Self-reflection: How a Fun Approach Sparked Real Impact for My Team During Performance Reviews

Let’s be real: when most people think of performance reviews, the focus often lands on “proving worth” rather than celebrating growth. But as managers—and more importantly, as coaches of talent, we’re in a unique position to shift that mindset and make self-reflection a powerful, positive experience.

End-of-year reviews always seem to arrive just when things are at their busiest - annual planning, budget meetings, and finalising projects. It’s like all the year-end chaos conspires against that quiet moment of calm for self-review. With all the noise, my goal usually is to get my team to actually feel energised about their reviews, not bogged down by them. I want them to experience good vibes!

Make performance reviews inspiring, a time to reflect with pride and look forward with purpose.

So, in time of need, I flip the script! I put together a list of self-reflection questions that considered the personalities on my team and are worded in a way that would encourage honesty, break down big challenges into manageable pieces, and keep the process less about checking boxes and more about sparking growth, celebrating achievements, and creating meaningful dialogues between us. And yes, I even throw in a few cheeky questions to keep things fun, because I know that lot - they love a cheeky question. I call that 'the red pill' approach

And the Result?

A team that felt genuinely motivated and energised to dive into self-reflection. Let’s just say they loved it, so much so that I now feel on the hook to keep those fun questions coming! But hey, that’s a challenge I’m more than happy to take on.

Here’s how I brought my approach to life with my team—and how you can bring a self-review spark to yours, too.

Below is the actual message I sent them (minus all the emojis!). My goal wasn’t for them to answer every question but to get their minds moving and start crafting their own story. Keep reading to see why that makes a difference.

It’s time to celebrate your wins, reflect on your growth, and get ready to level up! Self-reflection isn’t just about ticking boxes—it’s a chance to own your journey, highlight your strengths, and show how you've evolved. Below are a few thought-provoking questions, and maybe a chuckle or two along the way to get you out of the self-review blues.

Best Practices for Self-Reflection:

1. Be Honest but Kind: It’s easy to focus on what didn’t go well. Flip the script—acknowledge challenges, but give yourself credit for overcoming them.
2. Highlight Wins, Big or Small: Every feature shipped, stakeholder managed, and experiment run counts. Show off!
3. Connect to the Bigger Picture: How did your work contribute to the team and organisational goals? You’re the glue that brings ideas to life! You are Product Managers!
4. Celebrate Growth: What skills have you sharpened this year? Where did you step out of your comfort zone?
5. Keep It Balanced: Share your wins and the moments where you learned (a.k.a. the not-so-wins). Both are equally important!

Reflection Questions to Get You Started:

1. Let’s start with a brag! What’s that one moment that still makes you fist pump?
2. What’s the proudest moment of the year for you?
3. What did you learn about your product leadership style?
4. Did you lean more into data-driven decision-making or focus on stakeholder management? Or maybe you found your inner product whisperer?
5. Where did you add the most value to your team or product?
6. Was it an epic feature launch? Solving that sticky user problem? Find your sweet spot!
7. What was your biggest challenge, and how did you handle it?
8. Channel your inner hero—what was your product kryptonite this year, and how did you conquer it?
9. How did you grow as a collaborator with cross-functional teams?
10. Reflect on how you worked with devs, designers, and stakeholders. Did you unlock some Jedi-level collaboration skills?
11. What risks did you take, and what did you learn from them?
12. Maybe a daring experiment or a bold product pivot? How did it pay off—or what did you learn if it didn’t?
13. What feedback did you get this year, and how did you apply it?
14. (Yep, the good stuff and the constructive bits!) Reflect on how you’ve taken feedback on board and improved.
15. What processes did you help improve or streamline?
16. Did you find ways to make the team more efficient? How did you improve communication or product delivery?
17. What new skills or tools did you pick up this year?
18. Any new shiny product tools or frameworks in your toolbox? If not, is there something you’d like to learn next?
19. What’s one thing you’d do differently next year?
20. What’s your product strategy for?you? What would you tweak for a more impactful year ahead?

LFG Team!!!!

But wait, there's more! Crafting a moment of honest, fun self-reflection didn’t happen overnight. I had to put in the groundwork all year long, building a culture of honesty, psychological safety, and genuine encouragement. Just tossing out a list of questions at year-end is not enough! If you want this moment to resonate, you’ve got to set the stage for it months in advance.

