Great Leaders Know When to Say Yes and When to Say No

Confidant for High-Achieving Leaders and Visionaries

Great Leaders Know When to Say Yes and When to Say No

Published on March 28, 2025

with Doug Thorpe

Leadership is often viewed through the lens of decision-making. As Doug Thorpe expertly explains in our discussion, “Great leaders aren’t afraid to make that decision. They’re going to take in the information, but they’re going to know the moment and they’re going to be able to have almost impeccable timing for saying yes or no.” This ability to make clear, well-timed decisions is what separates truly exceptional leaders from those who merely manage.

The quick answer is that becomes the measure of a good leader. Great leaders aren’t afraid to make that decision.

The journey from individual contributor to leadership contains several critical transitions. The first challenge often occurs when a high-performing team member is promoted to manage their former peers. This transition creates an immediate psychological hurdle – how do you shift from being a friend and colleague to a position of authority? Doug points out that many newly promoted managers struggle with this dynamic, particularly as they try to balance their continued individual contributions with new management responsibilities.

As careers advance further, the burden of trying to maintain individual contributor status while managing increasingly larger teams eventually becomes unsustainable. This is when professionals start experiencing burnout, trying to “double down on the work effort” while also handling growing management responsibilities. The solution isn’t working harder but shifting perspective – recognizing that leadership requires a fundamentally different focus than individual contribution.

One fascinating insight from our conversation was the distinction between joining a company directly in a leadership role versus being promoted internally. Doug suggests that coming in as an external hire can sometimes be easier because “the people on the team, the employees around you, they don’t know you as a colleague.” This creates a clean slate for establishing your leadership identity, though you must be intentional about how you “show up” from day one.

Perhaps the most significant transition in professional development is moving from tactical execution to strategic thinking. Doug identifies this inflection point as occurring typically at the director or senior director level, where conversations shift from “How many widgets did we deliver today?” to “What’s our strategy for the bigger picture?” This expansion of perspective – from nose-down execution to head-up vision – requires developing new mental muscles and a longer time horizon.

The art of leadership decision-making becomes particularly crucial at the executive level. Doug makes a powerful distinction between the science of leadership (data, analysis, spreadsheets) and the art of leadership (reading the market, having that “gut feel”). He shares a compelling example from his banking days, where a chairman made the counterintuitive decision to delay implementing ATM technology for two years despite team recommendations to move quickly. This strategic patience allowed them to learn from competitors’ mistakes and ultimately build a more profitable infrastructure solution.

Values-driven leadership emerged as another crucial theme. Whether it’s Chick-fil-A’s unwavering commitment to closing on Sundays despite Wall Street criticism, or a construction company’s dedication to absorbing costs for their own mistakes rather than passing them to customers, strong values create distinctive organizations. As Doug’s construction client explained, “doing the right thing” created a reputation for transparency and honesty that ultimately attracted loyal customers willing to pay premium prices.

The conversation highlights that leadership development isn’t just about acquiring new skills, but about developing a different way of seeing the world. From managing former peers to making high-stakes decisions with limited information, leadership requires comfort with ambiguity and confidence in your values. As Doug’s military friend wisely noted when asked how he maintained calm despite facing extreme situations: focus on what truly matters and what you can control. For leaders navigating daily business challenges, this perspective is invaluable.

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