Self-development is critical to effective leadership. Leadership reflection is a critical mechanism to accelerate this process.
Why is leadership reflection important and why does it get ignored ?
By three methods we may learn wisdom: first, by reflection, which is noblest; second, by imitation, which is easiest; and third by experience, which is the bitterest.
Reflection is not glamorous
Look up the brochure for any MBA or executive business program and you are bound to come across words like strategy, decision-making, and leadership sprinkled generously amongst others. What you are less likely to find are words like reflection or the reflective mindset.
And yet, it is the art of skilled reflection that can make us good at all those advertised skills. We don’t pay attention to it because it is neither hip nor does it fit our standard notions of quick results.
Reflection is an underutilized superpower
Richard Kilburg, after doing a survey of human history, credits our power of reflection in enabling all the progress humanity has achieved. 
For 97% of the time between the age of stone tools and the development of agriculture, our human ancestors were hunters and gatherers. However, once Homo sapiens invented writing, mathematics, and philosophy, it took us only 7,000 years to land on the moon, create nuclear power plants, and develop string theory. I insert this extraordinarily brief history to make a point.
I believe it has been the evolution of the reflective capacity of the mind of Homo sapiens that, in the end, accounts for all that we have accomplished.
– Richard Kilburg in Executive Wisdom 
Our ability to think about ourselves, to think about our thinking, what Adam Smith called “being an impartial spectator”, is what differentiates us from the rest of the living world. 
Yet on a daily basis we do not use this extraordinary ability. Because it is so obvious and second nature, it does not get utilized.
Skilled reflection. Not rumination or self-absorption.
Many of us think we already reflect enough and there is no need to practice this skill. However, skilled reflection is different from plain rumination or worry where you are in an infinite doom loop and never gaining any perspective.
Most people—even people who would describe themselves as comfortable with the reflective as well as the “doing” mode—have never engaged in focused, structured, persistent, and active reflection.
– Robert Kegan & Lisa Lahey in Immunity to Change 
What many of us think of as reflection or even self-awareness is often just plain self-criticism or worse self-absorption. Those tend to come to us more naturally. And to boot this kind of reflection can make matters worse rather than help. 
[T]he habit of rumination that our narcissistic society encourages actually might make things worse.
The ESM research shows that when people think about themselves, their moods are usually negative. When a person starts to reflect without being skilled at it, the first thoughts that pop into the mind tend to be depressing. Whereas in flow we forget ourselves, in apathy, worry, and boredom the self is usually at center stage.
So unless one has mastered the skill of reflection, the practice of “thinking about problems” usually aggravates whatever is wrong instead of alleviating it.
-Mihaly Csikszentmihalyi in Finding Flow 
In contrast, skilled reflection enables us to gain perspective, unlock possibilities, and increase our available set of possible actions.
Reflection as the key to learning
Given the proliferation of information and ease of availability of online learning, one would think that our skillsets would be more widely developed. But clearly that's not the case.
One possible reason is the lack of skilled reflection. Consumption of information and even applied experience on its own does not guarantee learning and development. Reflection is that missing piece.
Reflection is what ties action and experience into learning and eventually development.
This is doubly true in fields where there is no clear feedback or common benchmarks of performance. Management and leadership fall squarely into this category. This is why reflection is even more important in these fields.
How can one learn the truth from thinking? As one learns to see a face better if one draws it.
— Ludwig Wittgenstein
Leadership reflection and performance
Whether leaders and managers can cope or even thrive in an environment of increasing change and complexity depends on their ability to adapt and respond to emerging, complex-adaptive challenges that do not have known solutions. And this adaptive capacity is a direct function of their ability to skillfully reflect.
Intelligence and information is generated when we take action but these cannot be harnessed and leveraged if the action is not balanced in a loop with reflection. When individuals and teams are under-performing or heading in the wrong direction, it is usually because they are skewed towards one, forgetting to balance one with the other.
In strategic terms, this is akin to Boyd’s OODA loops, where observing, orienting, and deciding are active reflection steps before we take actions, thus forming an infinite loop. 
