The Anatomy of a Decision
How High-Stakes Choices Take Shape
This article is an adaptation of a presentation I gave at ProductTank Tallinn on January 28, 2025.
Decision-making is at the heart of product management. Whether we enjoy it or not, the ability to navigate high-stakes choices is what drives progress—both for our businesses and our own careers.
Over the years, I’ve made good, bad, and ugly decisions in fintech, SaaS, and B2B environments. These days, I mentor and coach product managers while also offering financial education. This shift in my career has given me a new perspective: I now help others make decisions a lot more than making them myself.
Instead of adding another tool or framework to your already overflowing toolkit of product managers, my goal here is to share how I think about decisions and invite you to think critically about how you make them. Perhaps you will relate to my own mental model, perhaps you will uncover yours.
How I see it, decisions are seeds that can grow into a set of changes or die. Depending on how we nurture them they will take a shape and growth into one thing or another and the better we understand this, the better we will get at making high stakes decisions.
The Three Stages of a Decision
I like to think of decisions as organisms that go through three stages of development:
1. The “What If” Stage – When a potential decision is just a thought, a possibility.
2. The “Should We?” Stage – When it has gathered enough weight to be considered seriously.
3. The “Let’s” Stage – When it transforms into an action that impacts reality.
To make this more tangible, imagine a fictional company, Money Smart Humans (MSH), which offers a mobile app to help individuals manage their money. The team is now considering a shift into the B2B space. Let’s see how this decision might evolve through these three stages.
Stage 1: The "What If" Stage
At this stage, decisions are fragile. They may not survive beyond conception, and that’s okay. What determines whether they move forward?
Potential Impact
Is this decision worth pursuing? The key question here is: Will this have no impact, minimal impact, or could it drastically change reality for better or worse? Many ideas die here, and that’s a good thing. Not all decisions are worth the effort. If a decision is low stakes, spending too much time on it leads to overthinking.
The Decision Maker
Who has the final say? Understanding the decision maker is crucial. Their biases, experience, energy levels, and priorities will shape the outcome.
If you are the decision maker, be aware of your decision-making threshold—the point where fatigue sets in and choices become harder. Planning around this threshold can prevent poor judgment. If you’re presenting the decision to someone else, study how they operate. When and how do they make big calls? What have they decided in the past?
In our Money Smart Humans example, is there a structured way for the leadership team to evaluate big strategic shifts like moving into B2B? If not, that lack of process might kill the idea before it even gets serious consideration.
Stakeholders & Data
Decisions don’t happen in isolation. Who needs to be involved? Who will be affected? Who has influence, even if they aren’t the formal decision maker?
For Money Smart Humans, shifting to B2B means assessing:
Does this require changing the product itself or just repositioning our marketing?
Do we have the necessary skills in our team to sell and support B2B customers?
Who in the company is likely to resist the change?
Is there someone influential behind the scenes who can help?
Equally important: What data do we have to back this up? If key information is missing, is it critical to making a call, or can it be gathered later?
Stage 2: The “Should We?” Stage
If a decision survives the “What If” stage, it becomes a serious contender. Now, we must answer: Should we do this?
Considering Alternatives
High-stakes decisions usually involve high risks. The best way to manage risk is to generate options—but not too many. If we work with too many options we will find ourselves facing what is referred to in psychology as the paradox of choice, when up to a certain limit having several options is good but after that point it makes deciding more difficult.
I find that a good rule of thumb is sticking to three clear alternatives. In our Money Smart Humans scenario, these might be:
Partnering with a few B2B companies instead of a full expansion.
Adding an optional B2B extension to the core product instead of changing the existing offering.
Encouraging employers to subsidize subscriptions for their employees rather than selling directly to businesses.
Each of these options allows for different levels of risk and investment, helping refine the decision before committing.
The Role of Tools & Frameworks
This is the right time to bring in decision-making frameworks—not to overcomplicate things, but to clarify thinking. Whether it’s a prioritization matrix, a cost-benefit analysis, or a structured team workshop, the right tools can help different people involved make the right decision. This becomes more important the more data that needs to be considered by different people, and working together with them in helping them make sense of it will help transition into action if the decision is positive.
For example, in our fictional company, Money Smart Humans needs to ask:
What triggered this B2B shift? Was it a well-researched opportunity or panic due to competitors doing the same?
If competitors are moving to B2B, does that open up a gap in the B2C market that we could exploit instead?
Having a structured way to evaluate these questions ensures we don’t get caught up in assumptions or blind spots.
Stage 3: The “Let’s” Stage
Now comes the moment of truth. The decision either:
Moves forward
Gets killed
Gets postponed
Too often, decisions linger in limbo, which is a waste of energy. Saying no is often more valuable than a weak maybe because maybes take up mental space, and people tend to expect something to happen failing to fully focus on what we really need to make happen.
Similarly, if the decision is postponed, it is important to make it clear what conditions need to change before revisiting it so that, once again, no unnecessary mental space is taken up wasting ours and our teams’ valuable energy.
And when a yes is the clear answer, these are the critical things I believe we need to consider:
Commitment & Execution
A decision is only real when teams commit to execution. This is where the principle of “Disagree and Commit” comes into play. Even if not everyone agrees, once a decision is made, it is important that those who need to act agree to do it even if they initially disagree with the decision. That is why it is important to differentiate between decision-makers and stakeholders and their different roles in the process.
Without real buy-in, execution stalls. Status updates and clear accountability structures help translate decisions into action. They don’t have to be overcomplicated, but they have to be in place and clearly stated.
Reflection & Learning
Even after action has been taken, the work’s not done. Every high-stakes decision should be followed by structured reflection:
Did the decision achieve the intended impact?
What worked? What didn’t?
What can we learn for the next time?
Intentional reflection is key because high-stakes decisions don’t happen every day. The longer the time between decision and outcome, the harder it is to connect the dots. That’s why tracking and revisiting past decisions matters—it builds better instincts in the team for the future.
Epilogue
When I originally shared this mental model as a presentation in January 2025, I invited the audience to challenge me and help me refine my thinking during the networking break.
One participant and colleague from the Tallinn Product Community did just that: he suggested that rather than discarding low stake decisions we should also consider how several low stake decisions compound over time.
Yes, we should avoid overthinking them, but we should consider how the low impact a decision could have might interact with several other decisions. This requires being analytical, observational, paying attention to detail, and actively seeking the perspectives of others involved from different angles of the product and business.
So now I am trying to integrate that thinking into smaller decisions I make every day.
Before I finish, I would very gladly welcome new perspectives into this thinking so just as I did with the original audience, I ask of you: Would you be kind and challenge me in the comments? 🙏