Product Helmsmanship: Balancing Strategy, Execution, and the Storms in Between
How constant recalibration and tough decisions shape the craft of Product Management.
Product Management often feels like steering a ship through unpredictable seas. Over my career, I've learned when to dive into execution, when to step back into strategy, and when to simply let the crew steer.
I call this balance Product Helmsmanship.
When I first stepped into tech, I started from the lower decks. I began in execution, first as a developer writing code since I was 12, then as a Business Analyst turning requirements into documents and diagrams right after university, and later as a Project Manager focused on delivery.
The transition into Product Management felt natural, but in the early years my role often felt like translation, helping business leaders and technical teams understand one another, sometimes mapping business requirements to technical jargon and vice versa!
Over time, I realised Product Management is less about translating and more about helmsmanship.
A good PM, like a skilled helmsman, does not simply sit at the wheel and do what they are told. They know when to change course with the wind, when to slow down in a storm, and when to hold steady on a path others may not yet see.
-------------------------------------------
Recalibration Is the Default
Every new role, every project, every employer, and every wave of technology or market movement has forced me to rebalance between strategy and execution.
Sometimes I've had to lean into hands-on execution to get a product unstuck. Other times I've needed to step back, recalibrate, and focus on the bigger picture.
Like a helmsman reading the sea, Product Managers constantly adjust to shifting winds.
Here are some examples of recalibration:
- Long-term market strategy: When we lost interest in doing government projects, I shifted heavily towards strategy. Through a series of rapid experiments and quick discovery work, we pivoted toward building for the private sector. We launched a market-leading CRM with sustainable revenue growth and laid the groundwork for a Business Process Management solution, rolled out nation-wide for an enterprise client. Those became my legacy when I left the company. More on this story in How I approached building 0–1 product.
- Start-up vs Enterprise: When I moved into a leaner team earlier this year to work on new products in unfamiliar domains, my focus shifted from long-term strategy to short-term execution. To recalibrate, I got more hands-on while using AI as a copilot to cut manual and admin tasks time. This freed me to shift from creator to reviewer and keep a strategic view while still working closely with feature teams.
- Biggest pain point: When I joined a new company to help with execution and meet high client demand on reporting, I realised the root cause was not execution speed but strategy. Over the next six months I worked with the development team to build my vision of self-service analytic reporting and dashboards product. We moved from customer dissatisfaction and additional load on the dev team to a new upsell revenue stream, with happier customers who could build their own reports, or use a low-cost support team to do it for them on demand and as a fee-for-service task.
My Recalibration Framework
These recalibrations taught me that good decisions follow recognizable patterns.
To know if it's time to recalibrate, ask yourself these questions:
- Where are we losing momentum? (Execution issue)
- Where are we losing direction? (Strategy issue)
- Where are we losing trust? (Communication or alignment issue)
---------------------------------------------------------
The Balancing Act of Decisions
Helmsmanship is not just about steering toward the final destination. It is about judgment on the very next move, every single one of them.
Good PMs gain as much knowledge as time and resources allow, analyse the data they or their team can gather. Then, they make the best decision possible at the time.
They know:
Every PM faces these recurring tensions, Here are a few from my career:
- Customer feedback wakeup call: When we saw a spike in complaints about lagging price updates in a fintech SaaS solution through social media monitoring and surveys, I influenced stakeholders to prioritise background changes to the core platform for more frequent updates and smoother client-side transitions. CSAT lifted by three points in the next survey and complaints disappeared from social posts. No new features, just small improvements that made a big difference.
- Stakeholder misalignment: When conflicting priorities arrived from regional GMs in the US, EMEA, and APAC, I ran joint prioritisation workshops. We reshaped and sequenced features that could be reused across different installations with small customisations. We still delivered what we were supposed to deliver, but in the shape and order we chose that maximised the impact. We landed multiple multi-million-dollar projects globally in parallel.
- Technical sustainability: When major technical debt threatened a client-funded initiative, I convinced the client to agree to extend the delivery time by two months to complete the critical refactoring first. This gave us a sustainable product and a motivated team. Be the bad guy for one day if needed, save the product and earn the trust for the long term.
- Market movement: When we faced a major market shift and urgent client demand to align our products under a tight deadline, I parked strategic tasks. I created a plan across five cross-functional teams over night, clarified purpose and outcomes for each team, and set frequent checkpoints, sometimes daily. With clear client communication throughout, we delivered two weeks ahead of the deadline, giving our clients the buffer to make the right call without rushing.
My Decision-Making Principles:
If you want something that works every time, follow these principles:
- Be curious. Question everything, especially your own assumptions. Frameworks and processes keep us steady, but curiosity drives the breakthroughs that turn good products into transformative ones.
- Be humble. Don't start the discussion with "my way or the highway" attitude. Talk and listen with an open mind. Agree when convinced (whether it's you or your team), disagree but commit, or step aside.
- Be Agile. Choose the most valuable option, start small, run a proof of concept if needed, then scale up iteratively. Keep reviewing. Continue if you're on track, pivot if you're not.
----------------------------------------------------
Helmsman's Guide to Product Decisions
Not all storms are the same! Below are my go-to frameworks for common product questions.
Tech Debt vs Client Needs
Do we trim the sails for speed, or strengthen the hull for the long voyage? Should we keep pushing for client-funded features or make room for some refactoring?