‘The only thing of real importance that leaders do is to create and manage culture’ , Edgar Schein

If you're just here for the questions, feel free to skip to the end! But if you're curious about how to make this happen, here's how I approached it.

1. Celebrate Progress, Not Justify Worth

One of the biggest obstacles in performance reviews is the feeling that team members have to “prove” their value to the company. This can turn self-reflection into a high-pressure exercise, and let’s face it—nobody does their best thinking under pressure. To overcome this, I shifted the focus from “proving” to “celebrating.”

Practical Tip: Encourage your team to start their review with questions that highlight achievements and growth. They can reflect on things like, “What was your proudest ‘nailed it’ moment this year?” or “What accomplishment made you say, ‘I deserve a high-five!’?” By beginning with positive self-recognition, the review becomes a celebration of what’s been achieved, not a justification of worth.

Best Practice: Set the tone for celebration well before review season. Create a culture where successes are regularly shared and celebrated, whether in team meetings or chat channels. When celebration becomes the norm, team members will approach self-reflection from a mindset of pride rather than defensiveness.

2. Make Self-Reflection Fun

There’s often a stigma that self-reflection must be a serious business. While it can be deep and introspective, there’s no reason it can’t also be engaging and enjoyable. I found that by adding a touch of humour, my team opened up more readily and reflected more honestly on their experiences. It gamified the storytelling, it broke down big questions into smaller ones. It felt achievable, not overwhelming.

Practical Tip: Encourage your team to think about their year as a story, not a report. Ask questions like, “If this year was a movie, what would it be called, and who would play you?” or “Describe a time when you turned a facepalm moment into a win.” Humour takes the pressure off and turns the process into a conversation rather than a formality.

Best Practice: Model this tone yourself. When sharing your own reflections or feedback, add a dash of lightheartedness to show that growth can be serious without being sombre. This “light but meaningful” approach makes reflection more accessible and authentic.

3. Create a Feedback Loop

Traditional self-reflection can feel like a one-way report rather than a conversation. When it’s treated as a “box to check,” it loses meaning and becomes just another task. To make it more meaningful, I always make sure it’s framed as a two-way dialogue, where feedback flows both ways. While self-reflection is a solitary experience, it is still a step towards a dialogue and that dialogue is not just with me as their manager/coach but also with the organisation as the support system for their growth and the playground for realising their value.

Practical Tip: When it comes to reviewing the self-reflection, use open-ended questions that promote dialogue rather than a list of achievements. Questions like, “What’s one area where you’d like more support?” or “What do you want to achieve next year, and what help do you need?” not only empower your team members but also make the manager a part of the journey. This collaborative approach fosters trust and makes performance reviews a platform for growth.

Best Practice: Check in regularly with your team throughout the year, not just at review time. By building a continuous feedback loop, you make the review a natural extension of ongoing conversations rather than a once-a-year event. Regular dialogue ensures that reflections are grounded in consistent support and engagement.

4. Turn Setbacks into Stepping Stones

Reflection doesn’t mean only focusing on the good stuff. It’s also about dissecting the struggles, learning from the challenges and deep honesty.

But instead of viewing challenges as failures, you can encourage your team to see them as stepping stones toward growth.

When we talk about what we’ve learned from difficult experiences, we shift the narrative from defeat to development.

Practical Tip: Normalise the conversation around challenges. Ask questions like, “What was a big challenge you tackled, and what did you learn?” or “What’s an ‘oops’ moment that taught you something valuable?” This perspective builds resilience and helps teams see setbacks as essential parts of their journey.

Best Practice: As a manager, share your own learning moments. By being open about your own setbacks and what you learned from them, you give your team permission to do the same. This openness builds a culture of trust and growth, where people feel safe to reflect honestly.

5. End with Vision and Goals, Not Just Evaluation

A powerful self-reflection should leave team members feeling excited about the future, not just reflecting on the past, or worse, not good enough. By ending the review process with forward-looking goals, you aim to empower your team to envision where they want to go next, turning performance reviews into springboards for the future.

Practical Tip: If they have done a great self-reflection which has become the base for a meaningful conversation during the performance review, it’s only right that you close by setting a collaborative vision for what’s next. Ask, “What are you excited to achieve next year, and how can we support you?” This question creates a shared commitment to growth and aligns individual aspirations with the team’s mission.