In Donald Sull’s adaptation of strategy loops, reflection forms the basis of the three steps of making revisions, making sense, and making choices, before we are making it happen. 
Ron Heifetz calls this “getting on the balcony” and identifies it as a core leadership skill.
Leadership is both active and reflective. One has to alternate between participating and observing. Walt Whitman described it as being “both in and out of the game.”
Although the principle may be easy to grasp, the practice is not. Rather than maintain perspective on the events that surround and involve us, we often get swept up by them.
Consider the experience of dancing on a dance floor in contrast with standing on a balcony and watching other people dance. Engaged in the dance, it is nearly impossible to get a sense of the patterns made by everyone on the floor. Motion makes observation difficult.
To discern the larger patterns on the dance floor-to see who is dancing with whom, in what groups, in what location, and who is sitting out which kind of dance-we have to stop moving and get to the balcony.
– Ronald Heifetz in Leadership Without Easy Answers 
Developing our complexity and capacity to deal with volatility, uncertainty, complexity and ambiguity is a critical skill-set. Reflection plays an important role in developing this skill.
Balancing action and reflection is key to managerial competence
As a group, high-performing managers and execs are already good at execution/action. What is usually missing is balancing that action with regular, skillful reflection.
It's what Richard Kilburg calls the “tao of reflective engagement” – the Ying of engagement (action/execution) is balanced by the Yang of reflection. 
Any executive who wants to increase the likelihood that he or she will do a good job for an organization and become an increasingly wise leader over time must become superbly adept at both the arts of execution and the arts of reflection.
It is in the systematic and creative synthesis of both of these forms of executive activity that the wisest answers and actions will be found for the dilemmas facing most modern organizations.
Those who have such metacognitive and reflective abilities and who work to improve them are able to do a better job and that their organizations perform more effectively than those whose leaders seem blind to such capacities and skills.
– Richard Kilburg in Executive Wisdom
In their HBR article The Five Minds of a Manager, Mintzberg and Gossling emphasize the importance of balancing reflection with action in developing managerial competence. 
Two aspects establish the bounds of management: Everything that every effective manager does is sandwiched between action on the ground and reflection in the abstract. Action without reflection is thoughtless; reflection without action is passive.
Every manager has to find a way to combine these two mind-sets—to function at the point where reflective thinking meets practical doing.
– Henry Mintzberg & Jonathan Gossling in Harvard Business Review
This importance of reflection in leadership development has gained some traction as evidenced by it’s adoption in some corporate programs and even academic programs.
One such program is the IMPM program at McGill. The reflective mindset is their first module and undergirds the whole curriculum. A good example of a corporate program is the Search Inside Yourself program at Google. 
But you don’t have to enroll in an MBA or work at Google to harness the power of reflection in your own development. As with anything that is simple in theory but harder in practice, the trick is to take on methods that you like to work with and then consistently do it.
What got you here wont get you there
Effective action and prompt execution leading to results are what got managers and executives to where they are today. However, without skilled reflection they are unlikely to catch the blindspots that can ultimately derail them.
These days what managers desperately need is to stop and think, to step back and reflect thoughtfully on their experiences. Indeed, in his book Rules for Radicals, Saul Alinsky makes the interesting point that events, or ‘happenings,’ become experience only after they have been reflected upon, thoughtfully:
‘Most people do not accumulate a body of experience. Most people go through life undergoing a series of happenings, which pass through their systems undigested. Happenings become experiences when they are digested, when they are reflected on, related to general patterns, and synthesized.
– Henry Mintzberg & Jonathan Gossling in Harvard Business Review 
Action and execution are also areas where we are naturally inclined to look for opportunities for improvement and learning. This is what Chris Argyris and Donald Schon call single-loop learning where we adjust and improve based on direct feedback from our actions.
However, in order to grow we have to develop their metacognitive abilities — thinking about our thinking. Argyris and Schon call this double-loop learning. 
