Reflection Rituals Every Leader Needs in January

“If only I had time to pause and reflect” responded a collaborator to the idea of a reflection & goal-setting activity around the upcoming New Year. And honestly, that reaction is common. When we’re moving fast, reflection is often the first thing to slip off the calendar.

But what happens when we don’t take the time to reflect on what’s working and what isn’t? We stick with unhelpful habits. We allow interpersonal friction to build and fester. And we miss out on opportunities sitting right in front of us.

The New Year season is a natural prompt - a moment to step back, reset, and make intentional adjustments before the next wave of work begins. Reflection doesn’t have to be heavy or time-consuming; it just needs to be done.

Here are three simple reflection activities to consider this season:

1: Team Retrospective

A strong team builds a habit of periodic retrospectives for adjusting their approach and learning from their collective experiences. The New Year is a good time to start and aim to do it again every 2-3 months or meaningful seasonal shift.

Gather the team that works closely together - your leadership team, a functional team, or a product-focused pod - and focus the conversation on a recent period of time (the past quarter, the few months since a prior milestone, etc.). The format isn’t what matters; you can use a whiteboard, Post-it notes, or a shared Google doc, just begin the conversation.

There are dozens of team retro formats, and they often get at the same general themes:

• Identify what worked well - a great opportunity to appreciate your colleagues for their efforts or point out an action you’d like to see become a habit. If someone did something helpful, and you celebrate it, they’ll be more likely to continue to do it.

• Identify what was missed - where did some action not happen or some information wasn’t shared or some opportunity was forgotten? How can you spot and fill the gaps in your processes?

• Identify new learning - what trends did you notice? Is there a change in the ecosystem or the underlying assumptions such that you need to change approaches? Did you get actionable results from a recent experiment in your ways of working?

By including these three areas, not just finding what didn’t work, you can positively reinforce the good things and find adaptations for what could be improved.

Wrap up the session by identifying action items or explicit experiments you can try.

Remember: any action item must have a single owner who is on the hook for making that change. Set a reminder to check in on these actions or experiments in a few weeks to see what’s making a difference.

2: Systems Review

Does it feel like your tools are telling you what to do instead of the other way around? Tools and systems have a way of accumulating, each brought in to solve a particular problem, but their overlap in capabilities means you may have multiple tools covering the same needs.

Start by mapping what tools you use, who owns them, and how information flows between them. What’s missing or being done in a tool that you’ve outgrown? Are you still using a Google Sheet as a CRM? Are new employees unable to find SOPs because they’re haphazardly stored?

Then look beyond the tools themselves and examine the habits around them. Even the best tracker (Asana, Trello, Jira, etc.) ceases to be useful if half of the team doesn’t keep their tasks updated. If there aren’t processes or habits around how work gets input and updated, the tool isn’t actually helping bring a shared understanding of the work.

Lastly, look at the costs - have you been adding “seats” to a subscription as your team grows and suddenly a low-cost tool has a large monthly bill? Review your team’s tools to identify what is contributing value and what is just draining resources. What new challenges in 2026 will require new or different systems? Set aside the time and budget to review, remove, or upgrade accordingly.

3: Individual Reflection

Self-reflection is important, and not just when you’re prompted to populate an end-of-year performance review. Sit down with a nice cup of tea (or glass of wine, I won’t judge) and ponder these questions:

• What areas of your work bring you satisfaction or even joy? A favorite frame for this question in my coaching is “when were you so in the zone that you forgot to eat lunch?” Note: this rarely happens to me, as my stomach growls loudly enough to break focus, but the sentiment is right.

• What areas of your work sapped your energy? What activities did you procrastinate on so hard that you did all sorts of other nonsense to avoid them?

Then ask yourself how you might shift the balance toward the joyful and away from the energy-sapping. Can you take on more of the energizing work? Delegate the draining pieces? Redesign responsibilities to better match your strengths? What new opportunities do you want to take on this new year?

And don’t forget accountability! Who can help you succeed in your goals in 2026? Setting up accountability structures can make the difference between a nice idea and an actual change.

Bringing Intention into the New Year

Reflection and adaptation don’t require a blank calendar or a week-long retreat, just intention and a little space. The New Year simply gives us the nudge many of us need. By taking time to look back, adjust what isn’t serving you, and step into 2026 with more clarity, you’re setting your team, your systems, and yourself up for a stronger year ahead.

About the Author: Tiana Veldwisch is a tech team consultant, fractional product manager, and coach to tech leaders in the climate and sustainability space. She coaches individuals in job transitions and growth moments and supports growing technology teams in collaboration, communication, work habits, and trust, co-developing interventions, workshops, offsites, and more. She has an engineering degree from Olin College and an MBA from MIT, and currently lives and works in the Boston area.