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Your Single Most Important Tool for Managing the Uneven Downsides of Risk

Published 7/10/2026

The skills you build and the tools you master matter, but they aren't your most important asset when things go wrong — and something eventually will. In this episode, I work through why our careers and lives are governed more by avoiding catastrophic downside than by chasing upside, and why the single best tool for surviving a bad event isn't testing, insurance, or money — it's genuine trust with the people around you.

Here's a question to sit with: what is the most important tool you have as a software engineer and as a leader? Most of us reach for something technical, but the answer runs deeper than that. In this episode, I start with the humble premortem — the practice of assuming something has already gone wrong so we can pressure-test our plans — and use it to explore why so much of our work is really about predicting and mitigating risk. From there, I make the case that because we're all exposed to a far larger downside than upside on any given day, the tool that matters most is the one that helps you survive the bad event you couldn't prevent: your relationships with other people, built on real trust.

  • The Premortem as a Risk Lens: Learn why assuming failure ahead of time is such a useful counter to our natural optimism. Our plans quietly assume everything will go right, and a premortem forces us to inspect the gaps our best-laid plans never covered.
  • Life Is Already About Predicting Risk: Nearly every action we take — stepping forward, eating the sushi, merging into traffic — is a small bet on an outcome we can't prove in advance. Much of what we're managing isn't even our own behavior, but the risk other people put us through.
  • Why the Downside Dwarfs the Upside: On a typical Monday, your potential gain is limited, but your potential loss is not. A single catastrophic event — a breached customer, untested code shipped, an injury for an athlete — can undo far more than any single good action could ever build. This is why avoiding failure, not chasing brilliance, quietly shapes most successful careers.
  • Likelihood Times Impact: Even a one-in-a-hundred-days negative event can cost you your job or your company a fortune, while very few actions could produce a commensurate gain like doubling your salary. Our behavioral aversion to risk turns out to be rational.
  • Mitigate the Blast Radius, Not Just the Incidence: You can never be 100% certain a bad event won't happen. Good people who show up, stay reliable, and grow their skills still get laid off. So beyond reducing the likelihood of harm, you have to reduce its impact when it lands.
  • Relationships Are the Real Safety Net: The most important tool in your belt isn't technical — it's your relationships with other human beings. Invested in honestly, they pay you back forever, and they're the thing you fall back on when the negative event you tried to prevent happens anyway.
  • Trust Is the Core Currency: Genuine relationships require reality — real curiosity and care, not performed name-remembering, which people can see through. Trust compounds like an asset, while money spent to buy loyalty is gone the moment it's paid. When you hit a hard deadline or discover something's broken, a reservoir of trust is what lets people extend their best effort without you having to throw more money on the table.
  • Episode Homework: Go invest in your relationships regardless of your current risk profile. Spend extra time in your one-on-ones, with your team, and in your retros — and get curious about what the people around you actually want, instead of assuming you already know.

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Transcript (Generated by OpenAI Whisper)

What is the most important tool that you have as a software engineer, as a leader? I want you to think about this question and keep in mind what your answer is. We'll come back to it in a minute. One of the processes that a lot of teams use is a premortem. If you've never done this before, it's a pretty useful way to try to determine what your risks are. And the way it goes is essentially very much like a postmortem. If you were to look at something that has happened and try to describe what happened. And we've talked about premortems on the show plenty of times before. The. The interesting trick that a premortem provides you is it presumes it assumes that something has gone wrong. Because our natural bias is to imagine that nothing will. That our plans, our best laid plans will not go to waste. And in fact, they'll come true. And this makes sense because most of the time our optimism at least carries us forward. If. All we ever did was think about how everything is going to go wrong, then we probably wouldn't try anything new. We would. Live in fear. We would avoid taking any kind of risk. And every action we take is essentially us predicting risk. Every action that we take in our careers and our personal lives. As human beings. We are constantly. Constantly. Essentially. Taking some kind of action. For some kind of outcome. And we can never exactly prove what that outcome will be until it actually happens. Most things are basically very little risk in our lives. We take one step forward. And we assume in most cases that we're not going to trip. Right. We take a bite. Of sushi and we assume that the sushi is not bad. Sometimes it will be. We get in the car and we put our seatbelt on. We assume that other people are going to drive as rationally as we plan to. Even though we probably are not as good of a driver as we think we are. If you've ever pulled out your phone while you're driving, for example, or driven when you're a little bit sleepy. Well, you've experienced risk that you put yourself through, but also other people experienced risk that they