What would you do if you could start your leadership journey all over again? 

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I love the work I do at different universities – preparing our future leaders for all that lies ahead. More than anything, I hope that one day, they will look back and remember me as someone who made an impact not only on their education, but also on their careers. 

When I look back (over three decades ago now … shhh!), I still remember one lecturer I had who, on the very first day of my degree, said, “Look to your left. Now look to your right. Only one of you will get through this course”.  

He was absolutely right. Then in the very last lecture of my degree, the same lecturer said, “Just because you’ve earned your degree, remember it’s not what you know or what you’ve learned here; it’s who you know that’s going to help you go places”. 

He was right again. Building a professional network is extremely powerful.  

A few weeks ago, someone who has been in my network for a few years now, opened a door for me and invited me to do some coaching work inside a very large organisation that I would never have been able to get inside by just knocking on their door myself. 

The work initially involved running a series of 360 degree assessment debriefs with eight directors and this would be followed by a monthly executive coaching session with each director for the next 12 months. At the end of each 360 degree debrief, I asked each senior leader what they would do if they could start their leadership journey all over again, as I felt that this would be a good place to start our coaching journey. 

I found some of the responses really eye opening. 

“Gosh … if given the chance, I’d love a complete leadership make-over!” 

“I’d make sure I wasn’t so afraid to call out people’s bullsh*t”. 

“I wouldn’t let myself become such a martyr”. 

“I hope I’d learn from the get-go that it’s OK to ask for help when I have too much on my own plate”. 

“I’d tell myself early on that it’s actually OK to let my team fail so they can learn”. 

“I’d set better boundaries with time – and not drop everything to help others, only to fall behind in my own work”. 

“I would definitely want to be less critical about myself”. 

“Without a doubt, I would ensure I was actually more comfortable disappointing people. Goodbye people pleaser!”. 

When I meet up with each director again in October, my plan is to let each one know that regardless of how long they have been leading people, it’s never too late to make changes – or to even undergo a complete leadership overhaul! 

So, let me ask you the same question now. What would you do if you could start your leadership journey all over again? 

Whilst you might come up with some answers to what many may consider to be quite a confronting question, the hard part is doing something about it. Why? Quite simply because some senior leaders believe that after so many years building and running teams, that it’s impossible to change the way they lead; while others are actually afraid to make changes or to reinvent themselves. And it’s important to appreciate that there is a difference between these two barriers to change. 

Over the years, you may have developed a strong identity tied to your leadership style.  

Perhaps you see your style as a fundamental part of who you are, making it difficult to change without feeling like you are compromising your identity as a leader. Or maybe it’s a case that deep down, you have a stubborn personality, making you more resilient to change any aspect of your life, including your leadership style. 

Typically, one of the most common reasons a leader (particularly a very senior leader) will think it’s impossible to transform their leadership style is because it takes time, effort, and potentially external support or coaching. Some leaders may not be willing to invest in these resources, particularly if they are already stretched with no additional bandwidth given their current responsibilities. Of course, some leaders may not even realise that there are alternative leadership styles which could be more effective, or in some cases, the organisation’s culture may reinforce a particular leadership style. 

Having said that, it’s important to note that changing your leadership style is not impossible. Leadership development programs, coaching, and regular self-reflection can all be helpful in facilitating this transformation. 

As mentioned above, the fear of making changes or reinventing oneself is a distinct issue for many leaders from the belief that it’s impossible to change. 

One of the most common reasons is the fear of failure. Many leaders are concerned that if they try something new, it might not work out, and they could face negative consequences, including damage to their reputation.  

The stakes are undoubtedly high in leadership positions, and a fear of failure can be paralysing.  

There is no doubt that senior leaders can still have insecurities. Changing their leadership style may make them feel vulnerable or expose their weaknesses, which can be uncomfortable. Busy leaders responsible for big teams generally prefer what’s familiar as opposed to having to step outside of their comfort zone, which could lead to a loss of control or predictability, which can be unsettling, not to mention the fact that they may encounter resistance or scepticism from team members, peers, or superiors. 

For example, imagine the push back towards a leader who has, up until now, been a people pleaser, suddenly becoming more comfortable disappointing people, calling out their bullsh*t, or not dropping everything to help them to the detriment of their own workload. This is why I’m curious to see how open the directors I’ll be meeting with in the coming weeks will be to implementing their desired changes – particularly the one keen on a complete make-over! 

While these fears and concerns are only natural, they can also be limiting.  

Change, reinvention, or transformation are often necessary for both personal and professional growth, and leaders who overcome these fears and take calculated risks can often unlock new opportunities and achieve even greater success in their roles. 

Let’s get back to the question at hand. Have you thought about what you would do if you could start your leadership journey all over again? Would you focus on being less self-critical? Perhaps you might focus on becoming more transparent, empathetic, and open to feedback. Maybe time management and setting clearer boundaries are at the top of your list. Or could it be a commitment to embracing new technologies or methodologies? Hopefully if you are seriously considering the question, as a leader you will also recognise the importance of self-care and make appropriate changes to give you better work-life balance or work-life integration. 

Successful leadership is often about adapting one’s personal style in response to evolving circumstances and challenges. Even if you’re not in a position to undertake a 360 degree assessment and debrief, you might want to stop and ask yourself what you could start doing differently. Your reinvention can certainly involve small steps particularly if a complete overhaul isn’t at the top of your agenda. 

Remember, hellomonday can provide support to every leader, reinforcing habits through curated learning and impactful coaching, helping leaders become more open to self-reflection and growth and making changes that benefit both themselves and their organisations. 

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