Product Helmsmanship (P2): Recalibrate Between Strategy and Execution
Remember the product transformation I shared in my previous post, where we turned never-ending custom reports with an exhausted dev team into a self-service analytics engine that became a new revenue stream?
That shift from execution to strategy did not happen by accident. It came from asking three questions that have guided my career in product for years.
Today, I am sharing those questions with you.
Before diving in, revisit Part 1 to refresh your memory on the Helmsmanship mindset in product management: the art of balancing strategy, execution, and everything in between.
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The Problem
Most product management advice naturally focuses on the product work: interview techniques, discovery frameworks, data analysis methods, prioritisation matrices, roadmap templates, or PRD and user story formats. Older frameworks were even designed on the assumption that the product lifecycle is predictable.
These resources are often heavy on management tactics but light on leadership skills. They tell you what to do but rarely when to do it.
Real-world storms demand more.
Should you focus on strategy or execution this week? Should you dive into details or step back for the big picture in this project? Should you lead from the front or empower your team to take the wheel with a new team?
These are not just tactical choices. They are helmsmanship decisions that can navigate you through storms, make or break your product, and shape your career.
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The Framework
Over the years, I have learned that good decisions follow recognisable patterns. When something feels off with the product, team, or direction, or when starting a new initiative, I ask myself these three questions:
Question 1: Where do we need to accelerate momentum? (⚡Execution focus)
This is about speed and delivery. Are features taking longer than expected? Is the team bogged down in processes? Are we working hard and shipping but not moving the needle?
When momentum is the issue, lean into execution. Get hands-on. Remove blockers.
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| Where do we need to accelerate momentum? |
Sometimes, product managers belong in the engine room rather than on the bridge. It is not about working harder but working smarter, steering energy toward impact.
Question 2: Where do we need to clarify direction? (🧭 Strategy focus)
This is about outcomes and alignment. Are we building the right things? Do we know why we are building them? Are our actions aligned with the business mission, outcomes, and OKRs? Are teams pulling in different directions? Are we focusing on real impact?
When direction is the problem, step back into strategy. Challenge assumptions.
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| Where do we need to clarify direction? |
Sometimes, product managers need to climb the mast and look ahead. Realign on outcomes and impact.
Question 3: Where do we need to build trust? (🤝Communication and alignment focus)
This is about relationships and credibility. Are stakeholders losing faith and questioning the roadmap or progress? Is the team confused about the priorities? Is there anyone unsure if the product is on the right track?
When trust is the problem, focus on communication and alignment. Bridge gaps. Clarify decisions.
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| Where do we need to build trust? |
Sometimes, product managers need to function as translators, reopening communication channels and realigning everyone.
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How This Played Out in Practice
Here is how these questions guided three real-world decisions:
Momentum Problem: All Hands on Deck
As a PM at a fintech company, we faced a crisis head-on. Late on a Tuesday afternoon, we got an urgent call to join a meeting: our client was facing a major market shift and needed immediate changes to streamline their SaaS solution. The timeline was brutal, and failure could sink both their business and our partnership.
Question 1: Where do we need to accelerate momentum?
We had a capable team, but waiting for the next sprint and debating strategy would not meet the deadline. This was crisis mode.
The recalibration: We needed the momentum to meet the deadline. I immediately created a roadmap for the changes focus on MVP (not what customer asked, but what they really needed). Then I created a coordination plan across five cross-functional teams to meet this goal and scheduled an all-hands meeting the next morning. We started with the “why,” explaining the client’s situation and what was at stake. Then, clarified specific outcomes for each team based on the shared roadmap and set up frequent checkpoints, sometimes daily, to remove blockers and maintain momentum.
The outcome: Teams fully understood the urgency and had clear purpose. We delivered all changes two weeks ahead of the client’s deadline, giving them breathing room to navigate without rush. Not only did we save the partnership, but we also earned a big “THANK YOU” cake from leadership at the next team lunch.
Sometimes, momentum is not about forcing teams to work harder. It is about giving them a crystal-clear purpose to focus their energy.
Direction Problem: Conflicting Regional Priorities
At a global company, each regional sales team treated their client requests as separate projects with a compelling business case and claiming as the “highest priority.” The result? Competing requirements, too many projects in progress, and a stretched-thin dev team. When I joined the team, there were twenty -three projects in progress!
Question 2: Where do we need to clarify direction?
Everywhere. Team was trying to be everything to everyone, ending up as nothing to anyone. Developers were constantly context-switching, losing time and focus.
The recalibration: This needed strategic realignment. I ran joint prioritisation workshops across all regions. Instead of building client-specific features in parallel, we reshaped the strategy and sequenced features into one unified product with minimal customisations for each client/region.
The outcome: We delivered what each region needed in a way that maximised global impact. Multiple multi-million-dollar projects launched on one product, and the team gained sustainable focus.
