What’s the habit that once made you proud, but now holds you back? Try asking someone this and hear what they’ve got to say.

I asked a client this question recently, and her response was clear. ‘My ability to dive in and take control,’ and after a pause her brow furrowed, and she added ‘the problem is now everyone’s telling me to stop diving in and to stay firmly back!’

If you’re an executive reading this, then chances are you’ve had a pretty long and seasoned career. And I imagine that what has made you successful over those years has inevitably changed.

For many people, early career success often depends on an abundance of energy, a willingness to please, powerful ambition and a strong drive to deliver results. And in turn these qualities earn recognition, opportunities and typically… promotion.

Yet as careers progress, it seems that sometimes the very behaviours that once made a person effective can quietly become obstacles. They can become habits that keep leaders anchored to past definitions of achievements. The traits that have got people to a certain point, can be the ones that later in their career stop them dead in their tracks.

This must feel very confusing for a person.

And as an Executive Coach, I see this paradox lying at the heart of a lot of executive development. The strengths that once propelled my client up the ladder, can in fact harden into patterns that might limit effectiveness at the top.

So what’s does this mean?

The Early Success Formula

Many leaders begin their career by mastering a few fundamental things – solving problems and proving value.

Early career advancement clearly rewards people who are decisive, personally accountable and clearly willing to go the ‘extra mile’, and over time – reinforced by positive feedback and success – these patterns can become a kind of ‘default’ operating system.

If we think back to the start of our careers, we will all be familiar with people who embodied some of those ‘early career’ characteristics:

- Taking control – being the one who always ‘gets it done’

- Seeking approval – relying on feedback and recognition to validate performance

- Prioritising productivity over reflection – achieving through action and speed rather than pause and perspective

- Controlling variables – managing risk by staying hands-on with detail, process, or people

These traits work brilliantly in high-performance individual roles or first-line leadership. There’s no doubt that we have all met wonderful colleagues that display these traits. When used well, they create trust, momentum, and measurable results. All the things’ businesses like.

But what happens as the scope widens? When the role becomes less about ‘doing’ and more about ‘shaping’? As leaders climb the ladder and become more senior.

It seems to me that the very same behaviour that enabled success can begin to turn into behaviours that shrinks a leader’s impact instead…

When Strengths Turn into Stress Patterns

I recently worked with a COO who built her career on operational excellence. She was known for a meticulous attention to detail, and an incredible ability to follow through. She arrived in my coaching room with the following dilemma. ‘I need to learn how to delegate. Like really delegate. I know the principles but apparently, I’m just not doing it enough.’

As we worked through this together, the extent of the problem became increasingly clearer. She’d unintentionally created a deeply dependent team. And in this dependency, creativity and strategic thinking was becoming stifled. No-one could – or would – come up with their own ideas or solutions as they knew it had to come from her. Everything had begun to fall under her scrutiny. Her absolute strength – owning delivery – had become a significant and problematic bottleneck; and now she was being told it needed to change.

After decades in confidential conversation with executive Leaders, I’ve become more and more attuned to the way in which their previously successful habits can turn and become unconscious reflexes. A way of behaving that’s instinctive and lacking thought; and when pressure rises – as it inevitably does – the brain automatically reverts to what has always worked best. But instead of producing excellence, those overused strengths can in fact create problems, friction and fatigue.

I worked with a CEO recently who prided himself on ‘being the one with answers’. He told me he was always like this. He wasn’t arrogant, but he was quick, well read, and very persuasive. I’ve spent time observing how his team members behaved when they were around him and noticed how his behaviour suppressed contribution from others, bred passive agreement instead of bold debate. His people deferred to his insight rather than exercising their own. Underneath the surface they appeared to be getting deeply frustrated about it. At the time I suspected some would leave, some would stay silent and I could see that the organisations ability to co-create would plateau. From afar it looks like these possibilities are now becoming true.

It will be clear for you to see how the examples illustrate a really important truth which is that our qualities when unexamined, can harden into mechanisms that no longer entirely serve us. Instead they act as defences to protect a part of identify that says ‘this is how I succeed’ even when the context demands something new.

Moving from Habit to Choice

As with most behavioural change, escaping this ‘success trap’ begins with awareness. Leaders rarely abandon what’s working until they see the cost clearly. That cost may appear as others’ or their own burnout, team disengagement, declining agility, or stalled innovation.

If you’re a leader reading this, I’d like to highlight that recognising these signals is really important, as it invites reflection. Ask yourself, ‘which of my strengths are starting to overreach their usefulness?’ and see what ideas are thrown up.

If it helps, these are the principles I use with my clients when they are in this situation.

1. Pause to allow for pattern recognition

Create deliberate space for reflection – whether this is through coaching, journaling, or while you take your daily walk. It doesn’t need to be complicated, but reflective practise is critical to increasing awareness. Take this opportunity in the essential quieter moment to identify where your energy feels most compulsive or reactive. That’s often the sign of a strength turned automatic.

Time to think is not a luxury. It’s critical.

2. Invite challenging feedback

This is a tough call for all of us at times. But try where you can to ask colleagues, mentors, friends, peers and other trusted parties to tell you their truthful observations about when they see you at your best and when your impact diminishes. Frame the invitation around learning, not judgment. For example, ask ‘when might my drive to deliver get in the way of me leading?’

3. Distinguish identity from behaviour

Remember, you are not your habits. The behaviours that once defined success were contextually right, not eternally right. Adopting new leadership patterns doesn’t erase your past, on the contrary it provides the opportunity to expand it

4. Reframe ‘success’ for your current career stage

Early success is measured in contribution; executive success is measured in multiplication. The question shifts from ‘What did I achieve?’ to ‘What did I enable others to achieve?’

Reframing your perception of leadership success for the leader you are today, can help greatly.

5. Build tolerance for discomfort

Yes, without doubt, if we really want to learn, then we need to increase our ability to be vulnerable, and to sit with the ‘uncomfortable’. For most of us that’s a tricky place, and something we have to work on over time. But know this, ‘unlearning’ creates vulnerability, because you’re letting go of something familiar and trying something new.

Instead of resisting it, treat that discomfort as important data – it signals growth is happening.

The Power of Letting Go

Unlearning is not a rejection of past success, it’s an evolution of it.

The leader you were built the house, but the leader you need to become, will need to renovate that house from time to time. This often means swapping certainty for curiosity and effort for influence.

I’ll leave you with one question to ask yourself if this writing holds meaning for you right now. ‘What’s the habit that once made you proud, but now holds you back?’

The answers you find to this – maybe whispered – point to the direction of real transformation.

When Success Becomes a Trap: Overcoming the Habits That Got You Here But Won't Get You There