Asking the Right Questions

ILTA's Quarterly Magazine

Asking the Right Questions

Why, Why, Why, Why, Why?

by TJ Johnson

Let’s dig into whether the “Five Whys” or the “Three Whys” or even “One Why” are the right questions to ask to help lead your legal organization into the future. Could any number of Why? help advance innovation projects in your organization?

The Five Whys is an iterative interrogative technique to explore the cause and effect relationships underlying a particular problem. It was formalized by Toyota in Lean Manufacturing and later included in Six Sigma. A great use of the technique was the investigation into the deterioration of the Washington Monument (see image).


Asking a succession of Why? after each response helped understand the problem, find the root cause and eliminate it, which should prevent the problem from happening again. One of our biggest challenges in legal technology projects is making sure the projects do what we intended and meet the goals. When the client isn’t happy or the new system isn’t adopted by the users, or the innovation isn’t seen as innovative, we have to figure out what’s going on. We often address a symptom and move on. We are shocked when the problem repeats itself, and we have to start over. If instead of looking at symptoms, we dig into the real Why? of the problem, identifying the real cause(s), then eliminating the cause(s), we should be able to eradicate or at least face the real problem head on.

Sounds easy ☺. I’m betting it took awhile to figure out the answers to each of the Why? for the Washington Monument, and getting to the root cause that could be changed, that would eradicate each additional layer of cause must have been a nightmare.

Perseverance, analytical curiosity and good facilitation skills seem to be the key to the Five Why? approach. I used a Five Why? exercise with a group of project managers recently, asking the biggest challenge in their current project, then working to find solutions for them. Just asking “Why?” to a problem expressed as “We are way behind on the project and the guy in charge at the client won’t talk with us”, resulted in blank stares and/or listing additional symptoms. To tease out the real problem causes, we came at the Why? from different directions with questions like “Do you think the client as angry because he just didn’t like the way that meeting was run, or maybe he wasn’t briefed ahead of time about the problem that was going to be discussed, and he wasn’t prepared in that meeting?” We stopped worrying about how many Why? we were asking, just kept digging deeper and deeper into what was really causing the roadblocks. Once we got to the real crux of it, we talked through strategies to fix them properly.

So, Five Why? or Three Why? translates into asking the right questions to get to the cause, and digging deeply enough to solve it.

Applying all this to innovation projects is interesting because so often these projects are not well understood by all the people charged with executing them. There seems to be more mystique with projects that involve emerging technologies or AI etc., so a problem in that project “must” have some sort of magic cause that no one will understand. That’s not a good answer!! And probably again, the wrong question being asked. If the project plan for an innovation project has clear definitions of success and clear specifications, then when a problem arises, it should be possible to work through to the cause and decide what needs to be done. Is it that Innovation projects are harder to define success for? Maybe, but if we use the Why? questions in the requirements gathering phase, we should come to a place where we agree how success is defined. Why is the innovation needed? Client demand for process improvement. Why are clients demanding that? Dig deeper… You should get to a place where you have certainty on what success can really look like for this project at this time.

With clearly defined success, then use a few Why? questions to help decide where and how to insert quality gates. These are selected criteria that must be met to move past each stage in the project. Why does this specific test need to be passed at this point?

Once you are clear on what success looks like, make sure to do the measurements, don’t let it drop because everyone says “Oh, the project is going well”. Success metrics help in communicating the success of the project and add credibility for the next project you want to undertake. Dig deep into the results you get to the measurements. Why isn’t the metric being met? Dig deep for patterns that provide you either with comfort… or show you where there are issues, so you can deal with them before they become catastrophic.

Measurement and metrics needs to be baked into every stage of the project. Add the measurements to your project and engagement meetings, add them to your communications plan, and add them to your ongoing improvement and learning strategy. Use as many Why? questions and dig as deeply as you can at the right places in that process and you may not only save your monument but also achieve some real innovation.

If you aren't sure the best questions to ask in a situation, I'm happy to ask questions to help you figure it out, at

Watch for the next installment of “Asking the Right Questions” when we think about how to ask the right questions around What’s Next? How we can futureproof our organization? ILTA

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TJ Johnson
is Strategy Director at Olenick ( She has great fun focusing on “StrategicIT” – looking at innovation, internally and for clients, and thought leadership around new ways to help clients deliver successful projects. TJ has deep experience in legal technology. A familiar and well-respected figure in the legal technology industry, TJ worked in various capacities for law firms and legal departments. Most known for her recent role on the executive team of ILTA (International Legal Technology Association) where she led the strategy development and execution of ILTA’s global portfolio of events, was instrumental in growing their premier conference, ILTACON, and was responsible for the vison and execution of many strategic projects.