hoped they wouldn't have to at your hands. So a lot of what we're predicting is. Out of our control. Right. Right. A lot of what our choices end up being is trying to predict the risks that others will put us through. That we'll be subjected to circumstantially. And so, so much of our lives is already about predicting risk. So when we make plans, we imagine that the plans are hedging risk on their own. So a premortem. Very important tool. And just to spoil the earlier question of what your most important tool is, this is not it. But a premortem. Is. Kind of forcing our brains to imagine that we did get something wrong. Right. That. When we step into the car. What could go wrong. That we weren't really thinking about. That our plan to drive with our seatbelt on was not sufficient to cover. Right. Maybe we're driving on a two lane road when we could choose. A four lane road that has a median in the middle. And that hedges risk. We still can't say that it's going to provably. You know, solve a. A real material problem. We're preventing things. From happening. We're preventing bad things from happening. By inspecting and pressure testing our plans. So why is the postmortem so important? Again, it's not the most important tool. You have. It's important because it aligns us to. A heavy downside. A heavy downside. Most of the time. Most of the time. The thing that we face. In our lives and in our careers. The opportunities that we have in front of us. Are a result. Especially of a lack. Of failure. This is not very inspiring. Probably for us. For most people. A lot of your career. Will naturally. Fall into a success pattern. If you can avoid. Failure. Now you might think that that's. A pessimistic way to view the world. But this is. How many investors. For example, Warren Buffett. Look at their investing. It's also. How many high. High powered. High intensity athletes. Look at their careers. Well. If they can avoid injury. For example. That becomes. One of the most important. Aspects. For a professional athlete. Now why is that? Why is it that. Avoiding injury becomes more important than. Becoming a world. Class athlete. But because. That one injury. That one mistake. That one. Catastrophe. The one time that you. Breach. The privacy. Of your. Customer base. Right. The one time that. You know. You push code. That wasn't well tested. These are the events. That can have an outsized effect. That is far. Larger. In terms of baseline. So imagine you're at baseline. You know. On a given Monday. And your potential. Upside. For anything that you do. On that Monday. Is fairly limited. But you're. Downside. The downside. How much could you fall. What could the worst mistake do to you. Versus. The best. Action. The. You know. Most advantageous action. You know. Barring. You know. Incredibly lucky. Big strokes of luck. Like buying. The correct lottery ticket. Which you have. Basically zero control of. And nearly zero. Potential of. The likelihood that a risk. That you face. Is going to take you down. Is far higher. Far higher. Than the likelihood. That a good action. Will take you up. By a commensurate amount. In other words. Because of this reason. The. Outsized impact. Of risk aversion. Which has been shown. In many studies. Over and over. That we are. More averse to risk. Than we are driven. To gain. Right. This is actually rational. Or at least. Behaviorally rational. Because the likelihood. Again. The likelihood. That we're going to. Experience. A risky. Event. A negative event. That will have a large impact on us. Right. The likelihood. The utility function here. Likelihood. Times impact. Right. The likelihood. Let's say. I don't know. Ten percent. One in ten days. Hopefully it's not that high. But. Even if it's one percent. One in a hundred days. One in a hundred days. You're going to experience. A worse event. If. You know. Given. Given that you do nothing at all. To prevent it. One in a hundred days. That is. That could. End in you losing your job. It could end in you. You know. Losing a million dollars. For your company. Right. Now exactly. What that downside is. Is dependent entirely. On your situation. It's dependent on your career. It's dependent on where you are. And. You know. What. What. The event is. But there are. Far more events. In that category. Than there are. Events. That would. You know. Cause a commensurate gain. In other words. If you're. If you're. Talking about losing your job. Then the commensurate gain. Would be doubling your salary. Right. This is. And. And perhaps even more. Because. You know. In the job loss scenario. Now you. You have to go and look for a new job. Not only are you totally out of income. But you also have to look for a new job. So. The. The. The likely commensurate gain. How many actions. Could you take. To double your salary. Very. Very few. Very few actions. Right. So. What does this mean. Why are we going through this. This means that risk. Is an incredibly important thing. To pay attention to. In fact. It might be. The most important thing. To pay attention to. The most important thing. So. Of course. A lot of our jobs. A lot of our lives. Are about. That limiting. The. The likelihood. Of risk. Right. That we're. You know. We add testing. We try to. You know. Provide some kind of backstops. We. You know. Provide ourselves insurance. We have all of these things. To avoid. An outsized. Downside. But there's another tool. In your tool belt. That can help you deal with. The reality. Of a bad event. You can never fully prevent. A bad event. Right. You can never actually. Be 100% certain. That something bad won't happen. So what other. Mitigating factor. Can we introduce. If we've tried to reduce the likelihood. But there still is the possibility. Many of you who have had a layoff. Know this is true. You work on your career. You try your best. You do a good job. You show up every day. You're