In our last blog, we talked about why creating your leadership story matters. Today we’re going to help you figure out how to write it. And, we’ve created a downloadable workbook to help you with everything below. You can download it by filling out the pop-up form below.
Even the best writers have moments where they sit and stare at the blank page and most leaders never have a chance to think about their own story. So while this might feel very new to you, here are some tips to help conquer writer’s block and start drafting your leadership story:
Timing is everything: Find the time of day that you feel relaxed, creative, and can work on this uninterrupted for a bit. It’s possible that the best time for you will be in the early morning, over lunch, at the end of the day or before bed. Pick a time that you have the energy to dedicate to this task. Some folks do well writing in a long stretch of one or two hours, while others will thrive dedicating 15 to 30 minutes to writing a portion. Figure out what works for you and put it in your calendar (because nothing gets done if we don’t carve out time for it!). It’s possible that you might figure out your story quickly or you might need several writing sessions to work through it. Be realistic and give yourself the time you need to do it well. And if, after the time you allotted, you’re still ruminating – then that’s fine, build in a bit more time in the days ahead.
Get into a creative headspace: Just as athletes warm up before working out or a game, it can be helpful to get into a more creative, flexible mind space before writing. This is true for everyone, not just those of us whose talents tend toward the mathematical or scientific. If you’ve been busy all day with work or personal matters, give your brain a short break. Play some music that inspires you, watch a comedy that makes you laugh, grab a tea or coffee and have a quick snack because nobody writes well when they’re hangry. Try exercising, dancing or going for a brisk walk before you start writing – whatever gives you a fresh and different perspective and shifts you from a work zone to a creative zone.
Brainstorming rules apply: When you are drafting your leadership story, you start by brainstorming, not writing a flawless manuscript. This means that your creative zone is also a judgement-free zone where perfectionism is checked at the door. Let your ideas flow because sometimes the kernel of an idea is what morphs into or becomes a fantastic idea. Stay focused (put that cell phone on airplane mode so you’re not distracted or disturbed!) – but allow yourself to get a little crazy as you work. If music helps you focus and feel creative, crank up some tunes as you work on this.
Try different techniques for writing down your ideas and thoughts: Just because you’re writing your leadership story doesn’t mean you have to limit yourself to a pen and paper or a keyboard and screen. Often, a visual way to capture your thoughts can get those creative juices flowing. Have you ever seen a screenwriter’s board? They often use colourful post-it notes on a big board so they can visualize the story arc and move elements around. Other creative writers will use a doodle journal to work through plot points. Toss a ball or move around as you think because movement can help us unlock creativity. You don’t have to get it right the first time, you just need to get started. You can keep at this process for as long as it takes.
When you’ve got the time, space and tools to dive into writing, we have prepared some questions to help you with conceptualizing and writing your personal leadership story.
First, let’s remember the purpose of your leadership story. You’re getting to the essence of what your message as a leader is, touching on what has made you into the leader that you are and what you value most in your leadership and perhaps, what kind of leader you want to become. The more authentic and genuine your story is, the more people will feel they connect with you as an authentic and genuine leader who, essentially, walks the talk.
Ready to start? Here are some questions to help you work through the defining moments of your life and highlights of your leadership we have created a workbook you might find useful as you work through these questions.):
- If your life was flashing before your eyes, what would the highlights be?
Try to capture at least 10-15 in point form. These highlights can be from any point in your life – childhood, high school, university, career, romantic life – it’s your story. - What have been some of your biggest challenges?
Write down what comes to mind, whether that’s a big disappointment, a tragedy, a personal or career setback or struggles with a relationship. Jot down at least 5-10 examples. - What are the successes in your life that you’re most proud of?
Again, this could be related to education or career but it doesn’t have to be. Have you done anything that you didn’t think you could? What achievements come to mind? When or where have you made a difference? Jot down at least 5-10 examples. - Who has inspired you in your life so far?
As you reflect on your life from childhood to the present, who has meant the most to you and why? Think about family, friends, mentors, leaders and anyone who stands out. What qualities do you associate with each person? How did they shape you? You can consider people who have influenced you positively or negatively. Jot down at least 5-10 examples. - When you think of your goals in life, what comes to mind?
Think about goals you’ve met or attained, then goals that you still hope to achieve. Consider personal and work goals, and maybe even some big audacious goals that you’ve never told anyone about. Jot down at least 5. - When you think about what you value most in life, what stories come to mind that you feel show who you really are as a person?
This is going to vary for everyone, but if you’re not sure where to start, think about times you made a difference, helped someone or showed courage. What happened and what stands out to you? Quickly jot down 5-10 memories that come to mind. - How did you get to where you are as a leader?
Start jotting down whatever comes to mind, from career twists and turns to people or circumstances that gave you a break or opportunity. Another way to approach this is to consider what advice you’d have for your younger self. Jot down 5-10 thoughts. - What do you value as a person and as a leader? How do you live these values in your work and through your leadership?
In point form, write down whatever pops into your mind. What matters most to you? How do you demonstrate this day-to-day? Jot down 5-10 thoughts. - How have you made a difference as a leader?
Consider times you’ve had the most influence, either negatively or positively. What happened? What did you learn about motivating people? About yourself? Jot down at least 3-5 examples. - If you were at a dinner party or out with a friend, what are your favourite leadership memories to share?
These could be poignant stories or maybe they’re hilarious. What are the times in your leadership that you did something incredible? What are those moments you learned from? Jot down at least 5. - If someone was going to write your biography, do a television special about you or write your eulogy, what would they say about you and your leadership?
It’s one thing to pick our own highlights, but it’s another to see ourselves as others see us. Does how you see yourself match how others see you? You can guess and write down 5 thoughts or ask some of the people you’re close to what they’d contribute to an overview of your life.
Once you’ve worked through these prompts, you will have quite a bit of material to draw from. The next step is to consider how you want to share your leadership story.
- When you look over all the elements and moments you’ve captured, what are the key moments?
- Are there any themes that jump out at you?
- What are your favourite parts? Why?
- Do you want to tell a story that makes people think, laugh or feel inspired? If this was a movie, would it be a comedy, drama or suspense thriller? Every story is unique and it’s up to you to choose the angle.
- When you tell your story, how can you make it vivid and real for your audience? What are the elements that are most relatable? What points are the most important to your story?
As you write your leadership story, give yourself permission to take a run at a first draft that is truly a rough draft. Don’t limit yourself by insisting on perfection from the first paragraph, just run headlong into your story and see where it takes you. Many times it’s far easier to shape a rough draft into a masterpiece than to wait until you’ve got it all figured out.
The next step is arguably the hardest: Take your leadership story to a few people you trust for their feedback. Remember how good leaders handle criticism because it can be really hard to listen and hear feedback about something so personal. Take their feedback (you asked for it and most people will strive to be constructive and honest) and think about it.
Ultimately, it’s your leadership story and you get to determine the final draft. You can also test it out when you speak to your team members and refine it as you move forward. After all, it – and you – are a work in progress.
Coach’s Questions:
How do you feel about writing your leadership story? What helps you the most to get into a creative headspace? What can you do this week to work on your leadership story?
If you feel like this has been a good start but you’d like to delve a little deeper, we recommend Douglas R. Conant’s The Blueprint: 6 Practical Steps to Lift Your Leadership to New Heights.




