Exploratory Thinking

0043: Makes sense of today and you will see tomorrow.

0042: It’s not just “tech” and “the business” - it’s managing people, process, and technology holistically.

0041: Nothing is simple anymore that’s why it’s difficult to see things for what they are.

0040: A big part of what people at companies do as part of their jobs is figure stuff out, yet we don’t capture the problems encountered along the way or how they were solved.

0039: Which would you rather be: Really good at coloring within the lines, or really good at creating the lines?

0038: Most business “urgency” is artificially created by lack of planning and foresight.

0036: Why is it that when you explain and demystify something, it becomes less magical?

0035: Focus on solving existing problems before creating new ones.

0034: Structure gives us some permanence from one moment to the next.

0033: We’re all really just trying to find ways to get other people to do our work for us.

0032: Happy path planning is similar to believing your team will win the championship at the beginning of each new season.

0031: Why not just automate all the things?

0030: You can’t control, but you can be prepared.

0029: This time we’ll get it “right.”

0028: We think of making processes or workflows easier by reducing steps…what if we focused on reducing the number of times humans had to think about unimportant stuff?

0027: What if instead of corporations trying to use AI to make workers irrelevant, workers figured out how to use AI to make corporations irrelevant instead?

0026: We focus on outcomes when we should be focusing on creating the conditions for those outcomes to emerge.

0025: Patterns do not emerge locally. Patterns emerge at a level of abstraction.

0024: How is value valued?

0023: Stop telling people what they can or can’t do…show them what’s possible.

0018: Never let the people who use the system design the system.

0020: You don’t ask why something happened to cast blame, you do it to learn and to incorporate that knowledge into future thinking.

0014: Knowing how others think is an exercise in learning what mental models they know, use, and apply.

0021: Because tech companies strive for frictionless buying experiences, sometimes you need to add your own friction to cut down on the self-discipline needed to resist…because it’s too much to keep up with on your own.

0022: My vision of the ultimate enterprise technology platform is one where business and technology solutions can be implemented in a matter of minutes or hours.

0019: Automations should be focused on internal processes, not customer facing processes.

0015: At what point do you introduce structure?

0013: It is not your job to be understood, it is your job to be aware of how you were understood.

0017: Sometimes it takes me a long time to finish things…and I’m OK with that.

0016: “Knowing” means having been to the other side and having seen for yourself.

0012: You can never, by nature, have direct experience with some "thing" that occurred in the past.

0011: You have to want something if you have hopes of achieving it.

0010: When someone tells you to stop “overthinking” and just jump into something, it’s terrible advice.

0004: You cannot estimate the unknowable.

0009: System change efforts fail when they shift work from one person to another, or one team to another, as opposed to onto the technology and processes that were intended to automate or eliminate the problem to begin with.

0007: Every new connection establishes a new relationship that will need to be maintained.

0008: It’s never to say that the outcome you’re hoping for isn’t a good (or correct) outcome, it’s just one of several possible outcomes and you need to take that into consideration.

0002: You didn’t fail when success was never a possibility.

0006: Before we automate, let’s struggle through this the old fashioned way a little bit and learn what we need to learn.

0005: Design is the stuff you have to think about upfront because you have to have at least some mental structure of the software you’re going to write.

0003: The first one is always the hardest.

0001: The boundaries or constraints of an organization are formed by its ability to manage complexity.