Why Smart Leaders Make Bad Decisions

What if one of the best ways to make a decision is to imagine that you’ve already made it and it failed?In this episode, we explore the power of the premortem: a decision-making technique that asks us to mentally travel into the future, imagine a bad outcome, and work backward to understand what caused it.Through stories ranging from the contingency planning surrounding Apollo 11 to a near-disaster at Pixar, we discuss why asking “What could go wrong?” often isn’t enough and how imagining that failure has already happened can uncover risks, assumptions, and vulnerabilities we might otherwise miss.This is the second in a 3-part series around the launch of Matthew’s new book, The Upside of Downside Thinking, to introduce a deceptively simple idea for making better decisions: imagine the failure before it happens.The goal isn’t to predict the future. It’s to be less surprised by it.—Matthew’s Book on Premortem Thinking: https://www.theupsideofdownsidethinking.com/Learn To Lead is brought to you by Abilitie, a leading provider of experiential learning. Abilitie’s simulations and leadership programs have inspired over 100,000 professionals in more than 50 countries. To learn more about Abilitie and about our host Matthew Confer, visit the links below:Abilitie Leadership Development - https://www.abilitie.comHost Matthew Confer:LinkedIn - https://www.linkedin.com/in/matthewconfer/TEDx Talk on Decision Making - https://www.ted.com/talks/matthew_confer_before_you_decide_3_steps_to_better_decision_makingMake sure you subscribe to our show to ensure you get our next episode when it is released.

Smart leaders make bad decisions all the time. But why?In this episode, we explore the story of Kodak, a company that helped invent the digital camera yet still struggled to navigate the transformation of photography. It’s a fascinating example of how optimism, existing success, and our own assumptions can make risks surprisingly difficult to see before a decision goes wrong.As we prepare for the release of Matthew’s new book, The Upside of Downside Thinking, we use this episode as the first in a 3-part series to introduce a deceptively simple idea for making better decisions: imagine the failure before it happens.—Upcoming Book: https://www.theupsideofdownsidethinking.com/Learn To Lead is brought to you by Abilitie, a leading provider of experiential learning. Abilitie’s simulations and leadership programs have inspired over 100,000 professionals in more than 50 countries. To learn more about Abilitie and about our host Matthew Confer, visit the links below:Abilitie Leadership Development - https://www.abilitie.comHost Matthew Confer:LinkedIn - https://www.linkedin.com/in/matthewconfer/TEDx Talk on Decision Making - https://www.ted.com/talks/matthew_confer_before_you_decide_3_steps_to_better_decision_makingMake sure you subscribe to our show to ensure you get our next episode when it is released.

In this episode, we explore how past generations reacted to groundbreaking technologies like the telephone, ATMs,and spreadsheets and why so many confident predictions turned out to be wrong.Along the way, we’ll uncover Roy Amara’s famous observation that we tend to overestimate the short-term impact of new technologies while underestimating their long-term effects. As leaders navigate the AI revolution, history offersan important reminder: the future is almost never what we predict— Upcoming Book: https://www.theupsideofdownsidethinking.com/Learn To Lead is brought to you by Abilitie, a leading provider of experiential learning. Abilitie’s simulations and leadership programs have inspired over 100,000 professionals in more than 50 countries. To learn more about Abilitie and about our host Matthew Confer, visit the links below:Abilitie Leadership Development - https://www.abilitie.comHost Matthew Confer:LinkedIn - https://www.linkedin.com/in/matthewconfer/TEDx Talk on Decision Making - https://www.ted.com/talks/matthew_confer_before_you_decide_3_steps_to_better_decision_makingMake sure you subscribe to our show to ensureyou get our next episode when it is released.

What do shipping containers, barcodes, and time zones have in common?At first glance, not much. They’re ordinary, often overlooked systems that most of us rarely think about. But each quietly transformed the way the world works.In this episode, we explore the hidden innovations that made modern commerce, transportation, and retail possible, and what they reveal about leadership. While most people focus on visible outcomes, great leaders understand that lasting success is built on foundations that often go unnoticed. It’s a powerful reminder that the most important work isn’t always the most visible, but it is often the most impactful.—Upcoming Book: https://www.theupsideofdownsidethinking.com/Learn To Lead is brought to you by Abilitie, a leading provider of experiential learning. Abilitie’s simulations and leadership programs have inspired over 100,000 professionals in more than 50 countries. To learn more about Abilitie and about our host Matthew Confer, visit the links below: Abilitie Leadership Development - https://www.abilitie.comHost Matthew Confer:LinkedIn - https://www.linkedin.com/in/matthewconfer/TEDx Talk on Decision Making - https://www.ted.com/talks/matthew_confer_before_you_decide_3_steps_to_better_decision_makingMake sure you subscribe to our show to ensure you get our next episode when it is released.

History is filled with companies that became incredibly good at the current game, right before the game changed completely. Through stories from the mobile phone and retail industries, this episode explores why disruption often comes not from doing something better, but from asking a fundamentally different question.—Learn To Lead is brought to you by Abilitie, a leading provider of experiential learning. Abilitie’s simulations and leadership programs have inspired over 100,000 professionals in more than 50 countries. To learn more about Abilitie and about our host Matthew Confer, visit the links below:Abilitie Leadership Development - https://www.abilitie.comHost Matthew Confer:Upcoming Book: https://www.theupsideofdownsidethinking.com/LinkedIn - https://www.linkedin.com/in/matthewconfer/Matthew’s TEDx Talk on Decision Making - https://www.ted.com/talks/matthew_confer_before_you_decide_3_steps_to_better_decision_makingMake sure you subscribe to our show to ensure you get our next episode when it is released.

