Routine Reflection as a Leadership Development Tool

When most people think about uncovering their blind spots, they think about having someone else hold up a mirror for them, shine a light on an unknown for them, give them feedback, or otherwise point out the aspects of themselves they cannot see. Those tools are indeed wonderful to help leaders uncover their blind spots and develop self-awareness. However there is something missing here; the pursuit for greater self-awareness must include honest reflection with oneself. The full picture can only be gained by multiple perspectives, and one perspective central to the whole picture is the Self. There are several ways to support yourself in uncovering your own leadership blind spots. One powerful way is through routine reflection of your leadership.

To reap the rewards of self-reflection as a leader, you need to step into a mindset of being able and willing to look at yourself more objectivity, be open to your shortcomings, and be interested in closing the gaps on where you are and, 1) where your organization needs you to be and 2) where you want to be.

The Self-Performance Review as Routine Reflection

Having a framework, or pre-determined process for self-reflection will be helpful as you begin to make this a leadership habit. Think about the annual performance review process at organizations, only this routine is for yourself. These processes are huge efforts for managers to lead, and they are made possible by creating a feasible system for everyone in the organization to follow – key areas each team member needs to be assessed on and questions they need to answer based on the person’s role and performance, as well as the company’s goals and values.

Performance reviews are a moment where both manager and employee take a step back to reflect on the highs, lows, and everything in between, related to performance and career. My personal belief is that reflecting on performance and career once a year is not nearly enough to ensure you are focused, motivated, satisfied, and on track – both for yourself and for the organization. I believe it is even more important for those in senior leadership positions to reflect more often.

If you can begin to think about your leadership reflection routine as a self-performance review – one you are doing on and for yourself, this might be helpful. To make it more manageable and productive, create a process you can feasibly follow consistently and a cadence that is most beneficial for you.

Quiet Space to Slow Down and Pay Attention

“The quieter you become, the more you are able to hear.” Rumi

The heart of reflection is to give yourself quiet space and time to think. This sounds obvious and easy, but it is a rarity for the senior leaders I work with. In order to reap the rewards of a self-reflection routine, you must prioritize quiet time for it. This means creating that time, as it does not tend to just appear for senior leaders.

Reflection is about paying attention to what is below the surface, and in order to pay attention, you must slow down. Because you cannot pay attention to two things at the very same time, you will have to prioritize your attention. As you craft your questions for reflection, think about what deserves more of your attention or less. What should you be observing or noticing that you haven’t been? What you decide to reflect on will naturally steer your attention.

Because your attention is such an important driving force in your reflections and therefore your goals and behavior, choose carefully where it goes. Pay attention to what triggers you so you can proactively set up some guardrails to avoid falling into your traps and patterns. Pay attention to when you feel most energized so you can do more of the things that generate your energy. Pay attention to what exhausts you so you can eliminate, delegate, simplify, or otherwise minimize those aspects of your work. Pay attention to the people and contexts you work best in so you can optimize your performance. Pay attention to your biases so you can minimize how they interfere with your work and relationships. Pay attention to your assumptions and when you are holding onto your sense of right and wrong too tightly. Pay attention to the power dynamics in the room so you use your own power in the most intentional way. Pay attention. Pay attention. Pay attention – and you will make the most of your routine reflections and gain the self-awareness you need to enhance your leadership.

As you create space for silence and slowing down, also consider how you could embody a posture and attitude of learning and openness. If you are able to remain open as you observe yourself and reflect routinely, you will notice yourself more objectively and learn more about where you need to grow and develop as a leader.

There are many ways to set up your reflection routine, and this is something that can and should be tailored to suit your needs. Here is a simple framework you can use for routine reflection – feel free to adjust to suit your needs:

6-Step Framework for Routine Reflection

Once you commit to uncovering your leadership blind spots and building self-awareness through reflection, where do you start? Here are some steps you can follow to customize a self-reflection routine to suit your needs and situation.

1.  Decide How Often and When, Then Schedule It

Get specific as far as how much time and at what cadence you plan to spend reflecting on your leadership. Then make the time and commit to it by putting it in your calendar. This could be any combination of daily, weekly, monthly, quarterly, annually, biannually, etc.

