Over a year ago, I gave a philosophy workshop to a group of managers. The focus was on how to ask better questions, and why cultivating self-awareness, curiosity, and the habit of questioning our assumptions can make us better problem-solvers, managers, and leaders.
During the Q&A session, a department head said: “Your presentation was very interesting. You raised some good points and offered a few guidelines for asking better questions. But I have a question for you: in what way is philosophy different from executive coaching?”
I paused. I didn’t have a satisfying answer at the time. I replied that coaching focuses on providing actionable tips and tools to improve skills and performance. Philosophy, I said, is less about readymade solutions and more about first principles thinking. If coaching gives you a fish, philosophy teaches you how to fish.
My goal wasn’t to pit the two approaches against each other, but to explore how philosophy might offer something more foundational.
I thought it was a neat analogy. But it wasn’t quite enough. The question stayed with me.
Over time, I’ve come to believe that there is a deeper difference.
Coaching typically works within established management, behavioral, or psychological frameworks. It helps people operate more effectively within the systems they already inhabit.
Philosophy, by contrast, is concerned with how we think about those frameworks in the first place. It trains us to step back, question the assumptions beneath the system, model, or framework, and decide whether a different approach might be more appropriate.
In this sense, philosophy is not to be understood here as an academic discipline, but rather as a disposition, a mindset.
What is a philosophical mindset?
It’s not about learning the history of ideas, even though that can also be helpful. It’s about cultivating the habit of critical (self) reflection, questioning, and ethical clarity. It won’t necessarily make us more certain, but it can help us become more attentive to our beliefs, to ambiguity, complexity, and to our potential blind spots.
A philosophical mindset won’t magically make us better problem-solvers or more ethical. But it will help us become more self-aware about how we think, how we judge, and how we relate to other people’s assumptions, beliefs, and ways of being.
So what does it involve in practice?
Four pillars of a philosophical mindset
At its core, a philosophical mindset deepens our curiosity, sharpens our ability to identify assumptions, and encourages more thoughtful, collaborative approaches to solving complex problems. Here are four key components that support this mindset:
1. Self-awareness
The first step is understanding our values, biases, strengths, and blind spots. It’s about having a realistic grasp of how we show up, especially under uncertainty or pressure, and what areas and skills need improvement, both in our personal and professional spheres. Without this clarity, even the best tools or frameworks are likely to be futile.
2. Asking better questions
In many environments, having answers is often equated with competence. Admitting that we don’t know can be interpreted as a weakness. But the best solutions and decisions begin with the right questions.
One of the most effective methods for asking better questions is the Socratic method, named after the ancient Greek philosopher. It focuses on asking inquisitive, open-ended questions that help everyone involved think through the problem themselves, instead of giving them a readymade answer.
3. Understanding the difference between analytic and creative reasoning
Many of the problems we face, in the workplace and in life, arise from the constant need to make a case, prove a point, or win an argument. As Rory Sutherland points out, this can make the problem-solving and creative process feel narrow and tedious.
A philosophical mindset helps us recognize the difference between domains that require analytic reasoning and those that demand creative or synthetic reasoning, as Sutherland calls them.
Analytic reasoning is best applied in areas governed by strict rules, where the conditions cannot be otherwise. For instance, if you’re building a plane or designing a bridge, there are physical and safety constraints that must be respected.
But when you’re shaping a brand, launching a campaign, or exploring a new product line, what’s needed is creative (synthetic) reasoning. This involves gathering data, asking the right questions, and often working backwards from a desired outcome to determine the most effective approach.
A philosophical mindset helps us navigate this distinction. It encourages us to apply the appropriate mode of thinking to the problem at hand, to know when to analyze and when to invent. It also allows us to engage in disagreement without falling into ego-driven debate, and to foster more open, generative environments where complex problems can be explored rather than reduced.
4. Perspective shifting
As the term suggests, a philosophical mindset helps us shift our perspectives in an attempt to understand different points of view. It doesn’t mean that we should agree with other viewpoints. But by shifting our perspective, we put ourselves in other people’s shoes, aiming to understand the reasons that led them to subscribe to a certain belief or argument.
This exercise helps us find common ground with our colleagues, employees, customers, family members, and friends. It helps us become more empathetic toward people who don’t necessarily agree with our viewpoint, but it also makes it possible to bridge the gap between different views, especially in critical situations where compromise, consensus, or a difficult decision has to be made.
Why a philosophical mindset matters now
A philosophical mindset requires practice, reflection, and constant examination. Instead of defaulting to optimal best practices and predefined formulas, it equips us with tools and habits that help us adapt to, and navigate, a complex and uncertain world.
As such, developing a philosophical mindset can help leaders, professionals, and individuals:
- Make better decisions by recognizing assumptions they might otherwise take for granted
- Handle uncertainty and ambiguity with greater confidence
- Cultivate a culture of questioning and intellectual humility within organizations
- Avoid dogmatism and rigid thinking that often lead to poor decision-making
- Develop moral clarity when facing ethical dilemmas, rather than relying solely on predefined rules
Coaching can help us improve our skills within established frameworks and proven models.
A philosophical mindset, however, enables us to take a step further back, to examine those frameworks and question whether they still hold.
This can be especially valuable during periods of paradigm shift and increased uncertainty: times marked by rapid technological change and disruption, tense national and global politics, economic and social unrest, and a growing existential unease about where we are, where we’re going, and what it means to be human in the age of AI.