Five Whys is a technique I borrowed from Lean methodology for getting to the root cause of a problem. As shown in the example below, I use the method to identify many possible solutions to a particular productivity problem. 

The simple steps:

1. Ask “Why do I have this problem? / What is causing this problem?”

2. Make the answer as concrete as possible.

3. Ask yourself “Why do I have this answer?/  What is causing this problem?”

4. Repeat steps 2 and 3 until you run out of more ideas. (Aim for at least five times.)

5. Brainstorm solutions to each answer. What specific action might resolve that problem?

6. Choose 2-3 solutions to test. If these aren’t sufficient, you can go back to test others.

Many problems have more than one root cause, so you may need to repeat the above for different starting questions.

Example 

1. Why aren’t you exercising?

   • Because it’s difficult to stop mindlessly browsing the web in the evening to start exercising.

     • Possible solution: reduce friction to exercise, such as by having an exercise plan.

2. Why is it difficult to stop browsing?

   • Because I feel guilty about not getting enough done, so I don’t want to leave and hence admit that I’m not going to do more tonight.

     • Possible solution: Accept that the guilt is a counterproductive cycle. 

     • Possible solution: Learn to recognize clues that you’re caught in a bad cycle. 

     • Possible solution: Find better ways to relax, so that you aren’t out of steam so much and have something that feels good to switch to.

3. Why are you feeling guilty?

   • Because I care about what I’m working on, but I don’t prioritize well. So I never get everything done and always feel bad about being behind and not having done enough.

     • Possible solution: Rank tasks by priority and do the most important first.

     • Possible solution: Try aiming for a number of hours instead of tasks.

     • Possible solution: Read Rest in Motion.

4. Why don’t you prioritize well?

   • Because I’m constantly in reactive mode to what other people want me to do.

     • Possible solution: Let people know when you will get back to them instead of feeling guilty you haven’t responded for a week.

     • Possible solution: Block off time for your deep work and don’t accept meetings during that time.

     • Possible solution: Delegate or say no if you’re not the best person for a job, instead of accepting everything that people ask you to do.

5. Why are you in reactive mode?

   • Because I don’t have a system for managing tasks.

     • Possible solution: read Getting Things Done, try out a system.

Many thanks to Jonathan Mustin for transcribing my rambling cursive, and to Nora Ammann for feedback.