Start Strong: The Ultimate ‘Prepping’ Checklist for Your Next AI Design Sprint™ Workshop to be Successful.

Does this ring a bell?

“I still remember the very first workshop I helped organise. The excitement was palpable, teams buzzing with curiosity, decision-makers eager for quick wins. But there was a problem: the group walked in without a crystal-clear goal and incomplete data. As you can imagine, that caused some confusion.”

That’s precisely why preparing for an workshop is so important. A little groundwork can mean the difference between a chaotic session and one that yields practical, measurable outcomes.

Below, I’ll share the steps and best practices that have consistently helped clients approach these AI Design Sprint™ workshops with confidence.

We’ll also explore how OKRs (Objectives and Key Results) can keep your team laser-focused on what truly matters.

Why Preparation Really Matters

Planning for an AI Design Sprint™ isn’t just an administrative detail, it’s the foundation for a successful workshop. The methodology itself brings structure and rapid prototyping to the table, but only if everyone is on the same page.

• Well-defined goals: You don’t want vague ambitions like “automate something” or “improve efficiency”; you need a tangible aim.
• The right participants: Too many voices can derail progress, but too few means missing crucial insights.
• Aligned data strategy: AI is only as strong as the data you feed it. Weak or disorganised data kills momentum.
• Shared understanding of OKRs: Having a north star lets teams see why each workshop step matters, aligning short-term sprints to bigger business wins.

With proper groundwork, your sprint won’t get stuck in endless debate or overshadowed by unrealistic expectations. Instead, you’ll have a focused conversation that leads to actionable results.

1. Pinpoint Your Core Challenge (and Tie It to OKRs)

Align your sprint goal with broader business objectives.

Ask yourself, “Which aspect of our business needs AI-driven automation right now?” and “How does this align with our OKRs?” For instance, if your Objective is to “Boost Customer Retention,” your Key Result might be “Reduce churn from 10% to 7% by year-end.” An AI Design Sprint™ could address a specific pain point, like personalising support interactions or automating routine follow-ups, directly influencing that target.

In practice, this makes sure your sprint isn’t just about experimenting with AI for AI’s sake, rather, it’s about making a meaningful contribution to your team’s established Key Results. By explicitly linking the workshop’s focus to a Key Result (like a churn metric), you sharpen everyone’s sense of purpose from the outset.

2. Gather the Necessary Stakeholders

Balance expertise with efficiency.

You’ll want:

• A project sponsor/decision-maker: Ideally someone who tracks or owns the OKR you’re aiming to impact, ensuring they can champion results post-sprint.
• Subject matter experts: They understand the nuances of the user problem and the data you plan to use.
• A technical or data expert: Crucial for spotting feasibility issues early on.
• The facilitator: Often, this is a certified AI Design Sprint™ facilitator who keeps the session moving and ensures each voice is heard.

Aim for a group that’s diverse but purposeful. If the OKR is about reducing churn, having someone from the customer success or retention team would be highly relevant. This not only bolsters the depth of discussion but ensures better follow-through once the sprint concludes.

3. Conduct a Data Inventory (with OKR Relevance)

Clarify what data drives your Key Results.

AI solutions thrive on the right inputs. If your Key Result is “Reduce order-processing time by 30%,” gather data on order volumes, processing steps, and any customer feedback data on delays. Before your sprint:

• Identify relevant data points: Which metrics best reflect progress toward your OKR?
• Check data quality: Are there gaps or inconsistencies?
• Review ownership and compliance: Ensure privacy or regulatory hurdles won’t block you mid-sprint.

Doing this groundwork prevents you from designing an AI feature that’s impossible to support because the necessary data isn’t clean or available.

4. Define Success: From OKRs to Sprint Metrics

Translate big goals into sprint-level goals.

OKRs are typically broader and time-bound over months or quarters. Within your AI Design Sprint™, you’ll need a more immediate success metric. For example:

• OKR: “Reduce churn from 10% to 7% by Q4.”
• Sprint Metric: “Implement a feature that personalises account follow-ups and test with 10 beta users to measure a 15% increase in usage.”

By anchoring your sprint success in a real, measurable outcome, like improved user engagement, you keep everyone accountable to something tangible. This helps the team feel confident that they’re not just brainstorming but working toward a real result.

5. Map Out Workshop Logistics

Eliminate scheduling and tech roadblocks early.

