Embracing Reflection and Possibility This Holiday Season

As the year winds down and festive lights illuminate our homes, it’s the time of year when we take time off for the holidays to spend with family and friends. It’s also when quiet introspection and reflective thinking can bring fresh insights and perspectives.

For example, my wife and I have a New Year’s Day morning tradition. Over coffee and the quiet hum of a new year, we talk about the year that was and where to focus our time, effort, and attention in the year ahead. One of these discussions reshaped my career trajectory, leading to one of the best decisions of my life.

This personal tradition mirrors my work with clients—unlocking potential through purposeful questions and reflection. I aim to help clients become better versions of themselves. Whether it’s an individual leader, leadership team, or organization, there’s always potential for growth and improvement. To paraphrase the Beatles, sometimes we need a little help from our friends.

So, in the spirit of taking time to rest, reflect, and recharge over the holiday season, here are some questions to stimulate your reflective thinking:

1. How do others perceive me, and how do I wish to be perceived?
2. What kind of culture am I creating and encouraging—one that prioritizes personal accomplishments or celebrates collective contributions?
3. How do I currently show up for my stakeholders—customers, employees, peers, investors— and how do I want to show up?

Pondering these questions helps us break free from the shackles of our expertise and usual way of operating. When things are going well, we are less likely to question why, reimagine what could be, and experiment. They also help us understand where our focus should lie and chart the next steps toward personal and professional growth. And they illuminate our brand perception. Remember, your brand is what others say about you when you’re not in the room.

As you navigate this season of rest and rejuvenation, consider embracing the power of possibility:

• What if you could align what you’re known for with what others value, elevating your leadership impact?
• What if creating a culture of contribution over credit could amplify your team’s performance?
• What if showing up authentically for your stakeholders opened doors to opportunities you’ve only imagined?

The answers to these “what if” questions could redefine our trajectory in the coming year. So, as you reflect during this holiday season, dare to ask yourself: What if the best version of me is just one thoughtful question away?

Let’s unlock better—together.

– Kevin

P.S. Thanks for reading, sharing, and offering your thoughts on the Whatif? Wednesday Thought Letter over the past year. It’s genuinely appreciated. We’ll be back in the new year.