Thinking about Thinking

Clear decisions start from clear thinking. Clear decisions are robust and durable. They are flexible towards unknowns and simple to explain.

Clear communication starts from clear thinking. Clear communication is memorable and self-explanatory. It creates focus on the most critical topics and leaves room for interpretation on topics with ambiguity.

The best leaders of any discipline are noticed by their clear communication and decisions, which means two things: That they have developed a system to think clearly That the deliverables of thought are typically decisions and/or communication

So what does it mean to think clearly?

Thinking clearly means that you have a system for processing the available information in order to arrive at the best, or at least a good, outcome, consistently. A good outcome doesn’t mean that you always succeed, but rather that you have also prepared for failure. In failure you know how to course correct (and if it is still worth doing) and in success you have not just achieved a goal but solved the problem.

How do you think clearly?

Everyone’s process will be different and situational. But of course, I will operate from the perspective of a business that develops software for this example.

1. Establish the fundamental truths of your environment

You can’t have one hundred of these, they must be memorable and easy to gut-check against, probably 3-5 is right.

A business that develops software must:

• Produce value for its users that is commensurate but ideally much higher, to its cost
• Treat its software as a living organism.
• Software that is not fed and maintained, dies.
• Software that does not grow and adapt to its changing environment, dies.
• Software that does not plan for industry seasonality, dies.
• Plan for unknowns.
• Software is research and development. It carries both quantifiable and unquantifiable risk.
• Software is experimentation, it is not always steady and incremental progress. It is often failure after failure after failure, and eventually exponential success.

2. Establish what you know

You will never have enough information on any decision, in fact clear thinking is needed the most when you have the least amount of information. But here are a few questions that you can consider:

• What is the impact and scope of this?
• What are the risks of getting it wrong?
• What is the historical or entrenched context to consider?
• Who cares about this?
• Why is this coming up now?
• What happens in failure? Is this easily reversed?

3. Establish what you DON’T know

The most important thing about this list is deciding if you can find answers to things you don’t know and then, is it worth pursuing the effort of obtaining those answers.

• Do I need to better understand user behavior?
• Do I have telemetry/metrics on this topic?
• Do we need to better clarify options through discussion?

4. Read the room

This step may be considered optional but I think this is often the “secret sauce” for people with reputations for decision-making competency.

• When you talk about this topic with people are they excited, anxious or frustrated?
• Is the hard part of this problem Product, Design, Technical or Political?
• Is someone not voicing their opinion because it is too controversial?
• Is there urgency here and is it real or fabricated?

5. Decide Clearly

By this point you are probably leaning towards a certain direction and if you have done all of the previous steps then you are well on your way to a well thought out deliverable. Here’s a few questions to ask yourself:

• Does this make sense within the boundaries of your fundamental truths?
• Have you teased out all the spoken and unspoken implications?
• If this fails do you know what you would do next?
• Do you have a good sense of how people will react to your next steps?

If you have good answers by this point in time, congratulations you are about as confident as anyone can be in this situation! Also, sometimes the answer is: we don’t know enough to act on this or it’s too risky. We need to test alternatives or wait for new information.

6. Communicate Clearly

Now it’s time to synthesize all of this information. How much this needs to be communicated and to whom will vary widely. You might just need to write one sentence in Slack, you may need to prepare a presentation to your entire department or company. You may need to tailor your communication to engineers or executives.

In every case remember, communication must be simple, it must be memorable, and it must give focus to the important thing.

7. Listen to feedback

You have now communicated a clearly thought out plan or decision. Now it’s time to look for reactions, new information, things that could impact a previous step in your thought process. Did someone react strangely to your communication? Maybe they know something that you missed. It’s time to follow up and adapt, you will likely be iterating steps 2, 3, and 4 for sufficiently complex problems.

But look at that, people are starting to ask you to help them think clearly.