Season 05 - Newsletter 02 --> When Your Boss Wants Strategy but You're Stuck in the Weeds: A Product Leader's Dilemma

Jan 28, 2025

Hi Friends -

If you've been a product leader long enough, you've probably experienced that very moment when your boss says something like "stop focusing on the day to day" or "I need to see more strategic thinking." Hearing that can be a shock to the system especially knowing how hard Product Managers work to get their features to customers - it can feel frustrating and confusing.

A recent discussion in the product management subreddit caught my eye, where a Director of Product managing multiple PM teams shared this exact struggle. Their story perfectly captures a challenge many of us face: the delicate balance between getting things done and thinking strategically about what should be done.

Let's unpack what could be behind that guidance and why it matters:

Thanks for reading Product Hustle Stack Newsletter! Subscribe for free to receive new posts and support my work.

Generated by Flux 1 - Quote by Marshall Goldsmith

Q: As a director of multiple teams who has received feedback to be more strategic how should I balance between strategy and delivery?

This questions stems from a reddit post in r/productmanagement where the original poster shared that they were focused heavily on delivery (with new teams), that they felt as they were not appreciated for their execution and had gotten less than positive feedback from his boss on their strategy and insight generation.

Before we dive into some core areas, it’s important to identify the root of the problem here and that is there is a fundamental strategic misalignment. In other words the job is to ship to customers in the near to mid term, while providing a clear strategic roadmap for the mid to long term. The latter is what their leaders will be sharing with their peers and leaders.

Let’s dive into some core areas and what to do:

Operating at Different Altitudes

This altitude mismatch is more common than you might think. When you're deep in the trenches ensuring features ship and customers stay happy, it's easy to lose sight of the strategic forest for the tactical trees. Additionally, the mismatch may not be with your leader, but might also include his peers. Depending on how your leader likes to operate, he may want to come into a room already warmed vs having to it themselves.

What can a PM Leader do. Really understand your leader and their style. If you have a 1 on 1 already, you might want to modify it to be less here are my 3 issues and more geared towards their need. Connect the dots and be early. The week will be filled with fire drills, so prior to starting the week ensure you can answer how the upcoming work ladders up to quarterly goals, to next year etc etc. Make sure you think of not just your leader but also of their peers, especially those that play an important role in your roadmap. Make it a habit to translate tactical wins into strategic narratives.

Strategic Vision Gaps

Here's a telling quote: "The vision I put together last year wasn't sufficient enough." Sound familiar? Many product leaders I know excel at execution and the bigger picture, but the pull of the day to day and looming deadline means they struggle to find time to develop and paint the bigger picture their bosses need to see.

The fix? Working backwards. To do that, just start with a simple exercise: Write down your product's story three years from now. Not features, not roadmaps - but the story of how your product changed your market. Then work backwards. This isn't just about having a vision; it's about crafting one that resonates up and down the org chart. Share that vision with colleagues, leaders, their peers often.

Resource aka Constraint Management and the Art of Possible

2024 was and 2025 will be another year of constraints, of doing more with less, of shifting priorities and team transitions. But our unique burden as Product Leaders is that we must manage keep the lights on, which is on itself tough enough, squeeze out outcomes but also elevate our strategic game even if that feels impossible.

The solution? Turn the constraints to your advantage, turn your constraints into your strategy. A big part of strategy is what you say not to and where you choose to focus on. Limited resources force prioritization, and prioritization is strategy in action. Document these choices and their rationale and how they support your strategy - they're the building blocks of your strategic narrative.

Communication Deficits and Gaps

At the heart of any disconnect between leaders and their directs is not just clear communications but also enough communication surface. When you are heads' down delivering it’s easy to forgo building the communication surface. Each touchpoint, each email, each teams message increases that communication surface.

Here's what works: Create a simple "impact dashboard" that connects daily work to strategic outcomes. Every feature shipped, every bug fixed, every customer interaction should ladder up to strategic metrics your boss cares about. That dashboard could be an actual Power BI dashboard, a powerpoint slide or a weekly email. Whatever the format share, and share regularly.

🏁 Final Takeaway

The shift from tactical to strategic thinking isn't about doing less - it's about seeing more. It's about connecting dots between daily decisions and long-term impact. It's about speaking two languages fluently: the language of execution and the language of strategy.

Share your thoughts in the comments - let's learn from each other's journeys in navigating this crucial career transition.. 🚀

Before you go, please help us by completing the Three Actions:

1) Share this edition with others! It will help spread the word and get more upvotes. We like both of those things

2) “Star” this edition! Click the heart icon near the top or bottom of this edition 👇☝️

3) Reply! It only takes a few seconds, but the feedback is invaluable