20 Simple Questions To Guarantee Better Decisions

Avoiding being stupid is easier than trying to be smart.

Richard Banfield
7 min readNov 5, 2022
Being less stupid is easier than being smart. Photo by Benjamin Davies on Unsplash

When my wife died I realized I’d be an emotional and cognitive mess for a while. However, as a father and only breadwinner I still needed to make important decisions. In tough situations your ego tries to convince you that you can think your way through the situation with brute force. It is pure arrogance to believe you will. I prefer to think I’m not special.

To help myself be less stupid I created a list of questions that would be a forcing function for better outcomes.

1. Do you need to make this decision?

In many cases we feel like a decision is required, but that’s not always true. Sometimes you just need to sit with situation and contemplate what’s happening. As my late wife, Kristy, once told me after I jumped into a conversation to offer a solution, “Thanks, but I don’t really need you to solve the problem. I was hoping you’d just listen so I can get these thoughts off my mind.” Before jumping into problem solving mode just listen to your thoughts and ask what you can learn from this situation.

2. Are you being asked to make a decision or just share an opinion?

We used to call this a ‘drive by’ at my previous company. Your boss walks past your desk or drops a message in your DM, “Hey, I’ve been thinking about [insert something about work]. What do you think we should do?” While it sounds like you’re being asked to make a decision, it’s just as likely this is a request for an opinion. Confirm whether you’re being asked to decide or just provide an opinion before taking action.

3. Are you being forced to make a decision that is someone else's to make?

Similar to the question above, it’s possible we’re misunderstanding whether the decision is on us or just a conversation about who needs to make the decision. We might find ourselves being forced to make a decision we’re not ready to make or even qualified to make. Are you the right person for the decision? It it your responsibility? Are you assuming that the person is specifically asking you to make the decision?

4. What happens if you don’t make a decision?

We live in a society that values decisiveness. Particularly there is a famous quote by General Norman Schwarzkopf claiming that a bad decision is better than no decision at all. Considering there is a mountain of evidence that he led US military forces into a war that could've been avoided we might want to take that with a grain of salt. Sometimes the best decision is to reconsider.

5. What are the options you are deciding between?

Write them down. Knowing your options makes it easier to determine what path to take. Can you create or negotiate more options? Optionality is a key driver of anti-fragility. The wider the range the better. (Read Antifragile: Things That Gain from Disorder by Nassim Nicholas Taleb)

6. Do you need to make the decision now?

There is power in procrastinating too. More information can be gathered if you leave your decision to the last minute. Avoid prematurely converging on a decision before you absolutely have to. Thanks to John Cutler for this one.

7. Is this a Type 1 or Type 2 decision?

A Type 1 decision is a big, strategic decision that it’s hard to turn back from. It’s like a one-way door. There’s no turning back. A Type 2 decision is an everyday operating decision that you can reverse or unravel. Delay Type 1 decisions until you are confident you can move forward. Move quickly on Type 2 decisions to maintain velocity. This framework was borrowed from Jeff Bezos.

8. What’s the worst that can happen?

Worst case scenario planning is proven to reduce anxiety and improve preparedness. Tim Ferriss describes how you can do this in a few steps in his popular TED Talk. Also, read Jane McGonigal’s book Imaginable for more details.

9. Will this decision indenture you to someone or something for an unacceptably long time?

Think about how much debt (financial, tech, design, support, emotional, etc.) you’re creating by making this decision. Signing leases, taking big loans, leveraging assets, and asking for big favors can all lead to long-term shackles on your future options. This is especially important if your future choices will be restricted by this decision.

10. Is this decision going to create a temporary inconvenience but has long term value?

On the other end of the spectrum, some choices are a temporary inconvenience but generate long-term value or gain. To avoid recency bias and urgency bias, ask if the decision connects directly to your long-term vision or goals? if so, the temporary inconvenience might be worth it.

11. Who are you going to hurt if you make this decision?

Hopefully this is self-explanatory. Don’t be a dick.

12. What are the 2nd and 3rd order consequences of this decision?

Everything has consequences. Beyond the immediate outcomes, what happens next? What will happen in several months from now, or several years from now? Once you have considered what might happen after you make the decision, use your vision and values to help you consider which outcomes you are willing to live with.

13. Do you have data and evidence to support your decision?

Data can be very helpful in narrowing choices or providing precedent. While it’s become fashionable to use data-driven decisions, it’s often unnecessary to include data until further down the decision stack. If you follow questions 1 through 12 you’ll often find you’ll know what type of data will be useful. In some cases you might find you don’t need additional research or data to make a confident decision.

14. How good is your data?

Data that is incorrectly interrogated can be harmful. Selection bias is a good example of how data can be unhelpful if we only have half the story or if we’re asking the wrong question of our data. The quality and source of the data is important.

15. Do you need other’s opinions?

If you want to consider opinions, and you probably should, the easiest way to filter for usefulness is to ask if the source of the information has been in your exact situation. For example, investment advice from that stranger at the bar or the friend of a friend whose “in finance” are just opinions. If the person sharing their opinion had an experience 20 years ago in a different economic market and with a family trust fund to back up their risky choices, walk away. Context and timing in opinions are everything.

16. Can you run a small decision experiment?

A small ‘prototype’ of the decision might be all you need to qualify the decision. If you can’t run an experiment pretend you have already made a choice and imagine what consequences there are. For example, instead of moving your entire family overseas to seek greener pastures try living abroad for a few months in the city you’re anticipating moving to. Live like a local and objectively consider all the possible consequences.

17. How does it feel to live with this decision?

Pretending to make a decision can sometimes be the most informative thing you can do. Watch how your body reacts when you make the decision one way or another. Do you feel excited? Relived? Does the decision bring a sense of dread or foreboding? These feelings shouldn’t be ignored. Even if there’s a rational reason to go with a certain option, you feelings can be warning signs for what’s ahead. Your feelings can add an important clarification. In contemplating the future decision, does this feel like a “full-body yes” (mind, heart, gut) decision or do you have doubts?

18. What are your expectations?

We all have biases and preferences. It’s normal to want certain outcomes but our biases can also steer us towards particular options. As blind as love can be, so can all our desires lead us towards preferences that might not be the best for us. Are you ignoring the red flags just so you can get the outcome you’re hoping for? Are these expectations biasing you towards a certain decision? Thanks to Matt Watkinson for reminding me that expectations drive outcomes.

19. Would my parent/partner/child be proud of my decision?

Try seeing your decision through the eyes of someone your respect. Would this decision make them proud or ashamed of you? Of course, if you’re making a decision about them or that affects the status of your relationship, this might be harder to use a lens.

20. Is this decision aligned with your vision and values?

In many ways this is the most important question. Using your vision and values as a framework to make choices has long been the way people and businesses stay the course. Assuming you have a general idea of what your vision for the future is and a set of principles to live by, these can be a powerful forcing function.

21. Bonus question: What would a time-traveling me do?

Try time-traveling into the future and asking yourself if your future self would like the decision you’re about to make. This is particularly useful when considering a trade-off between instant gratification and future gains. Buying that expensive sports car now, verses investing that money in a guaranteed investment vehicle is rarely the wrong choice unless you have f*ck you money.



Richard Banfield

Dad, artist, cyclist, entrepreneur, advisor, product and design leader. Mostly in that order.