No One Taught You How to Do This
Most leaders didn’t choose leadership—they earned it.
They were great at their work, dependable, trusted. Then one day, the role shifted. Less doing, more leading. Suddenly they’re expected to guide performance, support growth, and have conversations that don’t always come naturally. We see this often, especially in organizations and communities where relationships matter deeply and leadership carries more weight.
Leaders care about their people—but that can make performance conversations feel heavier, more personal, and easier to avoid. So, performance planning gets treated like an annual task. A form. A conversation you brace for once a year. But that’s where things break down.
Performance Planning Shouldn’t Be an Event
When performance is only addressed annually, it creates pressure for you and your team.
It often looks like this: you sit down for the annual review, knowing there are things that should have been said months ago. Now, everything feels bigger, heavier, and harder to explain.
Annual reviews often feel difficult because they’re trying to do too much, too late. By the time you get to the conversation, the opportunity to support real change has already passed.
- Goals feel disconnected from the actual work happening day-to-day
- Feedback comes too late to make a difference
- Reviews feel more like judgment than support
What we’ve learned is this: performance works best when it becomes a rhythm, not a moment.
Instead of relying on one annual review, we use a 12-week rhythm:
- Set clear, realistic goals together
- Check in consistently
- Use week 13 to reflect, reset, and move forward
It can be as simple as agreeing on one or two priorities for the next 12 weeks—something that will have a meaningful impact on a behaviour the employee is working on.
I often ask, “What’s one thing we can focus on that would make your day-to-day work easier or more effective right now?”
Then it’s about checking in briefly every few weeks and having a clear conversation at the end about what worked and what didn’t.
It removes a lot of the guesswork, reduces pressure, and makes performance something you build together, not something you evaluate after the fact. It builds trust and it treats people like individuals—because no two growth paths should look the same.
This Is What Leadership Actually Looks Like
Most leaders aren’t struggling with performance planning because they don’t care; they’re struggling because no one ever taught them how to do it in a practical, human-centered way. It isn’t about having the perfect template. It’s about knowing what to say, what to do, and how to follow through. In many organizations, leadership is deeply relational. Performance planning needs to reflect that by balancing accountability with respect, humility, wisdom, and a clear understanding of community impact.
That’s exactly why we created our Leadership Fundamentals Training Program.
It’s designed for leaders who want real tools they can use immediately:
- A framework to set meaningful expectations
- A model for ongoing performance conversations
- A practical approach to supporting growth without losing accountability
Our next Leadership Fundamentals cohort starts in September, and it’s built for those who want to strengthen leadership in a way that reflects their values, their people, and their community.
Because when leaders are supported, performance planning stops being a task and starts becoming part of how your organization grows. Leadership isn’t built in an annual review—it’s built in the consistency of clear expectations, honest conversations, and follow-through.
And that’s where real impact starts.
This piece was shaped with some AI support, alongside our experience working with leaders in real organizations.
From the Owl Insight team and lead collaborator: Lisa Isaac, Founder/CEO, Senior HR Consultant
Lisa.Isaac@OwlinsightHR.ca
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Blog Photo by: Zyanya Citlalli - Unsplash
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