10 OKR prompts to flag risks early and prepare leadership reports

If you're a chief of staff or a manager, you already know the drill.

Someone has to make sense of all the OKR data before the leadership meeting. Someone has to chase updates, spot the risks, and turn a mess of check-ins into a clear story for the exec team. That someone is usually you.

AI Mode won't change your job. But it will cut the time you spend on that part of it. All the synthesizing, report-writing, the "wait, what's actually blocked right now" moments can be done or answered in seconds.

You'll find here 10 examples of prompts that you can use with Tability AI Mode.

What's AI Mode?

AI Mode is a conversational interface built directly into Tability. It's connected to your actual OKR data (objectives, key results, check-ins, initiatives, and owners) allowing you to interface with your team activity by using prompts instead of clicking around the app.

You can ask it to build a plan, write a report, surface risks, or create a custom view. It responds the way a knowledgeable colleague would.

The practical difference between using AI Mode vs. using ChatGPT or Claude:

• Zero setup required: anyone with a Tability account can start using AI Mode – no need to setup the MCP server.
• Way faster: AI Mode is already scoped to your workspace and has direct knowledge of Tability's data model. This means that you get better and faster answers
• Creation tools: with AI Mode you can create new OKR plans, views, and retrospectives

Describe what you need and AI Mode does the work. Most requests take a sentence. Most responses take seconds.

📝 Reporting prompts for OKRs

1. Generate a cross-team retrospective

Can you write a retro combining the Sales and Product OKRs? I want a summary of each objective with your own assessment (🔴 off track, 🟡 at risk, 🟢 on track) and your rationale for your assessment. Give your highlights and lowlights, and what the SLT should focus on.

Writing a retro that actually reflects what happened — across multiple teams, multiple objectives — normally means hunting through check-ins, chasing updates, and trying to synthesise everything into something leadership can act on.

This prompt does that synthesis for you. It pulls the picture together, adds a clear status for each objective, and tells the story in a format your leadership team can read in five minutes. What used to take an hour of wrangling can happen in a single prompt.

2. Create custom views in Tability

Create a view of all in-progress KRs that are off track or at risk

Standard dashboards show you everything. That's often the problem — you need to know what's actually on fire right now, and who's responsible for it.

This prompt cuts straight to what matters: blocked work, grouped by owner, with enough context to have a useful conversation in your weekly review. It's the kind of view that used to require a dedicated ops person to build manually, and now it takes a sentence.

3. Draft your weekly OKR report

Draft my weekly OKR update. Include wins, risks, changes since last week, and top priorities for next week. Keep it concise and leadership-friendly.

Stakeholder communication is important. It's also one of the first things that slips when you're busy — and when it slips, people start wondering what's actually happening with the quarter.

This prompt turns your existing check-in data into a clean update you can send with confidence. The structure is already right: wins, risks, what changed, what's next. You edit it, add your voice, and hit send. The hard part is done.

4. Run a pre-mortem on your quarter

Pretend it's the end of the quarter and we missed our top 3 objectives. Based on our current KRs, check-ins, and initiatives, what most likely went wrong? List the biggest risks now, early warning signs to watch, and the top 5 actions we should take this week to avoid that outcome.

Most risk conversations happen too late — after the quarter is already slipping. The pre-mortem flips that. You're not waiting to see what goes wrong; you're asking the question before it happens.

This is probably the highest-leverage prompt in the list. It forces an honest read of where you are versus where you need to be, surfaces the risks that are easy to rationalise away, and gives you a concrete action list for this week. It's uncomfortable in the best way.

5. Prepare for exec Q&A

Act as an exec reviewer and ask me 10 tough questions about our OKRs. Then suggest strong, data-backed answers.

A practical way to pressure-test your narrative before leadership reviews — not to polish the story, but to find the gaps in it.

🔮 Prompt to prepare the next quarter

6. Create an OKR plan from scratch

Help me create an OKR plan for Q2 for the [Team Name] team. Our priorities are [priority 1], [priority 2], and [priority 3]. Propose 3 objectives with 2–4 measurable key results each.

The blank page problem is real. You know roughly where the team needs to go, but translating that into well-formed objectives and measurable key results is where most planning sessions get stuck.

This prompt skips that friction. Give it your priorities and it gives you a structured draft — complete with initiatives and a first look at risks you might have missed. You won't ship it as-is, but you'll spend your team's time reacting and refining instead of staring at an empty template.

🔥 Prioritisation prompts

7. Prioritise when time is limited

If I only have 2 hours this week to improve overall OKR health, what should I do first? Rank by impact and urgency.

Useful when you need to be ruthless about where you spend your attention.

8. Practice de-prioritisation

If we had to cut 20% of current initiatives today, what should we pause first and why? Protect KR impact.

Helps teams stay focused on outcomes, not just staying busy.

Better questions lead to faster answers and clearer decisions. That's the unlock.

If you're already tracking OKRs in Tability, these prompts are one of the fastest ways to turn the data you're collecting into something you can actually act on.

❤️ Bonus prompts

9. Find what to celebrate

What are the top 5 achievements from this week across all objectives that we should celebrate publicly?

Great for all-hands, Slack shout-outs, and keeping momentum visible when teams are heads-down.

10. Ask questions in your own language

¿Cuáles son los objetivos que están en riesgo este trimestre y qué deberíamos priorizar esta semana?

AI Mode works in whatever language you think in. If your team operates in French, Spanish, Portuguese, or anything else, just ask in that language and you'll get a response in kind.

No switching tools, no translating updates. Your OKR data, in the language that's most natural for your team.

How to try AI Mode

1. Go to https://tability.app/signup
2. Create an account and start a trial
3. Run the prompts

Every new Tability workspace ships with sample data. You can use it to test all these prompts.