5 Essential Tools for Conquering Complex Decisions

Complex decisions drive us all nuts. We argue about them during the day, and we agonize about them at night. All of this struggling — with others and with ourselves — makes us unhappy, anxious, and less successful. Over and over we procrastinate, subject others to waffling, and often end up with a fear of regret.

The human mind was not built to handle much complexity, so we run into our limit frustratingly often. The other week I heard a room full of decision makers nearly erupt with concern when a colleague of mine presented options for a technical project that looked something like this:

6 considerations x 4 different options = 24 points of data, far too many to consider at once.

The mind only has a working memory of “seven plus or minus two.” Confronted with 24 pieces of data, we physically have no choice but to narrow our focus. When we fail to simplify problems deliberately, we leave the job to our subconscious, yielding sadly predictable results:

  • Circular conversations in which considerations revolve in airtime, but no forward progress gets made at a higher level
  • Inexplicable stubbornness by a friend or colleague to see things our way or to balance our concerns against his or hers
  • Arrival at a logical decision that doesn’t end up “feeling” right
  • Neglect for a foreseeable consideration that only came up in hindsight

As a product manager, I belong to a field that has built a profession out of helping teams to navigate complexity. Years of practice have taught me the hard way (i.e. repeatedly) that complex decisions may never come easily, but we do have valuable tools that can bring structure and confidence to an otherwise messy process:

  1. Surface hidden complexity
  2. Compress complexity with cognitive reasoning
  3. Creatively discard less critical considerations
  4. Let vision handle complexity for you
  5. Enlist gut feelings for difficult trade offs

Tool #1: Surface hidden complexity

Hidden complexity hampers us more than visible complexity because we only find out about it after wasting time and energy deliberating moot points.

Clarify your goals before assessing any options

Surprisingly enough, the most common consideration that product managers forget to incorporate is the end goal of a project or proposal.

Not long ago, a PM at Earnest held a meeting to determine the launch criteria for a new statistical model. The promise of automating significant manual workload led to a heated discussion about balancing risk against efficiency: maximum automation would come at the cost of greater possibility of error. We went back and forth, back and forth, until realizing that efficiency was not even the immediate goal. Rather, our desire was to increase the percentage of applicants who get verified at all, and the best approach for achieving that had nothing to do with replacing manual verification with automation. Neither efficiency nor risk remained relevant concerns. Had we clarified the goal at the beginning, we may have saved ourselves a good bit of time.

Great product management teams typically avoid neglecting considerations by self-imposing regimented processes. Companies like Dropbox force a formal review of a problem statement before granting an opportunity to pitch a proposal to product leadership. At Google, every product launch requires explicit, written sign-off by a long laundry list of approvers.

Seek the experience of others

Both in the workplace and in our personal lives we resist seeking advice for a host of reasons. We may worry about looking incompetent, conflating others’ opinions with our own (getting that nagging voice out of your head can be a pain), or inviting unwanted participation in future parts of the decision making process.

All one can recommend is that you balance the merit of these concerns against the value of seeing around more corners and diminishing the chance of feeling regret.

Get more advice about what to consider, and less about what to do.

Surface considerations that hide behind others

Seasoned negotiators know that colleagues can look at the same information and see very different pictures. Therefore, the best practitioners ask questions aimed at uncovering those pictures hidden in the minds around them (see Investigative Negotiation in the Harvard Business Review). In product management, we quickly learn that engineers demonstrating puzzling hesitation might silently, and maybe even subconsciously, sense dangers like throwaway work, execution risk, or structural fragility. Technical experience provides the familiarity required to surface and assess the relevance of these otherwise tacit concerns.

At the very least, take the considerations you already have on the board, and break them down into their basic components so as to avoid murky reasoning and unclear communication.

Detaching one consideration from another can provide valuable clarity.

Tool #2: Employ cognitive reasoning to compress complexity

Don’t think too little

My grandpa has always had a habit of reminding me to “use my noodle.” Similarly, Nobel-winning psychologist Daniel Kahneman teaches us that when we don’t take the time to consider a problem, our brains employ a library of metal shortcuts that don’t always do a great job. The limitations of what he calls “fast thinking” are fascinating and worth reading about in his seminal book, Thinking Fast and Slow.

Don’t think too much

“Type A” people in Silicon Valley (read: all people in Silicon Valley) exhibit less of a tendency to under-think and more of a propensity to over-think. I believe this stems from a fundamentally obsolete understanding of the power and purpose of conscious reasoning.

While philosophers as far back as Descartes have placed cognition on a pedestal (“I think, therefore I am”), modern research by neurologists like Anthony Damasio shows that emotions play a central role in making decisions. Patients who lose their neurological ability to feel emotion also endure pathological indecision, incapable of even picking a black or blue pen.

The mind should act as the judge, and the heart as the jury. The purpose of thinking through problems is not to make them less emotional but, in a sense, to make them more emotional — or at least more emotionally addressable.