reliable. You are growing your talent. You're growing your skill. And then you get laid off. It's a negative event. That you tried to mitigate. And it still happened. It still happened. So what do you do? What do you do in this scenario? Or not necessarily in the post event scenario. But all the time. The most important tool in your tool belt. The most important tool. Is your relationships with other human beings. It's that simple. It is that simple. Your relationship with other human beings. Is your best safety net. To deal with risk in your life. To deal with risk in your career. If you invest in relationships. Regardless of what your current risk profile is. Your relationships will pay you back. Forever. Now when I say invest in relationships. I want to be very clear about something. Relationships. With other people. Requires. Reality. It requires truth. It requires you to actually develop. A care. And an empathy for that person. If all you're doing is performing. The relationship. If all you're doing is. Learning somebody's name. Because you know it's important for you. So that you avoid risk in the future. Because you know somebody's name. Then. Because we are social animals. Because we've developed the. You know the critical skill. Of being able to see through other people. We've developed the ability to understand. Whether somebody's being genuine. Or not. If you are performing this. Unless. You are incredibly. Good or potentially sociopathic. People will know. People will know. That you're not actually developing. A relationship with them. This starts with a sense of curiosity. And it starts with. Developing an understanding. That we have a shared experience as human beings. Now this is a software engineering. Show or centrics show. We talk about technology. We talk about AI. We talk about all this stuff. That surrounds the human experience. If you lose your job. If you. Screw up production. Right. If you. If you hire poorly. If you. End up going into a difficult job. That you're not able to bridge the gap. Whatever the negative event is. You are better off. If you have good relationships. To fall back on. If you have good relationships. With your customers. With your co-workers. With your teammates. With your consuming teammates. The other teams who use your services. The people who are on call. The support services that you use. All of these people are relationships. All of them are relationships. And so much about. What we try to do in our jobs. So much about what we try to do with other people. Is centered. And kind of pivots on relationships. And so much about. What we try to do. The ability to motivate another person. For example. As a manager. The ability to motivate another person. Of course there are many different levers. That you can pull. Right. Of course there are levers like. For example. Pay. If you were to pay somebody. A significant amount of money. Then that gives them a higher motivation. To do something. Right. So there's a utility function. That you might run. If you are. You know. Thinking about. Do this in the most efficient way. There's a utility function. That you might run. That says. Okay. How much is my time worth. That I would have to invest in a relationship. Versus the pay. That I would have to give this person. To substitute for a relationship. What's interesting is. The compounding value. Of relationships. Lasts. The time you spend now. Compounds over time in the future. Versus the pay that you give now. Is gone. Immediately. Of course that person can go and invest it. And all of those things may. May be true. But the trust that you develop. Is foundational. And it lives on. It's like an asset. So if you're purely looking at things. Through an analytical. Investment portfolio perspective. The assets you build. Through relationship development. Are. An investment in something. Rather than. A spend on something. If you're just paying someone. In order to get their loyalty. For example. You're probably going to eventually find. The end of that road. In fact. It's almost certain. Plenty of studies have come out. Showing that pay. Compensation. Has a roll-off effect. In other words. There's a certain number. At which. That pay. Doesn't increase your satisfaction with life. There's a certain. And we see this. In the extremes. Right. We see. People who are. Uber rich. Ultra rich. People. Who are. Not yet satisfied. Or. You know. Are. You know. Somehow. They're missing something. Right. They either are continuing. To seek more money. Or. You know. Their relationships are falling apart. Around their lives. This is something that we see in the news. We see it on tabloids. Whatever. Right. And of course. So. So. So. If. If it was the case. That. Money was sufficient. For. Buying loyalty. For example. And. And. Certainly. It is not. A useless tool. I want to be clear. I'm not going to try to be. You know. Overly philosophical here. Money is not. A trivial thing. To put on the table. Of course. It's not. But there is a limit. And my argument. Is that. The most powerful lever. That every person. Listening to this. Has. Is relationship development. And it doesn't even have to be. You know. Deep relationship development. We're just talking about. A simple modicum. Of care. For another human being. So what this really looks like. Is being curious about. What that person cares about. Being curious. Being curious about. What this. What does their life look like. Right. What. What kinds of things. Actually motivate them. And how could you get them. More of those things. Right. This is very. Basic. You know. Negotiation. Right. And so. If you're. If you're a manager. You should be able to answer. In my opinion. I'm going to. Very. Try to avoid being prescriptive. On the show. But. You should be able to answer. What does this person want. In their career. If they're your report. You should have that conversation. With