Good To Great Decisions

by Barry O'Reilly

Having advised many leaders of large organizations over the years, I’ve realized that one of the most critical skills of leadership is making great decisions. That might seem obvious, but when I ask executives what process they use to make decisions, most of them don’t have a solid answer. 

They often stare at me for a moment and say, “Well, I think about it, then just make a decision.”

Personally, I learned the hard way that such an intuitive approach is less than ideal as I set about growing my own business, so I started to develop a system for understanding and improving how I make decisions. This simple tool, when used consistently, has proven exceptionally powerful for me and my clients.

I call it a “Decision Journal.” 

I realized that visualizing the way I was making decisions gave me a way to catalog several important factors over time, such as:

  • how I was making decisions
  • what information I liked to use (or was lacking) to make decisions 
  • why I made a given decision and under what circumstances, and
  • reflections and critiques to improve my method for making decisions in the future

In high-pressure, high-tempo situations, our decision-making capability is often tested to the maximum. We’re asked to make decisive calls under extreme uncertainty with incomplete data and limited time, but high stakes. It’s in these moments that great decision-making becomes crucial. Yet at the same time, we have the greatest potential for information and process loss, as well as a loss of discipline for making conscientious decisions.

We can experience a variety of emotional highs and lows—even a strong sense of progress from rapid-fire answers—but tend to forget the real details of, “What actually happened?” and “Why did I make that call again?” Bias clouds our memories, and it becomes easy to keep plunging forward, never truly retaining the important lessons we needed to learn.

Having a tool to leverage and regularly reflect upon gives you the means to intentionally and continuously improve your decision-making ability, because ultimately, our process for making decisions matters more than the results of any particular decision. 

Yes, that’s correct—read it again. Results matter less than how you make decisions. Why? The quality of our results is not fully in our control. It stems from a combination of the quality of our decision-making and chance. 

Learning to recognize the difference between quality of decision, quality of results, and chance is a powerful perspective to improve our outcomes. When we have this mindset, we can intentionally improve our decision-making systems and subsequent outcomes over time through reflection, refinement, and deliberate practice.

I’ve been using a Decision Journal for a number of years now, and every time I mention it, people always want to know more. So I figured that, given the current state of our lives in the midst of the coronavirus pandemic, it’s a perfect time to shed more light on this for you, dear reader.

 

Why Our Decision-Making Can Be Less Than Ideal

First, we need to be aware of how bad decisions can occur. From what I’ve experienced and observed, we set ourselves up for poor decision-making when:

  • We see decisions as simple, binary choices. 
  • We think too narrowly.
  • We fail to consider other alternatives or have a limited set of options.
  • We are biased by previous choices, personal values, and short-term emotions. 
  • We are overconfident about our past decisions expertise. 
  • We confuse quality of results with quality of decision making.
  • We’re not really aware of all the information we’re using to make decisions.

Now more than ever, we’re making decisions under uncertainty with a lack of all the information we may wish we had. So a system of capturing and visualizing our critical thinking becomes an even more powerful tool to help us learn our way through this time of heightened uncertainty.

The Inspiration for the Decision Journal

The first time I started a company, trying to figure out how to run and scale it, I found myself making decisions nonstop—from what type of Sharpies we needed, to what strategy to choose to scale our business. 

It was intense and endless. With such a high tempo and high stakes, and so much work in progress, it was difficult for me to look back on a week—nevermind a month—and understand why I’d made a certain call. 

This blind spot became especially troubling at times when the situation wasn’t going the way I wanted. I noticed I would start tricking myself into thinking I’d made the decision I wished I made over what I really did. 

I also got the sense I was making decisions I’d made before, and it started making me wonder if I was having further process loss—or if I was simply going crazy!

I was sensing patterns but missing essential pieces of the puzzle to get a complete perspective on what was happening and why.

Writing details in my Decision Journal helped me become aware of the information I had, what was missing, and which data was most important to me. It became the system of record, so I could start to understand my process—and its flaws and fallacies—over time. Then when I got results, I could go back and reflect on what was chance, what was me, and what was to be improved for next time.

