Why Great Products Don’t Result From Playing it Safe

And how I achieve outcomes safely (without knowing all the answers).

Have you ever spent months toiling over the perfect product plan? Do you spend countless hours prioritizing your features in an intricate ranking spreadsheet? Do you believe a solid business case, strategy, or proof of concept is what makes or breaks a great product?

If you answered, “Yes,” to any of these questions, I’ve got some bad news for you.

None of this makes much of a difference in getting to a successful result. In fact, it’s more likely to lead to a negative outcome because of all the effort, time, and cost you waste doing it.

Predicting product outcomes is in the realm of fortune-telling. It’s a scam. Nobody can actually see into the future. And don’t trust anyone who tells you they can.

Yet, that doesn’t stop many of us from trying. You see it play out day in and day out in product work.

• Strategic planning
• Yearly budgeting cycles
• Quarterly planning events
• Lengthy analysis and design
• Elaborate, predictive business cases
• Intricate, detailed plans far out into the future

I’ve seen companies spend months or years trying to build the perfect plan before taking one step to try it out. They think this reduces their risk. But it ends up sending them down the wrong path and destroys their chances of success.

Predictive, upfront plans don’t reduce risk. They aren’t safe. The control they promise is an illusion.

We are living out a fiction when we put our faith in planning.

Detailed plans are fairy tales.

A hard truth: precision aiming and risk-free execution aren’t possible in product work.

In the uncertain and complex world of product work, planning is riskier than action.

• You don’t know what you don’t know until it happens.
• You don’t know what will work for your customers until it does.
• You won’t know the best way to build it until you are building it.

We all wish we could control these things, but we can’t.

The faster we can admit this, the quicker we can get to what matters— action.

Planning is an obstacle to action. And it’s easy to get wrapped up in it and do it for too long. It becomes a form of resistance to taking a step.

The longer we plan, the longer we delay learning.

Then, why do we keep chasing the perfect all-in plan?

Bottom line, we plan with meticulous detail because we fear failing.

Fear of failure kills products. We end up trying to please our boss or stakeholders to stay in their favor. Or simply to keep our job. That beautiful plan might secure our job in the short term. But what happens when our grand blueprint fails to deliver results to real users? What is the reward for a failure to realize business impact? Nothing good.

You’re playing not to lose versus playing to win.

Now, I know many times, we feel we have no choice but to do this.

For instance, we are often forced to hit an imposed deadline. This drives us to focus on speed (to hurry). It makes us fall into the trap of optimizing to hit the target with one spectacular shot. And we often compromise quality (and our sanity) rushing to hit the deadline.

Our one shot is on time (sometimes). But it misses the target.

It’s not your skill that’s the problem. Rather, it’s the fallacy of believing your first try will work. Add fear as a driver, and you have a perfect storm beating against you. Sinking you.

Trying to hit an uncertain target, under stress, in one shot is foolhardy.

Product work takes many tries to get it right.

Without patient iteration, you are bound to focus on the wrong thing.

When we decide too early, we lock in before we get a chance to learn. We give up our optionality. Our only option is to deliver what we promised. This treacherous path leads to many failed products.

Realizing outcomes requires patience and evolution, not giant, one-time bets.

So, what’s the alternative? I’m glad you asked.

My 6 Safe Ways to Boost Your Product Outcomes With More Learning and Less Planning

Do breakthrough products come from the muse? Or do they emerge from day-in and day-out deliberate practice and experimentation? My experience points to the latter.

When I look back at my career, I’m better for all the defeats—the ideas that didn’t work—not the successes. Why? Because each defeat produced insight and learning. Learning is growth (when you act on it). And with product work, evolving from learning grows products your users love.

Safe product development derives from learning.

The more scared you are, the more you need to double down on learning (and loosen your grip on planning). Don’t be afraid to act. I’ve got 6 ways you can do this below.

Let’s dive in.

1 – It’s safer to plan lighter and near term.

Plans go stale fast.

So, if you are going to plan, make it a rough outline. A sketch. A guideline.

The lighter the plan, the easier it is to change.

Detailed plans take a ton of time and effort. When the inevitable happens (the plan doesn’t go as planned), you hesitate to throw it out. You don’t want all the effort you put into it to go to waste. Then, your plan is nothing more than wishful thinking.

I know this happens because I’ve done it many times. I’ve held on to a plan long past its expiration date. And a bad plan always decays until it spoils. You can’t save it. The only option is to trash it.

So, now, my teams and I plan light. And we keep our plans near term.

We may sketch out a goal for the day and a rough plan to get there. Any detailed plans are for the next hour only. This maximizes the number of learning loops. It allows us to move light when evidence presents a better path.

Plan for fast learning, not for precision.

2 – It’s safer to involve your user.

Most of our ideas suck—a hard truth.

And the faster we learn how wrong we are, the better.

How do you know if you are wrong? Talk to your users.

I engage with my user before, during, and after I build an idea. Here’s how you can do this:

1. Learn their situation before you build.
2. Get their input as you build a simple first solution.
3. Test a basic solution and get feedback on the experience.
4. Iterate, pivot, and keep trying until you delight and meet the need.

Let users be your compass.

3 – It’s safer to have a crooked path.

The shortest distance to a great product is not a straight line.

A plan usually charts the straight, shortest path to your destination. This would work fine if knowledge was perfect up front. But your ignorance is at its zenith before you start.

So, expect to take two steps forward, one step sideways, and one step backward as you learn and adjust. Your journey will look more like the sand-walk used in Dune to avoid a worm attack. While the effort is greater, so are your chances for a successful journey.

Use learning to chart a non-linear path to the right product solutions, sooner.

4 – It’s safer to take small steps.

Precision aiming bets on one large step (leap).

With one large bet, the only learning is at the end. You win or you lose. And unfortunately, we are often on the losing side. The house has the advantage in large product bets.

But many small bets allow you to have more tries at getting it right. And each step is better than the last because you inspect the evidence and learn as you go. This is how you beat the risk in product work. Many steps, coupled with learning, become your secret weapon.

Small steps use knowledge to put the odds in your favor.

5 – It’s safer to start simple.

We imagine more than we need.

It’s rare that the best thing we can imagine is what our users need in the time that they need it. I used to design elaborate features. Every bell and whistle I could dream up made it in. But users sometimes need a bicycle, not a Lamborghini.

Perfection is costly, takes excess time and money, and is unrealistic.

Practical is inexpensive, timely, and achievable.

Going big and grand out of the gate is reckless.

A simple, practical first step is safe. Favor this.

6 – It’s safer to release early and often.

Why hold up all value until you realize your grand vision?

I hear elaborate tales from teams who claim they can’t release in small increments.

• It’s too disruptive.
• It’s too complicated.
• It’s not aligned with yearly rhythms.
• It’s too difficult to change processes.

These are all excuses. One thing remains true, regardless of the reason. If you don’t release, you can’t earn value.

Don’t delay value until the end. You’ll likely find no pot at the end of the rainbow.

Instead, find a way to harvest value along the journey.

Realizing value early is safe. It’s a winning strategy. For your team, your customers, and your business.

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That’s it.

It’s safer to risk getting it wrong than to try to always get it right. This is how you discover what actually matters to your users. You put early ideas out there and adapt them until you hit a chord that resonates.

Detailed planning amidst uncertainty is not safe.

Safety emerges from:

1. Lightweight, short-term plans.
2. Involving your users.
3. Non-linear paths.
4. Small moves.
5. Simple fixes.
6. Early value.

Keep on learning. Leave detailed plans behind. Safe outcomes await. Good luck out there.

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