Making OKR Check-ins Work: A Practical Guide to Weekly Progress Review

Created

Oct 17, 2025 3:05 PM

Finding Your Rhythm: Weekly vs. Monthly

For quarterly OKRs, I always recommend a weekly check-in cadence. It provides just enough frequency to maintain momentum without becoming burdensome.

For annual goals, monthly check-ins typically suffice.

The key is consistency → pick a schedule and stick to it. At Leave a Mark we run them on Mondays at 1PM

The Five-Part Agenda That Actually Works

After years of refinement, I've found that effective OKR check-ins follow this simple but powerful structure:

1. Quick Reporting

Start with facts, not stories. This isn't about listing everything you've done → it's about what's actually changed since the last meeting. Focus on learning, not actions.

Pro tip: Require everyone to update their Key Results before the meeting.

No updates? No speaking privileges.

This might sound harsh, but it ensures everyone comes prepared and respects the team's time.

2. Review of Confidence

Here's where things get interesting. Ask everyone to show with their hands (on a scale of 1☝🏻- 5🖐🏻).

How confident they are that each Key Result will be achieved by the end of the period?

Then-and this is crucial-ask those with the lowest scores to explain why.

This simple exercise does something remarkable: it gets everyone engaged and surfaces concerns that might otherwise remain hidden. Silent doubts become visible, actionable insights.

3. Obstacles

When progress stalls, name the blockers explicitly. This is where OKRs reveal their collaborative power. Often, you'll discover that Team A is stuck because they're waiting on something from Team B-who may not even realize they're the bottleneck.

Remember: OKRs are about working together, not working in silos. This section brings interdependencies into sharp focus.

4. Actions

Transform obstacles into action steps.

Who needs help?

What can we do as a team to unblock progress?

Be specific about owners and timelines. Vague commitments lead to vague results.

5. Closing

Summarize all action items and take a final confidence vote on the Objective as a whole. This gives everyone a clear picture of where we stand and what comes next.

Tips and Tricks I’ve learned along the way

Through countless check-in meetings, I've learned what separates engaging, productive sessions from painful obligation.

Here are the game-changers:

Rotate the Facilitator

Don't let the same person run every meeting. Rotating ownership helps team members understand the full picture and feel collective responsibility for OKRs. You only truly understand the system when you have to guide others through it.

Make Confidence Visible

The hand-voting technique isn't just theater → it's psychology.

Making confidence levels physically visible encourages honesty and prevents the "everything's fine" syndrome that plagues so many status meetings.

Focus on Outcomes, Not Output

This is perhaps the hardest shift for teams to make. OKRs measure whether you're moving the needle, not how busy you've been. Train your team to answer one simple question: "What help do I need with this Key Result?" rather than reciting their to-do list.

Prioritize the Biggest Blockers

Time is limited. Spend it where it matters most. If everything is important, nothing is.

The Three-Strike Rule

If a Key Result shows no progress for three or four consecutive meetings, you have a problem. Either it wasn't a good KR to begin with, or there's a systemic blocker that needs escalation. Don't let zombies lurk in your OKRs.

The Truth About OKRs

Here's what nobody tells you about OKRs: they're supposed to be uncomfortable.

If your check-ins feel too easy, you're probably not pushing hard enough or being honest enough about progress.

The discomfort comes from transparency. From seeing clearly whether your organization's actions match its ambitions. But this discomfort is productive. It drives change, forces mid week prioritisation, and ultimately leads to better results.

The difference between OKRs that transform organizations and OKRs that become shelf-ware often comes down to the quality and consistency of these check-in meetings.

Make them count.

Get in Touch with me if you want to talk about your OKRs or Strategy Execution

Chris Kobylecki

Cofounder of Leave a Mark

Chris builds magical experiences that help people to excel.

He focuses on strategy and team development. Applying his decade long experience of Venture Capital & Private Equity Firms