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  • Vanessa Anstee

Stepping up into leadership - when the dream becomes a challenging reality

Gaining a promotion into leadership is often initially an exciting time for someone who has always dreamt of being at the top. But what happens when the dream becomes reality?


What is it really like for a star contributor to make the shift to be a leader?

In my experience employers often underestimate the role and change to identity that’s involved. I’ve seen people who were previously amazing at delivering results suddenly faced with big confidence crises as they face the challenge of having to let go and have faith in directing others to deliver. It’s not an easy place to be.


Take Steve as an example. He’s always wanted to be a director and he was given a role about a year ago. The functions targets are ambitious, and the climate is challenging. He can no longer rely on his own drive and contribution to close the deal; now he’s got four teams that need to deliver that. But the team inherited a team that are passive. They do the work but it’s never to the standard he expects. He’s tried explaining it to them and he’s always pushing back but ultimately, he often just ends up re-writing crucial board reports late into the night.


Steve comes to coaching full of frustration. He’s had on-going conversations with his 4 team heads about what needs to happen (the numbers they need to make and the standards they need to meet) but they always seem to deliver lack lustre results. It’s got to the point where Steve’s now questioning if he really is cut out for this director role. He’s asking himself if this is really what he wants and he’s wondering about whether self-employment might actually be more of his thing because at least then he’d have freedom to say and do what he wanted.


As we sit down and reflect on the situation it’s clear that Steve’s thinking is in figuring out. He’s ruminating about recent conversations and stuck in his own analysis. He’s unintentionally reinforcing his own limiting beliefs and activating his doubt that he is not good enough to operate at this level. He knows his team are frustrated but then so is he.

When we explore why he took this role Steve suddenly lights up. He describes the difference he wanted to make to the organisation and the impact that would have on their clients. It’s evident that he wanted the role but what’s also clear is that the reality of the situation is not how he thought it would be. Conscious that we could spend our time discussing the team and theorising about their issues we turn our attention to the one thing that Steve can influence – himself.


We explore what the frustration is giving Steve. It’s an odd kind of question – surely no one chooses to be frustrated. As we dig in Steve starts to see his ladder of avoidance.




We identify the anxiety levels with each stage and what becomes apparent is that what’s driving the avoidance is the fear that the team will be unhappy and disengaged. As a result of this avoidance, passivity has become the status quo and frustration reigns. The team are complaining that nothing seems to be good enough for Steve and this is in turn reinforcing Steve’s fear that he himself is not good enough.


We talk about Steve’s biggest fear that he will get fired from this role and everyone will know that he is in-fact an imposter. We identify that the one thing that will come true if he continues to operate in this way, this is a possible reality. It’s a tough conversation but it somehow relieves the pressure. Steve opens to the idea that his frustration wasn’t just with the team but with himself. He identifies that his thought process of being self-employed is an escape fantasy. He admits to himself that he is exactly where he wants to be and that up until now, he’s been waiting for permission to act. He’s seen that he’s been going through the motions with things like objective setting and nine box grids because he’s been avoiding the adult : adult conversations with his team about expectations, performance, motivation, skillset and mindset.


For the first time in a long time Steve says he feels clear. He is committing to this role and can see how his thinking and operating needs to be at a higher level. He sees how he has to let go of doing everything himself and build trust with himself, his peers, his boss and his team for the journey that they need to go on together to deliver the results.


It’s these conversations that matter. They may seem obvious to you but when you’re in the situation it’s often so difficult to see the wood for the trees. This is what coaching brings. It can be the difference between someone reacting and giving up to really stepping into their leadership. If you resonate with anything this, why not book a complimentary clarity call with me and we will get you clear about what’s going on and what your next step needs to be.

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