Prepare for your best year yet with 150+ team reflection prompts

‘Tis the season for reflection and planning with your team

December 15, 2021Yellow Squiggle

Reflection gives us an opportunity to both look back on what happened and think about (and name) where we want to go in the future. Through this process, we identify where we’ve focused our time and energy, what was and is important to us, and what we’ve learned.

When we come together with our team and share our reflections, we seize the opportunity to build alignment, identify and prioritize shared goals, and recognize ways to work better together. That’s one of the reasons we recently led a Lead Time Live workshop on the practice of reflection, where Range VP of Engineering Jean Hsu and co-founder Jen Dennard facilitated a reflection exercise with attendees.

Now is an ideal time to set aside synchronous, in-person (virtual) meeting time with your team to reflect on 2021 and begin planning for 2022. Projects are wrapping up, there are potentially fewer meetings on everyone’s calendar, and many of us have an appetite for more connection. But it won’t be too late to get to this important task even after the new year begins.

To help you and your team jumpstart the process of looking back and looking forward, we’ve created a resource full of reflection questions. Read on for a preview of what’s inside.

Download 150+ Reflection Questions for Teams

All the prompts you need to kick off your best year yet

Reflect, share, and prepare for the new year

This eBook of reflection questions was designed to help teams plan for the new year by looking back at the previous year.

For teams, this is a great opportunity to wrap up the year, reset, realign, and get everyone on the same page as you set off to make the most of a new year.

For managers who will be creating new goals and OKRs, leading your team through personal reflections, team reflections, and reflections for leaders (we’ve actually divided the over 150 questions into these three sections) will be incredibly helpful. The process will allow you to further elicit feedback from your team so you can better plan according to their needs and goals.

Sample questions and prompts

In each section, you’ll find a series of questions and prompts intended to help you look back at what’s happened this year. As a follow-up, you’ll see additional questions designed to guide you a level deeper.

Here are a few sample questions from inside the eBook:

(1) Share an example of a personal risk you took this year that paid off.

  • What worked about this particular risk? How might you apply what you learned from that experience to future situations?

(2) What's a skill you have gained confidence with in the last year?

  • From your perspective, what was the source of that growth in confidence? Was it internal or external? A shift in your mindset or actions? A combination?

(3) Share an example of a misunderstanding you had in the past year.

  • What helped you resolve it?

(4) During busy moments throughout the year, how did you choose what to focus on?

  • Would you change anything about that approach?

(5) What’s 1 risk your team took together this year that paid off?

  • How did you decide to take that risk? Why do you think the risk worked so well for your team?

Tips for using the reflection questions

There are a lot of questions within this eBook, but don’t let that deter you! In each section, you’ll find questions designed to help you look back on what happened in the past year and uncover learnings and themes from these experiences.

Here are some quick tips to help you set expectations for yourself and your team (we’ll go into these more inside the eBook):

  • You don’t have to answer everything
  • Embrace vulnerability and honesty
  • Go with your gut
  • Think big and small
  • Carve out dedicated time
  • Be gentle with yourself and others

Download 150+ Reflection Questions for Teams

All the prompts you need to kick off your best year yet

As you and your team head into the new year, we hope the questions in this eBook help you arrive at a deeper understanding of what to focus on next to grow as individuals and as a team.

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Prepare for the new year: 150+ reflection questions for teams
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