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HOW TO TEACH AN OLD LEADER SOME NEW TRICKS

7 min readMay 30, 2025

We’ve all seen one of these leaders. The leader who thinks they already know everything. The leader who does not recognise they still have more to learn. The leader who thinks they have made it.

I had exactly this conversation with a senior HR executive this week. She was telling me about a member of the executive team. Someone who is very strong in some areas of their role, but in other areas not so much.

She has spoken with him on several occasions about the potential for further professional leadership development. An opportunity to build his capability. And every time the conversation had been difficult as he does not see any need for his own development. He believes he already knows everything as a leader, or that is what he is saying to her anyway.

And as I was talking to this HR executive and she was relating this conversation, we tried to determine what might be the underlying factors here. Is it that this individual really is that lacking in self-awareness? Is it some fear of acknowledging that perhaps they do not know everything and admitting this will make them look less capable in their role? Is it that the individual does not want to admit any kind of vulnerability to somebody else because this might diminish their leadership or presence or alter what other people think of them in some way?

“The greatest enemy of learning is knowing.”

- John C. Maxwell

On reflection, she said this leader is a good person. They are a good contributor. However, she is concerned there are some limits in the leader’s capability, and if they do not get some growth into their leadership then unfortunately, they will be left behind. Yet they still have real potential to elevate.

She was a little frustrated because she had tried to approach this executive on several occasions and have a conversation that was useful, and it just was not going anywhere. The executive in question was a little bit defensive and the HR executive did not want to create a situation which neither of them could recover from.

I asked her what her objective was in this situation? And she was very clear; she wants to keep this executive. She simply wants him to be operating at a higher level. To recognise the need for this ongoing elevation of his leadership skill and leadership awareness, capability and capacity. A strong positive intention.

Next, we spoke about, how she might approach this conversation in a way that this executive may become more open to the opportunity that she is trying to create for him.

Life is a classroom. Only those willing to be lifelong learners will move to the head of the class.
— Zig Ziglar

What I am noticing in this space, particularly with executives, is that a leader may be quite good, competent, capable, with capacity right now. They are contributing at a level that meets the requirements, maybe even exceeds requirements. They are a good performer, a solid performer. However, the challenge is that the world continues to change very quickly. The environment in which work happens is evolving very dynamically.

While yesterday a leader may have been a good performer, if they do not keep up with the rate of change, their ability to continue to perform at the same level will decline over time. Relying on yesterday’s performance, relying on yesterday’s capability and competence, does not guarantee tomorrow’s success as a leader.

What can happen, if you look at the diagram, is that without making any change, without filling in any of the leadership gaps or developing some of the leadership opportunities, over time leaders can be left behind. If somebody does not choose to expand their leadership, as the world around them is changing, they become less able to meet the expectations of leadership.

In time they will find themselves and their performance on the red line. A declining level of leadership performance. Initially, it looks okay, but over time they become less and less able to perform to the changing expectations of leadership. Ultimately, they head towards a steep downward slide into poor performance, simply because they are not keeping up with the changes in the world.

If you need to have a conversation with a leader about their future and their opportunity, do not make it just about them, but rather consider focusing on the changes going on around them. Encourage them to consider how they are going to keep up with the change, so they do not get left behind.

Now the conversation becomes less personal, about them and their leadership limitations or leadership gap. It is more about how the world is changing, and if they want to continue to be a leader, they need to keep up. You can move the focus. It is about them creating a future opportunity for themselves. This future opportunity is what you can see on the green leadership performance line.

Taking small opportunities to grow, to round out their leadership now is going to set them up for the future. Incremental opportunities, incremental learning, incremental growth that allows them to continue to have the competence, the capability, the capacity to operate in this evolving world as an effective leader will move them towards the green line. They are setting themselves up for the future and therefore setting up their teams and the organisation.

No matter who you are, no matter what you did, no matter where you’ve come from, you can always change, become a better version of yourself.

— Madonna

Your opportunity here is to open their eyes to the possibility they can create for themselves, by recognising the need for ongoing adaption to a changing world.

By focusing on the world changing rather than the individual leader and what they might consider to be criticism of their leadership, this opens an opportunity for a different way to have this conversation. This might be the catalyst for an individual leader, who is good in lots of areas but needs to develop their leadership a bit further, to consider that maybe, just maybe, there is something they need to learn that will set them up for success now and in the future, rather than being left behind.

I’d love to know your thoughts.

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Stacey Ashley
Stacey Ashley

Written by Stacey Ashley

Focused on future proofing CEOs, Dr Stacey Ashley CSP is a Leadership Visionary. Stacey is often described as the leader for leaders.

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