Absolute Bottler or Train Wreck? If You Can’t Say Why, You’re Doomed to Repeat It
TL;DR: If you can’t explain why you succeeded or failed this year, you can’t repeat or avoid it. The fix: (1) Capture what happened immediately after important events—decisions, feelings, assumptions. (2) Reflect critically on the gaps between what you expected and what occurred, acknowledging your own role and the emotions that make this uncomfortable. (3) Build your theory—write down explicit hypotheses about what works in which conditions, recognising these are personal to you. (4) Test deliberately—treat your next decisions as experiments to validate or refine your theories. Repeat continuously, not just in December. Each cycle builds on every cycle that came before.
Had an exceptional year? A disastrous one? If you can’t articulate what drove either outcome, you’re operating in unconscious competence. Or incompetence. You got results, but you have no reliable mechanism to replicate success or avoid failure.
The solution lies in transforming unconscious experience into conscious capability through continuous, systematic reflection. Kolb’s learning cycle offers a practical framework for executives to extract actionable intelligence from their experiences in real-time, not in December when the insights have already decayed.
But here’s what matters: this isn’t about scheduling reflection sessions. It’s about recognising that learning didn’t start this year and won’t end next year. You’re already in the middle of a spiral that’s been turning your entire career.
A note on limitations: Kolb’s cycle has valid critiques. Egan (2008) notes it’s often misapplied as episodic snapshots rather than lifelong learning. Stirling (2013) highlights that individual learning styles aren’t as fixed as sometimes portrayed. The framework works best when you recognise these constraints—when you use it not as a rigid prescription but as a lens for understanding how learning actually accumulates across time, context, and experience.
1. Start With What Actually Happened: Concrete Experience (CE)
Your year wasn’t abstract. It consisted of specific decisions, interactions, wins, and failures. The cycle begins by capturing these concrete experiences as they occur, not retrospectively reconstructing them months later when memory has been sanitised by hindsight bias.
You don’t approach any situation as a blank slate. Every decision you made this year was filtered through pre-existing mental models, assumptions, and biases accumulated from prior experience. These aren’t just background noise. They’re the lens through which you perceived every situation, and they shaped every outcome before you even recognised there was a choice to make.
The question isn’t just “what happened?” It’s “what lens was I viewing it through, and how did that shape what I even saw as possible?”
Example: A CEO I worked with had just closed a difficult acquisition. Her immediate capture included: “Board meeting, 3 hours, felt defensive when questioned about integration timeline. Assumed they doubted my competence. Pushed back hard on their concerns about cultural fit. Got approval but left feeling hollow.” She wrote this within an hour of the meeting ending, while the emotional texture was still present. Three months later, she wouldn’t have remembered the defensiveness or the assumption about competence—only that she “got approval.”
After significant events—quarterly reviews, major deals, difficult conversations, strategic pivots—document the raw experience immediately. What happened? What did you feel? What were you trying to achieve? What assumptions were you carrying into the room? Write it down while it’s still fresh. But recognise this: you’re not starting from zero. You’re building on every cycle that came before.
2. Make Sense of It: Reflective Observation (RO)
This is where executives typically fail. Not through lack of intelligence, but through lack of structured time and psychological safety to genuinely reflect. Reflective observation demands that you step back and examine the experience from multiple perspectives, actively searching for gaps between expectation and reality.
Effective reflection is inherently critical and emotionally challenging. You must confront the discrepancy between what you intended and what actually occurred. This requires acknowledging your own complicity in suboptimal outcomes. Vince (1998) demonstrates through empirical research on management learning that executives are often “defended against experience”—subconsciously resistant to learning because genuine reflection provokes anxiety, threatens established identity, and exposes vulnerability. His work shows that managers mobilise strong emotions, particularly anxieties about their competence, that simultaneously promote and prevent learning.
Reflection isn’t just personal. It operates within organisational power structures. Admitting what you don’t know or acknowledging mistakes carries perceived risk, particularly in cultures that conflate competence with certainty. Your anxiety isn’t irrational. It’s a signal that real learning requires letting go of secure, tested ways of thinking.
Example continued: That CEO spent her next weekly reflection session examining the board meeting from multiple angles. She asked: Why did I assume doubt about competence rather than legitimate concern about risk? Where else have I interpreted questions as challenges to authority? She realised this pattern traced back to her first VP role, where a board member had publicly questioned her judgment. She’d been carrying that defensive posture for twelve years, applying it indiscriminately to contexts where it wasn’t warranted. The board wasn’t questioning her competence—they were doing their fiduciary duty. Her defensiveness had prevented her from hearing genuine concerns about cultural integration that would prove prescient six months later.
