5 Questions Every Leader Should Ask About Last Year
“LEARN FROM YESTERDAY, LIVE FOR TODAY, HOPE FOR TOMORROW.” – ALBERT EINSTEIN

5 Questions Every Leader Should Ask About Last Year

Written by Stephanie Flies , CEO and Founder of City Mom Collective

As a leader, every January I find it especially beneficial to spend intentional time decompressing and reflecting on the past year. While I know it’s tempting to run full steam ahead into the new year, leaders must take time to reflect before moving on into the future.

To give your soul (and mind) space to reflect, might I suggest that you carve out some time on your calendar to find a quiet place with just a journal, a pen, and a cup of coffee or tea? It might also be helpful to have access to your last year’s calendar so that you can review the major events of the year.

1. What were two or three major themes that kept recurring??

Reflecting on the recurring major themes from the past year can provide invaluable insights for our strategic direction. Identifying the two or three key themes that consistently emerged allows us to discover patterns, challenges, and opportunities that may impact our goals. By identifying these themes, we equip ourselves give ourselves the gift of perspective that informs decision-making and fosters a proactive approach to the challenges and opportunities that lie ahead.

These can be single words or phrases. For me, they were:

  • Transition seasons in life and business, while scary, are beautiful
  • The importance of self-awareness both personally and professionally

2. What did you accomplish this past year that you are the proudest of?

Recognizing and celebrating our proudest accomplishments empowers us to build on our achievements and approach the upcoming year with a clear understanding of our capabilities, ultimately fostering a desire for continuous improvement and success.

These can be in any area of your life—spiritual, relational, vocational, physical, etc. Be as specific as possible. Here are a few of mine:

  • Reached MILLIONS of moms online and offline
  • Prioritizing Sundays as a day of rest
  • Navigated the work/life shuffle of the summer season well

3. What do you feel you should have been acknowledged for but weren’t??

Reflecting on what you believe should have been acknowledged but wasn’t provides valuable self-awareness, helping you identify areas where your contributions may have gone unnoticed and allowing for a more intentional focus on recognition and appreciation in the upcoming year.

4. What disappointments or regrets did you experience this past year??

As business owners, addressing disappointments or regrets from the past year is crucial for personal and professional growth, as it enables us to learn from experiences, adjust strategies, and approach the new year with a clear understanding of areas for improvement and resilience.

5. What were the major life lessons you learned this past year?

Reflecting on the major life lessons learned in the past year is a valuable exercise for leaders.? By answering this question, you’ll glean insights that contribute to personal and professional growth into this next year.

Boil this down to a few statements. For example:

  • Discovered my “secret” to decompressing and thriving each day – daily walks!
  • When overwhelmed and not sure of what to do next, seek outside counsel
  • I’m my best self when I reserve time to learn from others (reading, listening to podcasts, meeting with my mentors, etc)

So often, life goes by so fast that we don’t take time to process it. I hope you’ll take the time to write out your answers to the above 5 questions.? Then once you’ve done so, it is time to acknowledge the past?and move on. It’s over. There’s nothing you can do to change it. This is super important. What was done was done. It’s time to close that year and look to the year ahead.


City Mom Collective's Mission is to empower, connect, and inspire moms through our media agency and membership community, providing the resources, networking, and support they need to succeed in entrepreneurship while nurturing their roles as mothers.



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