Sometimes, direction means finding a common path through different destinations.
Trust Problem: The Technical Debt Standoff
In one of my recent experiences and on a client-funded initiative, our Tech Lead flagged major technical debt impacting code maintainability. The client, however, were insisting to prioritise revenue-generating features. The dev team wanted to refactor for 6 months; the client wanted to expand right away. Both sides were complaining, and I was caught in the middle.
Question 3: Where do we need to build trust?
Neither the client nor the team trusted the other’s priorities. They both lost faith in each other.
The recalibration: This needed me to function as a bridge. After creating clear models and facilitating tough meetings, we brought everyone on the same page. We convinced the client to extend the timeline for their initiative by two months for critical refactoring. They fully acknowledged that it was in their long-term interest. The tech team also agreed to refactor in stages, starting with the minimum necessary. Yes, it was a difficult conversation. Yes, I was the “bad guy” for a day.
The outcome: We built a sustainable product roadmap with a motivated team and a satisfied client. They understood and trusted each other’s decision.
Sometimes, trust comes from defending what matters most, even if it makes you unpopular for the moment.
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Here is how I apply these questions in practice.
Checkpoints (When):
Regular checkpoints: I ask these questions weekly or per sprint. It is a quick gut check to assess where we stand and if I need to shift focus.
Starting a new project: Before diving in, I use these questions to determine how much time to allocate to strategy, execution, or communication.
Stakeholder meetings: When tensions arise, I listen for signals about momentum, direction, or trust to understand what is really at stake.
Crisis moments: When everything feels urgent, these questions help me triage: fix momentum first, then direction, then trust. You cannot steer a ship that is not moving.
After any change: When markets shift, new technologies emerge, or when I join a new team, I use these questions to spot improvement opportunities, quick wins and recalibrate.
Questions (Where):
In each checkpoint, use a whiteboard (digital or physical), or go for a walk then ask yourself these questions. Remember, don’t stop after the first one. Make sure you think about each question equally and objectively. Do this with the team if you must, but remember you are ultimately at the helm.
Signals (What to listen for):
Go deep in diagnostic mode and listen for the “Signals”: Features taking longer than expected (execution signal), Roadmap overloaded with tactical asks (strategy signal), Cross-functional partners working in silos (trust and communications). They help you pinpoint where you need to focus next.
Quick Wins (What to do immediately):
When you know where to focus, follow your verified playbooks to make “Quick Wins”: an immediate nudge to rechart the course: Reduce work in progress (to accelerate the momentum), run OKR check-in (realign the strategy) or publish short, regular updates as a newsletter or dashboard (communication)
Review and Repeat:
Set a reminder for a new checkpoint and evaluate the result of actions. Then repeat.
Check out the board below for Recalibration Checkpoints, common signals, and easy quick wins to boost momentum, refocus direction, and improve team communication.
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Why This Works
This framework simplifies complex leadership choices, helping you diagnose when to shift gears. Like Agile retrospectives, it makes the invisible visible, turning reactive actions into conscious decisions.
It is not about being perfect; it is about being deliberate and proactive. Sometimes, you may misjudge the signals, and it is OK. A momentum issue might be a trust problem in disguise, or a strategy problem might stem from poor execution. This is why you need to be Agile here, discover, plan, do, evaluate and repeat!
There is no single perfect heading, only a series of micro-corrections that keep us moving toward value.
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The Next Level
This framework does not replace long term strategy and OKRs but tells you when to recalibrate. It is also won’t tell you how to make decisions. A PM’s impact is not just because of big decisions or swinging between strategy and execution. It is from the small choices you make daily.
In my next post, I will share decision-making patterns and techniques for common PM dilemmas, evaluated in the storms I have navigated over the years. Decisions like: How do we choose between multiple solutions? How do we prioritise? Or when do we lead from the front, and when do we empower our team?
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Your Turn at the Helm
Try this exercise: Set a checkpoint this Friday and think about your biggest product challenge right now. Ask yourself:
- Where do we need to accelerate momentum?
- Where do we need to clarify direction?
- Where do we need to build trust?
Which question resonates most? From where do you get stronger signals? That is likely where to focus first.
I’d love to hear how this framework applies to your situation. The same if you are using a different approach. Drop your comment, I’d love to compare notes.
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This article is part 2 of my “Product Helmsmanship” series, adapted for Medium. Originally published here: https://medium.com/@alivahed/product-helmsmanship-p2-recalibrate-between-strategy-and-execution-d7c99e2fbfe9
Read part 1 for why PMs need a navigation philosophy. I explore the PM craft of knowing when to switch between strategy, execution, and everything in between. Future posts will cover decision-making frameworks for PMs and AI’s impact on product management.
⚓️ Join me on this journey and share how you recalibrate when your product drifts off course!
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