Build regular reflection intervals into your operating rhythm. Weekly 30-minute blocks where you ask: What worked? What didn’t? Where did my assumptions prove wrong? What am I avoiding examining? What patterns am I noticing across multiple experiences, not just this week but over months or years?
This must occur while the experience is still emotionally and cognitively accessible, not when it has become a sanitised anecdote. But don’t treat these sessions as isolated episodes. Each one should connect to what came before. What did you think last month? How has that changed? What’s building over time?
How past experiences shape present decisions: Each loop doesn’t just build incrementally—it compounds. That CEO’s twelve-year-old defensive pattern had shaped dozens of board interactions, vendor negotiations, and leadership team meetings. Once she identified it in reflection, she could trace its influence backward through her career and recognise how it had both protected her (in genuinely hostile early environments) and limited her (in collaborative contexts where it created unnecessary conflict). Past cycles create the interpretive lens for present experience. When you reflect, you’re not just examining what happened last week—you’re examining the accumulated sediment of every cycle that prepared you to perceive and act in that particular way.
3. Build Your Theory of Why: Abstract Conceptualisation (AC)
Observation without conceptualisation is merely anecdote collection. Abstract conceptualisation transforms specific observations into generalisable principles—your personal theory of what drives outcomes in your particular context.
This is where unconscious competence becomes conscious. You’re no longer relying on instinct you can’t articulate. You’re constructing explicit frameworks that explain causal relationships. Why did that negotiation succeed? What specific conditions enabled your team’s breakthrough? Which leadership behaviors correlated with engagement versus disengagement?
But here’s what you must understand: these frameworks are yours. They’re built from your experience, filtered through your perceptions, shaped by your history. They won’t work the same way for someone else. They might not even work the same way for you in a different context. This isn’t a weakness. It’s the nature of knowledge. As Stirling (2013) notes in her analysis of Kolb’s epistemological foundations, knowledge is constructed through the transformation of experience—meaning it’s inherently subjective and specific to each learner’s refined interpretations.
Context matters profoundly. The frameworks you develop must be situation-specific. A strategy that worked in a growth market may fail in contraction. Leadership approaches effective with experienced teams may backfire with new hires. The goal is not universal laws but conditional hypotheses: “In situations characterised by X, approach Y tends to produce outcome Z.”
Example of framework construction: That CEO developed what she called her “Question Interpretation Framework.” She wrote:
“When I receive challenging questions from stakeholders (board, investors, senior team):
- First response is often defensive (legacy pattern from early VP role)
- Defensiveness correlates with worse outcomes: I miss information, damage relationships, create adversarial dynamics
- Better approach: pause, assume good intent, ask clarifying question before responding
- Conditions where this works: high-trust environments, genuine questions (vs. disguised criticism)
- Conditions where defensiveness is appropriate: documented bad faith, repeated pattern of undermining
- Test: In next 5 board interactions, consciously pause and assume good intent. Track: my emotional state, information gained, relationship quality, decision outcomes”
This framework is specific to her, built from her history, applicable in particular conditions. It acknowledges both the pattern she wants to change and the contexts where her defensive instinct might still serve her.
After reflection, articulate your working theories explicitly. Write them down. “I’m noticing that when I involve the team early in decision framing—rather than presenting pre-formed solutions—both the quality of solutions and implementation velocity improve. Hypothesis: early involvement increases psychological ownership and surfaces information I wouldn’t have accessed otherwise.”
But also write down the conditions. When does this work? When doesn’t it? What prior experiences taught you to value this approach in the first place? Your theory isn’t emerging from nowhere. It’s part of a longer developmental arc.
The tension here matters. You’re trying to create general principles from specific experiences. You’re using reflective interpretation to understand something you initially grasped through immediate feeling. These are opposing modes of knowing, and they should feel like they’re pulling against each other. As Egan (2008) explains in his reconceptualisation of experiential learning, concrete experience is grasped via apprehension (immediate, tangible), while abstract conceptualisation is grasped via comprehension (reflective interpretation). That tension is where learning lives.
4. Test and Refine: Active Experimentation (AE)
Theories without application remain academic. Active experimentation means deliberately testing your newly formed hypotheses in real-world contexts. You treat your leadership practice as an ongoing series of experiments.
The cycle becomes continuous rather than episodic. You’re not reflecting once annually. You’re operating in a perpetual spiral: experience generates observation, observation produces theory, theory informs experimentation, experimentation creates new experience. Each loop builds on the last. The spiral constantly advances toward greater sophistication and conscious mastery.
Real-world problems are ill-structured and ambiguous. Your theories will be incomplete and sometimes wrong. The commitment is to systematic testing and refinement, not perfection. Each experiment generates data that validates, refutes, or nuances your working hypotheses.
Example of systematic testing: That CEO ran her experiment across five board meetings over two quarters. She documented each instance:
Board Meeting 1 (Budget Review):
- Question about marketing spend seemed challenging
- Paused, asked “What specifically concerns you about the allocation?”