A powerful tool to do that is the art and practice of skilled reflection. It entails taking an impartial view and becoming an observer of the observer, an impartial observer of our own selves.
We all intuitively recognize this in extreme situations. Imagine the last time you were in a highly stressful situation and you told yourself that you need a minute or went took a walk to “clear your head”. Your system intuitively knew that you needed a break to get some perspective. However this kind of active reflection does not have to be only in emergency scenarios.
It can become an integral part of our ongoing self-development efforts. Self-development can happen naturally when we actively develop our reflective mindset by exercising the muscle of reflection on a regular, planned basis. In the process we develop our ability to think about thinking and our metacognition.
Wisdom is not a given. Experience often comes alone.
The unexamined life is not worth living.
– Socrates in Plato’s Apology 
Socrates was talking about reflection. Perhaps the unexamined manager isn’t a manager after all.
We often equate number of years of experience with competence. But experience often comes just by itself. Wisdom and learning do not necessarily come packaged with it.
Experience is what connects theory with practice. However, reflection is what turns that experience into wisdom.
It’s reflection that cements the new knowledge and feedback from our experiences and converts it into learning which then gets used further, thus creating a virtuous spiral. Without reflection we cannot build on our experiences for growth.
In almost all well researched and documented theories of learning, the key factor that leads to learning from experience and knowledge is reflection. Experience or knowledge on their own do not turn into learning or wisdom.
If learning is the antidote to stay on top of the volatility and complexity that managers deal with, then reflection is the catalyst that accelerates this learning.
Reflection is a proven “technology”
The practice of skilled reflection as the core of developing our wisdom and capacity is nothing new. It’s origins range from ancient wisdom traditions to modern developmental, learning theories, and is backed up by evidence from the latest in neuroscience.
One of the reasons why practices like meditation, journalling and executive coaching are effective is because they enable or at least create the space for this kind of reflection to happen. Without reflection there is no breathing room for wisdom to develop.
Reflection is the technology in coaching
Reflection as a skill is underdeveloped in most of us. We typically don't have a long-term strategy towards developing skilled reflection.
People with a well-developed reflective mindset are self-generating and self-correcting. Good coaches knowingly or unknowingly help the client develop a reflective mindset. Same goes for managers.
And this ultimately is the goal of good coaching engagements — to develop your capacity to reflect and take action. Reflection ultimately increases your capacity for action by increasing the available action set.
Ray Dalio captures this idea in his formula for progress and personal evolution. 
Pain + Reflection = Progress.
There is no avoiding pain, especially if you’re going after ambitious goals. If you can develop a reflexive reaction to psychic pain that causes you to reflect on it rather than avoid it, it will lead to your rapid learning/evolving.
Your unique power of reflectiveness—your ability to look at yourself, the world around you, and the relationship between you and the world—means that you can think deeply and weigh subtle things to come up with learning and wise choices. Asking other believable people about the root causes of your pain in order to enhance your reflections is also typically very helpful—especially others who have opposing views but who share your interest in finding the truth rather than being proven right.
If you can reflect deeply about your problems, they almost always shrink or disappear, because you almost always find a better way of dealing with them than if you don’t face them head-on.
– Ray Dalio in Principles
Knowing or unknowingly a majority of coaching effectiveness stems from the power of reflection. It's one why regardless of what method the coach uses, the client walks away better than they were before.
Executive coaching as a reflective container
Skilled reflection is one of the key mechanisms that helps leaders in executive coaching. Every engagement and conversation is towards building what Richard Kilburg calls “a reflective container”.
This is where busy leaders and managers get a chance to step out of their whirlwind worlds and be able to see through the confusion by taking a different perspective from a different vantage point.
For managers and executives as a group, their time and energy is perhaps the most splintered compared to almost any other professional. It's one reason why a planned reflection strategy can work wonders by engineering breaks and slowing down the pace of things to provide extra space for wisdom to emerge.
Tools like the Johari Window model also help with eliciting feedback that might not otherwise reach the executive.
