Asking “Why” At Your School Can Be Dangerous. (Lean on a Design Process)

I thought this would be a funny picture.

Forget simply trying to deal with Cow Paths, the sacristy of time and resources makes many schools an act-now-ask-questions-never environment. Schools have limited time for teachers work with peers as much of a teacher’s time is with students, rightly, but that creates an issue, “Is our teacher/peer time a place to consider and study our problems or a place to act quickly?” Sadly, organizing teacher time to do both is quite hard and even more unfortunate might be the case of those deep thinkers and process oriented folks being viewed as a problem. For these folks, asking “why?” is a dangerous proposition.

A quick story you may identify with:

When I was a young 24-year-old teacher in my home state of Arizona, I never thought too hard about what we did because I was so good at execution, good at getting things done. I thought I had a six shooter at my hip and that I was a quick draw when I needed to get something done for my students or elsewhere on campus. I was quick and could make a quality product. Then, in waked in another 24-year-old teacher, a new teacher named Dan. He was from New York, tall, bald, goofy and paused often to think about what he was going to say. The guy was too darn slow to act for my pace.

Quickly, I was in meetings with him of various sorts where he openly asked why the school, teams, teachers would do what they were doing . He asked what our expected outcomes were, what problem we were trying to address and he would ask about the evidence we would collect to see if it worked. I had honestly yet to work somewhere where that kind of thought was being honored or valued, but there I was. My transition into the teacher/deep thinker felt slow at the time, but I was absolutely a different teacher after three years of working with him.

Factors that make it hard for schools to think deeply

First, I need to acknowledge the problem: every single person working in a school is crunched for time with so many roles and obligations that deeply considering the practices we put into place feels difficult to impossible for some. This makes for a slow-down in production to study the problems at hand very hard to do and makes folks who pose difficult questions less desirable in some situations.

Also important to note; many contrarians and would be progress-blockers will hide in debate to stall with an aim to ruin any possible progress. They may be some of the “dead wood” your school still has laying around and the process for progress at your school needs to be careful to deal with the land mines that some lay as “constructive dialogue.” Often, telling the difference between a progress-blocker and someone who wants purposeful progress can be hard. Well meaning leaders will often struggle to separate the discussion-wheat from the blocking-chaff with great skill.

What’s the Danger in Asking Why?

Across my teaching career, I’ve seen folks like Dan and later myself confront an act-now individual, committee or team and take on some bruises. It is the plight of those individuals who bring a design thinking or similar process to a group not ready to think and act within a methodology. Taking on DT and bringing it to a group not ready for a process can also interrupt a group that; may not be interested in accountability to results, may be interested in doing what they like or believe in regardless of the evidence, may not be engaged in a process because of their own lack of engagement.

Losing trust of your colleagues. There is a need to be productive and there are times when quick action is needed. Not fighting every batter for better work may be necessary to be ready and able to help establish a good working order that allows for meaningful efforts to be planned out.

Being perceived as too slow for the daily rush of a school. There is obvious value in doing things well and doing things right the first time, but with no established culture and no expectations for getting things right it’s possible that the priorities of a team will be to do something, to do anything in order to get though a day.

Elitism is another perception that can be hurtful for the deeper thinker. This may be especially true when others don’t feel well invited along in the processes of development or if they don’t feel well trained to be a participant. Here, the deeper thinkers need to work on how they bring others along and not to simply expect others to be with them and ready. Ill will is bound to happen.

Above Your Pay Grade is a common refrain I’ll hear when the desire to shift the thinker role away. It’s a solid argument that I think about often. Are we as teachers the Facilitator of learning or the Designer? I’d must admit that when you look at how most teacher’s roles and daily responsibilities are set, one could easily conclude that teachers are primarily facilitating learning with students. Any other roles are secondary at best. Therefore, decisions and the design of learning is “above” the teacher level. This works as a thought process as long as we pretend that there is an above that is tasked with team and classroom level decisions and as long as we pretend that meeting time is for reading announcements and other non-essential tasks. Teachers are the primary designers of our schools and we can use meetings in such a way.


  • Time and resources are limited in a school, choosing how to work is a critical step.
  • Prevailing culture will dictate the willingness of teacher/colleagues to engage in deep, process-driven development.
  • Some avoid a process-driven approach like Design Thinking in favor of quick action.
  • Process thinkers and deep thinkers may be most effective in establishing the culture than anything else.


Get a working order or group culture set around a process long before your first topic comes up. Spend time on developing your group in how they work and why they work the way that they do as it’s own important business. No matter how well intended a process-driven teacher or leader might be, their efforts are likely to be in vein should an established culture not exist to support their efforts. It’s personally taken me a long time to not take the negative attention I’ve received for years personally. It’s the culture that drives the arc of development, not individual inputs within the existing culture. When that arc of development has a path to success, it is often seen in a process, much like design thinking. That process needs a committed leader as well, or expect to feel like you’re on a bike with no handlebars, no matter how great the bike/process happens to be.

  • Train up! Look at attending Design Thinking or Facilitation training with a critical group from your school
  • Hire facilitators and trainers to go to your school and dedicate time for implementation.
  • Read! Here are a few blog posts that help your investigation of a good working process:
  • DT Step 1 Define
  • DT Step 2 Collect Information
  • DT Step 3 Brainstorming

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