Leadership Journaling: Why It Builds Better Leaders and How to Start

Walk into any bookstore or office supply store and you will see an entire section on journals: journals to document your dreams, journals for sketching, journals for list-making, journals with questions and simple, blank books for any journaling purpose you deem appropriate. For those who enjoy technology, numerous apps are available for the mobile device or computer, some even with the ability to include photographs and automatically document the date, time, weather and music you were listening to when you wrote an entry. PPS International Limited has long used journaling as part of our learning processes, especially for leaders. As far back as the early 1990s, we integrated journaling into our Management Skills for New Leaders program, allowing new managers to capture their ideas and insights in a specific learning journal. We’re in good company! Those who journal and see its value were Leonardo da Vinci, Albert Einstein, John D. Rockefeller, George Patton, Ben Franklin, Thomas Edison, Winston Churchill and Ernest Hemingway (to name a few). What is the appeal and value? Here are just a few of the benefits to anyone, but especially to leaders:

1. Better Decision Making: Did anyone ever tell you when you were stumped on an issue of importance, “Make a pro and con list”? Well, their advice was sound. The act of writing allows the writer to consider various points, clarify needs and process options. In addition, journaling can channel energy into solutions in a way that for many people talking does not. Those who journal may find that their ability to make decisions in a timely manner with a better outcome will improve over time.
2. Improved Self-Knowledge: We work diligently to build awareness into our training programs and coaching processes. This is because we know that leaders who can examine their own behavior and outcomes will continuously improve their relationships and results. Journaling can provide writers with better self-insight, a look at patterns in their behaviors and a means of stopping the cycle of repeating self-defeating actions.
3. More Positive Outlook and Attitude: If leaders include gratitude and positive intentions in their journaling, their internal outlook can improve. Through a more balanced lens of gratitude and goal-setting for improvement, leaders’ outward behaviors can begin to shift to be calmer and appreciative. Leaders live very public and influential lives, and their demeanors can be a positive force for an engaged workforce.

The benefits come with continued practice: starting and keeping a pattern of writing that can be as brief as a few minutes a sitting. From an instructional designer’s perspective, the act of journaling is as relevant to our leaders’ development today as it was to those who included this habit in their lives hundreds of years ago.

This article keeps those three reasons and adds the practice around them: what a leadership journal is and how it differs from a work journal or a decision log, what the research on reflection shows, how PPS has built journals into leadership development programs since the early 1990s, how to start and keep the habit, a set of leadership journal prompts, ten reflection questions for a weekly or monthly review and a simple decision log. If you lead talent development and want to build reflection into a population of leaders rather than into your own routine, the section "Building journaling into leadership programs" covers program design, privacy, evaluation and what other organizations do.

What a leadership journal is

A leadership journal is a private, regular written record of the situations a leader faces, the decisions and conversations that come out of them and what the leader notices about their own behavior and results. The entries are short. The value comes from writing them consistently and reading them back, which is where patterns show up that are difficult to see day to day.

The word "journal" covers several tools that overlap but serve different purposes. Knowing which one you are keeping helps you decide what belongs in it.

Most leaders end up with a hybrid: a leadership journal that includes a short decision log and a line or two of gratitude. The sections below assume that hybrid.

What the research says about reflection

The three reasons above line up with what researchers have found about reflection and writing.

Donald Schön described professionals learning by reflecting during an action and afterward, and argued that this reflective practice is how experienced practitioners handle the situations that the textbook did not cover [1]. David Kolb placed reflective observation as one of the four stages of experiential learning, between having an experience and drawing the generalizations that shape the next attempt [2]. A journal is the simplest way to make sure that stage happens rather than being skipped on the way to the next meeting.