Another productive time to self-reflect is following a project or difficult conversation – to reflect on how it went and what could go better next time. Once you finalize a new project timeline or schedule a tricky meeting or conversation, make sure to add reflection time after it launches or completes.

2. Outline Questions

Ask yourself which questions will serve you best at which cadence, and what areas for reflection will be the most supportive for your goals. These questions will help steer what you’ll be paying attention to and observing – and should be based on the areas you hope to grow. They will also change over time, as your situation, role, and goals will naturally shift (and presumably expand as you grow as a leader).

Draft some questions to align with your personal leadership goals, some questions to align with your team goals, and others to reflect on your organizational goals. See the sample list of questions I outline in the exercise at the end of this article for ideas and a starting point.

3. Answer with Specifics

Hold yourself accountable for keeping that quiet time to reflect, and make sure you write down your answers. Be as specific as possible when you answer the questions, including examples along the way. The more color you provide in your routine reflections, the more you will learn and the more momentum you will build with your leadership reflections.

4. Look for Patterns and Themes

Over time, review your reflections and search for common themes that surface repeatedly. What threads do you notice are woven into your responses more often than not? Are there patterns or commonalities among what you write week over week, month over month, or quarter over quarter?

If you notice common threads, what might they mean for your leadership? What might you want to shift as a result of the patterns you see? Reflect on your reflections and note what you discover.

5. Share Your Questions and Reflections

Don’t keep your routine reflection process to yourself. Share it with your team members in an effort to motivate others to do the same. The more people who know about your routine reflection and practice it, the more a growth mindset becomes part of the team’s culture and shared language.

If you’re stuck on questions, you can also use the opportunity to ask others for feedback. You may be clear on how to answer certain questions one month and stuck on the same questions the following month. Asking for feedback from others is most helpful as an ongoing process, rather than a one-time conversation. See tips in the article, 11 Steps to Getting Honest Feedback as the Boss.

6. Change, Refine, Revisit

Do not treat this as a static checklist. Reflection is not something you will ever be “complete” with. It is an ongoing practice and development tool. When you ask yourself questions such as, what is the single biggest thing I can do to amplify my career, elevate my leadership, or drive my team’s goals forward?, your answers will change over time as your career, team, and success expands.

I often see clients continuing to solve problems that are no longer relevant or spend energy on issues that are no longer priorities because the focus hasn’t shifted quickly enough. Maintaining the same goals over time will hold you back, which is why reflecting routinely is key. We live in a fast-changing world and our reflections must keep up with the pace of change in life and business.

Exercise and Example: Routine Reflection

I recommend starting with daily, weekly, monthly, quarterly, and annual reflections. This does not need to be extensive, but it should be consistent. Here, I outline some ideas for a reflection routine to serve as a thought starter for you as you create your own:

Daily – 1 Minute:

Check in with yourself at the beginning of each day and set an intention for how you want to show up. For example, if you are a leader working on being more curious, focused, empathetic, or confident, you might set an intention aligned with one of those traits. Then, check in with yourself at the end of each day to see how you measure yourself according to your intention. The final step is to decide what you plan to do differently tomorrow to be more aligned with that intention.

Another idea I really like is to use Marshall Goldsmith’s Daily Question format. It is simple and fast – and should change based on the leadership competencies you are working on at the time.

The format is simply outlining between three and seven questions starting with, “Did I do my best today to…?” The way he phrases the questions removes any inclination you might have to answer with a story, excuse, or blaming someone else. This format allows you to fire off answers to these three to seven questions every day in about one minute. It also allows you to focus on the leadership competencies you truly want to develop. Some examples include, Did I do my best today to empower my team?; Did I do my best today to project confidence?; Did I do my best today to lead with curiosity? Did I do my best today to stay focused on top priorities?; Did I do my best today to remain fully engaged? Did I do my best today to build positive relationships? Did I do my best today to respect my boundaries?

Weekly – 5 Minutes

Spend five minutes at the end of each week in quiet reflection. Here are some sample questions suitable for weekly routine reflections:

• What wins or accomplishments can I celebrate from this past week?
• What challenges did I face and how did I manage them? What could I have done differently or better?
• What did I learn or observe in the last week that was valuable to me?

