How to Connect OKRs to OSTsDear Reader, OKRs (Objectives and Key Results) help you measure strategic progress. OSTs (Opportunity Solution Trees) are a visual structure for connecting solution and problem spaces to business goals. Let me break down how the layers of an OST connect to the practices of OKR drafting and execution: Layer 1: The Outcome Teresa differentiates between business outcomes, product outcomes, traction metrics to sit in this level. The goal is to provide orientation for the exploration of the problem space. As defined here, the Desired Outcome best connects to the Key Result you'd find in company- or department-level OKRs:
So, if you feel lost in your OSTs, it comes from a lack of strategic specificity in your higher-level OKRs. Remember: Goals are not a strategy. There needs to be a strategic intent to form actionable OKRs. Other narratives would call this level of metrics also an Impact. Representing a higher-level business interest. Layer 2: The Opportunities Opportunities emerge from understanding the problem space a customer experiences. Compared to layer 1, OKRs don't inform the filling of this layer, but are informed by it. When you understand a specific customer problem space like "Updating our shift planning availability manually creates a high error rate," you can perform what I like to call a positivity flip to describe how customers, whose problem got solved, behave differently, which you can use to design Outcome-focused team-level Key Results: High error rate from manual data input → Increase shift planning automation by x%; Reduce error rate in shift planning to 1 per customer per week Layer 3: The Solutions Solutions are outputs. The activities or artifacts you provide to solve a customer's problem and drive the team-level KRs. The connection between Outputs and OKRs can be two-fold:
Note: Output OKRs are a crutch for you to use on your way to steering through measuring changes in customer behavior. They're more useful than staring at lagging metrics without change, but not an indefinite state. Layer 4: The Experiments Similar to solutions, experiments are executed to increase the chances of success of your solutions. So, they serve the OKRs, but aren't informed by them. You should align the priority for executing an experiment with the progress you want to make in your OKRs (rather than purely chasing opportunistic ideas). Alternatively, you could temporarily steer experiment-focused behavior through team OKRs to cultivate experimentation: Number of A/B tests run OR Pre-order revenue generated. But the same caveat as for Output OKRs applies. Next week, I'll translate the fundamentals of this connection to changes you might see in the context of building AI products and using AI to accelerate your work. Thank you for Practicing Product, Tim As a Product Management Coach, I guide Product Teams to measure the real progress of their evidence-informed decisions. I focus on better practices to connect the dots of Product Strategy, Product OKRs, and Product Discovery. |
1 tip & 3 resources per week to improve your Strategy, OKRs, and Discovery practices in less than 5 minutes. Explore my new book on realprogressbook.com
Product Practice #418 The Essence of Every Mapping Technique PUBLISHED Jul 24, 2026 READ ON HERBIG.CO Ways we can work together 1️⃣ Order my book: Real Progress: How to Connect the Dots of Product Strategy, OKRs, and Discovery, which readers call "a practical guide you can return to again and again." 2️⃣ Join my Workshop From Staring at KPIs to Prioritizing with OKRs, in 6 Hours, for turning generic dashboard metrics into useful goals, helping you prioritize and measure your work. 3️⃣ Join...
Product Practice #417 User Outcomes are Positively Flipped User Problems PUBLISHED Jul 17, 2026 READ ON HERBIG.CO Dear Reader, Last week, I mapped how OKRs connect to the layers of an Opportunity Solution Tree. But especially the Outcome layer deserves its own issue: turning a customer problem into a team-level Key Result. I first wrote about it in 2023, before I had a name for it. Since then, the positivity flip has become one of the most-used tools in my OKR and Discovery workshops, so...
Product Practice #415 Accelerated Context and the Validation Sparring Partner PUBLISHED Jul 3, 2026 READ ON HERBIG.CO Dear Reader, Most of the AI conversation in product management right now is either describing doomsday scenarios, exaggerated improvements, or warning about what might go wrong. But I am more interested in what changes for product teams doing real work. When a product team adopts an AI tool, what specifically changes about their day? What benefit do they keep coming back for,...