Defining “Great” Decisions

Before we look at improving decision making, it’s useful to consider what constitutes a great decision.

For me, great decisions are not just about making logical or data-informed choices. It’s important to consider that the rest of the team, executives, and stakeholders can support and understand your decisions, even if they disagree. 

I actually like to gather dissenting opinions, and if I don’t have enough of them with a given idea, it often makes me worried that I’m making a decision in isolation, or people aren’t really thinking about it.

If you don’t have any dissenting opinions, it means you might have too many people thinking just like you, which is actually dangerous. If that’s the case, it’s imperative you find someone (even yourself) to play devil’s advocate.

Even worse are situations where people aren’t willing to speak up—they feel unsafe and thus offer silence. If that’s the case, it’s on you to set the tone. Admitting errors, discussing them more often, and showing people this system helps everyone understand that you don’t have all the answers—you struggle with tough questions just like everyone else. 

Great Decisions Have A Great Process And Results

Often when you ask people, “What’s the best (or worst) decision you made in the last year?” they’ll tell you a story based on the result. Very few people will talk about the process they used to make a decision, regardless if the result was good or bad. 

But what I realized is the best way to test the quality of a decision is to test the process I used to make the decision. Again, we’re not always in control of the outcomes of our choices, but we are in control of the process we use to achieve them.

This notion was crystallized for me further in poker champion Annie Duke’s book, Thinking In Bets. Like product innovation, poker is a game in which new information emerges over time. You can’t know in advance exactly what is going to happen in a hand, so you need a system to make decisions in the face of uncertainty. The better you understand, refine, and improve your system—the higher the probability of achieving the outcome you desire.  

Great decisions are the result of a great process. That process must include attempts to accurately represent our own state of knowledge—the true facts and our honest intent based on the situation. 

Often we don’t know all the answers, but having a system to note what information we do and don’t have, to make decisions becomes super powerful as a tool to reflect and refine how we make better decisions over time. It also helps to separate our process for making decisions from the results. 

It’s easy to tell ourselves we made the best possible decision yet were unlucky with the results. Believe me, there’s a massive difference between those that can differentiate between poor results stemming from a good decision and poor results from a poor process.

 

How to Use a Decision Journal

So what actually goes into a Decision Journal? 

The basic idea is to capture, then reflect on what decisions you made, how you made them, and how they could be better in hindsight. 

It’s important that you capture the data you have in context at the time of a decision. As American physicist Richard Feynman often highlighted, we view a situation differently if we already know the outcome—analysis is always clouded with bias and beliefs based on the real results. This makes it difficult to truly critique our capability in the face of uncertainty. 

Here are some of the decision characteristics I usually include (especially when I’m running experiments):

  • What are the desired outcomes I’m aiming for?
  • Which experiments did I choose to run, or not? 
  • What options for running them did I pick, and forego?
  • What data did I have, and what were the “known unknowns” (what information was I missing)? 
  • What insights or takeaways do I want to remember in the future?
  • Did I knowingly incur any debts (costs that will have to be sorted out or improved in the future: e.g. starting with a solution that isn’t scalable in order to quickly test an idea)?
  • What tradeoffs did it include, along with dissenting opinions, and why?
  • What do I expect to happen?
  • A series of prompts to ask myself if I can make the decision smaller and safer-to-fail, and how soon I wish to see results 

A recent, simple example of my system in action was trying to find an effective way to keep all the participants from one of my client companies up to date and aligned on their coaching program. This effort faced multiple time zones, work from home situations, and difficulties finding collaborating hours everyone could make. 

I needed to decide how to deliver the program once the pandemic was announced. Did we need to fix times? Have a rule that you make it or miss out? What if people were pulled into crisis meetings over course modules? 

I wanted to make a decision that was easy to apply and empathic to the situation but couldn’t wait as the coaching was critical to their business continuity initiatives. 

I quickly pulled out my Decision Journal and mapped out what I believed mattered most. Reviewing other decisions I’d made helped me identify the components I wanted to consider for my critical thinking ahead of the decision. 

