Part 2: How to Lead Your Team Through a “Wins, Losses, and Lessons” Reflection

Last week, we talked about the power of pausing at the end of the year to remember what God has done, to celebrate the people who faithfully carried the mission, and to honestly acknowledge what stretched us. This kind of reflection doesn’t just close a year; it strengthens a team’s heart for the work ahead.

But knowing why reflection matters is only the beginning. This week, let’s walk through how to lead your team through a meaningful “Wins, Losses, and Lessons” session.

Whether your team meets in person or gathers virtually, this process can become one of the most unifying moments of your year.

1. Set the Tone With Intention

Reflection cannot be rushed. Before your meeting begins, open with prayer and a scripture-based reflection. This can help center your team’s hearts, remind them of God’s faithfulness, and prepare them for honest conversation.

You may also choose to send the questions and worksheet to your team ahead of time so each person has space to think, pray, and prepare. When people come with hearts already softened by reflection, the conversation becomes deeper and more meaningful.

Encourage your team to approach the time with:

• Honesty

• Grace for themselves and others

• A posture of gratitude

When expectations are set gently, people open their hearts more freely.

2. Start With the Wins: Celebrate God’s Faithfulness

Ask your team to begin by sharing their wins, not numbers, but stories. Provide space for each person to share moments when:

• They sensed God’s presence in their work

• A small victory made a big difference

• Someone on the team showed unexpected compassion or strength

These stories often spark laughter, tears, and a renewed awareness of God’s provision. Celebrating wins reminds your team that their work, seen and unseen, matters deeply.

3. Acknowledge the Losses: Create Space for Honesty

Every ministry year includes difficult moments. Missed goals, unexpected challenges, emotional exhaustion, none of these should be carried alone.

If your meeting is virtual, intentionally slow the pace. Allow pauses after each person speaks. Silence gives others permission to reflect more deeply.

As a leader, model vulnerability. When you name losses without blame, others feel safe to do the same. Losses are not necessarily failures, they’re often markers of growth, resilience, and faithfulness in more difficult situations.

4. Identify the Lessons: Turn Reflection Into Growth

This is where reflection becomes transformation.

Invite your staff, volunteers, and board members to share:

• What this year taught them

• What adjustments could strengthen the ministry moving forward

• What practices they want to carry into the new year

When participants receive the questions ahead of time, they often uncover deeper insight instead of surface-level responses. And in virtual meetings, prepared reflections help ensure every voice is heard.

Lessons often emerge from unexpected voices—new team members, quiet contributors, or those carrying unseen burdens. Make space for all.

5. Close With Encouragement and Vision

End the meeting by speaking life over your people, whether they’re seated around a table or showing up courageously through a screen.

Affirm:

• Their faithfulness

• Their resilience

• Their impact

• God’s continued presence

Remind them that every step of the mission, every intake, every conversation, and every private prayer, has eternal value.

Offer a word of hope for the year ahead. Encouragement fuels energy, and energy fuels mission.

6. Make Reflection a Rhythm, Not a One-Time Ritual

A single gathering is powerful, but consistent reflection is transformational.

Consider adding a a brief “Wins, Losses, and Lessons Moment” throughout the year. Just 10 minutes once a quarter can:

• Build gratitude

• Prevent burnout

• Strengthen communication

• Keep the mission centered

  
  

Reflection is not a pause from the work, it’s part of the work.

As You Lead …

Whether your team is at one table or spread across screens, your leadership creates the environment for meaningful, Spirit-led reflection. Your willingness to slow down and guide your team through this process may be one of the most life-giving gifts you offer.

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If you would like to access to a sample Wins, Losses and Lessons worksheet to get you started, send me a DM or and email and I will send one your way! ehale@lifeadvancementgroup.org