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Leadership Journaling: 15 Prompts, 33 Uses, & Quick-Start Guide

September 16, 2022

Leadership is difficult because it’s dynamic, and you only become a better leader by growing through experiences. No one wakes up one day as a phenomenal leader. You may have qualities that help you lead well, but a leader only becomes experienced through challenges, tough decisions, and experiences with their team. 

Those who want to become truly exceptional leaders must take their experiences one step further by practicing self-awareness, observation, and reflection. How do we do this? Through leadership journaling. 

leadership journaling

What is leadership journaling?

Leadership Journaling is an effective tool for leaders who want to improve their leadership skills. It helps them reflect on their strengths and weaknesses as they lead others.

Leadership journaling is a simple way to learn how to become a better leader. This technique encourages reflection and self-awareness, which will help you develop new habits that will benefit your team.

After all, leadership and management author and expert Peter Drucker says, “Follow effective action with quiet reflection. From the quiet reflection will come even more effective action.”

Why Should I Start Leadership Journaling?

Taking time to reflect through leadership journaling helps leaders break through the cycle of rumination, or thought patterns that cycle over and over again. Ruminating in thought patterns achieves nothing and keeps our growth stagnant, but journaling, reflecting, and exploring new paths forward helps us break that cycle and develop new paths forward. 

Journaling is the best way to reflect on your leadership, get out of your own head, process decisions, think through team interactions, seek new and exciting possibilities, and – most importantly – see new paths forward toward growth. 

If you’re interested in learning more about leadership journals, here are some benefits you might enjoy:

There are several reasons why you should write your own journal. First, you will gain insight into yourself by reflecting on your experiences. Second, you will develop skills such as critical thinking, problem solving, and decision making. Third, you will build relationships with other people through sharing your thoughts and feelings. Fourth, you will become more aware of how you think and act. Finally, you will improve your ability to communicate effectively.

What Are the Benefits of Journaling for Leaders?

Studies show that reflection through journaling at the end of every work day can solidify what we learn and increase our effectiveness by up to 25%.

Taking that one step further – what if we could become 25% more effective each and every day? After one year, we would be over 9,000% more effective. What could we accomplish or achieve at this rate of development and growth?

Journaling and self-reflection does even more than increasing effectiveness. It also helps you:

  • Reflect on your life experiences and choices
  • Understand who you are and where you came from
  • Uncover your own story
  • Reflect on your strengths and weaknesses
  • Discover new opportunities to learn new things
  • Practice critical thinking.
  • Improve your communication skills.
  • Build relationships through reflection & planning
  • Build and maintain self-confidence

How to Start Leadership Journaling Right Now

Many people think that writing down what they feel is a waste of time. However, research shows that leaders who write down their thoughts and feelings before making decisions are more likely to make better decisions than those who do not.

In addition, leaders who keep a journal tend to perform better at work, process stress, and navigate or heal from burnout. Here’s how to start journaling today:

Pick a Format

To start a leadership journal, first decide whether you will use an online journal or paper journal. If you choose to use an online journal, there are several options available. You can use a simple text editor such as Microsoft Word or Google Docs. Or, you can use a specialized software program designed specifically for journaling like Evernote or Notion.

Identify Your Strengths, Not Weaknesses, First

Start by listing three things you do well FIRST. Then list three things you wish you were better at. Finally, write down three things you’d love to try out. You’ll find that these lists will give you insight into your own strengths and weaknesses.

Get Started in Whatever Way Feels Easiest

Once you’ve identified your strengths and weaknesses, start journaling. This process involves writing down your thoughts and feelings about yourself and your role as a leader. If you’re having trouble coming up with ideas, ask yourself questions such as “What does it feel like to follow my leadership?” or “How would I describe my leadership style to a friend?”

Optional: Share Snippets with Your Team

You’ll find that when you share what you write with your team, they will appreciate your honesty and support your decisions and efforts more. They will also learn from your experiences and gain insight into how they can better serve their teammates.

Write Through Tough Decisions

If you’re looking for ways to improve your leadership skills, consider writing down your thoughts and ideas in a journal. This process allows you to think through your actions and decisions, and gives you the opportunity to reflect on your successes and failures.

Take Action to Make Leadership Progress

Once you’ve written down your thoughts and ideas, take action based on what you’ve learned. You’ll find that by taking action, you will learn more about yourself and how you work with others. 

Begin by asking yourself a question that will help you focus on what you learned from your journal. This introspective question should prompt you to think about how you can apply what you learned to improve your leadership skills.

To evaluate your leadership journal, ask yourself these questions: What did I learn from my journal? Did I accomplish anything significant? Was there any new insight into myself or others? If not, why not?

Organize Your Leadership Journal

Once you have decided what type of journal you want to use, you need to determine how you will organize your entries. There are two main ways to do this: chronological order or thematic order. In chronological order, you write down everything that happened during a particular period of time. Then, you move on to the next period. In thematic order, you write down each event according to its theme. This allows you to focus on one aspect of your life at a time.