them. What do they care about. Are they the kind of person. That. You know. Very much cares. About. The next level. In their career. Or do they care about. Stability more. Which one of those things. Is more motivating. To that person. And now. I. I'm starting to develop. Like. A true picture. Of who this person is. And what they want. Just knowing. What another person wants. Instead of assuming. What they want. Is already a good basis. For her relationship. Right. So. If you're developing. And this. This goes for. Not just for. Reports. And their bosses. This goes for. Your cross. Functional relationships. It goes for. You know. Through other teams. What is that. Teams incentive. What do they care about. Right. They have a roadmap. For example. How can I make sure. That what I'm asking for. Is respectful. Of their incentives. That I'm not just coming in. And bulldozing them. And. How can I do. Do so in a way. That isn't just. Pulling power. Right. That isn't just. Trying to throw money. Or trying to throw. Something else at them. That doesn't. Fundamentally. Understand. What they care about. And their experience. As a person. In. In my personal. Experience. In this career. And. In. What I've watched. In others. I believe it is. A high. A much higher. ROI. A much higher. ROI. Because here's what happens. If you. Let's say. You have. An unlimited amount of money. To motivate people. And somebody else has. An unlimited amount of money. To motivate people. If you're just going. Pay versus pay. When things get hard. On either side of that fence. What is left. Right. This is. This is kind of an. An endless runway. Or a runaway problem. Right. It's a game theory problem. What. What is left. For that person. To. To stick. To stick with you. To. Similarly. On the flip side of this. You know. The relationship development. Really. Fundamentally. The kind of core unit. Of relationship development. Is trust. Right. Trust is. Is the core currency. The core unit. To. That you deal in. With relationships. Right. Because. What I care about. Is that this. I trust this person. To do. What is best. For both me. And them. That is the. The kind of. Basis. For trust. In any good relationship. Particularly. In professional relationships. I trust that this person. Is not going to do something. That will harm me. Just to get ahead. That is. That is a fundamental basis. For. For any. Professional relationship. Okay. And I'll trust that this person. Is. Is. Truthful. And honest with me. That. What they say. I can depend on. That they're reliable. Etc. Right. So if you develop. Trust. Trust. With another person. Then. When they come to you. Asking for something. That is an extension. That is. Inconvenient. For you. When they come. And ask you. When your neighbor. Comes and asks you. For a cup of sugar. Right. That's. That's. Obviously. Very mild. But that is an inconvenience. To you. You're out. A cup of sugar. What if you needed that? Well. Of course. If you. Have a trusting relationship. Then you know. Well. They wouldn't ask me. They actually needed it. They're not going to try. To take advantage of me. We trust each other. And so. If you're a manager. And. If you are coming up on. You know. The end of the quarter. And you have a deadline. And you have good trust. With your people. They trust. That you. Wouldn't ask them. For something. Unless you actually need it. They. They. They trust. That you're not just. Playing the urgency card. To make yourself look good. You have. Much more. Potential. To deal. With risky. Scenarios. We've. Come up against. A hard deadline. We. Suddenly realize. Something's broken. In a non-trusting situation. Or in a situation. Where somebody is redlining. Because of what you've paid them. In order to get them. To extend. Their. Best effort. In that situation. What do you have to do? You have to throw more money. On the table. What. What is the. What is the. Recourse. Where is. The. The reservoir. Right. Hopefully. Hopefully. This person cares enough. About their own career. About their own. Professionalism. Or whatever. Right. But. If they don't trust. You. Fundamentally. If you've. Developed a. Contentious relationship. Or. A purely transactional relationship. And you don't have any trust. For each other. As human beings. It's much less likely. That that person is going to. To their best effort. On your behalf. Especially. If it happens. Multiple times. Over and over. Right. So. You know. If. If your track record is. That every time. A quarter. Is up. And we're close to the end. We're at. You know. Near. The finish line. On a. On an OKR. And you're asking. Every single time. For somebody's. Extended effort. And. You know. They find. They. Especially. If they find out. After the fact. Oh. Well. You know. It wasn't. A big deal. You're going to. Erode. Trust. With that person. The next time. That you ask. For that. You know. The likelihood. That they're going to. Extend their best efforts. Very low. It's very low. Or they may. Say you know what. I'll keep doing this. But you got to keep paying me more. Right. Or you got to. We have to change the. The agreement here. Because. Because we don't have. A reservoir of trust. I have to protect myself. From you. Right. And so. Your best. Most important tool. Because. Of. Your risk. Because. We are all exposed. To a greater downside. Every day. Than we are. The potential upside. So we should be focusing. Heavily. On the likely downside. The. The. Risks. That we are facing. And mitigating the effects. Of those risks. We can try to mitigate. The incidence. Of a risky event. And. But we should also mitigate. The blast radius. Of risky event. And your best tool. To do that. Your best tool. To deal with. A bad event. Is relationships. Go and. Invest. In all of the relationships. Spend extra time. In your one-on-ones. Spend extra time. Talking with your team. In your retros. Spend.