Some ideas don’t fail because they’re bad, they fail because something is missing. In this episode, we explore how QR codes, online grocery delivery, and ride sharing all struggled before finally taking off, and why something as simple as a tin can took nearly 50 years to become usable. Each story reveals a powerful leadership insight: great ideas don’t exist in isolation, they depend on timing, technology, and behavior coming together at the right moment.—Learn To Lead is brought to you by Abilitie, a leading provider of experiential learning. Abilitie’s simulations andleadership programs have inspired over 100,000 professionals in more than 50 countries. To learn more about Abilitie and about our host Matthew Confer, visit the links below: Abilitie Leadership Development - https://www.abilitie.com Host Matthew Confer:Book: https://www.theupsideofdownsidethinking.com/LinkedIn - https://www.linkedin.com/in/matthewconfer/ Matthew’s TEDx Talk on Decision Making - https://www.ted.com/talks/matthew_confer_before_you_decide_3_steps_to_better_decision_making Make sure you subscribe to our show to ensure you get our next episode when it is released.

Some of the most extraordinary successes in history didn’t happen early, and they didn’t happen easily. In this episode,we explore the stories of people who stayed relentlessly committed to their passions long after most would have quit. From Orville Redenbacher’s decades-long quest to perfect popcorn to Colonel Sanders launching KFC at 65, these journeys show how persistence, curiosity, and passion can turn unlikely ideas into global successes.—Learn To Lead is brought to you by Abilitie, aleading provider of experiential learning. Abilitie’s simulations and leadership programs have inspired over 100,000 professionals in more than 50 countries. To learn more about Abilitie and about our host Matthew Confer, visit the links below:Abilitie Leadership Development - https://www.abilitie.comThe Learn To Lead Podcast - https://www.abilitie.com/learn-to-lead-podcast/Host Matthew Confer:LinkedIn - https://www.linkedin.com/in/matthewconfer/Matthew’s TEDx Talk on Decision Making - https://www.ted.com/talks/matthew_confer_before_you_decide_3_steps_to_better_decision_makingMake sure you subscribe to our show to ensureyou get our next episode when it is released.

Sometimes the best ideas have unexpected outcomes. In this episode, we explore how a pizza delivery guarantee, a public bike-sharing program, and safer playgrounds all changed behavior in surprising ways. Each story highlights a powerful leadership insight: when you design a policy or system, you’re not just shaping results — you’re shaping how people respond. The most effective leaders look beyond first-order outcomes to consider what might happen next. —Learn To Lead is brought to you by Abilitie, a leading provider of experiential learning. Abilitie’s simulations and leadership programs have inspired over 100,000 professionals in more than 50 countries. To learn more about Abilitie and about our host Matthew Confer, visit the links below:Abilitie Leadership Development - https://www.abilitie.comThe Learn To Lead Podcast - https://www.abilitie.com/learn-to-lead-podcast/Host Matthew Confer:LinkedIn - https://www.linkedin.com/in/matthewconfer/Matthew’s TEDx Talk on Decision Making - https://www.ted.com/talks/matthew_confer_before_you_decide_3_steps_to_better_decision_makingMake sure you subscribe to our show to ensure you get our next episode when it is released.

In crowded markets, most organizations fight to be slightly better than everyone else. But some of the most successful companies in history took a different path. They chose to stand apart instead of blend in. In this episode, we unpack how AOL, Red Bull, and IKEA each broke industry norms, challenged conventional wisdom, and built enduring brands by leaning into what made them unconventional. These stories reveal a powerful insight for leaders: sometimes the smartest move isn’t to improve the playbook, it’s to throw it out and write your own.-Learn To Lead is brought to you by Abilitie, a leading provider of experiential learning. Abilitie’s simulations and leadership programs have inspired over 100,000 professionals in more than 50 countries. To learn more about Abilitie and about our host Matthew Confer, visit the links below:Abilitie Leadership Development - https://www.abilitie.comThe Learn To Lead Podcast - https://www.abilitie.com/learn-to-lead-podcast/Host Matthew Confer:LinkedIn - https://www.linkedin.com/in/matthewconfer/Matthew’s TEDx Talk on Decision Making - https://www.ted.com/talks/matthew_confer_before_you_decide_3_steps_to_better_decision_makingMake sure you subscribe to our show to ensure you get our next episode when it is released.

What is it about a new beginning that makes us feel more motivated, more hopeful, and more ready to change?Behavioral scientists call it The Fresh Start Effect — the idea that temporal landmarks create psychological separation from our past selves and give us permission to begin again.In this episode, we explore three fascinating examples: why people are far more likely to run their first marathon at ages ending in nine, why searches for “gym” and “diet” spike everyMonday morning, and why birthdays trigger major goal resets.The leadership takeaway is powerful: momentum isn’t just about discipline, it’s about timing and framing. Great leaders know how to intentionally create “January moments” throughout the year.— Learn To Lead is brought to you by Abilitie, a leading provider of experiential learning. Abilitie’s simulations and leadership programs have inspired over 100,000 professionals in more than 50 countries. To learn more about Abilitie and about our host Matthew Confer, visit the links below:Abilitie Leadership Development - https://www.abilitie.comThe Learn To Lead Podcast - https://www.abilitie.com/learn-to-lead-podcast/ Host Matthew Confer:LinkedIn - https://www.linkedin.com/in/matthewconfer/Matthew’s TEDx Talk on Decision Making - https://www.ted.com/talks/matthew_confer_before_you_decide_3_steps_to_better_decision_makingMake sure you subscribe to our show to ensure you get our next episode when it is released.