Reflecting on Your Leadership Journey in 10 Steps

I recently joined the DisRHupt program to share insights from my leadership journey. As I was putting my thoughts together for the talk I realized that the reflection process I used to articulate my journey was, perhaps, more valuable than sharing the journey itself. There are 10 key elements of this reflection process. Thinking through each one of these is what allows for deeper insight and learning. This reflection process has been developed and adjusted over years of coaching global leadership development program participants and supporting their growth journey.

1. Mentors – Who are and who were your mentors? Reflect on the mentors you’ve had and the impact they’ve made on you. What did they leave you with?

One of my first mentors left me with a phrase I still believe in and use today, “If you don’t know the business, you have no business being there.” It helped me to appreciate the importance of understanding the whole business in order to add more value from within my functional area.

2. Values – What do you value? What are your company’s values? Have your values changed over time? If so, in what way? Which of your values align with your company’s values?

Humility and vulnerability are values that have evolved and strengthened for me over time. As a new leader it was hard to believe that showing these values to my team would have a positive impact. Now, I’m certain and have evidence to prove that humility and vulnerability support and strengthen the team. Now, I want to help other leaders identify the values that are important to them faster than I did.

3. Inflection points – What has happened that changed the course of your life? What decisions have you made that have altered your life’s direction? What have they taught you?

Our lives are like real-time “Choose Your Own Adventure” novels with our decisions shaping who we are along the way. One of the first big inflection points in my life was walking away from a career as a singer. I learned valuable lessons in being agile and open to change, making difficult decisions, and that life is full of opportunities.

4. Behaviors – What behaviors do you typically exhibit? How might they change when emotions are high, such as when you are stressed or angry? What behaviors would you define as your strengths?

It’s so easy to stay action-oriented and focus on what we need to do to be successful. We can forget to ask ourselves who we need to be to support that success. Through honest reflection I could see my journey from being a compulsive and emotionally charged leader that didn’t always end up with a desired result to a leader that can be and stay composed and calm when necessary. I can still get triggered, but it’s become much easier to recognize the trigger and be able to make a choice and decide what I want my reaction to be instead of reacting before thinking.

5. Motivators – What motivates you? No matter where motivations come from (i.e. success, joy, titles, money, fear), be honest with yourself to understand what gets you going and keeps you going. How have your motivations guided the choices you’ve made?

Admittedly, when I started my career I was motivated by upward career progression and titles. This guided my choice of only going into new roles that were promotions. It was all about me. That motivation gave way fairly quickly as I realized the transformative power coaching can have in supporting someone else’s success. My motivation became seeing the success of those I coached. It was all about those around me. Seeing how I can support others in making an impact helped me to further evolve my motivators. Now I look for where I can make a larger impact together with others. It is now about the collective impact we make together.

6. Shifts – What shifts have you made so far? What shifts do you still want to make? Why are they important?

The classic HBR article by Michael D. Watkins, How Managers become Leaders articulates 7 different shifts we can make toward becoming a leader. It was a “light-bulb moment” for me when I first read this article and realized how much I had shifted from warrior to diplomat over the years and how much more I needed to continue on my journey from problem solver to agenda setter.

7. SWOT analysis – What are your strengths, weaknesses, opportunities, and threats? Which stand out to you? Which are you most proud of and which are you most concerned about (and why)?

The first time I used a SWOT analysis for self-reflection I had a hard time coming up with threats until I realized that self-limiting beliefs, like imposter syndrome, were my threat. Reflecting on your own strengths, weaknesses, opportunities, and threats can help you identify areas of opportunity and growth.

8. Skills – What skills have you built over time? Which skills were the easiest to master? Which have been the hardest? Which are you still mastering today?

Skill building can take different shapes and sizes from experiential learning and formal training to reading a book or participating in a round table discussion. Some skills I’ve built to become a more well rounded business person, like taking accounting for non-finance managers and sales training. Other skills I work on out of joy, such as coaching. Even though I have been coaching for over 15 years, I seek to learn and sharpen my skill with each new coachee.

9. Wheel of Life Assessment – What are the 8 most important areas of your life and how satisfied are you with each of them (on a scale of 1 to 10)? Are you comfortable with the level of satisfaction that you are at for each area? If not, why? If so, what do you do to maintain it?

When you are not satisfied with some important area of your life, the other areas will invariably be affected. This simple assessment tool can help you reflect on what’s most important to you. I use the wheel of life assessment as a reflection tool every few years to review my satisfaction with and commit or recommit to the things most important to me.

10. Themes – Reviewing all the other reflection points, what themes have come up? Looking at your whole life, are there other themes that come out?

When I look back and reflect on my whole career, there are a few themes that stand out. Coaching and mentoring, for example, has been a theme from first receiving good mentorship and coaching, then becoming a coach, and even teaching other to build their coaching capability. It’s been a theme a part of who I am, what I do, and how I work for as long as I can remember.

I hope these 10 key elements of reflection prove as useful for you as they have for me and many of the people I coach.

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