

Randall Stutman, Apr 13, 2026

“the majority of coaches that do this for a living don't have answers. And, and I actually, some of them are very proud with the idea that they process people and, and the answers are in other people. I believe the answers are in all of this, but, but at the same time, if you went to a tennis coach and you wanted to…”

Randall Stutman, Jul 27, 2020

“what you learn really quickly is that being able to size people up and adapt to them in an ongoing flow of interaction is almost impossible. So you've got your own goals. You've got other competing things going on. You've got the noise of the context. It's very, very difficult to do. So what most people do is they go…”

Randall Stutman, Jul 27, 2020

“And that by being a great fan of other people, and showing your fan-ness, and asking yourself the question in almost every context, what would a fan do here? What would somebody who's your fan do? That becomes a very different thing because you can work on your fantasy and be a better fan all the time, and now you…”

Randall Stutman, Jul 27, 2020

“If you tell me that you've got some, you know, stress, anxiety, trait anxiety, I can't coach for that. If you tell me that you have bad judgment, I probably change your judgment time. Take me 20 years. If you've got poor judgment, that is not a coachable thing.”

Randall Stutman, Jul 27, 2020

“rather than waste time in group settings, trying to make decisions in group process, what you do is You do it away from the table after a target position's made, you create consensus or near consensus, then you come to the table, and then you validate the decision.”

Randall Stutman, Jul 27, 2020

“And in many cases inside places like hedge funds or private equity firms or other places where allocators would invest, there's a high degree of respect on skill and a low degree of respect on character. And that creates division inside those teams.”

Randall Stutman, Jul 27, 2020

“I'm always amazed at how many people take one of the self-diagnostic tests, whether that be DISC or Myers-Briggs or Hogan or whatever it might be. They'll sit down with me and they'll say, Randall, that really nailed me. I can't even believe how good that diagnostic was. It just grabbed me and just nailed me right on.…”

Randall Stutman, Jul 27, 2020

“It is amazing the research about being side by side and walking with people. People get much more disclosive when they're actually walking shoulder to shoulder than they ever are face to face.”

Randall Stutman, Apr 13, 2026

“Once you do that for a handful of weeks, three, four, five, six weeks, it become a routine, it become a habit, and then it will be yours.”

Randall Stutman, Apr 13, 2026

“What you have to do is pick a behavior that you're going to work on. Just one. Not 20.”

Randall Stutman, Apr 13, 2026

“Because if you do them for effect, you won't keep them up. You'll only do them in some situations. You won't get very skillful at them. As soon as they don't work on somebody, you'll give them up. You got to pick the behavior that you believe in that represents what you value, that you're passionate about, and the kind…”

Randall Stutman, Apr 13, 2026

“That power has a consequence. It creates resistance. People naturally become a little bit reluctant, if not totally defensive, to things that come at them from power.”

Randall Stutman, Apr 13, 2026

“What I tell leaders all the time, Ted, is they need to get out of the feedback business and get in the recommendation and suggestion business. They're going to be able to give a lot more feedback a lot more often with a lot less resistance and defensiveness just by what they call it, by how they introduce it and frame…”

Randall Stutman, Apr 13, 2026

“Internalized feedback is feedback that's going to get acted on, remembered, has real duration to it, and has a longer-term impact.”

Randall Stutman, Apr 13, 2026

“Anytime I can get you to give yourself your own feedback and using a third party is the easiest way to do it.”

Randall Stutman, Apr 13, 2026

“right after success, right after mission accomplished, right after tasks have been achieved, people are much more receptive to feedback. Why? Because they've just succeeded. They've got an armor to them because of their success, their effectiveness. They're much more sensitive right after defeat, right after mistake,…”

Randall Stutman, Apr 13, 2026

“There's a bias that almost everybody has across the whole world. You have it, I have it, everybody has it, and that is, we're generally more critical of people based on our own strengths. Whatever it is that we're good at, we're more critical about other people about it.”