If it's so effective why isn’t everyone doing it ?
Unfortunately, reflection typically does not get factored into improving managerial performance. Let’s examine some of the reasons.
- First, is the lack of awareness of its importance to the process of development. In Managerial Reflection, Siebert and Daudelin outline the three prerequisites that are important to life long learning: awareness of the need to learn, an intentionality about learning, and awareness of the importance of reflection in learning.  We are usually pretty good about the first two but do not have a strategic approach to the third prerequisite.
- Second reason is because we think we already do it. However, for most of us it is not skilled reflection but rather plain rumination, and we do not have a strategic approach to leverage it for our learning and development.
- Third is because we think we don't have the time. But it’s worth considering how many mistakes might be avoided if we built skilled reflection into our schedules and how much time and money those mistakes cost us.
- Lastly, we tend to have stereotypes. The typical image that accompanies reflection is the meditating monk, completely detached from everything.
But meditation is just one way of reflecting. You don’t have to be an expert meditator to reap the benefits of skilled reflection. There are numerous other ways of getting better at it.
Being aloof is clearly not an option either. But setting aside even 15 minutes of dedicated time is doable and can be transformative. A simple reflective practice like capturing thoughts in a journal on a regular basis can have an extraordinary return on investment.
A caveat to the emphasis on reflection
I emphasized reflection in this article, because action/execution seems to come more naturally to us. Also, the ecosystems that we operate in naturally force us to be in the action and execution mode by default, often without any breathing room or time to think. Reflection looks like a waste of precious time we do not have.
In order to balance this perspective, here’s Peter Vaill, who reminds us not to wallow too much in reflection. 
At some point, you have to dial down the reflection, dial down the double-loop learning, dial down the reflexivity and the phenomenological reductions, set aside the speculations about the nature of the leader’s consciousness—just lower the volume on all these things that we’re telling executives they need to be able to do. We need to dial that down and dial up the energy required to move people to action and enlist people in projects, which is the content of leadership.
– Peter B Vaill as quoted in Extraordinary Leadership
When asked if leadership was choosing between the two, he said
No, it certainly is not either-or. It is balance and integration, but I wonder if those of us with a passion for developing leaders sufficiently emphasize the need for a balance between an action mentality and a reflective mentality. The best practitioners have a sense of the balance.
– Peter B Vaill as quoted in Extraordinary Leadership
Thus the key is to balance both action and reflection and adjust it based on our own biases and habits.
- What do you need to do more of or less of?
- What are some new practices that you need to start?
- How can you structure reflection into your existing processes?
📚 You also get a curated spreadsheet of 100 best articles Harvard Business Review has ever published. Spans 70 years, comes complete with categories and short summaries.
I did a deep dive into the ladder of inference - a practical tool you can use for ongoing reflection when making decisions and otherwise.
For more on the mechanics and finding the time to reflect, having a basic set of design principles for reflection can help immensely.
An effective way to improve reflection is to the mechanism of double-loop learning which is significantly different from our default way of single-loop learning.
Sources and references
- Executive Wisdom by Richard Kilburg.
- Theory of Moral Sentiments by Adam Smith.
- Patricia Werhane elaborates on impartial spectator in this paper in the Philosophy of Management journal.
- Immunity to Change by Robert Kegan & Lisa Lahey.
- Finding Flow by Mihaly Csikzsentmihalyi.
- OODA loops, John Boyd.
- You can read more about strategy loops here.
- Leadership Without Easy Answers by Ronald Heifetz.
- The Five Minds of a Manager by Henry Mintzberg & Jonathan Gosling.
- International Masters Program for Managers at McGill.
- Search Inside Yourself program.
- Double Loop Learning in Organizations by Chris Argyris.
- Socrates quoted in Plato’s Apology.
- Principles by Ray Dalio.
- Role of Reflection in Managerial Learning by Marilyn Daudelin & Kent Seibert.
- Interview with Peter Vaill in Extraordinary Leadership by Center for Creative Leadership.