A Harvard Business School working paper by Giada Di Stefano, Francesca Gino, Gary Pisano and Bradley Staats tested the point directly. Across ten studies with more than 4,000 participants, people who spent time reflecting on what they had learned tended to improve more than people who spent the same time on additional practice, with the largest benefit early in the learning curve, once some experience had accumulated to reflect on [3]. That is the decision-making benefit in the first reason above: writing about a decision and its outcome is a form of reflection that practice alone does not supply.

The outlook benefit has evidence as well. James Pennebaker's research on expressive writing found that writing about emotional experiences over a few short sessions was followed by improvements in physical and mental health, an effect he attributed to organizing and making sense of the experience through language [4]. Robert Emmons and Michael McCullough found that people who kept a brief record of things they were grateful for reported higher well-being and more optimism about the coming week than people who recorded hassles or neutral events [5].

None of this requires long entries. The reflection studies asked participants for short reflections, and the gratitude studies used a few lines a day or a week.

How PPS uses journaling in leadership development

PPS has used journaling in leadership programs for more than thirty years, and the practice shows up across our work in a few forms.

• A learning journal in Management Skills for New Leaders, in place since the early 1990s, gives new managers a place to capture ideas and insights between workshops. The program is one of the foundations we offer organizations that are building a new manager training program.
• The senior manager development program created with GE HealthCare by the SyNet Americas (PPS) design team won a Gold Brandon Hall Group Award for Excellence. It combined "skills assessments, personal reflection and journaling, self-study, social learning and instructor-led training" to help experienced leaders reflect on and refine their leadership identity, and the award announcement describes the design.
• In a program that built leaders' ability to deal with ambiguity for an Asia-Pacific medical devices organization, learning journal reflections about behavior change were one of the success indicators, alongside a baseline skills assessment and peer feedback in social learning settings.
• Our guide to individual development plans lists journaling among the development resources that run beyond training, and its example plan includes keeping a short journal after each presentation as a way to practice a skill. Reflection has its own entry in our 20 employee development ideas.

The common thread is that the journal is attached to something: a program, a skill someone is practicing or a coaching relationship. A journal with a purpose tends to get written in, and one without a purpose tends to stay blank.

How to start a leadership journal

The journals that last are the ones that ask little of the writer. A routine that survives a busy week has four parts: a fixed time, a format you will keep using, a small structure and a habit of reading back.

• Pick the time. The end of the workday works for many leaders because the material is fresh and the writing closes the day. Ten minutes is enough. A recurring calendar appointment protects it from the last meeting of the day.
• Pick the format. Paper suits people who think while they write and who want the journal away from notifications. An app or a private document suits people who want to search entries later or who travel. Either works; the format that matters is the one you will still be using in three months. If you write digitally, use a tool your organization approves, since entries often mention colleagues and decisions.
• Use a small structure. Three questions cover most days: What happened today that mattered? What did I do, and what did I notice about how I did it? What will I try next? A line of gratitude at the end takes a few seconds and carries the outlook benefit.
• Read it back. Reread entries. This creates new connections and knowledge. A weekly skim and a monthly read are enough to see the patterns described above: the repeated situations and the repeated responses to them.

Here is a cadence that fits around a leader's calendar.

Leadership journal prompts

Prompts help on the days when the three questions produce nothing. The prompts below follow the three reasons above, so a leader working on one of them can pick from that group.

Prompts for better decisions

• What decision did I make today, and what did I know, assume and not know when I made it?
• Which decision am I avoiding, and what would make it easier to make this week?
• Whose input did I use today, and whose did I skip?
• What is the smallest version of this decision I could make now and review later?
• Which recent decision would I make differently with what I know today, and why?

Prompts for self-knowledge

• What is the biggest lesson I learned today?
• What positive feedback did I get today?
• When did I feel most and least effective today, and what was I doing in each case?
• What did someone see me do today that I did not intend?
• Which of my reactions today was a pattern I have noticed before?
• What feedback have I received in the last month, and what have I done with it?
• What did I say I would do differently, and did I?
• What resources do I need to reach my goals?
• What new skills can I learn? How can I learn them?
• What skills can I strengthen? How can I improve?
• What is my job satisfaction level?
• What can I do to increase my job satisfaction?

