CTO Compass

8 tips for improving your decision-making

CTO Compass series

I don't know about you, but I wasn't taught how to make good decisions. The only advice I ever got was to bust out a piece of paper and make a list of the pros and cons. Mostly, I'd sit and contemplate or endlessly "research", which was really code for sitting and procrastinating.

Often, the decision would get made for me because I procrastinated so long that the opportunity passed, or I’d have to make a knee-jerk decision at that moment. I might as well have flipped a coin back at the beginning and saved a lot of angst because the end result was the same. 🙄

And that’s also how I said yes to my girlfriend when she asked me to marry her!

Now, that turned out to be a great decision. I have two amazing children, and we’ve been very happy for the last 17 years. However, procrastination and coin flips are not exactly good strategies for making successful decisions.

Most decisions we make are a combination of learned behaviours and risk aversion as we blunder our way through life. Annie Duke says that “decisions are bets on the future”, so if you want a better future, you must make better decisions.

8 things you can do to improve your decision-making

  1. Remember, most decisions are reversible. When the stakes are higher, it’s easier to lock yourself into poorer ways of thinking, which constrain you unnecessarily. Aside from learning to ask yourself better questions to open up your thinking, you can pre-plan by thinking about how you might reverse a given course of action or noting which decisions are genuinely one-way doors.
  2. A common trap we fall into when deciding is narrow framing. It’s easy to think there are only two or three possible options. When listing your choices open to you, constantly challenge yourself to develop several other options.
  3. Be aware of your biases. There are many cognitive biases we can be susceptible to, often without even being aware of it, as we’ve often conditioned ourselves by naturally thinking that way. Here are three of the most common ones worth considering: Outcome probability. Humans generally tend to incorrectly estimate the likelihood of events occurring or not compared to their statistical probability.The Sunk Cost Fallacy. What’s past is past. If you base decisions on past investments of time, money or effort already spent instead of evaluating the best prospects moving forward, you’ll likely get bogged down and constrain your thinking. Instead, think about what you would advise someone else if they were in your situation. A bit of objectivity goes a long way.Short-term bias. Bigger decisions have longer-term ramifications. We are often driven toward short-term gratification, especially in today’s culture. Make sure you’re considering more than just the short-term benefits.
  4. Consider your intrinsic values and your personal principles. To make decisions easier, think about how the choices align with your values or principles.Your intrinsic values are the things you value for their own sake. When a decision is more aligned with them, you will generally feel better about it being the right choice.Similarly, perhaps you have a set of principles–I like to call them operating principles–, a form of default action which leads you toward being the person you want to be. For example, “Family comes first”. Use these principles as a guiding light to pick the right action.
  5. Align with goals. Decisions you make should help you move toward your long-term goals. If you haven’t got clarity on your goals and making sure they’re effective, then you’ll have a more difficult time making a good decision because you won’t know if your decision will likely lead you closer to what you really want. While it might be tangential to making an immediate decision, putting time aside to get clear on your goals will make future decisions easier.
  6. Learn from the past. Reflect on past decisions you’ve made, especially those that did not go well, and try to identify the patterns of thinking and behaviour that led to that choice. Don’t ignore your successful decisions either. Was it more luck than judgment? What can you learn from them?
  7. Use a decision journal. I encourage you to create a decision journal. Writing down your thinking is always helpful since we can only hold so much in our heads. You can also be more structured in learning from your past by reviewing the journal periodically; you can more accurately assess the impact of your choices, what you did well, and where you can improve in the future.Don’t use it for every decision; reserve it for those that matter.

​By applying these tips and following a more disciplined process, you’ll make better decisions that will weigh less on your mind. Make it a habit to keep practising and refining your decision-making skills, and you’ll see the impact of your improved decision-making process on your life.

⚡️ Thinking Time ⚡️

When faced with a decision, use your Thinking Time to think it through, either using the structured Thinking Time process or be guided by this advice.

Be sure to document your decision-making process as you go, and set a reminder to review it in the future.

CTO Compass series