Why Are Strategy Activities Remarkably Hard to Fit into Our Schedule
Two pervasive challenges and what to do about them.
Product teams constantly do discovery and delivery activities to validate and understand what they need to build, and then ship it successfully to their customers.
These activities are mostly opportunity-driven (or initiative-driven, or idea-driven, meaning that you execute them for a given “thing” that you want to explore and build). For this reason, we manage backlogs for delivery and usually a similar artifact to organize and prioritize discovery (like an opportunity solution tree).
But what about Product Direction activities? Strategy, Roadmapping, and Objectives are not backlog-driven. They are time-based.
Starting with objectives, most teams have quarterly OKRs. Every three months, we go through a crazy period of a few weeks in which we verify results and decide what to focus on next quarter (FYI, it doesn’t need to be stressful if you have a strong strategy in place).
Similarly, if you have strategic roadmaps (FYI, those are the useful ones, based on outcomes rather than features), you probably review and update them on a regular cadence, usually between 1 and 3 months, depending on your speed and maturity.
And finally, Strategy is a bit less normalized but still affected by time triggers. Some companies have a more formal annual planning, and strategy is adjusted on that cadence (alongside resources needed and annual business objectives). Other companies do specific product strategy reviews that can be every 6, 12, or 18 months.
(*) Note: there may be times when they are context-driven, a reaction to a major change in the situation (external condition, competitor move, or even an unexpected result of your execution) can trigger a change in strategy, roadmap, and objectives.
Why do we fail then?
While all of this may sound clear, most companies still fail to create solid product strategies and successfully connect them to their discovery and delivery activities.
While there are many challenges (described in chapter “The Job of Product Direction”), today I want to focus on the scheduling and managing activities complexities.
Challenge 1: Time management
Planning time for strategy is completely different.
Of course, we have a tactical inclination. The client issue that can cost us thousands in revenue, a competitor's move that we need to react to, that bug in production that is hurting the conversion rate. All of those are (rightfully) high-priority and time-consuming activities that we need to fit into our schedule. How many “strategy-time blockers” have been crushed due to emerging problems or requests?
We usually have regularly planned ceremonies for our delivery and discovery work (planning, refinement, standups, retros, demo, etcetera).
But unless there is a formal deadline (like submitting a yearly budget), strategy is something we usually create ad-hoc, that tends to be forgotten or postponed indefinitely. Furthermore, this work is not easy to “timebox,” which leads to prolonged periods with scarce progress in between (an easy example: based on a first strategy conversation, you will find out you need more information, which will trigger a new strategy session once you get it).
What to do about it?
The best “tool” I have found so far is to do quarterly strategy reviews alongside the OKR results review. While it may sound obvious, many teams treat OKRs separately from strategy (when, in fact, OKRs should be your main tool to execute your strategy).
This frequency allows keeping track of major strategic initiatives and their results and keeps strategy “present” to action on any follow-up that arises from the reviews.
Challenge 2: Synchronizing both types of activities
Even when you manage to do the strategy work with the proper cadence, you can hardly predict how it would match with your ongoing discovery and delivery efforts.
For example, you will be working on a major intiative while preparing the strategy for what will happen in the next 12 months. And it may still be very uncertain the time it will take to complete the initiative and the result it will have, both of which will impact your strategy.
This has the profound implication of contradicting everything I just said about strategy being time-based :)
While this is not entirely true, you still need to be open to constantly reviewing your strategy.
Considering you did good strategy work, most of the time, your strategy will remain constant, and you will only add more information (insights, confidence, clarity) based on your execution results.
But sometimes, the per-initiative results of discovery and delivery will trigger a non-time-based strategy update.
What to do about it?
I have already mentioned OKRs as a key tool to direct your discovery and delivery efforts. Similarly, on your opportunities (a.k.a. iniciatives, ideas, etc) you should describe their contribution to the strategy. In this way, you keep the connection present and can relate to any information discussed during strategy updates.
In the opposite direction, when a major discovery or delivery result has an implication for the strategy, you need to call for an ad-hoc strategy review. Given the time-frames of most companies, usually it is enough to keep the quarterly review (it is unrealistic and undesired to do major strategic changes faster than that). But the format of the strategy review will be quite different if you are facing a major change versus when you are just doing a check-in.
While it's always nice to provide a few hints, my main advice is to pay attention to this pervasive time management issue and explore what solution works best for your context.