Prompts for outlook and attitude

• What went well today, and what part did I play in it?
• Who helped me this week, and have I told them?
• What am I grateful for in this team, this role or this organization right now?
• What am I worried about, and what part of it is within my influence?
• What do I want people to experience from me tomorrow?

Leadership reflection questions for a weekly or monthly review

Review questions look across entries rather than at a single day. Ten are enough, and a leader can rotate through them over a quarter.

1. Where did my time go, and how much of it went to the work only I can do?
2. Which conversation did I put off, and what did the delay cost?
3. Which decision did I make quickly that deserved more thought, and which did I slow down that deserved less?
4. What did my team need from me that I did not provide?
5. Where did I hear the same concern twice, and what have I done about it?
6. Which strength did I overuse?
7. Who on the team grew this month, and what did I contribute to that?
8. What did I learn about myself that I would have disagreed with a year ago?
9. What would my direct reports say my mood was this month, and would they be right?
10. What one behavior, if I changed it next month, would matter most to the people I lead?

Keep a decision log inside the journal

A decision log is a short, structured record of significant decisions, kept alongside the daily entries. The first reason above, better decision making, comes partly from the act of writing a decision down and partly from reading the entry months later, when the outcome is known and the reasoning can be compared with it. Without the record, memory tends to rewrite the reasoning to fit the result.

A leader who keeps a decision log for a year has a dozen or two entries to read back, which is enough to see a tendency: decisions made late, options not considered or confidence that ran ahead of the evidence. The log pairs with our tool on dealing with ambiguity, which covers six ways to make progress when the situation is unclear.

Making the habit stick

Many leadership journals stop within a few weeks, in our experience, and the reasons tend to be the same. A few practices that help include:

• Lower the bar. An entry can be two lines, and a missed day is a missed day rather than a failed habit.
• Keep it private. Writing changes when a leader expects someone to read it. Share themes with a coach or mentor if that is useful and keep the entries to yourself.
• Attach it to something. A program, a new role, a coaching engagement or a specific skill you are practicing gives the journal a purpose and a natural end point, after which many leaders keep going anyway.
• Keep tasks elsewhere. Tasks belong in the work journal or the task manager. If an entry has turned into a to-do list, add one sentence about what you noticed and stop there.
• Reread on a schedule. The monthly read is the step most people skip, and it is the step that produces the self-knowledge.
• Expect the outlook benefit first. Many leaders notice the calmer, more appreciative demeanor described above within weeks; the decision-making benefit takes months of entries to show.

Building journaling into leadership programs

For talent development leaders, the question is how to build reflection into a population of leaders rather than into a personal routine, and how to know whether it is doing anything. Learning journals are one of the least expensive components of a leadership program and one of the most often skipped, because they depend on time that agendas rarely protect.

Where a journal fits in a program

A journal works when each program element gives it a job. Here is how we typically place it.

Value to the organization

Reflection is the step where a program's content turns into behavior on the job. A leader who writes about trying a new conversation process, and about how it went, is doing the transfer work that a workshop cannot do for them. The journal also gives the organization evidence it rarely has: written, first-person accounts of behavior change, which in the ambiguity program above sat alongside assessment scores and peer feedback as a success indicator. Journal themes feed individual development plans and give leadership coaching a running start, because the participant arrives with situations already thought through.

Cues that a leader population is not reflecting

• The same mistakes recur across cohorts, and after-action reviews stay at the level of events rather than decisions.
• Feedback from assessments or multi-rater surveys is received and then not acted on; the debrief is the last time anyone mentions it.
• Decisions are made fast and rarely reviewed, so nobody knows which judgments were good and which were lucky.
• Program evaluations report satisfaction and learning but carry no evidence of applied behavior change.
• Leaders describe development as something that happens in the classroom and stops at the door.

