Mirror, Mirror…

Robyn Ward
4 min readDec 5, 2019

Tis’ The Season…To make time to reflect and learn from 2019 before you look forward and plan for 2020.

“Success is a habit.” “Leadership is a practice.” I find myself repeating both of these mantras often — whether coaching founders, teaching students or giving leadership talks.

Since it’s already December, which is generally a forward-thinking month, where people and companies engage in planning and goal-setting for the New Year, I wanted to share some thoughts on the important practice of reflection.

Reflection tends to be an activity that isn’t given the same importance as planning and is often rushed or skipped entirely. Many a client has said to me, “But I am so busy moving all the balls — individual, family, business — forward. I mean, really, who has the “luxury” to sit back and reflect?”

Reflection is by no means a luxury. We look back to get perspective, to make meaning of our actions and experiences, to learn, and to grow. If you are looking to be your best self and best leader, and to build your best company, reflection is a necessity, not a luxury.

Famed leadership guru, Warren Bennis, shared that the most successful leaders build “reflective structures” into their lives, meaning they make time and space for self-examination. I have also found this to be true. The high performers I know build reflection into their calendars — end of the day, week, month, quarter and year. I encourage all my clients to do the same to facilitate making it a habit.

Reflection, of course, is beneficial for everyone so I also suggest my clients build this practice into and across their teams and companies. As reported by Harvard Business Review, studies have found that ”employees who spend 15 minutes at the end of the day reflecting about lessons learned performed 23% better after 10 days than those who did not reflect”. This is which is why I call reflection a “high-leverage habit.”

At the broadest level, self-reflection examines how you showed up for yourself, your family, your team, your company, your community, etc. It can also be more specific and include questions around thoughts, feelings and behaviors you deem important for success and/or are working to improve. For instance, “how much time did I spend listening vs. speaking?“, “was I mostly directing and telling or asking and co-creating?”, or “was I mostly on offense/proactive or defense/reactive?”

Here are some ideas for self-reflection questions from industry and company leaders:

Marshall Goldsmith, Leadership Guru, promotes the following 6 Daily Questions:

1. Did I do my best to increase my happiness?
2. Did I do my best to find meaning?
3. Did I do my best to be engaged?
4. Did I do my best to build positive relationships?
5. Did I do my best to set clear goals?
6. Did I do my best to make progress toward goal achievement?

Steve Schlafman, Investor and Coach, recently shared his new reflection practice:

- What new thing did I do today?
- What worked well, what didn’t?
- What did I learn?
- What one thing will I do differently tomorrow?
- What am I grateful for?

Shivani Siroya, Founder/CEO of Tala, reflects on the following:

- What efforts/actions/people have contributed the most to my results?
- What efforts/actions/people consumed my time and energy but didn’t lead to results?
- How could I have been more focused and productive?
- What habits have been essential to my happiness, productivity, and energy?
- What can I learn from blindspots or unforeseen events that presented themselves?

The above are questions for you to examine and assess yourself. As a business owner and/or leader, you should also set frameworks and processes for reflection on specific projects and teams, as well as the overall organization. A simple way to kickstart a culture of reflection is to ask your team to share their weekly wins and weekly learnings every Friday. And, of course, share your own.

At this time of year, we suggest our FounderForward clients email the following questions to their team members and then hold a meeting to share and discuss answers. This can be done with teams all the way down the organization and/or can be done between managers and direct reports.

1. What was the best part of last year for you here at Company X?
2. What was the most challenging part of your year?
3. What did you learn?
4. What are you most excited about with regard to your role, team and/or the company overall in 2020?
5. What are 3–5 skills or behaviors you want to improve upon next year?

Another approach we like for incorporating team reflection on an ongoing basis comes from the Navy Seals. As shared by Daniel Coyle in his book The Culture Code, the Navy Seals use an effective tool called the AAR (After-action Review). The AAR process uses the following five questions:

1. What were our intended results?
2. What were our actual results?
3. What caused our results?
4. What will we do the same next time?
5. What will we do differently?

If you don’t already have a reflective practice in place, hopefully what you will do differently after reading this is start one. As the philosopher, John Dewey said, “We do not learn from experience, we learn from reflecting on experience.”

  • Download our FREE FounderForward Year-End Review Questions HERE!
  • Also, we are talking about goal-setting later this month so sign up for our newsletter HERE.

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Robyn Ward

Startup Coach/Company and Community Builder/Investor. Mentor@Techstars, BoD@Women Founders Network, Entrep Teacher@USC