7 Insights from Interviewing More than 200 Brilliant People

Key Takeaways

• Good decisions require good “decision hygiene”. Daniel Kahneman emphasized “decision hygiene”: using structured methods that prevent errors, even when you don’t know what mistakes you’re avoiding. One tip is to assess each important quality of an option before making your judgment.

• Negotiation works best as collaboration. Raffi Grinberg suggests moving away from a win-lose mindset. You’ll get better results by asking how both sides can benefit and starting the conversation with clear intentions.

• Success stories can mislead you. Elspeth Kirkman highlights survivorship bias: focusing on winners while ignoring failures. To get real insight, always ask what you’re not seeing.

• Blame ruins relationships. David Burns found that blame strongly predicts dissatisfaction. Taking responsibility and dropping defensiveness is often the first step to healing relationships.

• Consistency beats emotion in investing. Jim O’Shaughnessy says the biggest threat to good investing is fear and greed. Automating your plan helps you stay the course and avoid bad decisions.

• Avoidance holds you back in therapy. Matthew Smout argues that progress often comes from facing what you’ve been avoiding.

• Lasting happiness isn’t about achievement. Stephanie Harrison warns that chasing perfection and success often backfires. Deeper happiness comes from meaning, connection, and authenticity.

What could you learn from a Nobel prize winner, a clinical psychologist, and a successful investor?

Spencer Greenberg has now interviewed more than 200 brilliant thinkers on the Clearer Thinking podcast, covering a wide range of expertise. Guests are invited to the podcast to bring "ideas that matter" that they are excited to discuss.  In this article, we’ve collected together 7 insights from these interviews that we think are important and worth hearing. 

1) How can you improve your decision hygiene?

Daniel Khaneman, who recently passed away, was a Nobel laureate and a giant in the fields of psychology and behavioral economics. When he joined us on the Clearer Thinking podcast, one of the things he talked about was the concept of decision hygiene.

Physical hygiene is important for your physical health, but it isn’t like vaccines or medication, which target specific diseases. When you wash your hands (an act of physical hygiene), you don’t know which germs you’re preventing from harming you; you just know that you’re lowering the risk of being harmed by germs. Decision hygiene is a similar idea but applied to thinking. There are things you can do (like the mental equivalent of washing your hands) that will help you avoid mistakes, even when you don’t know which mistakes you’ll be avoiding.

For example, there’s something Kahneman called ‘Mediating the System Protocol’, which is an un-catchy name for a very important idea. Imagine you’re hiring someone for a job. You might take one of the following two approaches:

1. The unstructured interview: You talk with the candidate, trying to form an overall impression of them.

2. The structured interview: You first define the qualities you’re looking for (e.g., reliability, originality) and then you spend the interview evaluating each quality independently, one by one. Only once you’ve done that for each important quality do you zoom out and make an overall judgment.

If you want to employ the best candidate for the job, research has found that the second approach is better. In typical unstructured interviews, interviewers make up their minds very early and spend the rest of the interview confirming what they already believe. Interviewers who delay their judgments until they’ve assessed important qualities independently get a more reliable impression of their candidates.

The same is true of decision-making. When you’re choosing between options, think of each option as a ‘candidate’ and identify the qualities you want from an ideal candidate. Evaluate candidates on those qualities before making an overall judgment. The key is to delay your intuition and your overall judgment of each candidate or option until after you’ve gathered information about their desirable qualities.

To hear Kahneman discuss this idea, along with other elements of decision hygiene and much more, you can listen to the full podcast episode here:

2) What’s the best way to negotiate?

Negotiation is a core career skill, but Raffi Grinberg argues that many people approach it the wrong way. Popular culture teaches us to think of it as a battle of wills, where one person asks for more, the other offers less, and they meet somewhere in the middle. In reality, the best way to think of negotiation is usually in terms of expanding the pie, not fighting over slices. Or, to put that more literally: finding ways for both parties to benefit as much as possible from the exchange.

Whether you’re hoping to negotiate a pay raise, a job offer, or something else entirely, Grinberg offers some advice.

He advocates shifting away from an adversarial mindset and to a collaborative one. “It’s often less of a zero-sum game than people think,” he says. And you’re likely to get better results if you approach negotiation with the question “How can we make this situation mutually beneficial for both of us?”

Another tip is to start by stating your intention. For deeper discussion of this and other tips for negotiating, check out the full episode here:

3) Are you misjudging success?

What would you say is “the bias that rules all biases”? 

