TBM 39/52: Monthly Strategy Prompt Exercise

You may be in the throes of annual planning right now.

If so, you likely spent the last nine months heads down. On cue, you were expected to have a grasp on where things are headed. To be strategic. You lost the muscle, and the delta was huge.

Instead of waiting nine months next time, try staying grounded with some MONTHLY prompts. Fill these prompts out monthly. Snapshot your responses. And review the history.


1. I expect we’ll see increased signals that _________. The implications here are that _________.

Example: I expect we’ll see increased signals that our existing approach to content personalization is falling flat as we pivot to new user profiles. The implications here are that we may be losing opportunities to retain those new user profiles which—in theory—are valuable to our advertisers.

2. I expect to see an increased threat coming from _________. We’ve been operating under the assumption that _________, but that could change if _________.

Example: I expect to see an increased threat coming from nimble DTC brands hyper-focused on younger anglers. We’ve been operating under the assumption that our product selection was broadly attractive to all age-groups, but that could change if these upstart find an untapped niche and get organic traction.

3. I see us continuing to focus on _________, but with a slight shift in tactics. Instead of trying to _________, we may pivot a bit and focus on _________.

Example: I see us continuing to focus on breadth of data sources, but with a slight shift in tactics. Instead of trying to proactively build our own integrations, we may pivot a bit and focus on existing ecosystems that would give us access to many sources using a single integration.

4. I expect a concrete shift in focus from _________ to _________. This will manifest in many ways, the most notable of which include _________.

Example: I expect a concrete shift in focus from physical only games to hybrid physical/digital game experiences. This will manifest in many ways, the most notable of which include bridging existing silos in the organization and pairing game designers with digital product teams. We’ll also need to coordinate synchronizing product releases to support cross-format play.

5. We are going to need to strengthen our ability to _________. We’ll need to experiment a bit, but if we can _________, we’ll be set up well for future challenges.

Example: We are going to need to strengthen our ability to onboard property management companies with >150 units under management. We’ll need to experiment a bit, but if we can bring time to 100% activation down under 2x the time for small <30 unit customers, we’ll be set up well for future challenges.

6. A new puzzle we’ll need to wrap our heads around is unraveling the complexity around _________. There’s a lot to consider, but a promising place to start is _________.

Example: A new puzzle we’ll need to wrap our heads around is unraveling the complexity around non-rental car mobility in Europe. There’s a lot to consider, but a promising place to start is researching the public transit and ride-share ecosystem in [Some City] and maybe standing up a experiment there using legacy partners.

7. We’ll likely need to revisit our assumption that _________ . Operating based on this assumption has served us well by allowing us to _________ . But that will likely change because _________.

Example: We’ll likely need to revisit our assumption that larger accounts have similar collaboration patterns to smaller accounts . Operating based on this assumption has served us well by allowing us to offer a single experience to both account types . But that will likely change because we’re seeing increasing churn among champions at the larger accounts.

8. We’ll need to lay the groundwork for _________. If we delay any longer it will introduce significant risk because _________.

We’ll need to lay the groundwork for a full contact-less payment experience. If we delay any longer it will introduce significant risk because research points to major shifts in expectations around contact-less payments.

9. I foresee a tangible shift in strategy. Until now we’ve been able to _________. Now, because _________, it will be necessary to change our approach to something more _________, and less _________.

Example: I foresee a tangible shift in strategy. Until now we’ve been able to avoid directly competing with AcmeCorp. Now, because we’re actively offering a viable alternative to FluxFeature, it will be necessary to change our approach to something more integrated into the rest of the product (which is a differentiator), and less bolted on.

10. I expect our key internal bottleneck to shift from _________ to _________ as we _________. I’m not exactly sure how we’ll tackle the problem, but some promising directions include _________.

Example: I expect our key internal bottleneck to shift from how quickly we ship to how quickly we learn as we level-off hiring after the huge increase in team size. I’m not exactly sure how we’ll tackle the problem, but some promising directions include regularly reviewing feedback and instrumenting new releases for basic situational awareness.