How organizations solve for it

The organizations that get reflection to happen design the time in rather than hoping for it. A few practices to consider include:

• Protected writing time on every workshop agenda, with the prompts on the screen, so the journal is used in the room before it is expected to be used outside it.
• A journal that participants own. The privacy rule is stated on day one: facilitators and managers see only what a participant chooses to share. Voluntary sharing tends to rise once people trust the rule.
• Prompts that change between workshops and arrive with a date, so the journal follows the learning path instead of sitting in a bag.
• Reflection built into group coaching meetings, where part of each session is reserved for individual application commitments that participants write down.
• A closing reflection that doubles as evaluation evidence, collected with consent and reported in aggregate.
• Digital journals inside the learning platform for global cohorts, under the same privacy rule, with paper available for those who prefer it.

Our leadership development programs and coaching engagements build reflection in as a standard component, from the assessment debrief through the closing evaluation, and the program pages describe where it fits in each design.

Frequently asked questions

How long should a leadership journal entry be?

A few sentences on most days. The reflection studies asked for short reflections, and the gratitude studies used a few lines. Length matters less than regularity and rereading. An entry that records one situation, one observation about your own behavior and one thing to try next is complete.

Paper or digital?

Whichever you will keep using. Paper keeps the journal away from notifications and suits people who think by writing. A digital journal is searchable, travels well and can live inside a learning platform for program use. For anything digital, we recommend a tool your organization approves, because entries mention colleagues, clients and decisions.

Should a leader share the journal with a coach or manager?

Share themes rather than entries. The journal works because it is candid, and candor drops when a leader expects a reader. A useful practice is to bring one or two situations from the journal to each coaching session and to keep the pages themselves private. In programs, we recommend stating the privacy rule on day one: the participant owns the journal and decides what is shared.

What is the difference between a leadership journal and a work journal?

A work journal records what was done: tasks, accomplishments, blockers and notes for status updates or performance reviews. A leadership journal records how it was done and what the leader noticed about their own decisions, behavior and effect on others. Many leaders keep both, often in the same notebook, with the work log at the front and the reflections at the back.

Can an AI tool help with journaling?

It can help after the writing rather than instead of it. Draft the entry yourself first, because the thinking is what the journal is for. Then, if your organization approves the tool, an AI assistant can summarize a month of entries, surface recurring themes or suggest questions for the next review. Use the company-approved tool only, since entries contain names, decisions and sometimes confidential information, and treat its output as a prompt for your own reflection rather than the reflection itself.

Where to start

For an individual leader: tonight, ten minutes, three questions and one line of gratitude, then the same tomorrow, and read the week back on Friday. For talent development leaders: pick one program in the current cycle, add ten minutes of protected writing time to each workshop day, send two prompts between sessions and ask for a voluntary closing reflection. One cohort's journals will show whether the practice is worth extending to the next.

References

1. Schön, D. A. (1983). The Reflective Practitioner: How Professionals Think in Action. Basic Books.
2. Kolb, D. A. (1984). Experiential Learning: Experience as the Source of Learning and Development. Prentice-Hall.
3. Di Stefano, G., Gino, F., Pisano, G. P. and Staats, B. R. (2014). Learning by thinking: How reflection can spur progress along the learning curve. Harvard Business School Working Paper 14-093. https://doi.org/10.2139/ssrn.2414478
4. Pennebaker, J. W. (1997). Writing about emotional experiences as a therapeutic process. Psychological Science, 8(3), 162–166. https://doi.org/10.1111/j.1467-9280.1997.tb00403.x
5. Emmons, R. A. and McCullough, M. E. (2003). Counting blessings versus burdens: An experimental investigation of gratitude and subjective well-being in daily life. Journal of Personality and Social Psychology, 84(2), 377–389. https://doi.org/10.1037/0022-3514.84.2.377