25-Day Calendar of Leadership Reflection Questions
Soft, restorative prompts to help you and your team slow down, reflect, and lead with intention—no matter the season.
We originally shared these prompts as our "Winter Wayfinding" series in December. We didn't want to encourage everyone to be online during the holidays. We knew that rest is personal and that the right time for reflection is simply when you are ready.
Whether you are navigating a busy season, recovering from burnout, or just looking for a way to ground your team, these questions are designed to be a "little nod or hug from a supporter."
This collection offers 25 days of introspection alternating between "For You" (personal leadership grounding) and "For Your Team" (collective culture building). You don't have to do them in order or in a single month. Treat this as a library of moments to pause, breathe, and reconnect with the human side of leadership.
The Wayfinding Markers
Each of the prompts below links to its original visual card. Click on any day to open the visual—feel free to screenshot it, save it for your own reflection, or drop it into your team chat to spark a gentle conversation.
Slowing Down & Grounding
Day 1 (For You): What’s one thing your mind or body is asking you to slow down on this week? Take one unhurried breath before answering.
Day 2 (For Your Team): Where do you feel stretched thin right now, and what’s one small support that would make things feel lighter?
Day 3 (For You): What’s something you’re carrying from the past year that it may be time to gently set down?
Day 4 (For Your Team): What’s one ritual or habit that helps you recharge? How can we honor that more?
Day 5 (For You): What’s one thing you’re proud of from this week or month? Let it be small, steady, or quietly meaningful.
Growth & Boundaries
Day 6 (For Your Team): What’s one small win from the past week you want us to pause and celebrate? Remind the team that growth often happens underground.
Day 7 (For You): Where in your life or work do you feel the need for clearer boundaries?
Day 8 (For Your Team): What’s one thing we can remove, simplify, or stop doing to reduce pressure?
Day 9 (For You): Which relationships or collaborations nourished you recently? How can you nurture them in return?
Day 10 (For Your Team): What’s one creative spark or curiosity you haven’t had space to explore yet?
Energy & Rhythms
Day 11 (For You): What quality of rest is your body actually craving? (Quiet, movement, solitude, or laughter?)
Day 12 (For Your Team): If work felt 10% more spacious this month, what would that allow you to show up for?
Day 13 (For You): Which emotions or stories feel ready to be honored, acknowledged, or released?
Day 14 (For Your Team): What’s one thing you wish more people understood about the way you work or think?
Day 15 (For You): Where does your energy naturally rise right now? Listen to your natural rhythms.
Connection & Care
Day 16 (For Your Team): What is one boundary you want to protect? How can we support you in upholding it?
Day 17 (For You): What do you want to remember about yourself as a leader right now?
Day 18 (For Your Team): What is something you’ve learned that you are grateful to have mastered, even if it was challenging?
Day 19 (For You): Where do you need gentleness rather than grit right now?
Day 20 (For Your Team): What’s one way our team can create a little more warmth, connection, or care this month?
Looking Forward
Day 21 (For You): What’s one moment of beauty or stillness from the past week you want to hold onto?
Day 22 (For Your Team): What’s something you’d like to express appreciation for—in yourself, someone else, or the team as a whole?
Day 23 (For You): If you step back and look at your year like a landscape, what did the valleys and peaks teach you?
Day 24 (For Your Team): What intention do you want to carry forward for how you work, lead, or collaborate?
Day 25 (For You): What do you want to leave behind, and what do you want to carry forward with care into the next season?
We hope these prompts serve as a signal fire for you—a place to return to when you need warmth, direction, or a moment of pause.
We’d love to hear which days resonated with you or how your team responded to these moments of reflection. Drop us a message on our LinkedIn page or let’s connect directly—we’ve got your back if you want to chat through what’s going on for you.
