Making OKRs Operational - Cadence, Reviews, and Leadership Behavior
Keith Johnson Keith Johnson

Making OKRs Operational - Cadence, Reviews, and Leadership Behavior

Most OKR systems don’t fail during planning. They fail once the quarter starts.

Pressure builds, priorities collide, and leaders begin making exceptions that feel reasonable in the moment. Over time, alignment erodes. OKRs stay effective when cadence, reviews, and leadership behavior reinforce focus and intent. Execution exposes whether alignment was ever truly in place.

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OKRs as an Alignment System, Not a Goal-Setting Exercise
Keith Johnson Keith Johnson

OKRs as an Alignment System, Not a Goal-Setting Exercise

Alignment doesn’t fail because teams lack goals. It fails because intent and tradeoffs are unclear.

OKRs only create leverage when they operate as an alignment system that connects strategy to daily decisions. Strong objectives represent explicit strategic bets. Key results show whether those bets are paying off. When OKRs are treated as a reporting artifact or layered on top of misaligned priorities, they add noise instead of clarity. Alignment starts with structure, not ambition.

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OKRs as a Product Alignment Tool
Keith Johnson Keith Johnson

OKRs as a Product Alignment Tool

Most product organizations don’t fail because teams aren’t working hard. They fail because strategy doesn’t travel. OKRs only create alignment when they define shared outcomes and act as a decision filter across product, sales, and execution.

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Measuring Portfolio Health and Strategic Success
Jennifer Jaffe Jennifer Jaffe

Measuring Portfolio Health and Strategic Success

In Parts 1-3, we explored why roadmaps fail, how three-horizon thinking creates advantage, and the operational systems that make it work. Now we tackle the final critical piece: measurement, communication, and the compound competitive advantages that make all this effort worthwhile. Here's how to prove your portfolio strategy is working—to your board, your team, and yourself.

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The Three Horizons: Reframed for Scale-Ups
Jennifer Jaffe Jennifer Jaffe

The Three Horizons: Reframed for Scale-Ups

The hardest part of three-horizon thinking isn't understanding the concept—it's defending strategic capacity when everything feels urgent. In Part 3, we tackle the organizational reality: how to maintain portfolio discipline when customers are demanding Horizon 1 features, how to structure teams across different horizons, and how to avoid the four pitfalls that kill most strategic initiatives.

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Why Your (Standalone) Roadmap is Failing You
Jennifer Jaffe Jennifer Jaffe

Why Your (Standalone) Roadmap is Failing You

Your product roadmap looks impressive. It's packed with features your customers want, capabilities your sales team needs, and improvements your engineering team knows are necessary. You're executing well, shipping consistently, and hitting your quarterly commitments. So why does it feel like you're falling behind strategically? If you've achieved product-market fit but can't seem to build lasting competitive advantage, the problem isn't execution—it's how you think about your product portfolio.

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Want Your New Team or Leader to Succeed? Start with Clarity.
Keith Johnson Keith Johnson

Want Your New Team or Leader to Succeed? Start with Clarity.

Most teams don’t stumble because the new hire wasn’t good. They stumble because no one aligned on why the team exists or how it connects to the rest of the company. Add a new function without clarity, and people start guessing. That guesswork slows everything down.

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From Features to Focus: Getting Back to Why We Started
Jennifer Jaffe Jennifer Jaffe

From Features to Focus: Getting Back to Why We Started

Few product teams set out to become feature factories. It happens slowly, even accidentally. At first, you’re solving real problems. There’s energy, clarity, a nearly singular purpose. Then the roadmap starts to splinter. Stakeholders get louder. Metrics get fuzzier. And before you know it, you're shipping work without being sure why it matters.

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How to Sequence Tech Debt vs. New Features
Keith Johnson Keith Johnson

How to Sequence Tech Debt vs. New Features

Few topics spark more tension between product and engineering than the balance between addressing tech debt and delivering new features. Product wants to ship value fast. Engineering knows the cost of ignoring debt. When these priorities collide, roadmaps stall, trust erodes, and both teams feel unheard.

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Turning Sales Losses Into Roadmap Opportunities
Keith Johnson Keith Johnson

Turning Sales Losses Into Roadmap Opportunities

Every lost deal tells a story. Too often, product teams dismiss sales objections as noise or excuses. In reality, they are one of the most underutilized sources of product insight. The problem is that most companies lack the structure to separate valuable patterns from one-off complaints.

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Creating Feedback Loops Without Derailing the Roadmap
Keith Johnson Keith Johnson

Creating Feedback Loops Without Derailing the Roadmap

Feedback is the lifeblood of great products. Sales hears objections in the field. Customer success sees adoption challenges firsthand. Executives bring insights from investors and the market. Every team has valuable input. The problem isn’t getting feedback—it’s managing it.

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