A Leader’s Guide to Pausing & Reflecting: Lessons from the High Holy Days

  • Post category:General
You are currently viewing A Leader’s Guide to Pausing & Reflecting: Lessons from the High Holy Days

I married into Reform Judaism 27 years ago. All of it was new to me: shabbat dinners, Hebrew school, and prayers in a different language. But one aspect that I happily adopted immediately was observing the High Holy Days.

These are the 10 days book-ended by Rosh Hashanah and Yom Kippur. The purpose of this time is to pause, reflect on our actions and impact over the past year, and commit to doing better. Some people use the term “High Holidays” but I prefer the term “High Holy Days” used by many Reform Jews to distinguish the personal and introspective aspect of this time as compared to the communal celebration that the term “holidays” connotes. I love the ancient wisdom that humans need a specific time of the year to intentionally pause, take stock and set an intention to be a better person. Even back in the olden days, people were caught up in the day-to-day busyness of life.

The idea that the High Holy Days come around every fall also fits well with our modern secular schedule of starting a new school year, and the rituals of getting fresh notebooks, school clothes and schedules.

But once we start working and are no longer in school, for most of us the year becomes a big blur. Sure, there is looking forward to summer and the holidays, but how often do we really pause, reflect and recommit to being some version of our best selves? As leaders, we have a responsibility to ourselves and to those around us to periodically step back and look at our life and work from a higher altitude, to be intentional about how we spend our finite time and energy. When does that happen for YOU?

One of the hallmarks of an exceptional leader is that they lead with intention. What do we mean by that? It’s about leading with purpose, with presence and with care. Some of the core behaviors we look at when assessing leaders in high impact roles are whether they are able to:

  • Remain energetic and confident during the rollercoaster of successes and disappointments
  • Maintain composure under pressure
  • Have presence and positive impact when dealing with others
  • Evaluate competing priorities and make balanced decisions
  • Actively listen to both verbal and non-verbal cues
  • Recognize when it is time to shift direction

These capabilities require clarity about our purpose and priorities. They require resiliency and presence. They require the ability to “choose our response,” as Viktor Frankl once said. They require pausing to free us from the reactive “stimulus-response” autopilot that runs so much of our typical day.

It is very hard to choose our response when we are stressed out, reacting to the latest request and committing to far more than is humanly possible in the finite hours of our day. It is hard to choose the right response when we aren’t clear about our purpose as leaders and the priorities that will truly move our teams and organizations forward.

So what can we do to be more deliberate about our impact?

  1. Schedule the time to pause and reflect. Take a day or half a day annually (I prefer fall, but others like January, their work anniversary or a birthday).
  2. Get out of the office and away from Slack and email and consider:
    1. What are your top 3-5 priorities for the next 6 months?
    2. Who are the people you need to set aside time for?
    3. How are you currently spending your time? (Try reviewing your calendar for the past month)
    4. What meetings can you delegate, cancel or redesign for higher impact?
    5. What impact do you want to make as a leader, at this time and place?
  3. Now get your team together. Use the time to discuss, debate and decide on priorities and ways of working. Also to play and connect. In-person time is too precious for report-outs. Anything that can be done asynchronously has no place in a team agenda anymore. Use the time together to pause, reflect and commit to your priorities and to each other.

We just had a company offsite last week in San Francisco. It was a collective team pause. We picked just three topics for a 1.5 day agenda, starting with our top priorities for the final quarter of the year. Because we didn’t overpack the agenda, we had plenty of space for discussion, creativity and fun (including sharing a reflective moment about our accomplishments from the past year inside a yurt! ). We also linked our offsite to a client event to keep our focus on the purpose of our work. We returned to our remote offices refreshed and reconnected.

In addition to these major pauses of individual and team offsites, we need more frequent mini pauses. Some leaders do this on Sunday evening. I prefer Friday afternoon to set myself up intentionally for the following week. Our team does this on Monday morning. The point is to look at our purpose and priorities for the week. It’s a deliberate pause to ensure that we are using our most valuable resources, our time and energy, on what really matters.

This season let’s make our work intentional. Let’s make the time to reflect and recommit to being the most impactful leaders we can be.