How to Make Hard Decisions

Making tough decisions is messy—no perfect answers, just trade-offs and courage. Here’s how to keep moving forward without letting complexity hold you back.

I started my career as a developer in the Israeli Air Force. We designed and built mission-critical systems, some of which were recently retired after having served the field for over twenty years. It was a prestigious job, and after five years, when I decided to move on, I knew that I could find my dream job out there. 

I took it very seriously. I interviewed for over thirty companies. A friend explained to me that when a company gives you an offer it’s for a limited time, so you should try to get all the offers you want more or less at the same time – and so I did. I ended up having five or six offers that I needed to choose from. 

They were all great offers but very different from each other.

Some were for managerial roles, while others were for an IC role. They were from companies of different sizes, cultures, and industries. And they had different pay grades accordingly.

It wasn’t an easy decision to make. None of these offers were perfect, and I needed to understand the tradeoffs that I was willing to make.

Being as methodological as I am, I created a spreadsheet with the various criteria I had for my dream job. It included hard considerations like the role, compensation, and travel, but also softer criteria like culture, interest, and how much I liked the product I would work on there.

Trying to keep it as objective as possible, I gave each criterion a weight, scored each offer accordingly, and calculated the overall score for each.

But when I looked at the results, I wasn’t happy. It didn’t make sense to me that some offers – that I felt were lower on my list – ranked high, and vice versa. I ended up fine-tuning the weights and the individual scores to reflect what I thought should be the right order.

But if I knew what the right order was, why did I need the scoring to begin with?

It’s because the company I wanted most (and chose eventually) wasn’t the best choice on paper. It was for an IC role with no explicit path to managerial roles; it was the one with the lowest compensation and a company where I had no connections whatsoever.

Deep down, I knew what I wanted, but I wanted it to be the right choice and not simply my choice. Choosing what’s objectively right is much easier than choosing what’s right for me, but perhaps not for everyone. If there is a right answer that no one can argue with, it’s clear that I should go with it. But if it’s subjective, and there is no perfect solution, the decision becomes more complex. Eventually, it would not be the data that makes the decision but me, and therefore, I needed to own it fully. It takes courage, and in an attempt to overcome the lack of it, I sought a method that would tell me that I was making the right call.

But then I realized how ridiculous it all was. Manipulating the data to support the choice I wanted to make was not what I needed. Instead, I needed the courage to go with what I felt was right. 

This decision was about me and my career, so I fully owned both the decision and the outcomes, and hence, all I needed was that bit of courage.

In our professional decisions, we often face similar situations where there are no right or wrong answers, and we still need to choose. As product leaders, we are involved in complex decisions day in and day out. It’s tricky, and the fact that there is no clear cut could even be paralyzing and cause us to avoid any decision whatsoever. 

But endless debates – with ourselves or others – are not what we are here for. Our companies need us to help everyone decide and move forward, even when there is no right answer.

Here is what you can do to not let complexity stop you.

Your Decisions Are Complex

Acknowledging the problem is a huge step toward the solution. When you understand that most of the decisions you need to make are complex and have no right or wrong answer, it allows you to operate differently. 

Instead of trying to justify it with objective arguments, you need to consider a broader perspective in which there are multiple options, none of which is perfect.

When perfection is out of the discussion, you enter the world of carefully considered trade-offs instead. 

Thinking in trade-offs means that there will always be some risk involved. You would always be giving up on something in the favor of someone else, and it’s not always a happy one to make. In other words, many times, these trade-offs are a result of one or more constraints that you would happily remove if you only could, except that you can’t.

Choosing between imperfect options puts more emphasis on you as the decision maker (or recommender if it’s not your decision to make) rather than on the data or the objective truth. It means that no matter what you do – it won’t be what you really want. Instead of letting it overwhelm you, look at the freedom it gives you: If all decisions are imperfect, and you can’t know in advance which one is right, it’s more important that you choose and move on than to debate this forever.

Adopt a Risk-Management Mindset

Since the decision you made is not a perfect one, it’s a risky decision by definition. That’s what makes it so scary. To eliminate the risk – and the hesitation – you need to operate with a risk-management mindset.

It means that you must look the risk in the eye: What happens if you choose wrong? What is the worst-case scenario? How bad is it? 

There would be different answers for different options, so you should consider these worst-case scenarios per option.

Sometimes, you will discover that the worst case isn’t that bad. In other cases, you will see that a worst-case scenario is so bad that you can’t afford to even take the chance that it will happen.

But in most cases, you need to choose between moderate risks. Once you choose, or even as part of the decision, you need to understand how you are going to manage the risk.

You wouldn’t go bungee jumping without a safely secured rope, right? Likewise, you shouldn’t take major risks without understanding the measures that will keep you safe.

And measures are really the first step.

If you want to manage a risk that may or may not materialize, you must understand where you are in terms of the odds it would. Ask yourself how you would know that the risk is getting closer, and make sure to monitor these signals (typically more than one) closely.

Next, prepare your mitigation plan. At which point would you need to operate? What would you do?

Preparing that plan in advance will not only help you decide better but also allow you to look at the risk objectively as you go. After we choose a certain path, changing it is never easy, so our tendency would be to overlook the signals and continue as originally planned. But if you add these safeguards in advance, it will be much harder to ignore them when they are most needed.

This risk management process doesn’t have to be a heavy one. For some decisions and some risks, it’s only a matter of pointing it out to the team and being aware of it. For other risks, closer consideration and monitoring are required. Use your judgment to find the right level for each decision. Remember, we are in the business of deciding and moving forward, not analyzing everything forever.

You Don’t Need to Have All the Answers

As product leaders, we often need to make decisions or lead decisions on things that are beyond our direct control or knowledge. Some decisions we make would impact sales, marketing, finance, and other areas, and other decisions require their input, even if they wouldn’t directly affect them.

Some product leaders find this overwhelming and are unable to take action. To overcome this, you must remember that you are not expected to have all the answers yourself.

Your job is not to come up with a great answer but rather to make sure that there is one eventually.

To do that, it is more important that you facilitate a proper discussion and make sure the hard questions are answered than preparing the full argument in advance.

As the facilitator, you need to give room to multiple perspectives and engage in the complexity. Crisp up your thinking by understanding what question, if answered, would allow you to decide, and find out who can answer it and how.

Only then can you make your recommendations or decide.

Communicate the Complexity

To get everyone’s buy-in to your decision, you must communicate your thought process properly.

Compile an end-to-end narrative that explains what led you to the specific decision. This narrative must include the multiple options you considered, the information you gathered, and the considerations you applied when choosing between the various trade-offs.

Don’t try to make it look like a trivial decision if it isn’t. People would find it superficial and hard to follow.

You must reflect all the perspectives to management or relevant stakeholders, including things they don’t necessarily want to see. For example, when someone doesn’t understand why a certain solution contradicts another, you can’t ignore it and must explain it clearly. If you can’t explain something, perhaps it’s not as solid an argument as you think. 

Remember that if someone is trying to lead to a different path than yours, they usually do so because they think it’s what’s best for the company. Assume there is at least a grain of truth in it, and build from there. Understand what bothers them in your suggestion, and seek an alternative that addresses everyone’s concerns.

The decisions you need to make are often not trivial. Don’t let it overwhelm you. Remember that since there are no right or wrong answers, the only bad decision you can make is the one you didn’t think through and can’t explain.


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