In minutes I captured and visualized all the information that was swirling around my mind. I got clarity, then created and considered my options. Taking a moment to think through what mattered and was missing helped me crystallize everything, but also recognize the gaps.   

Outcomes

  • 100% of participants actively partake in the program
  • 90% participant satisfaction with coaching
Insights

  • No one wants to fall behind or let team members down
  • Lots of competing priorities, especially related to business continuity concerns
  • Participants love the program and don’t want to miss out
  • People have access to share digital collaborative workspaces
Data

  • 4 pilots, 16 program participants overall
  • 4 time zones
  • 50% of participants are working together on the business continuity initiative
  • 80% have families at home
  • Unsure home working situations—70% chance not ideal work set up
  • Unsure when crisis meeting will strike—40% chance participants will miss class
Trade-Offs

  • Keeping momentum over not leaving people behind
  • Easy to catch up over waiting for perfect everyone to be available
  • Short and sharp over large time commitments
  • Easy to consume over only one format
Smaller, Safer, Sooner?

  • Could I make the class shorter?
  • Could I know who is failing to follow the content?
  • Could I know who needs to catch up or is falling behind without shaming them?
  • Modules allow me to learn what works and doesn’t each week—could I learn faster?
Options

  • Fix class time
  • Repeat classes
  • Record class
  • Slice classes
  • Coach others to train classes
Dissenting Opinions 

  • Who should I ask?
Decision

  • Slice module into smaller sections
  • Record and post them in video, audio, transcript and subtitled format on collaboration channel, e.g. Slack
  • Be available for an office half-hour at module launch and an Ask-Me-Anything three days later. Otherwise, monitor thread asynchronously
Debts

  • Invest the manual time, for now, to see if it’s useful—then automate afterwards with Otter.ai, Loom, and Rev
Notes For the Future, and what to reflect upon after results

  • What were your key results?
  • What effects did you observe?
  • What behaviors led to your desired aspiration or outcome?
  • What behaviors led to unintended consequences?
  • What corrective actions (if any) will you take?
  • How will you scale out, scale back, or iterate your next action or behavior?

 

Going through this method gave me confidence in the decision I wanted to make. It also created an easy model to share my thinking with the team asynchronously—saving the hassle of finding and waiting for a time to hold ANOTHER MEETING. 

Interestingly, the team started confirming their agreement (thumbs up emoji) with the decision quickly, and offered real data for who was in what situation (struggling to work from home or with other competing missions). I got all dissenting opinions in the thread, which aligned with each other and thus played the Devil’s Advocate role for me unsolicited. 

That afternoon I delivered the shorter module and published it straight on our collaboration workspace. I automated subtitling and transcription in minutes via Otter.ai, shipped to Slack, and we were live. Almost immediately, people started asynchronously debating the principles and how they might practice them on their work. 

 

Notes For The Future and Reflecting Upon Results 

The following week I pulled out my Decision Journal to go through the “Notes For The Future” I’d left myself so I could reflect on the results. 

Many new and interesting unintended consequences had emerged from the team. One that stood out was how participants had started to coach one another. If someone missed a module in real-time, one of the attendees would offer a catch-up session and Q&A—both to help the team but also test their own understanding of the content. This doubled the impact for all involved and became a power multiplier for scaling the methods out in the company. 

How Will You Measure A Great Decision Now?

I often joke that if I make just one good decision a day, it can actually be my most impactful moment on any day. Decision Journals are a great tool to show us how we’re making decisions, so we can raise our chances of getting the results we want, or at least learning something along the way. 

Being aware and able to separate quality of decision from quality of outcome is a powerful skill to identify our gaps and improve over time. 

So here’s a challenge for you: every day for the next week, track your decisions in a journal, and then go back and review at the end of the week. Reach out and let me know how it goes and what you learn.

Recent Articles

Subscribe to our newsletter and we’ll send you news you can use. No spam, ever.

Barry O'Reilly 2020. All Rights Reserved ©