Finish Strong to Start Strong: Reflection with Intention

As leaders help their teams finish the year strong, pressure ramps up quickly to align on new goals, new expectations and new priorities for the year ahead. In the rush to ‘get ahead’ there is one step most managers skip, miss or forget: Taking time for intentional reflection.

For new, emerging and seasoned leaders, REFLECTION is one of the most powerful tools that you have. Slowing down long enough to understand what worked (and what didn’t) creates clarity, confidence and intention for the year ahead.

Why reflection matters (more than people think)

When done well, reflection can help:

• Celebrate wins & successes and recognize your team

• Sharpen your priorities

• Prevent repeating the same issues next year

• Understand what motivated or drained your team

• Create alignment and reduce misunderstandings

• Make the planning for next year more smooth and realistic

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If you haven’t done a reflection exercise before or aren’t sure where to start, read below for a simple, 4-step framework to guide you through this important practice

Step 1: Start with your own reflection (30-60 minutes)

Before you invite your team into a reflection conversation, spend time doing it yourself. Ask yourself a few questions and be honest with yourself about the answers:

• What went well this year? What am I most proud of?

• What do I wish I had done differently?

• Where did I feel clear? Where did I feel overwhelmed?

• What external factors impacted our results? Where did we get in our own way?

• Where did we miss our goals? Why did we miss them?

• What patterns am I noticing in my leadership? In my team?

Write your answers down and don’t overthink it. Honesty matters more than being polished. This self reflection will become your anchor as you lead your team through the same process

Step 2: Lead a reflection exercise with your team

Choosing the right format for your team will depend on a few different factors to make it effective. Reflection with your team can be as simple as a 10 minute activity or as in-depth as a half or full day session together.

Choose the right format based on:

• Team size

• Trust level within the team

• Overall workload & bandwidth

Formats to consider:

• 10-20 minute team session (use an existing team meeting or schedule as a standalone meeting)

• A 60 minute standalone meeting (recommended)

• A half or full-day off-site/on-site

• A series of shorter conversations across the week (not recommended)

While this can be done in shorter sessions if needed, I recommend starting with a designated 60 minute meeting to allow you and your team time to go through this exercise thoughtfully and without feeling rushed. Some people take time to process and think before they are ready to share and you want to create an environment where your team feels safe to share as they are ready. Attempting to do this across several short discussions throughout the week will likely see it get deprioritized and lose momentum due to the discussion being interrupted several times

Remember: the format matters less than the intention behind it. If you can only dedicate 10-20 minutes, that is better than nothing. Send your team the questions in advance so you can have a more focused and efficient discussion when you meet together live.

Step 3: Use a simple reflection framework

When facilitating this discussion, you don’t need anything complicated or overly formal.

Prompts/Questions for reflection:

• What worked well this year and what are we proud of?

• Of the things that worked, what do we want to keep doing next year?

• What didn’t work well? What slowed us down or caused frustration?

• What should we stop doing because it no longer adds value?

• what do we want to change or do differently in the year ahead?

Another way to frame these questions is the classic Start/Stop/Continue framework:

• START: What should we begin doing?

• STOP: What no longer helps us that we should stop doing?

• CONTINUE: What is working well that we don’t want to lose?

To make this more actionable and specific, ask these questions of each area of your team separately:

• Our team (communication, culture, routines)

• Our work (output, processes, priorities, tools)

• Our cross-functional collaboration (how well we partnered with others, which partners were difficult or easy to work with)

Breaking the discussion and reflection down this way helps go deeper, brings specificity and helps create clarity in the true opportunities to address.

Step 4: Lead the conversation with neutrality and curiosity - keep an open mind

This part is crucial. If you want honest reflection, your team needs to feel safe to share without repercussion.

This means:

• Stay neutral

• Don’t get defensive

• Don’t explain decisions in the moment

• Listen deeply and ask clarifying questions

• Don’t fix issues or provide solutions as issues are raised

Your role during this session is simple:

• Ask Questions

• Listen

• Facilitate the dialogue / encourage sharing

• Take notes

If someone says something that is hard to hear, try responding with:

• “Tell me more about that” or “Can you elaborate on that?”

• “Can you help me understand what made that challenging?”

• “What do you feel would have made this easier"?”

The safer the room feels, the more insight you will get and the better your team will be at working together and with you to achieve your goals

Once you have completed the exercise with your team, gather and review all of your notes. Identify themes and start to prioritize areas to address in the short term or long term. Share this information with your team, gain their alignment on the prioritization, and look for volunteers and leaders to help drive solutions to any of the areas of opportunity that came up.

The goal of reflection is CLARTITY

Reflection isn’t about dwelling on the past. Its about understanding it well enough to lead your team with confidence in the future.

When you take time to reflect with intention, you simplify your focus, stop carrying over unnecessary work or burden, you gain alignment and build trust.

Your next steps

1. Block time over the next few days to complete your own reflection exercise and give yourself enough time to be thoughtful, honest and intentional.

2. Decide how you want to facilitate a reflection exercise with your team

3. Let your team know you will be scheduling this and walk them through the framework and the questions so that they can start to think about their answers in advance. Some people struggle to come up with this in the moment so giving them a preview in advance will allow them to do their own personal reflection ahead of time.

4. After you have facilitated this with your team, be sure to send out notes that include a summary of themes, priorities and next steps. Follow-up and follow-through are the next most important things you can do to be intentional with how this reflection will influence your growth as a leader and as a team

If you can get in the habit of doing this with your team at least 2x/year or 1x/quarter, you will create an environment where voices feel heard, problems get solved, and performance excels. You will be seen as a confident, intentional and valuable leader and you will be teaching your team how to lead well.