How often do you revisit your product strategy? What is your framework for reevaluating it?

I generally believe product strategies should be evaluated more frequently the earlier a product is in its lifecycle. A zero-to-one team I worked closely with found the right pace to be testing a new direction & goals every month or so, whereas a scaled team I led had sufficient visibility to establish a high-level strategy that lasted well past a year. 

At Patreon, we aim to set strategies & goals that cover 6 months or so for each team. In tech, unless you're working on a platform or infra initiative that is largely independent of evolution in user need, I'd generally recommend somewhere between 3-6 months for early-stage or growth companies and 6 months to a year for more mature companies.

At each of those milestones, I'd suggest confirming your core assumptions about your customer, the problem space, the competitive landscape & your strategy to maintain or grow your market position. If any of those elements change in a fundamental way during that window, you should consider whether you need to update your product strategy even if it's not quite on schedule.

At GitLab, we revisit our product strategy once a month. During these reviews, we document our progress and what we've learned. It's important to align on what you're working on next to make progress against your direction. Monthly reviews ensure that you keep your high-level objectives in mind as you execute day-to-day work.

Many times, these strategy updates will be pretty straightforward. Some cases warrant more extensive changes. Product Managers and leaders will maintain a pulse on the market to identify when these situations arise. To name a few examples:

• Change in company strategy

• Market trends change drastically (i.e. AI)

• A competitor's product launch

• User research uncovers new opportunities

• Discovery of unforeseen technical challenges executing on the path charted out

The frequency of revisiting our strategy depends on its altitude, but I'm continuously reassessing various aspects of it. Let's break this down to better understand how to keep a strategy fresh within an organization.

The highest strategy altitude most organizations focus on is the 3-5 year vision, as anything beyond that tends to be more of a dream than a strategy. Typically, I assemble a cross-functional team to conduct thorough analyses of the industry, market, competitors, prospects, and customers every 2 years. In cases of significant shifts in company goals, I've revisited it sooner, though every other year has generally proven effective.

This overarching strategy is then broken down into objectives, key results, investment areas, projects, epics, stories, and metrics we hope to change over time. The higher-level components (Objectives, Key Results, Investment Areas, and Projects) are usually consolidated into an annual plan that's a subset of the 3-5 year vision. This plan should outline specific elements within the vision that we intend to progress within the upcoming year. It's also an opportunity to seek increased investment by demonstrating an attractive ROI. This part of the strategy is reviewed annually.

The subsequent layer involves project priority and sequencing, planned quarterly and ideally, on an ongoing basis. Planning without assessing progress against the existing strategy is considerably less effective, which is why we conduct quarterly reviews to track our advancements and proximity to our goals. This approach also enables us to pivot if a particular aspect of our strategy no longer serves us or aligns with our intended outcomes.

I employ several frameworks to evaluate different components and objectives of our strategy. A few examples include:

• JTBD (Jobs to be Done) Framework - I find this approach valuable due to its impartial nature. It assesses whether customers can perform a specific job quickly, easily, or delightfully. This framework is instrumental for evaluating how well our quarterly product investments address the tangible needs of our customer base. This assessment should result in a noticeable improvement in the quality or volume of jobs accomplished by our product. This evaluation is done quarterly or continuously at the initiative level.

• RICE (Reach, Impact, Confidence, and Effort) Framework - I favor this method for assessing early to mid-stage investment ideas. When considering a significant investment not already staffed by current teams, I recommend using the RICE framework. It provides a holistic view of potential projects for prioritization, making it simpler for the team to provide consistent assessments compared to detailed ROI analyses that often prove inaccurate. This assessment is conducted quarterly or continuously at the initiative level.

• SWOT (Strengths, Weaknesses, Opportunities, Threats) Framework - I employ this framework to evaluate our market competitiveness. Tailoring the SWOT analysis to the target buyer or market segment is crucial, as it can significantly differ based on the competitive landscape. This assessment occurs annually or on an as-needed basis, such as when facing new competitors or observing disproportionate losses in target buyers.

To gauge the effectiveness of our strategy, I conduct the following analyses annually (or more frequently, if necessary due to market changes):

• Market Analysis

• Value Proposition Analysis

• Messaging and Positioning

• Competitive Analysis

• Business Model

By employing these methodologies and analyses, we ensure our product strategy remains agile, responsive, and aligned with evolving market dynamics."

I revisit the strategy whenever there is new information. Usually, customer needs do not change that much. What changes is company visions and organization structure, budget, risk, etc. So every time there is an internal shift, propose how you think the strategy should adapt to meet the company vision with the new current reality.

You can even propose to leadership that you are planning to do this. Or depending on their needs, ask them how they would like to discuss strategy (when and how). Once I had a leader ask me to give a roadmap update once a month in a leadership meeting. I had ten minutes. As you can imagine, that is not nearly enough time to have a rich conversation. So I told them I need more time, or we bore the risk of misunderstanding each other. Partner with them on the best way to discuss strategy.

Cadence for evaluating strategy is often set by the business. I have been at companies that will redo their company strategy every 3-4 years, and then as a result product strategy is reevaluated every 3 years in suit. I

I traditionally plan strategy using 1,3,5, and 10-year product strategy horizons.

• 1-year strategies are very tactical and get iterated on continuously

• 3 years are revisited 2-3 years

• 5-year strategies are revised every 5 years

• 10-year strategies are sometimes only created once and often I have exited the company (IPO, sold the company, or got a new job before I could fulfill that strategy cadence)

Revisiting the strategy looks a lot like rewriting it I conduct competitive analysis, and research, and often completely rewrite the strategy with new inputs and targets.

These are the main criteria for reevaluating your product strategy:

• At regular intervals to keep up with developments in your market. The exact timing depends on how fast your industry goes through changes. For software products, have a discussion to check that your strategy is in line with the market every 3 months and do a deeper-dive into external developments and their alignment with your strategy every 6 months.

• When there are significant events that are shifting the dynamics in your ecosystem. Examples for these are when a competitor launches a major new product, when a new technology comes out or when the regulatory environment changes and it affects your product.

• When there are major changes in your company's business and organizational strategy. If the objectives and structure of your business changes, then so does the product strategy need to change.