From Checkbox to Conversation: Rethinking Annual Reviews
Oct 30, 2025
Written by Susan Kuepfer
Picture this: It’s November. Your inbox is full of reminders — annual reviews are due. You’re scrambling to find time, your team is anxious, and you’re already exhausted before the first meeting begins.
The problem isn’t the review itself — it’s how we approach it.
Most leaders make the same mistakes year after year. They schedule at the last minute, skip preparation, and mix performance feedback with development conversations. The result? Team members leave feeling unseen, leaders feel drained, and everyone treats it like a box to tick rather than a meaningful conversation.
But what if it could be different? What if annual reviews became one of your most powerful tools for building a high-performing team?
The Shift: From Evaluation to Contracting
So what’s the alternative? Instead of treating reviews as evaluations, think of them as "contracting conversations."
What’s contracting? It’s about designing the working relationship — getting clear on how you want to work together, what you need from each other, and how you’ll navigate the year ahead. Most leaders skip this step entirely. They jump straight to feedback and goal-setting. But without a clear contract about the relationship itself, everything else wobbles.
When you use annual reviews to contract with your team members — to design how you’ll work together — everything changes.
(Want to dive deeper into relationship design? Read more about the A.L.I.G.N.™ framework.)
Here are three practical shifts to make it happen.
Tip 1: Prepare to Design, Not Just Deliver
Common mistake: Spending prep time reviewing performance data and crafting feedback.
Better approach: Prepare for a conversation about the relationship, not just a monologue about performance.
Most leaders prepare by gathering evidence: What did this person achieve? Where did they fall short? What feedback do I need to give? That’s necessary — but it’s not enough.
High-performing leaders also ask: How did we work together this year? What worked? What didn’t? What does this person need from me that they’re not getting?
Before the meeting, reflect on these questions:
- What do I know about how this person works best? What don’t I know yet?
- How do we communicate? What helps or hurts our conversations?
- What impact is this person trying to have? Am I helping or hindering?
- What’s our exchange? Am I giving what they need — and are they getting what they need from me?
- What needs to change or continue for us to work better together?
Ask your team members to reflect on the same questions. When you both prepare this way, the conversation shifts — from delivering feedback to co-designing how you’ll work together for the year ahead.
Tip 2: Split Performance from Development
Common mistake: Trying to discuss past performance and future growth in the same conversation.
Better approach: Have two separate conversations — one week apart.
Mixing performance feedback with development planning creates confusion. Imagine spending 30 minutes discussing what someone did well and where they fell short, then immediately asking about their career aspirations. How open do you think they’ll be?
Not very. They’re still processing feedback, wondering how it affects their future.
Split the conversations instead:
Meeting 1: Performance Conversation
- Focus: What happened this year?
- Topics: Results, achievements, gaps
- Outcome: Shared understanding of performance
Meeting 2: Development Conversation (one week later)
- Focus: What’s next?
- Topics: Aspirations, strengths, growth areas, development plan
- Outcome: A contract for growth
When you separate these discussions, people can receive feedback without fear — and be honest about growth without judgment. You create space for both accountability and possibility.
Tip 3: Schedule a Year Ahead
Common mistake: Scrambling to find time weeks before reviews are due.
Better approach: Schedule annual reviews twelve months in advance.
It might sound ambitious, but here’s why it matters: when you schedule reviews at the last minute, you send a message that it’s not important. People feel that. They get anxious and wonder if the conversation will even happen.
When reviews are already blocked in your calendar for next year, it sends a different message: This relationship matters. Your development matters.
How to make it work:
- Schedule two separate meetings — one for performance, one for development
- Block preparation time for both of you
- Share your contracting questions ahead of time
- Ask your team member, “What do you want to focus on in our conversation?”
When you schedule with intention, you create space for real dialogue: not rushed, not squeezed in. Real.
The Paradox
The paradox of leadership is this: the more you try to control performance through evaluation, the less engagement you create. But when you consciously design how you work together, performance follows — built on trust, clarity, and shared purpose.
Annual reviews don’t have to be dreaded. They can be transformative: Prepare to contract. Split performance from development. Schedule a year ahead.
Three simple shifts. One powerful outcome.
You’re not just managing performance — you’re contracting for it.
Start Now

Open your calendar and schedule next year’s reviews. And... don't forget this year's reviews if not scheduled already 😁
Share your contracting questions with your team, and invite them to co-create what’s possible when reviews become real partnerships.
That’s how you turn pain into performance.