• Dates and timing: Traditional sprints can span four or five days, though variants exist. Ensure participants block calendars.
• Location or platform: Whether virtual or in-person, make sure everyone is comfortable with the tools (sticky notes or digital whiteboards).
• Pre-reads and materials: Provide a brief introduction to the AI Design Sprint™ structure, any relevant data dashboards or research findings, and an outline of your OKRs so participants arrive informed.

The more seamless the logistics, the easier it is for attendees to dive straight into creative problem-solving.

6. Consider Ethical and Data Privacy Boundaries

Spot potential pitfalls before they derail your sprint.

If your AI solution touches user data, you’ll want to set or revisit guidelines around:

• Bias and fairness: Could the model disadvantage certain user groups?
• Data handling: Who can access sensitive data, and how is it anonymised?
• Brand trust: Are we transparent about how AI interacts with user information?

Walking into the workshop with clear guardrails means no one panics halfway through upon realising they don’t have permission to use a certain dataset.

7. Prepare the Right Tools and Resources

Equip your team with a collaboration toolkit.

From personal experience, having the following can accelerate the process:

• AI Design Sprint™: Process Automation Canvas© to structure the day.
• AI Cards© and GenAI Cards© to spark creative brainstorming about how AI might fit into different workflows.
• Data Sources Cards© for quick reference to data sets that might power your AI solution.
• OKR or scoreboard visual to keep the session anchored in your strategic goals.

Simple as they are, these resources ensure you don’t lose time re-explaining the sprint flow or data sources.

8. Set Clear Expectations on Deliverables

Emphasise that it’s a sprint, not a full build.

While you can prototype an AI-driven solution or produce a technical brief, you won’t come out the other side with a fully polished AI system. The sprint’s purpose is to validate ideas, assess feasibility, and produce a plan aligned with both user needs and your OKRs. Approaching the workshop with this mindset prevents frustration when people realise they’re not launching a final product on day five.

OKRs in Action: A Brief Example

Let’s say your company has an Objective to “Elevate the Customer Support Experience.” A supporting Key Result might be “Reduce average resolution time from 48 hours to 24 hours by the end of Q2.”

1. Core Challenge: You define a sprint around automating the initial ticket triage—where simple requests can be handled by an AI-driven chatbot.
2. Stakeholders: Pull in your Head of Support (owns the OKR), a data specialist (knows ticket data), and a subject matter expert on FAQs.
3. Data Inventory: You confirm you have reliable transcripts of past support tickets, plus relevant user feedback.
4. Sprint Metric: Build a prototype AI chatbot that can handle at least 50% of FAQs correctly, reducing queue time for agents.
5. Logistics: Two-day workshop, meeting room booked, data sets vetted.
6. Ethical Boundaries: Decide the chatbot should never handle legal or financial queries without human review.
7. Resources: The AI Design Sprint™: Process Automation Canvas© and a Slack channel for real-time collaboration.
8. Deliverables: At the end, you have a tested chatbot prototype that can classify queries and answer top FAQs. You also produce a technical brief explaining how to train it further, plus a roadmap for integrating it into your existing support platform.

This neat alignment means your AI Design Sprint™ doesn’t float in a vacuum; it’s embedded within a bigger vision of improved customer support and ties directly to key targets.

Wrapping It Up

By linking your preparation steps to clearly defined OKRs, you add an extra layer of focus and accountability to your AI Design Sprint™. Instead of “cool AI” ideas floating around, your team can see exactly how this work contributes to the company’s bigger picture, whether that’s lowering churn, boosting customer satisfaction, or streamlining internal processes.

Ultimately, a great sprint starts long before day one. It begins with assembling the right people, clarifying data, aligning on goals, and ensuring your ethics and privacy considerations are sorted out. If you do all of that, you’ll walk into the workshop ready to create a prototype (or technical brief) that truly moves the needle.

For Companies

If you’re eager to see real ROI from AI initiatives and align them with tangible OKRs, an AI Design Sprint™ is the perfect launchpad. As a certified facilitator, Jacobus van Niekerk from CATICS , I can help you map out exactly how AI can serve your unique business goals. Want to learn more? Simply comment “Workshop Ready,” and I’ll get in touch to discuss how we can shape the sprint to align with your strategic objectives.

For Aspiring Facilitators

If you’re excited about running your own AI Design Sprints™ by 33A led by Michael Brandt, and maybe even weaving OKR thinking into the mix, why not take the next step? Consider joining a specialised boot camp for AI Design Sprint™: Products & Services or Process Automation to learn the ropes. Unsure if you’re ready for the deep dive? Try an AI Design Sprint™ Experience Session first. Just drop “Facilitator Ready” below, and I’ll DM you a special link and coupon code.