• What was my worst day or moment at work this week, and why? What happened that made it so? What about my week did I outright dislike?
• When was I at my best this week? What happened that energized me this week?
• What do I need to focus on and how do I need to show up next week in order to create more five-star days?

Monthly – 30 minutes

Spend a half hour each month to gauge where you are on a larger set of leadership development goals you have. Here are some sample questions suitable for monthly routine reflections:

• What are the three biggest wins or accomplishments I can celebrate from this month? How will I celebrate them?
• Where am I in relation to each of my goals? Get curious about anywhere I may be falling behind.
• What conflicts arose this month, and how did I handle them? What could I have done better?
• What am I sick and tired of?
• What am I avoiding? What needs to be said that is not being said?
• Where might I need help? And who might I ask for help?
• What did I learn that was valuable this month?
• What do I need to do or focus on in order to develop myself in the next month?
• How can I get the honest feedback I need to develop my self-awareness next month?
• Are there any patterns or trends I am noticing?
• What do I want to focus on creating in my leadership next month?

Quarterly – 1 Hour

Once a quarter take a quiet hour to reflect on where you are and where you want to be. Here are some sample questions suitable for quarterly routine reflections:

• What are the biggest wins or accomplishments I can celebrate from this quarter? How will I celebrate them? Who contributed to these wins and how can I acknowledge them for their efforts?
• Where am I in relation to each of my goals? Get curious about anywhere I am falling behind, and notice places where I have been consistently falling short.
• How can I take a more proactive approach in my personal and professional development? What or who do I need to help me with this?
• What is the most important thing I need to focus on or learn regarding my leadership, in order to reach my goals? How will I do this?
• What am I challenged by or tired of, and how am I responsible in some ways for creating the conditions for this challenge? What are ways I could shift this?
• How can I get honest feedback from multiple perspectives regarding my leadership over the last quarter?

• What needs to be acknowledged, expressed, surfaced, or communicated?
• Are there any patterns I am noticing? Review reflections from past weeks, months, and quarters and look for trends, surprises, or possible blind spots.
  • Are there any trends that point to my discontentment or unhappiness that I need to address?
  • Are there any patterns that lead to my satisfaction and fulfillment that I can highlight?

Annually – A Day or Weekend

At least once a year, get away from it all for a day or a weekend to focus on yourself. Try to change your environment and really take a step back for this annual routine reflection. I recommend answering all of your quarterly questions at the annual mark and spending more time with each question. In addition, you can add other questions to your annual routine reflection, such as:

• What am I most proud of this year?
• Who was I closest to this year?
• What and who did I appreciate most thing year? How can I acknowledge others for their participation in my success along the way?
• What were my biggest lessons learned this year?
• Am I living in in alignment with my core values? My mission in life? My purpose?
• Where am I on the path to becoming the leader I want to be? If off track, how can I get back on track?
• Where am I stuck?
• Do I have any regrets from this year? If so, reflect on them.
• What kind of leader have I been in the last year, and what kind of leader do I want to be? What is the delta and what are some things I can do to close the gap?
• How can I get into a better rhythm of garnering honest feedback from those around me? How can I create a culture of generosity in giving and receiving feedback?
• What do I need to invest in – financially, energetically, time – in order to achieve what matters most to me?
• What zapped my energy and joy this year? How can I create more boundaries next year so I can minimize this?
• What fueled my energy and joy this year? How can I design my schedule going forward to include more of these things?
• Review reflections from the past year and note any trends or patterns.
• What do I need to focus on for the next year to bring me more success and fulfillment? Outline metrics and questions for next year’s routine reflections.

The questions I’ve outlined here are just examples you can use as a starting point; the invitation here is to customize these questions to suit your needs and goals. The intention of routine reflection is to help you get to the essence of who you are, what is most important to you, what are the ways you want to grow as a leader, and how you can effectively reach your aspirations. The starting point in all of this is self-awareness. As former tennis champion of the world and trailblazer for female athletes, Billie Jean King said, “I think self-awareness is probably the most important thing toward being a champion.” I think this applies to leadership as well.