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Strategy Development

In most organizations, long-term strategies (spanning months or years) are owned by senior leadership. Regardless of title, many leaders contribute to shaping strategy, whether at the company, division, or product level. Leaders have to figure out how the work of their teams pays into larger strategic objectives. Understanding a strategy and communicating what this means in terms of plans or tradeoffs is a crucial leadership activity on any level.

The recommended resources on this page focus on strategy fundamentals, what good and bad ones look like, and how to create an effective strategy. An effective strategy doesn’t try to please everyone - it forces tradeoffs, clarifies priorities, and reduces decision fatigue at every level of the org (see ⚖️Decision Making).

Objectives and key results (OKRs) deserve a special mention here due to their popularity and frequent misuse. OKRs are a goal-setting framework used to translate strategy into measurable outcomes and track execution over time. They help teams align around what success looks like, but they don’t define what to pursue or why. OKRs are sometimes seen as a synonym for strategy, although they are better described as a strategy deployment tool. You will find one of the very best yet brief OKR primers below.

Recommended Resources

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WTF is Strategy: Vince Law offers one of the best metaphors to introduce the topic of strategy and how it connects with a vision or an organization’s execution. He humorously shares how you can technically “start driving” without a strategy, but that thoughtful strategies clarify the key decisions and preferences that align a team. (8 min read)

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Crossing the River by Feeling the Stones: Simon Wardley shares one of the most compelling yet vulnerable leadership stories focusing on strategy. He introduces many complicated concepts, personal stories, and a visualization technique called Wardley Mapping. If you enjoy this kind of content you can also read his free e-book on Wardley Mapping, but this content is technically complex and not aimed at leaders who are just getting started with strategy. (51 min watch)

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Notes from “Good Strategy / Bad Strategy”: Jeff Zych shared his notes on Richard Rumelt’s seminal book. I keep sharing with folks who are interested in strategy as Jeff doesn’t just summarize key points with a crisp description of the kernel of strategy. He also shares personal experiences and anecdotes throughout that provide real-world examples that may be a bit more relatable than Rumelt’s examples in his book. (10 min read)

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What is Good Product Strategy: Melissa Perri offers both a crisp strategy primer as well as a tool for product strategists - the product strategy canvas. She wonderfully lays out typical roles and responsibilities in larger organizations and gives concrete examples to keep things measurable when it comes to objectives or descriptions of current versus desired future states. (6 min read)

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How to Define Your Product Strategy: Gibson Biddle with a free twelve-part series on creating a compelling product strategy. While this adds up to a much longer read, he manages to break things into smaller chunks and always adds examples from his impressive career as a founder and product leader at Netflix and Chegg. So, how will your product delight customers in hard-to-copy, margin-enhancing ways? (45 min read)

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How to Write a Strategy Statement Your Team Will Actually Remember: Effective strategies don’t have to be long, especially considering your team should remember them when they’re busy executing, making decisions rapidly. Try these “X even over Y” statements to spell out preferences and clarify tradeoffs in simple words. If these statements end up sounding like boilerplate and like they could apply to any of your competitors, give it another try. (3 min read)

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The Art of the OKR, Redux: Christina Wodtke gets the prize for “best free OKR primer” that I could find on the internet. Derived from management by objectives (Peter Drucker) and popularized at Intel and later Google, objectives and key results are the most popular way for organization’s to deploy their strategy today. Christina doesn’t just explain the basics, she also describes various ways OKRs are used incorrectly today. (13 min read)

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Team-Level OKRs in 7 Steps: Ben Lamorte doesn’t waste time re-explaining what OKRs are, but rather gives tactical advice for any leader who wants to create coherent OKRs for their team. If you’ve accepted the fact that objectives shouldn’t be filled with business metrics, most of your planning will go towards key results. Ben’s advice to avoid tasks as key results, challenge whether KR sets achieve the respective objective, and refining key results systematically will absolutely improve your OKR quality. (8 min read)

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OKR Examples & Resources: John Doerr’s team curates an OKR database in the spirit of his bestselling book “Measure What Matters”. While some of these don’t meet the quality bar laid out by Christina Wodtke and Ben Lamorte above, it’s still a rich and diverse resource of examples to show demonstrate the flexibility of objectives and key results. (3 min read)