Making Smarter Bets
- Michael Kellman
- Apr 29
- 4 min read
Updated: 4 days ago

Have you ever been there? In the thick of creating something new – a product, a feature, a campaign – and you hit that wall? That tension between the relentless push to move faster, to ship, to deliver... and the quiet (or not-so-quiet) voices asking, "Are we sure this is the right thing?"
It's a feeling I know well. We want to innovate, to be bold, but we also dread that costly mistake, that launch that falls flat, that feature our users actively dislike. So how do we navigate this? How do we know when to put the pedal down and when to tap the brakes and ask more questions?
I believe the answer lies in understanding two fundamental forces that shape every single decision we make: Risk and Uncertainty. Let's take something simple – imagine our team is considering making some changes to the "Save to Favorites" functionality in our product.
Let's start by looking at Risk – that's the consequence if we mess it up. What if we change where things are saved and users can't find them anymore? That’s a big risk – frustrated users, support calls, and maybe even bad press that hurts our sales numbers. But what if we're just changing the color of the button and some users don't love it? That's obviously lower risk. It's about the impact of getting it wrong.
Now let's look at Uncertainty – that's about how much we confidently know. Are we using a standard heart icon, placing it where users instinctively look? That'd be low uncertainty – it's a familiar path and we know where it leads. But what if we're proposing a radical new gesture to save to favorites? Suddenly, uncertainty skyrockets. It’s about the solidity of our knowledge.
If we plot these two forces on a graph with Risk on one side and Uncertainty on the other we can see four zones that inform our decisions:
Low Risk, Low Uncertainty: Standard icon, standard placement, minimal tech effort. This is the "Ship it" zone. Let's get it out the door and take the win.
High Risk, Low Uncertainty: Maybe we're considering changing the location of the button to increase usage, but saving to favorites is critical for our product. There's an obvious new location for it, but the impact of failure is huge. This is the "Measure Twice, Cut Once" zone. Test rigorously and deliver with confidence.
Low Risk, High Uncertainty: Let's say we want to automatically favorite items based on use. Will users like it? Highly uncertain. Will there be major disruption if we get it wrong? Maybe favorites gets a little cluttered? Maybe we can mitigate that somehow. This is the "Investigate" zone. Talk to users, run some A/B tests, or launch a small beta. Reduce uncertainty to acceptable levels and ship it.
High Risk, High Uncertainty: Maybe we're introducing AI into both saving and organization favorites. We're unsure what users will think (high uncertainty) and there's huge potential disruption (high risk). This is the "Investigate AND Measure Twice, Cut Once!" zone. Dig in to understand the unknowns, then move thoughtfully before committing the resources.
See how this reframes the conversation? It’s not just "fast vs. slow." It's about understanding where we need more information based on our tolerance for risk and uncertainty. Often our tolerance is based on the stakes involved. If this is a big bet in terms of resources we're investing, we may want some insurance on that bet in terms of low uncertainty and risk. Conversely, if this is a small bet, we may be willing to tolerate higher risk or uncertainty in exchange for a potential quick win.
So how do we get clarity on all these factors? We don't have to guess alone! We tap into the collective intelligence around us – our very own "mixture of experts." It always starts with the core team: PM, Engineering and Design – each one will have their own view on the risks and uncertainty. But don't be afraid to extend beyond that core group! Ask support about current user frustrations. Ask marketing about brand implications. You can even ask leadership for their view before you make your decisions and present to them. Different perspectives illuminate different facets of risk and uncertainty.
Even when we're in the "Research" zone it doesn't mean a six-month detour! It means targeted investigation. Wield this research like a scalpel, not a sledgehammer. What specific uncertainty carries the most risk? Find the fastest, cheapest way to shed light on that. Maybe it's five user interviews focused only on the new save interaction. Maybe it's a quick technical prototype. Start close, expand only if needed.
This lens – Risk and Uncertainty – isn't just for buttons. It applies to everything. The initial project goal. Understanding the core user problem. Evaluating potential solutions. At each stage, ask: What's the impact of getting it wrong? How much do we confidently know?
Embracing this process doesn't mean analysis paralysis. It means making smarter bets. It gives us the confidence to act decisively when the path is clear and the stakes are low, and the wisdom to pause and learn when we're navigating uncharted, high-stakes territory. It helps us find that crucial balance between speed and certainty.
So, the next time you hit that wall, that tension between moving fast and being sure, take a breath. Ask yourself: What's the risk? How certain are we? Let those questions guide you. Because by navigating with this map, we don't just build products faster – we build better products, with more confidence, and ultimately, deliver more value to the world.