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Sean Ryan

Challenge Your Thinking

Updated: Oct 8

Want better results? Challenge your thinking.

Smiling diverse group of people giving thumbs up.

You’ve had your rest.


Now it's time for reflection.


As Labour Day approaches, it’s the perfect time to get into the right headspace for a solid fourth quarter.


I’ve often said that leaders really only have two assets: their brains and their time. How you harness the latter to maximize the former is the great differentiator.


So, use this last stretch of summer to actively examine your underlying thinking – the mental models, beliefs, assumptions and perceptions that shape your actions and, ultimately, your outcomes.


Because exceptional leadership starts in your head.


The TAO of leadership

Your thinking has a far more dramatic impact on your leadership outcomes than anything you say or do. Until you get clear about your motivations and assumptions, shine a light on your mental blind spots, and examine those unconscious things driving your actions, you can’t begin to draw others into the collective work that will take your organization to the next level.

Thinking Action OutComes

This idea is so important and powerful that it’s our core philosophy about how leaders grow and thrive. We call it Thinking-Action-Outcomes or TAO. It answers a simple question: what is that voice in my head, why does it say what it does, and what are the implications of listening to it?


Being able to identify and question your underlying mental models is foundational to your journey to becoming a more thoughtful, empathetic, and effective leader.


Leadership roles come with big blinders. Part of your job is to keep removing them, questioning and challenging yourself and others.


Thinking IS work

This might be a tough assignment if you have a bias for action. Most leaders like to be busy, getting the work done and knocking down deliverables. But while it might look like nothing’s happening, this kind of deep reflection is actually one of the best investments you can make in your leadership development.


And, frankly, it’s one of the most challenging things you can do to make a real change. This kind of deep, personal learning means challenging your unconscious idea about how the world operates. That can be challenging and uncomfortable. But it can also unlock more of your leadership (and personal) potential.


Remember: Focusing exclusively on doing is not necessarily the best use of your time. It’s too easy to get caught up in the task treadmill. You can’t outwork every problem.


Real change goes deeper.

When it comes to making change for better outcomes, most leaders engage in what Chris Argyris, the brilliant business theorist and professor emeritus at Harvard Business School, calls “single-loop thinking,” devising intelligent solutions to external issues.


But the complex challenges and accelerated change we’re contending with today cannot be solved by slight tweaks to what we’ve always done. Pre-conditioned responses result in predictable outcomes that can only deliver slight variations on previous results.


Nothing much is likely to change when nothing really changes about our thinking.


Simply put, better actions that lead to more successful outcomes rest on better thinking, which starts with becoming conscious of what you believe, assume and perceive.


That’s why it’s so essential to develop a habit of self-reflection or self-interrogation. Your thinking isn’t just in your head: it affects every action, which in turn generates a three-dimensional ripple effect:

  • An effect on the present situation

  • An impact on the culture via the story that action creates

  • Lessons learned by those who hear the story over time.

The forces that shape us

Where and when you were born, your family’s finances, education, your religion, gender, sexual orientation, race, and many other factors affect your worldview.


Challenging how those influences shape your thinking and actions can feel existential like you’re questioning the core of yourself. But the ability to self-reflect doesn’t necessarily mean abandoning your beliefs and worldview, just becoming more aware of them and how they influence your choices.


For instance, “Don't just stand there, do something” was a phrase I often heard growing up, and it taught me to put a premium on action. It’s taken me years to identify how this kind of thinking has influenced how I work. Once I was able to name it, I could tame it.


How to start challenging your thinking

The prospect of examining everything you think, feel and believe may feel overwhelming. But like any other challenge, you can train for it. Here are some concrete ways to start the process of challenging your mental models:

  • Read—a lot. Go outside your usual reading list to expand your thinking. (Check out our summer reading list for leaders for recommendations).

  • Talk to strangers. Seek out people with different points of view. Cultivate curiosity about their perspectives and experiences. And listen.

  • Reflect upon your leadership. Some questions to ponder:

    • What do I think about leadership?

    • What is my role as a leader?

    • When faced with tough decisions, what are my thoughts, beliefs and assumptions about the situation? What about this situation may be different from what I perceive? What data am I missing? Am I filtering anything out? Who has a different perspective from mine?

    • What are the unintended consequences of my decisions on critical stakeholders?

    • What challenges do I face? What have I done about them? What were the results?

  • Argue another point of view. When making a decision, make a case for taking action different from your default. When debating a course of action with others, have everyone “flip” their thinking and argue a different point of view.

  • Keep an open yet critical mind. Apply it to everything you read and hear.

  • Keep a journal. Record your thoughts, feelings, beliefs and assumptions about your role as a leader. Watch how your mental model may change as you are exposed to new perspectives or experiences.


This work is challenging. But if you can build a practice of self-reflection, you’ll develop the awareness, empathy and flexibility that leaders today need.


And while you’re here, I’d love to know what mental models you’ve noticed guiding your thinking and, thus, your actions and outcomes?


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