10 Tools to Improve Your Thinking 🤔

Photo by Lucas Benjamin on Unsplash

If you’re leading an organization one of your most important roles is to make high-quality decisions. What can you do to improve your chances of making better decisions while resisting poor thinking and limiting decision fatigue?

Decisions matter in leadership. According to Sahakian and Labuzetta (2013), the average adult makes about 35,000 decisions a day.

In today’s post, I’d like to offer 10 tools that have helped me improve the quality of decisions I make.

Don’t set out to create a “better” wheel.

I believe in the discipline of mastering the best of what other people have figured out.

-Charlie Munger

Learn from the genius of others. When I started my podcast in 2015, I invested in a program called “Podcaster’s Paradise.” It cost me $1200 for a lifetime membership. This was the most I had ever invested in my growth.

This course and community were created by John Lee Dumas, host of the Entrepreneur on Fire podcast. I took his free podcasting course and was “sold” on the idea of joining his program.

Was this a wise investment?

I believed that joining this community would accelerate my own understanding of creating, marketing, and growing a podcast. Nearly six years later, I have shipped 100s of episodes each Wednesday and never missed a week. The podcast has been downloaded millions of times.

The show started off with incredible momentum because I leveraged the wisdom and experience of the “paradise” community and applied it on Day One.

Everything JLD taught me I could find on the internet for free or learn through years of experience. So my choice was a quicker route embedded with mind-blowing value or go the financially cheaper and more expensive timeline letting experience be my teacher.

I could also argue that it is actually more costly to have not invested in Pod Paradise. The impact I’ve had and the revenue generated from the show would have occurred years later. Instead, I was able to enjoy the harvest just a few months later.

What am I wearing today? (Just one of 35,00 choices I need to make)

Steve Jobs had a uniform. It was a pair of jeans and black turtle neck. Steve knew what he would wear each day and didn’t use any of his finite brain power contemplating his outfit.

I haven’t gone full “Jobs” in terms of a wardrobe, but adjusted this approach to fit my needs. I bought 5 white and 5 black V-necks for a top. I wear a Patagonia hoodie, pullover, or fleece every day. I love going to my drawer because I just grab the closest shirt. My only decision is, “White or black today?”

I didn’t mention pants. Most of my calls are done on video from the waist up. I’ll let you decide how you want to write the rest of my wardrobe story …

Delegate driving, groceries, chores.

Hire an Uber or Lyft. Use the time commuting to prep for a meeting, presentation, etc. Don’t worry about traffic or the route you need to take. Make some calls to invest in relationships or generate sales while you enjoy being a passenger.

Everything is delegate-able. When I arrived in New York last August and had to quarantine for two weeks, I didn’t starve. Groceries were delivered to my house via InstaCart.

In Upstate New York it snows, a lot. I could spend an hour clearing my driveway or I can use that time doing things only I can do and that creates value for my organization.

Exchange one of your hammers in for a screwdriver, drill, and a table saw.

If all you have is a hammer, everything is treated like a nail.

-Abraham Maslow

I am indebted to the work of Shane Parrish and his blog Farnam Street. Shane introduced me to the idea of “mental models.”

Mental models are concepts from a variety of disciplines that are useful when applied to your specific leadership context.

For example, when someone does something that results in a bad outcome, it can be tempting to think that this individual was “out to get you.”

On a recent coaching call with a client, she relayed a story of how the central office of her school district handled a specific situation. It’s clear that the outcome was bad, but where my client went astray in her thinking was believing that central office was doing it specifically to make her life harder or taint her reputation.

Hanlon’s Razor is the mental model that works in this case. It states, don’t attribute to malice what is better explained by stupidity.

Other mental models include:

  • The map is not the territory: I remember this when seeing events trend on Twitter, it doesn’t make it reality.
  • First-principles thinking: If you understand the building blocks, you can make some educated guesses when things get too niche and specific.
  • Second-order thinking: Estimating the first-order result of a decision isn’t difficult. How often do you pause and think of second and third-order effects?

Shane Parrish and the Farnam Street team have written two great books on mental models. I encourage you to pick up Volume 1 and Volume 2.

If you are looking for something free and useful: Here is a great guide that Shane wrote on making smarter decisions.

How did I feel when I made that decision? 6-months later what did I learn from the result?

Shane Parrish also taught me the idea of a “decision journal.” I read his article, downloaded the template, and put my own spin on the decision journal.

There are four components of a decision journal:

  • Prepare: Consider and identify your mental and emotional state.
  • Set the context: Describe the situation you currently face.
  • Explore options and decide: Consider the multiple options available to you (really dig in here). Place some “bets” on each option (How likely is this scenario? Write it as a percentage.). Make a decision.
  • Review: Set a calendar reminder for 6-months into the future. What did you learn from this decision? What did you learn about yourself?

You can download the decision journal for free on my blog here.

