My key takeaways

Following are some hints I noted from the book, in no particular order or structure. Be sure that the book itself is way more organized than that. If you resonate with those points, I highly recommend you grab a copy of the book and read it for yourself, as I’m sure I did no justice to those insights and their accuracy by rephrasing them here.

• Decisions require a process. Understanding our shortcomings in making decisions is not enough for fixing them. Following a process also allows us to feel more confident when making bold choices.
• The commonsensical approach of ranking pros versus cons is familiar, but is profoundly flawed (for reasons below).
• We naturally establish quick beliefs about every matter, and then try to confirm it rather than seriously analyze it. This is referred to as the confirmation bias. We need to take very clear actions to overcome this bias; being aware of it is not enough.
• A process for better decision-making consists of four steps: (i) widen your options, (ii) reality-test your assumptions, (iii) attain distance before deciding, and (iv) prepare to be wrong.
• When widening our options, it is often enough to be exposed to a tiny hint of existing alternatives in order to account for them and avoid being locked on a limited set of options. You need to actively seek those additional options, however. You will not naturally think of additional options unless you actively realize that you are neglecting them.
• A clear indication of neglecting to think of all options is when you think in lines of “whether or not”, not considering other possible combinations.
• To avoid narrow-framing, one trick is to ask yourself: “What if I couldn’t do any of the things I’m considering, what else might I try?”
• Multitracking (considering more than one option simultaneously) is a good way to avoid emotional bias towards your approach. If you favor three projects, you are more likely to accept unpleasant truths about any of them than if you support only one project. In this regard, exploring ideas sequentially is not as powerful as exploring them simultaneously. Also, by considering multiple options simultaneously, you get a better feel for the “shape” of the problem.
• It is a good idea to toggle between a Preventive mindset (focusing on the avoidance of negative outcomes) and a Promotion mindset (pursuing positive outcomes). We need both.
• Analyzing “bright spots” in our past can often help us find solutions for a problem. For example, if you want to go to the gym regularly but can’t fit it in your schedule, think of a past time when you were successful and ask yourself “how exactly did I manage to get myself to the gym on those four days?”. This is a powerful technique also because it tries to reproduce your own success rather than try to implant an approach that was helpful for someone else.
• We need to develop the discipline to consider the opposite of our initial instincts. This starts with a willingness to spark constructive disagreement, particularly when decisions are made by a group in an organization.
• When trying to gather good information for basing a decision, go talk to an expert. An expert doesn’t have to be a heavily credentialed authority, just someone who has more information than you do. (“If your son wants to be a carpenter, go talk to a carpenter. Any carpenter.”) However, don’t trust the expert for making predictions, just for providing missing information. If you ask for an opinion — you get an inside view, which has its biases and inaccuracies. Stick to asking facts about the present rather than about the future.
• A useful exercise when disagreeing on an idea is Roger Martin’s brilliant question: “What would have to be true for this option to be the very best choice?” Asking this question changes your frame of thinking. Similarly, if you think of an approach that you think is entirely not good, ask yourself: “what would have to be different for this approach to work?” Asking this question will change your frame of thinking.
• To gather useful information, we need to ask disconfirming questions. One extreme case for that is by forcing ourselves to consider the very opposite of what instinctively feels as the best approach.
• One trick that helps see the objective picture more clearly, as demonstrated by a CEO in one example in the book, is by asking: “What would my successor on the job do?”
• When we give advice to others, as opposed to when deciding on our own cases, our thought process features two advantages: (i) it prioritizes the most important factors in the decision, and (ii) it downplays short-term emotions. Therefore, when facing a dilemma, it is often useful to ask yourself: “What would I recommend a friend to do in this situation?” This has a similar effect to the question presented before of “what would my successor on the job do?”, but is more suitable for personal situations.
• Agonizing decisions are usually ones where there is a conflict between core priorities. It is important to be able to actively identify and enshrine those core priorities. It will add a lot of clarity to the decision and to other decisions.
• Another useful trick is the premortem, combined with the need to imagine the future not as a single point we must predict, but as a range between worst and best possible points. First, define the best and worst versions of the future following your decisions (not knowing yet what your decision is). Then, try to trace back how those situations might have been reached. On the worst case, ask yourself why you failed, and on the best case, ask yourself if you are ready for such success. Anticipating problems makes it easier to cope with them.