Whether you're mastering the skill of espresso art or learning to have the kind of difficult conversation that builds rather than breaks relationships, the path to new capability follows surprisingly similar terrain. The the leader learning to communicate strategy in ways that actually land and the 50-year-old learning to kitesurf for the first time are fighting the same battle - against the stories we tell ourselves about learning, failure, and what's possible. At Oasis, we describe these as Enemies of Learning.
I want to offer five habits that quietly sabotage our development, whether we're picking up a new craft or growing our leadership capability. More importantly, here's how to recognise them before they undermine what you're working toward.
1. The Trap of Premature Certainty
We're pattern-recognition machines, constantly linking new experiences to familiar ones. It's how we make sense of the world. But this strength becomes a liability when we dig up an historical experience too quickly and say to ourselves something like "this is just like that time when..."
Watch a new leader facilitating their first strategic conversation. If they've decided it's "just like running a project meeting," they'll miss the entirely different listening required when people need to think together rather than report out. Or consider the experienced Executive learning to coach rather than direct… if they conclude "this is just softer language for the same thing," they'll never develop the curiosity that makes coaching powerful.
The antidote isn't to abandon pattern recognition. It's to hold your conclusions lightly enough that something genuinely new can emerge. Before you decide "I know how this works," ask yourself: "What am I not seeing because I think I already understand?"
2. The Perfectionism That Prevents Growth
This one shows up early and often in leadership development. The senior leader who won't practise giving feedback in front of peers because "I should already know how to do this." The Exec leader who avoids coaching conversations because they might not get it right. The manager who won't admit they're struggling with strategic communication because, well, isn't that what leaders are supposed to be good at?
Brené Brown talks about vulnerability as the birthplace of innovation and creativity. But in professional contexts, we often convince ourselves that admitting we don't know something, particularly about leadership, will cost us the respect of those we lead. The truth is more nuanced: refusing to be vulnerable about your learning edges is what limits your growth (and 9 times out of 10 wins the respect of those we lead!).
I believe that effective leaders have learned (or are learning) to separate their worth from their current capability. They've discovered that "I'm still developing this skill" isn't a confession of inadequacy… it's a declaration of commitment to growth. Start by reframing: your mistakes aren't signs you're failing; they're evidence you're in the arena.
Note: One of our clients, a former school principal, embedded the word “Flearning” into the culture of the school – a powerful and simple way to reframe what we think of as failure to a learning moment.
3. The Resignation That Masquerades as Realism
This is the quiet voice that says, "Learning facilitation skills won't change the fact that our meetings are dysfunctional anyway," or "Why bother improving how I deliver difficult feedback when the performance management system is broken?"
Resignation is particularly insidious because it often sounds reasonable – Alan Sieler describes it as ‘intelligent cynicism”. It dresses itself up as wisdom, as if the person who's given up has simply "seen how things really are." But resignation isn't wisdom, it's a mood that causes us to opt out of the very practices that could shift our reality and make new things possible.
When you catch yourself thinking "it won't make a difference," that's your cue to reconnect with what drew you to this learning opportunity or development in the first place. What lead you to think it mattered to learn to have more effective difficult conversations? What made you curious about developing a coaching approach? Return to that original commitment, not because you were naïve then, but because you saw something worth pursuing.
4. The Impatience That Undermines Mastery
It’s easy to want the download, packet-mix, or AI-shortcut version of development. We want to attend the two-day workshop on strategic communication and emerge fully formed. We expect that reading three articles on coaching will somehow transform decades of directive leadership.
This shows up particularly in how we approach leadership development. We try a new approach to difficult conversations once, it feels awkward, and we conclude "this doesn't work for me." We experiment with a coaching question instead of giving direction, it doesn't land perfectly, and we retreat to what's familiar.
But here's the thing: inner work isn't instant. We aren't machines to be fixed. We're living organisms that grow over time, and you can't rush growth any more than you can tell a seedling to hurry up and give you shade.
The research on skill acquisition is pretty clear: the period where something feels most uncomfortable is often the precise moment when neural pathways are being rewired. That awkwardness isn't a sign you're doing it wrong - it's evidence that real learning is occurring.
Mel Robbins captures this beautifully in The Let Them Theory:
"If you can be honest with yourself about what you truly want, and take responsibility for creating it, you will. You don't have to be special. You just have to get up every day, put one foot in front of the other, and work hard to do a little better, and be a little better than you were yesterday. And one of these days, you are going to wake up and realise that you not only changed yourself, but you are in the middle of living the life you were once jealous of" (p. 150, emphasis mine)
The practice is to slow down enough to observe yourself as a learner. What happens in your body when you try to stay curious instead of jumping to solutions? What stories arise when you're facilitating strategy and people seem confused? Getting comfortable with the discomfort of the learning zone isn't just necessary for skill development… it's where the most significant insights about yourself emerge. You don't need to be special. You just need to show up, day after day, a little better than yesterday.
5. The Blindness to What We Don't Know
This might be the most dangerous habit because it's invisible to the person experiencing it. It's the leader who doesn't realise their strategic communication isn't landing because everyone nods in meetings. It's the manager who thinks they're having coaching conversations when they're actually just giving advice with question marks attached. It's the executive who believes they're good at difficult conversations because people don't push back… not recognising that people have simply stopped bringing them honest (and perhaps hard-to-hear) perspectives.
Now, let’s be kind to ourselves here: cognitive blindness doesn’t equal stupidity - it's a natural consequence of not having the distinctions to see what we're missing. Before you learned about distributed leadership, you couldn't see the ways you were creating dependency. Before someone showed you the difference between coaching and advising, they probably looked the same.
Breaking this pattern requires two things: honest self-assessment and trusted feedback. Where are the gaps between your intention and your impact? Where might your current approach be limiting rather than enabling? And crucially: who in your world will tell you the truth, even when it's uncomfortable?
The Learning That Awaits
These habits, premature certainty, perfectionism, resignation, impatience, and blindness, don't simply disappear. They're part of being human. But when we recognise them, we can work with them rather than being ruled by them.
The capabilities you need, whether it's mastering sourdough or transforming how you lead through conflict, are on the other side of these habits. The question isn't whether you'll encounter these obstacles. It's whether you'll recognise them when they show up and choose to move through them anyway.
Because here's the truth: the leader you need to become, the capabilities your role demands, the conversations you need to have, they're all waiting in the learning zone. And the only way to get there is through the discomfort of not yet knowing.
You Don't Have to Navigate This Alone
What skill have you been putting off developing? What habit might be standing in your way?
Sometimes the most powerful step isn't trying harder on your own. It's inviting someone into the learning journey with you. A skilled coach doesn't give you the answers, they help you see what you can't see yourself, challenge the stories that limit you, and hold you accountable to the leader you're becoming.
If you're ready to develop the leadership capabilities that will transform how you navigate conflict, communicate strategy, or develop your people, Oasis People and Culture is here to support your growth. Whether through individual coaching or our leadership development programs, we partner with you for the long haul.
Reach out to explore what's possible.
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Enemies and Allies of Learning
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