Don’t ship just yet: Here are 10 reasons your project will fail.

One of my favorite decision-making tools is a pre-mortem. You can do this alone or in a group. Before launching a major initiative or project, ask yourself: why might this project fail?

The point of the pre-mortem is to explore as many reasons as possible a project might derail. Doing this allows you to make a better decision moving forward. You can either plan for and address challenges you predict will occur or you might wisely choose to end a project before even launching. This is essential in proactive versus reactive leadership.

As a man, I feel very comfortable wearing a dress.

I actually haven’t ever worn a dress, but it is useful to understand why some men might enjoy doing that.

My point here is to force yourself to think from different perspectives. Imagine if our politicians actually spent more time thinking about why their opponent’s plan is better.

What if they actually had to argue their opponent’s perspective at a debate?

The community would end up winning as a result and the best of each perspective would be more likely included.

The present version of myself must really hate my future self.

I’m currently reading Thinking in Bets within a leadership community I facilitate.

One of the stories the author, Annie Duke, shares has to do with “Night Jerry.”

In this story, Jerry is that Jerry (Jerry Seinfeld). I guess one of his standup bits has to do with how Night Jerry doesn’t like Morning Jerry. Night Jerry likes to stay up late, drink an extra beer or two, eat way too many sweets. Morning Jerry dislikes how he wakes up each day: lethargic, bloated, and unable to focus.

The problem is Morning Jerry feels like he has no control over Night Jerry. This is untrue, but human beings do a lousy job of doing what is right in the present moment because it will have a greater reward in the future. This challenge is called temporal discounting. We see it when it comes to diet, fitness, sleep hygiene, investing, etc.

The trick is to pause just for a moment to allow your version of Night Jerry to collide with Morning Jerry and to consider the future consequences of the present decision.

When I think of trees, I think of monkeys, bananas, birds, and … decisions.

I’m currently coaching another cohort of the altMBA by Seth Godin and Akimbo. As a student and now as a coach, I can confidently say that this is the best investment I ever made in my personal and professional growth.

The altMBA is a 4-week sprint on the topic of leadership and making change. Part of the curriculum asks students to consider their decision-making process and level up the quality of decisions they make.

An easy way one might do that is by using a decision tree. Here is a great article that describes how to use a decision tree and how to apply some probabilistic thinking to various potential outcomes.

Done well, a decision tree will show you all the potential pathways forward you may not have seen at first. This brings me to my last point …

You mean you offer this couch in more than black and white?

I recently moved from overseas back to the USA. My wife and I were in various European countries for just over three years living in furnished apartments. When we settled in New York, we had no furniture to our name.

It took 6-months, but our couch arrived today, Thank God!

Why did it take 6-months??? (I’ll reveal that answer in just a sec …)

I used to go to a therapist years ago to work on myself. Joseph was an amazing therapist. His office was in downtown Chicago and it had a beautiful view of Michigan Ave.

I remember discussing some event where my perspective was “clearly right” and anyone who disagreed was “clearly wrong.” Joseph helped me understand that most people probably wouldn’t agree with me.

This was like learning about gravity or that the Earth revolved around the sun! Seriously. Learning that my way of thinking about what’s right and wrong in the world is just my one perspective. This was an earth-shattering revelation!

And I think it applies to decisions as well.

We often don’t see all the different ways we can approach a decision because we are too close to it.

It’s hard to read the label when you’re inside the jar.

-Joel Weldon

Surrounding yourself with a trusted board of advisors who can help you see what you cannot see is essential to upgrading your decision-making quality (and that is also a stealthy 11th tool I snuck in there).

Back to my couch …

We had initially ordered our coach from another store. We waited 5-and-a-half months and it arrived at our door, only to find out that it wouldn’t fit inside(Don’t get me started on how the delivery guys didn’t even try to bring the couch in nor did they attempt to take the legs off the couch to get it inside).

So we ordered our new couch from West Elm.

My wife and I found a sectional we liked. There were literally 55 different choices of color from Dark Horseradish or Rust to Pebble Stone and Shelter Blue. We went with Feather Gray because not only did it look nice, it was also in stock and would be inside our house in two weeks.

What I learned about decision making from purchasing my new couch:

  • There are more options than we originally think
  • Sometimes the best option is the one that gets you to the goal in the shortest time possible. Sometimes not. It’s very good to know which options exist.

One last note on outcomes.

This post is about decision quality.

You can make a great decision and arrive at a poor outcome.

You can also make a terrible decision and it ends up working out for you.

Don’t confuse decisions with outcomes. They are two separate parts in the same leadership equation.

My last bits of advice:

  • Focus on what you can control and commit to a sound process.
  • Surround yourself with amazing people that will push you to be a clearer thinker.
  • Hold outcomes loosely.
  • And celebrate something positive every day.

Host of the Better Leaders Better Schools podcast with over one million downloads 🚀