The power of rational thought lies in its ability to combine and translate the abstract, lifeless concepts of a financial plan into a confident decision backed by feelings of fear or greed. Consider how well this works for the related concepts of financial sensibility and how poorly for the unrelated factors behind picking a college:

As a high school senior, I agonized for weeks trying to “logic” myself into a decision for where to go to college. As you can imagine, I didn’t get very far with that approach. No cognitive reasoning can help further distill such disparate considerations as location, academic strength, and student culture because the factors already map cleanly to emotional triggers such as wanderlust, curiosity, and community. As a result, my thoughts kept running in circles, which should have indicated it was time to try out a different tool (probably Tool #5: Using your gut!).

Tool #3: Ruthlessly discard less critical considerations

Stay intellectually honest with yourself and with others about what you believe should truly factor into an important decision. At the end of the day, our little minds can only balance so much complexity, and those factors you do not find the courage to remove explicitly will inevitably haunt you from the depths of your subconscious. Acknowledge the cost in time and energy required of you and others to discuss and reason about your most marginal consideration. Especially remember that all time spent on one decision equals time not spent on another. Holistically budgeting your time across a portfolio of decisions (and other activities) may help you to select the most responsible number of considerations for each.

The workplace presents a special set of nefarious complications. Not only do we desire to steer course toward the best direction, but we equally desire to win the respect of those around us. This can lead to undesirable behaviors like bringing a kitchen sink of considerations to a decision, or trying to insert minor points that matter little. These two afflictions share an antidote: try to win alignment on considerations prior to debating the particular approach to take. This affords the group the opportunity to collectively create focus after everyone has had the opportunity to look smart.

Avoid rudderless meetings by allowing everyone to select a focused set of considerations prior to debating plans of action.

You might foster an appetite to discard a consideration by agreeing to remove any options that fail a basic threshold of acceptability. For example, we might do this on websites like Yelp, where we filter by price before sorting by quality and distance. Likewise, in product management we typically try to identify solutions that will provide long-term value before we explore the priority of a short-term “workaround.”

Tool #4: Let vision handle complexity for you

The most complex environment our minds can handle is the one we see around us. Consider that computers can beat us in chess and reply to our emails, but they can hardly read elongated words on funny backgrounds. Fortunately, the entire field of Data Visualization exists to hijack our visual system in support of better decisions.

Numbers are nonsense

Arabic numerals make efficient use of space and writing time, but let’s never forget that they deprive us of the visual cortex’s deep channel into the mind’s ability to comprehend. For example, the characters “6” and “9” look incredibly similar, when in fact they mean the difference between:

The difference between “6” and “9” makes more sense in chart form than in numeral form.

The problem only compounds for tabular data, for which a viewer has even less capacity to establish an accurate mental image. Therefore, please turn data tables into charts and unconditionally chastise those who do not.

Turning this data table into a chart better reveals that Projects B and C lost desired resources, while Project A became overstaffed.

The exercise of effectively turning data into graphics requires the scope of another article. In the meantime, one can reference Jacques Bertin’s authoritative Semiology of Graphics: Diagrams, Networks, Maps.

Jacques Bertin wrote the authority on on how to visualize different kinds of data.

All considerations can map to preferability

One visual technique that makes particular sense in decision making involves color coding a consideration matrix by how “preferable” or “acceptable” each option lands in that respect.

Color coding the options makes A and C quickly stand out as ideas on which to spend the most time.

With any luck, mere visual inspection will enable you to discard options down to a select two or three.

Tool #5: Enlist gut feelings for difficult trade offs

When you find yourself reasoning in circles and staring endlessly at the same set of options, you have positively identified a decision comprised of alternatives “on par.” Philosopher Ruth Chang impressionably describes these as existing “in the same neighborhood of value, in the same league of value, while at the same time being very different in kind of value.”

Philosopher Ruth Chang explains in How to Make Hard Choices that big decisions require discovering one’s personal identity more than reasoning in pursuit of an objective optimum.

Whether a big decision like picking a romantic partner, or a smaller one like ordering a dessert, we sometimes find ourselves wrestling with multi-faceted problems having no visibly obvious solution. Ruth argues that these opportunities let us define ourselves — they force each of us to let go of asking which option is better in favor of asking which option is me.

One old-school method to force this release involves assigning each option to opposite sides of a coin, flipping the coin into the air, and momentarily searching for a subconscious hope that one side will win. Analogously, you can scan your emotions after the coin lands for subtle cues of excitement or disappointment.

Regardless of your situation, remember that oftentimes the failure to make a decision can cost more than the downside of a wrong decision. Jeff Bezos reminds us that especially in organizational environments we can experience “slowness, unthoughtful risk aversion, and failure to experiment sufficiently,” as a result of misapplying heavyweight decision processes to entirely reversible decisions (see this Business Insider summary of Type 1 vs. Type 2 decisions).

In summary

Sound decision making relies on logical reasoning as a means of distillation, visualization for accurate comprehension, and gut-driven values analysis for breaking important ties between alternatives “on par.” In the frustrating angst of choosing a path, we ought to keep in mind that many decisions have reversible outcomes and that failing to choose a direction may lead to the worst outcome of all.


Daniel leads Product Management at Earnest. Prior, he was a Product Manager at Google and an alumnus of their Associate Product Manager program. Daniel holds a bachelor’s degree in Computer Science from Harvard University and loves flying airplanes.

Earnest is a San Francisco-based technology company building a modern bank for the next generation. Our Product Management team is a nascent group of technical, entrepreneurial, jacks and jills of all trades, and we are actively hiring!