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
🛠️ How to predict the future of your OKRs (and why it matters)
How to predict the future of your OKRs (and why it matters)Dear Reader, Ever sat in an OKR review meeting feeling like you're just going through the motions or reporting without meaning? You're not alone. As a Head of Product, I've been there too. But what if I told you there's a way to make your OKRs truly useful for decision-making? Let's dive in. The power of predicting the futureOne of my favorite ways of helping teams pressure-test their OKRs is by trying to predict the future. I want them to think about the answer to “Imagine a check-in 4 weeks down the road. With whom will you look at these OKRs and discussion emerges from looking at the changed values and confidence?” This is similar to a premortem exercise. By predicting the future, teams can anticipate how useful their OKRs are for making decisions. Why typical OKRs fail the "check-in-ability" testLet’s use one of the first (documented) KRs I wrote as a Head of Product 6+ years (don’t judge me): KR1: Understand 'feature' map of product status quo and compare with user expectations. KR2: Develop design guiding principles for product simplification. Imagine a check-in four weeks down the road: A: “How are we doing on KR1?” B: “I think we better understood the feature map.” A: “Ok, by how much?” B: “I think would put the confidence at 80%".” A: “But…why?” B: “Because it still feels on track.” A: “And KR2?” B. “We have scheduled a first meeting to discuss the design guiding principles. So, I estimate the progress to be about 20%.” A: “Will you do anything differently based on the progress of these KRs?“ B: “No, I think everything works according to plan.” A:
How would you rate the check-in-ability of these KRs? Spoiler: NOT GREAT. They can neither demonstrate real progress nor guide a conversation about priorities. But fixing KRs like these by just adding numbers would be too short-sighted. After all, how check-in-able is a KR with a number, if you can’t influence it, if it’s too lagging, or if it’s a generic KPI? Predicting the future of your OKRs isn't about being psychic. It's about understanding what they will help you do differently later, so they can be more useful now. Did you enjoy this one or have feedback? Do reply. It's motivating. I'm not a robot; I read and respond to every subscriber email I get (just ask around). If this newsletter isn't for you anymore, you can unsubscribe here. Thank you for Practicing Product, Tim What did you think of this week's newsletter?
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. |
Product Practice Newsletter
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 #416 How to Connect OKRs to OSTs PUBLISHED Jul 10, 2026 READ ON HERBIG.CO Dear 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...