How to Use Leadership Journaling to Self-Coach

Just like we use coaching to help our team members arrive at new ideas, identify goals, prioritize paths forward, and commit to taking specific action – we should be doing the same for ourselves as leaders

I utilize the GROW coaching model developed by John Whitmore in his book Coaching for Performance both for myself and others. 

The GROW coaching model is broken down into steps:

  • Goal: What is your ultimate goal? What does success look like for you in this situation, project, or endeavor?
  • Reality: What is your current situation? What’s currently happening?
  • Options: Name ALL the paths forward you could take. Get creative, leave no stone unturned. 
  • Will: Identify the one path you will commit to taking right away. Define your steps forward clearly.

As a self-coaching tool, we can use these focal points to ask ourselves pointed questions that help us move through difficult decisions, thoughts, beliefs, feelings and emotions. 

How to Journal the “Right” Way

When done correctly, journaling can be one the best and most effective tools in a leader’s developmental toolbox. Journaling done “right” simply means you’re not holding yourself to a specific standard of perfection, editing your thoughts or feelings, or criticizing yourself for what shows up on the page. 

Instead, journaling should be a judgment-free place of freedom, where any and all thoughts are welcomed to the page. This is your space to practice self-awareness, not self-censorship – and to do that you have to erase all standards of perfectionism. 

Additionally, Chade-Meng Tan writes that “journaling is an important exercise to help you discover what is on your mind that is not in a clear, conscious view… You are trying to let your thoughts flow onto paper so you can see what comes up.”

It’s not about processing what’s top-of-mind, it’s about digging deeper to uncover your subconscious approach to leadership!

15 Leadership Journaling Prompts to Become a Self-Coaching Leader

Here are some journaling prompts to help you practice self-awareness and begin to use leadership journaling as a tool to self-coach, develop, and grow into a next-level leader. 

  1. What am I feeling right now?
  2. How would I paint a picture of my leadership right now?
  3. If I were one of my team members, how would I evaluate myself as a leader right now?
  4. If I were honest with myself, what do I really want right now? 
  5. What is important to me right now?
  6. What is important to my team right now?
  7. What is the difference between what my team wants and what I want? 
  8. What are the commonalities between what my team wants and what I want?
  9. How far away am I from what I want?
  10. How far away is my team from what they want?
  11. How can we merge our two sets of goals into an all-team goal? How can we find common ground?
  12. How can we work in alignment to achieve what we all want together?
  13. What are all the paths forward we can take right now to achieve those goals?
  14. If I knew the right path forward, what would it be?
  15. What single action will I commit to taking today toward this path?

You Can Even Use AI to Help You with Your Journaling!

I think we can, by now, agree that leadership journaling is a hidden gem. It can help us get to know ourselves as leaders better, sharpen our decision making, and see how far we’ve come so we can celebrate our wins.

Did you know you can use AI to help you with your journaling journey? Here’s how:

  • Documenting Thoughts and Reflections: Simply start a conversation with ChatGPT, sharing your thoughts, experiences, or challenges of the day. The AI can understand and respond appropriately, often encouraging further introspection.
  • Exploring Leadership Scenarios: Describe a leadership situation to ChatGPT and ask for its perspective. The AI can provide diverse viewpoints, simulating a brainstorming session or even role-playing different outcomes.
  • Learning New Concepts: Ask ChatGPT about leadership theories, management styles, or practical skills like conflict resolution. It’s like having a leadership guide at your fingertips.
  • Tracking Growth: By regularly engaging with ChatGPT, you have a chronological record of your thoughts, decisions, and development as a leader.

Remember, the effectiveness of leadership journaling, even with a tool like ChatGPT, comes from consistent engagement. Make it a part of your routine, and watch how the insights unfold and enrich your journey as a leader.

Best Ways to Use Your Leadership Journal

In their book Leading Minds, Howard Gardner and Emma Laskin conclude that the commonality between objectively outstanding leaders is the simple act of taking time to reflect. 

Want to become an outstanding leader? Here are many ways to use your leadership journal:

How will you use your leadership journal? What ways or prompts stick out to you?

A Super-Simple Kickstart to Leadership Journaling

If tons of journaling prompts feel overwhelming to you, and you want a simpler way to kickstart your leadership journaling experience, here is an easy way to start. 

  • First set aside 5-10 minutes both morning and evening – before and after your work day – to write in your leadership journal. 
  • In the morning, ask yourself simply, “What am I curious about today?”
  • And in the evening, ask yourself simply, “What am I learning today?”

As a leader, if you’ve been feeling stuck, burnt-out, anxious or stressed, self-reflection is one of the best antidotes and cures. Make it a practice and see the transformation it will have on your leadership experience and growth!

I'm Kaylan, leadership educator, podcaster & speaker

What are you searching for?

Reading suggestions

Crafting a 90-Day Onboarding Plan

Job Postings that Attract Top Talent

Mapping Your Leadership Style