Best Practices for Agile Strategy Workshops

This week, I facilitated my first-ever two-day workshop to build a value architecture for a company—a model connecting day-to-day actions with value. Here's how the process went: BEFORE THE WORKSHOP 1. After a discovery session, the company provided me a bunch of strategy artifacts; OKRs, previous launches, roadmaps, business model info, dashboard screenshots, strategy decks, competitive landscape, etc.. 2. We fed the business context into our business modeling AI to create three potential value architectures for the company: - A Business KPI tree that decomposed their primary revenue metric into its logical components. - A growth loop model focusing on the network effects in their business. - A North Star map that focused on cultivating their most loyal user profiles. THE WORKSHOP - DAY 1 - We discussed the concepts of how you can use value architecture to shift from an output-driven ("feature factory") way of working to an outcomes-driven orientation. - We reviewed value architectures from other companies, looking at diversity of examples from different industries and different types of models. - We reviewed the three models I generated prior to the meeting and discussed the merits and drawbacks of each one. - After the discussion, we decided that a business KPI tree model was the right place to start, given its explanatory power and alignment with the metrics they were already using. - We spent the rest of the day refining the model. The model I generated before hand was 70% on point, but there were a few structural elements and nuances that required iteration. THE WORKSHOP - DAY 2 - To test the value architecture we created on day 1, we added their previous OKRs and product bets to the canvas with their value architecture. We pressure tested the value architecture by using it to explain the rationale behind their previous bets. - The value architecture held up well, but it became increasingly complex as we added more influencer metrics to the canvas. For a moment I worried we were about to fall off a complexity cliff that would undercut the utility of what we had created. - So we simplified our value architecture to be the bare minimum model needed to contextualize their 2025 corporate objectives. - Instead of mapping individual bets and OKRs to the model, we took a step back and mapped their teams to the model. - The process revealed that 2 of their 3 corporate objectives required collaboration b/w multiple teams. - So we created nested value architectures for each goal. This allowed the top-level value architecture to stay simple, while allowing the teams to create more granular value architectures with inputs laddering up to each goal. - At the end, we had a multi-level value architecture with appropriate views for the executive- and team-levels of the company. Overall this was really fun and I'm excited to do more in-depth session like this in the future.

I didn’t like 90% of my time in offsite strategy sessions leading up to starting Stitch. Sitting in conference rooms hour after hour. No windows. Whiteboards. Markers. Set agendas. No flow. No thinking. No decisions. No priorities. No focus. Endless swirl. Yeah…90% of them sucked. We wanted something different with Stitch. So for the past year, strategy sessions have been unlike any strategy session I’ve ever experienced. And I’m never going back. Within a six-hour block, we make big decisions quickly. We say no to some things we are doing now. We move faster. We have focus. We actually have fun working in these sessions to better our business. What do they look like? Well. The high-level agenda is simple. We start with some prompt or question. This week it was, “What does Stitch ideally look like in three years?” From there, we get into a very generic guide for our conversations. Not a true agenda: • What is working?  • What is not working?  • What needs to change?  • What do we need to prioritize?  • Clear next steps and ownership of those action items While we obviously know what city the session will happen in, we don’t even decide until the night before where we will start the day. The point of this is that we want less predictability. And we don’t want to stay in one location. As the flow of our time together changes through the day, so does where we meet. This week the order ended up being: coffee shop > smoothie place > reserved room > beachside restaurant > coffee shop/brewery > wrap up over Mexican food. Some big decisions can happen quickly. Even over that first cup of coffee in the morning. Like really, really big decisions that we decide upon in minutes. Some other topics require more thought and processing. We may need to touch on a subject without a resolution three to four times across the day before we finally gain clarity. What makes these rather organic and unformed sessions work is the prep that goes into them. It’s not easy to show up without having any thought at all. The prep work happens in a document where we share topics, context, and ideas before we meet. We prep for positive and constructive reflection. Strenghts. Weaknesses. Opportunities. Threats. In all, we typically respond to 25 to 30 prompts we need to answer before meeting. These are not perfect sessions. Not every moment of the day is an eye-opening moment. But damn…these are powerful sessions. I always come out of them ready to execute with even more focus.

Your Agile ceremonies aren’t broken ↳ your facilitation is. It’s easy to start implementing Agile. ↳ It’s harder to lead conversations that drive results That’s the difference between an Agile Practitioner and a Strategic Facilitator. Here are 12 lessons from years in enterprise environments: 1. They Set a Great Agenda ↳ Keeps the meeting focused and goal-oriented. ↳ Aligns everyone from the start. 2. They Do In-Depth Research About the Topic ↳ Shows up with authority, not just curiosity. ↳ Anticipates challenges and steers with confidence. 3. They Find Out Who’s Attending ↳ Tailors engagement and language to the audience. ↳ Builds relevance and rapport. 4. They Set Appropriate Expectations ↳ Clarifies purpose, process, and outcomes. ↳ Prevents confusion and misalignment. 5. They Walk Through Meeting Norms ↳ Creates a safe and respectful environment. ↳ Encourages productive participation. 6. They Interrupt Ramblers ↳ Protects time and focus. ↳ Keeps the discussion meaningful. 7. They Handle Naysayers with Grace ↳ Manages resistance constructively. ↳ Maintains psychological safety and flow. 8. They Bring the Meeting Back on Track ↳ Refocuses when things drift. ↳ Anchors discussion to the objectives. 9. They Ask Participants to Keep Moving ↳ Maintains momentum and engagement. ↳ Prevents stagnation and fatigue. 10. They Speak with Confidence ↳ Commands attention and earns trust. ↳ Sets the tone for decisiveness. 11. They Don’t Lose Their Calm ↳ Models composure under pressure. ↳ Defuses tension and keeps energy stable. 12. They Close with a Summary and Clear Outcomes ↳ Reinforces clarity and accountability. ↳ Ensures everyone leaves with shared understanding. In complex Agile environments, facilitation isn’t soft skill work. It’s executive function. And if you’re leading SAFe, Lean Portfolio Management, or enterprise-level PI Planning, then strategic facilitation becomes your edge. Not every coach has it. Not every leader values it. But the ones who do? Move faster, with less friction. If your leadership sessions feel like checkbox meetings instead of transformational touchpoints. It’s time to upgrade your facilitation game. I help tech execs lead these moments with precision and presence. Book a conversation: DM me.