Powerful Reflection Supports Leadership in a Long Game

Stacey Ashley
6 min readDec 15, 2023

It is the time of year the suggestions for reflecting on the year past and preparing for the year ahead are everywhere around you. And I agree with some of the principles, yet I believe the timeframe could use some adjustment.

Leadership is not a short-term game. Leadership happens over long periods of time. Sometimes you may not even recognise the outcomes until many years have passed. As you create the time and space for some reflection, regrouping and setting yourself up for the new year, my suggestion is to go bigger. Use a bigger leadership lens, with a broader perspective, and deeper insight.

I suggest that you do not just reflect on the year past, but rather years past.

There is so much insight to be gained into yourself, your progress, your growth, and your achievements, when you look over a longer period of time. You can begin to see your patterns of success, and also the patterns that do not serve you as well. So I encourage you to go bigger and be more purposeful with any reflection you might choose to do.

You might like to reflect on some of the questions below. Reflecting over a longer duration of time than the last 12 months. You might choose the previous 3 years, 5 years, or perhaps even 10 years.

I know for me, things have changed significantly over this period. I have learned so much over the past 10 years, and I have had influence and impact over this same period. If I chose to reflect over a shorter period, I would not notice all of these things.

What I want for you is the opportunity to recognise yourself in the outcomes that have taken place, and to recognise your achievements and the progress along the way.

Here are a few questions to help with your bigger reflection:

  • What have been your wins?
  • How have you grown?
  • Where have you made progress?
  • Where have you achieved?
  • Where have you perhaps reached goals, or in fact set new ones?

Whenever we summit a mountain, there is always another one to conquer. It is important to recognise the progress along the way.

  • Who have you supported in their achievements and progress?
  • What have you been part of that has really mattered?
  • What do you look back on with pride?
  • What would you like to celebrate?

Now, not everything is a win. Sometimes it is a lesson. And when we look back over a longer time, again, I find it is easier to recognise the lessons. To see the things that have served us and to take those lessons forward. It may be a lesson of something that worked, and it may be a lesson of things that did not work quite as you had hoped. Or perhaps you did not get the outcome you wanted. Or maybe it was an epic failure. Yet these are all lessons that have value for you, that sometimes can only be seen from further away. It takes a much broader, longer perspective, a longer look in the rear-view mirror to notice the value in them.

A few questions for you:

  • What are your lessons?
  • What have been the learnings you have taken?
  • What have you learned in terms of things going well?
  • What have you learned in terms of things not going well?
  • What have you learned that you are good at?
  • And what have you learned that perhaps is not an area of strength for you?
  • What have you learned from other people?
  • And what are the things in these lessons that you would like to take forward with you into the future?

So first is to reflect on the past, and in so doing gain insights, make observations about yourself. Next you can determine how to take this information into the future.

Let’s look into the future. Again, I encourage you use a horizon lens. Not simply looking at the next 12 months, but further, considering a longer time period.

What I am hearing from leaders at the moment is that they are in a highly reactive mode, they are incredibly busy, chasing the next bright shiny thing, and juggling priorities. And this is not serving their strategic leadership.

I believe it is much easier to be clear about what to say ‘yes’ to and what to say ‘no’ to if you have a more informed perspective. A perspective that is not only about the immediate future, but also about the longer term future. This is one of the ways you can begin to future-proof yourself, your team, and your organisation. Do not look only at the immediate for tactical responses, but rather include a much longer term strategic perspective. Go for bigger leadership, with a bigger vision and plan.

“Without reflection, we go blindly on our way, creating more unintended consequences, and failing to achieve anything useful.”

~ Margaret J Wheatley, respected elder in the field of Leadership and Organizational Change and Author of Best Seller, ‘Leadership and the New Science’

Here are a few questions for you to consider about your future, now and towards your horizon.

  • What is your focus?

This may be about the things that you would like to make progress with or accomplish. It may be about your leadership growth. It may be about the specific plans that you have or the milestones that you would like to reach.

I also want you to consider the kind of leader that you would like to be. I had this first question asked of me a few years ago, and I found it very powerful.

  • What is your leadership narrative?
  • What is the story you want others to tell in a few years’ time about you and your leadership?
  • What do you want to be known for?
  • Who do you need to be in order to be known for this?
  • Who do you need to be to achieve your big, hairy, audacious goals?
  • How do you need to change and evolve into the leader you want to be?

I want you to think on a bigger scale for yourself and for your leadership. I want you to ponder what is possible, not just for now, but well into the future. You do not need to have a specific plan for every step just yet, because we know things will continue to change. I do really want you to start thinking about some of the essence of these things because it will allow you to stay your course, to be on your path, to become the leader who can inspire, influence, impact, and be leading possibility.

With your big leadership lens, I want you to consider the big opportunities and create big outcomes for yourself, your people and organisation.

When you create the space over this end of year period to reflect, be purposeful when you think about your leadership. Be intentional and use a bigger frame for both your reflection, and your pondering about your future. You might be surprised about what you realise you have accomplished and the journey you have been on, and also about what now becomes possible for you in your future.

I’d love to know your thoughts.

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Stacey Ashley

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