Randall Stutman, Apr 13, 2026

“You need an ongoing high cadence of feedback on the smallest issues over time. What you'll see is you'll slowly move people from negative to positive in terms of climate attitude, other kinds of affect. That's the key. If I save it up and I never give it to you, I never really deliver the hard message, then I'm…”

Randall Stutman, Apr 13, 2026

“A how question, if it's done and carries feedback, actually embeds the feedback inside the question. When I say to you, Ted, how are you going to upgrade the talent on your team? The feedback is that your team talent needs to be upgraded. But I don't say that. Instead, I simply ask a how question. The feedback is…”

Randall Stutman, Apr 13, 2026

“The highest performing teams are the ones where the leaders have really high standards, really high expectations, unusual focus on certain kinds of details, and people feel relational closeness.”

Randall Stutman, Apr 13, 2026

“Most athletic coaches can have a bigger range of tone and style than you and I can as team leaders. We need to have a more positive, it doesn't have to be warm, but more engaging, more validating style to the way that we engage people.”

Randall Stutman, Apr 13, 2026

“Most smart people start on the negative. Because it's a differentiator, because it illustrates differentiation and distinction, as well as it illustrates, at least in most people's mind, that you understand something at a deeper level.”

Randall Stutman, Apr 13, 2026

“Good followership leaders tend to be high fans of other people. They tend to be relationally close to other people, but in particular, they tend to invest in other people in a multitude of ways, and that builds a sense of loyalty and a connection that they get to enjoy the benefits or the fruits of.”

Randall Stutman, Apr 13, 2026

“I'd argue that you need to organize yourself more about relationships and conversations than about tasks. That too many leaders think about tasks, and by the way, that's a perfectly acceptable majority of the world does that. But if you're going to be good at this leadership thing, you need to organize yourself around…”

Randall Stutman, Apr 13, 2026

“some people are so overscheduled they've never had unstructured time to think freely and let decisions and strategy and other things bake. They make poor quality decisions as a result.”

Randall Stutman, Apr 13, 2026

“Start celebrating decision processes that are great processes that produce bad outcomes. What you're going to find is you make for people willing to take more risk, willing to invest their time and energy, hone in and be specific with the process. Long term, they will make better quality decisions.”

Randall Stutman, Apr 13, 2026

“Most Hedge funds, private equity firms, small ones that start to grow, recognize that they have growing pains, and that their expertise is limited to investment, and they really don't know how to create an organization, how to create team culture, how to both select people, but most importantly, how to engage the…”

Randall Stutman, Jul 27, 2020

“one of the things that they do is they rely on a target proposal decision that basically they put out there, but they go out of their way to say, here's the target, and now they get people to weigh in against that target, and that saves tremendous amounts of time. People can respond much more quickly and clarify their…”

Randall Stutman, Jul 27, 2020

“You might have a rule that says, when conflict occurs, I immediately go to voice-to-voice conversation, because I don't do conflict vis-a-vis texts or emails, because those are inflammatory mediums, because we get to hide behind the words and not the, the face and the voice, we will often say things we normally don't…”

Randall Stutman, Jul 27, 2020

“So all of us have weak performance, but very few of us are truly weak performers around everything. If we're known as weak performers in organizations, generally because we're weak at the most critical thing.”

Randall Stutman, Jul 27, 2020

“So, so when we study the best leaders, people that are really good at elevating performance and getting the most out of teams, we were interested in finding, is there something that they do differently? And the answer is, yeah, they do. And they basically confront those people with information. So what does that mean,…”

Randall Stutman, Jul 27, 2020

“My belief is most leaders want to be better, but they don't know how. You have to give them the tools, the specific things to do to make them better.”

Randall Stutman, Apr 13, 2026

“When you study admired leaders, they always have an echo question going on with somebody about something.”

Randall Stutman, Apr 13, 2026

“In case good leaders have time value congruence, they schedule their priorities rather than let their priorities schedule them.”

Randall Stutman, Apr 13, 2026

“You can't play high-level golf that way. You gotta play for yourself. You can't be distracted like that. You can't be a social performer.”

Randall Stutman, Apr 13, 2026

“too many people treat reading as something they have to complete. And something that represents them in some physical way, I treat books like they're candy.”

Randall Stutman, Apr 13, 2026

“You can't debate like that and not like each other and still work together.”

Randall Stutman, Jul 27, 2020

“reading doesn't mean anything unless you're able to capture. And the capture is about grabbing the insights and then being able to put it in some place where you can review it and see it over and over again.”

Randall Stutman, Jul 27, 2020
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