Best Practice: Encourage each team member to set “stretch goals” that challenge them to grow. When setting these goals, frame them as experiments rather than pass/fail objectives. This way, team members feel encouraged to try new things without fearing failure, creating a more innovative and growth-focused team dynamic.

6. Encourage Ownership and Empowerment

When self-reflection is done well, it empowers individuals to own their growth journey and take pride in their achievements. Rather than feeling like a top-down evaluation, self-reflection should be an opportunity for team members to step up, celebrate their own progress, and actively shape their future path.

Practical Tip: Empower each person to lead part of the reflection process. For example, invite them to identify key goals or development areas they’re passionate about, rather than only focusing on company-set objectives. Ask, “What personal or professional growth area excites you most for next year?”

Best Practice: Recognise team members as co-creators of their growth journey. Empower them by giving them flexibility and resources to pursue development in areas they’re passionate about. This builds motivation and ownership, making self-reflection not just a process, but a pathway to real impact.

Final Thoughts

Performance reviews shouldn’t feel like a burden or a defence of one’s worth. By flipping the script, we can transform it into a platform for growth, self-recognition, and meaningful dialogue. When self-reflection is fun, constructive, and forward-looking, it becomes a tool for empowerment for our teams, ourselves as leaders and our organisations.

As managers, we have the power to shape how performance reviews are perceived. Let’s make them inspiring, engaging, and something our teams actually look forward to.

Performance isn’t about proving worth; it’s about celebrating growth. When self-reflection shifts from defence to discovery, growth becomes a team culture—not a checkbox.

I believe that Leaders and managers hold a unique social responsibility: to care for and nurture the growth of their team members, regardless of the organisation they’re in. We have the privilege of guiding people’s journeys, and that, to me, means fostering skills, resilience, and confidence that stay with them even if they move on. When someone leaves our team, they should feel more empowered, more capable, and better prepared than when they joined. That’s the legacy of true leadership—investing in people so they’re equipped to thrive, wherever they go next.

Because when self-reflection is done right, it doesn’t just empower individuals; it strengthens the entire organisation.

A selection of questions that you might want to pass on to your team, or even try yourself!

1. What was your proudest “nailed it” moment this year? (Bonus: Were you tempted to high-five yourself?)
2. Describe a time you went above and beyond—like, “I deserve an extra-large coffee” beyond.
3. What’s one skill you mastered that could be added to your LinkedIn “Superpowers” section?
4. If your year was a movie, what would it be titled, and who would play you?
5. What project challenged you most this year, and how did you ninja your way through it?
6. Name one time you turned a “facepalm” moment into a “fixed it!” win.
7. What’s something you accomplished this year that, a year ago, you’d have said, “Yeah, that’s not happening”?
8. If you had an “employee highlight reel,” what would be your top three plays of the year?
9. What’s one “oops” moment that taught you more than you ever wanted to know?
10. What’s a new skill you picked up that you think would impress even your future self?
11. How did you help a teammate this year—and did it involve heroic amounts of coffee or snacks?
12. Describe a time when you saved the day. (Bonus: Did you feel like a secret agent?)
13. What’s one task you now do better than a “professional procrastinator” version of you would have thought possible?
14. If you could give your past self one piece of advice for this year, what would it be? (No time machines allowed!)
15. What’s one thing you tried this year that didn’t go as planned but was totally worth it?
16. What would be your “unofficial title” based on your best qualities? (e.g., “Master of Diplomatic Emails” or “Spreadsheet Ninja”).
17. What’s one area you’d like to improve next year, and what’s your battle plan?
18. If there were an award for “Most Unexpectedly Useful Skill,” what would you win it for?
19. What’s one goal you crushed this year—and can we assume there was a celebratory dance?
20. Finally, in three words, describe your year… now add a fourth word that gives it an extra spark!

Disclaimer: Remember, every team and organisation has its own unique vibe! This article isn’t about a one-size-fits-all, copy-paste approach. Use your best common sense, leadership judgment, gut feeling, and maybe a pinch of humour to figure out what resonates with your team. Adapt, experiment, and make it your own—because great leadership is all about knowing what works best for your people.

Got you thinking, feel inspired? ??

?? Hit like, drop a comment, and share it with your network! ????