Elspeth Kirkman offers a case for thinking survivorship bias is the answer, because it colors almost everything we believe, often in ways we don’t notice. Survivorship bias occurs when we draw conclusions from success stories without paying proper attention to cases of failure. For example, if you only study billion-dollar startups to figure out what makes a company succeed and see that they all have strategy X in common, you’ll miss all the failed startups that used the same strategy and might end up thinking that strategy X is a surefire method for success. Without comparing successes and failures, it’s easy to think you have insight when you don’t. This bias is amplified in the age of internet algorithms selecting content for us to see: we mostly encounter the viral extremes that survive algorithms’ filters, not the full range of ordinary opinions or moderate voices. This can lead us to misjudge things like public opinion.

Kirkman reminds us of an important lesson: Whenever we see a success (including things that have successfully made it through algorithmic selection), we should ask what’s missing and whether we’re only looking at ‘survivors’. True insight usually requires contrasting successes with failures.

4) What’s the best way to solve relationship problems?

David Burns argues that the biggest reason relationship problems persist is that most of us aren’t willing to pay the enormous price required to truly fix them. What is that price? The death of our egos. We must give up the impulse to blame issues on the other person and take a hard look at our own role in the problem. To truly resolve these problems, he says, we must be willing to experience the difficult feelings that come with humility.

In a large study he conducted at the University of Pennsylvania, Burns expected to find complex patterns predicting relationship success. Instead, he says the data pointed to one simple predictor: blame. When partners blame each other, he argues, satisfaction plummets; when they take responsibility for their part, relationships thrive.

The painful truth, Burns says, is that the things we’re most likely to complain about in a partner is often something we are provoking ourselves with our actions and reactions. He discusses what he calls the “five secrets of effective communication” which he claims can suddenly turn conflicts around. These are techniques like disarming criticism, empathizing with feelings, and sharing your own emotions openly. But the first step is the hardest: dropping your defenses and letting go of blame. We all have instincts to get defensive and protect our egos, and that’s why the death of our egos is so scary. It’s also why Burns argues that “Love is kind of like the opposite of human nature.”

5) What’s the best investment strategy?

Jim O’Shaughnessy argues that the best edge most people can get, when it comes to investing, isn’t beating the market; it’s beating their own fear and greed through disciplined, automated investing. His “ultimate investment secret” is simply consistency. And the biggest threat to good investing, he says, is human emotion. Fear, greed, and even hope can lead investors to buy and sell at exactly the wrong times.

His advice is to build a process you can stick to, and make as much of it automatic as possible. For most people, that means regularly contributing to a low-cost, broad-based index fund or ETF and resisting the urge to time the market. When the market plunges, fear can make you want to pull out; when it soars, greed can push you to pile in at the top. O’Shaughnessy notes that even legendary investors struggle with these impulses. For example, Sir John Templeton placed orders in advance precisely so he wouldn’t let fear stop him from buying at low prices.

Automation is powerful because it bypasses the emotional “base code” we all share. Instead of reacting to headlines or short-term losses, you keep contributing steadily, letting decades of market growth work in your favor. O’Shaughnessy points out that the U.S. stock market has never produced a negative return over a 20-year period, despite wars, crashes, and depressions. “Ninety percent of success,” he says, “is just showing up.” When it comes to investing, that means showing up consistently, no matter what the market is doing.

6) What makes therapy effective?

How can you tell which kind of therapy is right for you? CBT, person-centered, … The options can be overwhelming. Well, clinical psychologist Matthew Smout argues that good outcomes in therapy are not as dependent as you might think on the specific type of therapy you engage in. Instead, he says that it’s important to have a strong working relationship with your therapist (in which you agree on things like the goals of the therapy), and he argues that “pretty much anything effective” involves addressing things that you’ve been avoiding. 

Avoidance can feel like relief, but it tends to maintain or worsen problems, so effective therapy usually involves helping clients face what they’re avoiding. This can mean changing the way clients evaluate themselves and the situations they fear, and it ultimately demands courageously facing discomfort. Our path to change runs through the fears we most want to avoid.

7) How should you pursue happiness?

Stephanie Harrison argues that although pursuing happiness is worthwhile, we are conditioned to chase it in ways that backfire. She distinguishes between what she calls “old happy” and a deeper version of happiness that includes meaning, purpose, connection, and authenticity.

“Old happy,” she says, is a conception of happiness derived from things valued by our culture; things like individualism and achievement. It instills values like perfectionism, competition, and hyper-independence that don’t deliver lasting well-being and often make us more miserable. She reminds us that lasting happiness comes from elsewhere: from recognizing our talents and strengths and using these gifts to connect with others - for instance, by using them to help others in meaningful ways.

We hope you found those episode takeaways insightful. The Clearer Thinking podcast has more than 200 episodes. To listen, just search for "Clearer Thinking with Spencer Greenberg" on your favorite podcast app, or take a look at our full list of episodes here.