The Two Critical Discussions Missing From Your OKR Workshops
It's planning season again. Whether you're wrapping up annual planning or preparing to kick it off in January, there's one thing I keep seeing in leadership team OKR workshops that makes me nervous:
Having the wrong conversations.
After facilitating countless OKR sessions both as a Chief of Staff and now as a workshop facilitator, I've noticed that even the best-run workshops often skip two critical discussions. These gaps can mean the difference between OKRs that drive real change and ones that look great on paper but fall flat in execution.
Let me show you what I mean.
The Reality Check Discussion
Here's a scene I see play out often:
The leadership team comes together, energized, and ready to set ambitious goals. They prioritize challenges, align on metrics, and maybe even map out tactical steps. Everyone leaves feeling good about their objectives.
Then reality hits.
A week later, those carefully crafted OKRs start to feel... disconnected. Leaders find themselves caught between "business as usual" and these new strategic priorities. The enthusiasm fades as they realize they haven't actually figured out how to change the way they operate to achieve these goals.
The problem isn't the goals themselves – it's that we skipped the reality check discussion.
This discussion needs to center on one key question: Are we setting idealistic goals that sound good, or are we identifying the actual changes we need to make in how we operate?
Think about it like this: If your company is struggling financially, should every function really have its own independent OKR? Or should every team be focused on the one thing that matters most – financial health?
The reality check discussion forces us to:
Ground our objectives in what the business truly needs right now
Identify what needs to change about our current operations
Focus on fewer, more impactful goals instead of trying to improve everything at once
The Resource Alignment Discussion
The second missing piece is what I call the resource alignment discussion. Here's what typically happens:
Each functional leader comes to the workshop thinking about their area first. Marketing focuses on marketing goals, sales on sales goals, and so on. Even when these goals align on paper, we're missing a crucial conversation about how teams will actually work together to achieve them.
The truth is, no functional leader can achieve their OKRs alone.
Sales needs marketing's help. Marketing needs product's support. Product needs engineering's resources. And everyone needs people ops and finance to make it all possible.
When I was a Chief of Staff, I learned to facilitate a specific pre-OKR discussion where leaders would:
Share their proposed objectives with peers
Explicitly state what support they'd need from other functions
Have direct conversations about resource trade-offs and compromises
This process often led to something interesting: instead of having six separate functional OKRs, we'd end up with three powerful, cross-functional objectives that multiple leaders would own together.
Why These Discussions Matter
Skip these conversations, and you risk:
Setting "set and forget" OKRs that look good but don't drive change
Creating siloed objectives that don't leverage your team's full capabilities
Missing critical dependencies between functions
Failing to address what's truly holding your business back
Making It Work
Here's how to incorporate these discussions into your next OKR workshop:
Before setting any objectives, have the reality check discussion:
What's actually keeping us up at night?
What needs to fundamentally change about how we operate?
What's the one thing that matters most right now?
Before finalizing OKRs, have the resource alignment discussion:
What support would you need from other functions to achieve this?
What compromises are we willing to make?
How might we combine our capabilities in new ways?
Remember: The goal isn't to have a perfect set of OKRs that cover every aspect of your business. The goal is to identify the critical changes you need to make and ensure your entire leadership team is aligned on how to make them happen.
The Bottom Line
Your leadership team OKRs shouldn't just match your org chart. They should reflect the real challenges you need to tackle and the actual way your teams will work together to tackle them.
Don't skip these discussions. They might feel uncomfortable or messy, but they're essential for turning your OKRs from impressive-looking slides into real organizational change.
Need help facilitating these crucial OKR discussions with your leadership team? Let's talk about how I can help →