- Board member explained concern about CAC trends in Q3
- Legitimate concern I’d missed in my analysis
- Outcome: Better decision, relationship intact
- Emotional state: Initially anxious, then relieved
Board Meeting 2 (Strategic Planning):
- Question about international expansion timing
- Paused, assumed good intent, asked clarifying question
- Discovered board member had relevant experience from previous company
- Gained valuable knowledge I wouldn’t have accessed if I’d defended the timeline
- Outcome: Modified approach, better result
Board Meeting 5 (Crisis Response):
- Aggressive question about supplier failure
- Paused, but recognised pattern: this board member consistently undermines in crisis
- Provided direct response, didn’t seek clarification
- Framework condition met: documented bad faith
- Outcome: Appropriate boundary, maintained authority
She tracked: emotional state, information gained, relationship quality, decision outcomes. Over ten weeks, she validated her framework in 80% of cases and identified one condition (crisis + bad faith pattern) where her old defensive response was actually appropriate. Her theory evolved. She refined it. The framework became more nuanced and more useful.
When implementing decisions based on your theories, explicitly frame them as experiments. “Based on my hypothesis about early involvement, I’m going to structure this quarter’s planning process differently and track engagement metrics, decision quality, and implementation speed against last quarter’s baseline.” Document results. Refine theory. Repeat.
But recognise what you’re doing. You’re not just testing a theory. You’re creating a new concrete experience that will feed the next cycle. And that next cycle will be informed by every cycle that came before it. Your learning isn’t contained in quarterly blocks. It’s accumulating across your entire career.
Moving From Accidental to Intentional Performance
The fundamental problem isn’t that executives are incompetent. Many are unconsciously competent, achieving results through pattern recognition and accumulated wisdom they cannot articulate, examine, or reliably replicate. When contexts shift or new challenges emerge, unconscious competence becomes a liability.
The learning cycle transforms this dynamic by making the implicit explicit. But it’s not a technique you apply to discrete events. It’s a way of understanding how you’ve been learning all along, whether you realised it or not.
Learning is a holistic process of adaptation that requires the integrated functioning of your total organism—feeling, thinking, perceiving, and behaving. You can’t just think your way to mastery. You can’t just act your way there either. You need the full cycle, and you need to recognise the tensions within it. Immediate experience versus reflective interpretation. Specific observation versus general theory. These tensions don’t resolve cleanly. They generate growth.
What holistic looks like in practice: That CEO didn’t just change her cognitive framework about board questions. The learning integrated across dimensions. Emotionally, she became less reactive to perceived challenges. Perceptually, she developed capacity to recognise contextual differences—same question, different intent depending on who asked and when. Behaviorally, she built new habits—the pause, the clarifying question, the documentation. Cognitively, she constructed theories she could articulate and test. The change wasn’t in one dimension. It was systemic. That’s what makes it sustainable.
The cycle acknowledges that reflection is not a comfortable, rational exercise but an emotionally demanding, politically complex practice that requires deliberate cultivation. As Vince’s empirical work (1998, 2002) demonstrates, organisational learning is fundamentally political, involving power relations that shape what can be learned, discussed, and changed. It recognises that learning is not an event but a continuous process. December is categorically too late to extract meaningful insight from January’s decisions.
But more than that: you didn’t start learning in January. You brought decades of prior cycles into every decision you made this year. The question is whether you’re conscious of those cycles or whether you’re letting them run on autopilot.
If you crushed it this year, can you explain precisely why? In sufficient detail to repeat it? Can you trace the decision back through the cycles that prepared you to make it? If you struggled, what specific causal factors drove the outcome? What would you change? And what prior learning led you into that situation in the first place?
If you can’t answer these questions with clarity and confidence, you’re gambling with next year’s performance.
Build continuous reflection into your leadership practice. Not as isolated episodes, but as a spiral that connects each experience to what came before and what comes next. Transform each experience into extractable wisdom before the insights fade into generalised memory. Recognise that your frameworks are personal, contingent, and context-dependent—and that this makes them valuable, not less so.
This is how unconscious competence becomes conscious mastery. How accidental success becomes intentional, repeatable performance. How you stop being lucky and start being capable.
References
Egan, T. (2008). A comparison of the Kolb and Illeris learning cycle models. Proceedings of the Adult Education Research Conference.
Stirling, D. (2013). David Kolb’s Experiential Learning: A critical evaluation. Journal of Perspectives in Applied Academic Practice, 1(1).
Vince, R. (1998). Behind and beyond Kolb’s learning cycle. Journal of Management Education, 22(3), 304-319.
Vince, R. (2002). Organizing reflection. Management Learning, 33(1), 63-78.
Justin O'Brien 