My Decision Framework:
- If customer churn is accelerating, fix their problems first.
- If pipeline is at risk, address immediate client needs, but set a strict timeline for technical investment.
- If team velocity or morale is dropping, tech debt wins. You cannot sail with a broken mast.
One Problem vs Multiple Solutions
One of the biggest challenges isn't a lack of a solution for a problem but having too many. Imagine different technical options, features or customer journeys to address the same problem.
In those moments, the PM's role is to clarify the problem, weigh trade-offs, align on principles, and choose the path that delivers the most value with the least regret.
My Decision Framework:
- Do not fall in love with any solution. Fall in love with the problem. It helps you choose objectively.
- Create an Opportunity Solution Tree, an Impact Map, or even a simple post-it board to visualise options and see pros and cons with some distance.
- Bring other eyes. The team can assess solutions with less bias. Multiple minds beat one.
One-Way vs Two-Way Door Decisions
Some choices are one-way doors, irreversible once taken. Examples like architecture choices, key hires, major platform bets, etc.
Others are Two-way doors, let you adjust course if conditions change. Examples like feature experiments, UI changes, pricing tests, etc .
My Decision Framework
- First ask, can I make an irreversible decision reversible without excessive cost. Techniques like A/B testing, canary rollouts, or beta releases for selected users, with clear rollout and rollback plans, can help.
- If not, what is the last responsible moment to decide. Delay until then if it brings more clarity.
- Make the call when it is due and move forward. Nothing demoralises a team more than an indecisive PM.
Leading vs Empowering
Sometimes the PM must grip the wheel and set direction. Sometimes influence is enough to shift course. And sometimes the best call is to hand the helm to the crew and trust them to steer.
My Decision Framework
- Grip the wheel: crisis, unclear requirements, cross-functional misalignment.
- Influence: the team has context but needs direction, stakeholders are aligned but need nudging.
- Hand over: the team has the expertise, the decision does not hinge on PM judgment, empowerment builds capability.
---------------------------------------------------
Learning from Rough Seas
Not every storm ends well. Here are moments when my approach broke down.
- Over-correction: A tight deadline pushed me from strategy into execution, and I micromanaged for a few months. We delivered but created dependency. It took just as long to restore autonomy. Micromanaging felt like steering the ship while tying everyone's shoelaces. Effective for a while, but the crew forgot how to sail!
- Reading the wind wrong: When we lost one client, I thought it wouldn't affect the main roadmap. I missed it as a signal to pivot. We recovered and moved into a new domain eventually, but I still think I should've seen this coming.
These failures taught me that helmsmanship isn't about perfect navigation. It is about recovering quickly when you get it wrong.
-----------------------------------------------
AI and the Latest Storm
The rise of AI has been another storm on my journey.
At first, I leaned into execution, experimenting with vibe code, building prototypes, and chasing speed over stability. It was exciting, but I soon saw the limits. Like sailing full sail into a thunderstorm, the energy cost was higher than the return.
At times, the push for PMs to use AI for execution also feels like steering with the map upside down. You are moving, just not where you intended. Read more about this in this blog post.
So, I recalibrated.
Today I use AI as a strategic copilot rather than a coding engine. It helps me think through options, sharpen discovery, and set clearer direction.
I use it to expand ideas into stakeholder-ready PRDs or prototypes, prepare for important client meetings, and draft documents in my tone in no time. More about how I tried to delegate 30 percent of my product work to AI in this post.
I am in the captain's seat. AI is my copilot, my compass.
Navigating the AI storm required the same helmsmanship principles. Execution still matters, but strategy is where PMs bring lasting value.
------------------------------------------------------
Helmsmanship as a Mindset
For me, Product Management is less about being a mini-CEO- position and status perspective, and more about being a helmsman- ownership and impact.
- Steady when seas are rough.
- Flexible when the winds shift.
- Decisive when the rocks are close.
- Empowering when the crew is ready.
It is about balancing execution and strategy, making trade-offs visible, and never forgetting why the ship set sail in the first place.
-----------------------------------------------
Your Navigation Toolkit
For PMs wanting to develop this mindset, here are the essentials.
Regular Recalibration Check
Every Friday, at the end of each sprint or release, when you join a new company or project, or even during your half-yearly review, ask yourself:
- What shifted since last time that I didn't see coming
- Where did I spend time that didn't drive value
- What decision am I avoiding that is slowing us down
Decision Documentation Template
For significant decisions, write down:
- Context: what signals led to this decision point
- Options: what were the alternatives
- Reasoning: why this path
- Success metrics: how will we know if this was right
It doesn't need to be fancy, just enough to document and refine your choices over time.
----------------------------------------------
Ready to take the helm?
This Friday, set aside an hour and imagine yourself at the helm of a ship (or even a spaceship).
Pick one product decision you've been avoiding this week and ask yourself:
- Is it a navigation issue (unclear direction)?
- A crew issue (people or process)?
- Or a weather issue (external factors)?
Then use the navigation toolkit and decision frameworks from this article. With helmsmanship as your mindset, decide whether to lean into execution or pull back into strategy to move that decision forward.
Set the sail and let me know how it goes.
And remember:
The seas will always change. New storms will always appear. With helmsmanship, we do not just survive. We build the capability to navigate whatever comes next.
Comments
Post a Comment