Before You Solve the Problem, Make Sure You Actually Understand It
- Eric Kebschull

- Dec 10, 2025
- 4 min read
Most people in positions of management or executive roles are wired to solve problems. They were hired for their problem solving skills at the front line, and that skillset got them promoted (eventually) to their current position.
This makes logical sense: if you can solve my problems for me, I will offer you "x": x might equal higher pay, higher title and role, and usually a greater degree of authority.
This is no different in organizational life than it is in politics. People get elected from our communities, to our states of origin, and all the way up to the President of the United States to solve our problems for us.
Regardless of your industry, private nonprofit or public, the expectation is relatively the same for those in charge: come up with solutions.*
*I emphasized the above to indicate what the main focus of the expectation is. This will be important to note a little later.
The first questions tend to be:
What should we do?
What’s the fix?
What’s the plan?
The action occurs relatively quickly after these questions are asked and answered with some form of unified "agreement". The action occurs:
Launching initiatives.
Tighten processes and policies.
Roll out new tools.
People may see progress nearly immediately. The solution worked!
But:
6 months pass, 1 year passes… and yet the same problems keep coming back again.
Why?
Two reasons:
1) You need to ask better questions to understand the problem.
2) You need to consider the system in which the solution is designed and implemented in.
Let's break it down further on each point. Ask Better Questions
The very basis of great problem solving begins with better questions.
For example, "what is the problem you are trying to solve?" should not be a question people breeze by or get to the "answer" to so quickly. This should take considerably more time than is usually allotted or used. How can you possibly know what you are trying to solve without truly understanding what the answer is to this question? Remember earlier the noted point about the expectations for solutions? Well, if your focus on on finding solutions first and foremost, then you are more than likely to get what you want. However, the "solution" might not be the one you need, as the focus was not on understanding the problem first. This is an incredibly common mistake, and one that costs organizations and taxpayers time, money, and resources. Another important set of questions that follow are beyond the "single loop" of thinking and learning, versus incorporating "double loop" learning.
Let me explain.
Perhaps your organization asks slightly better questions than "what is the solution to this problem?", such as:
What went wrong?
How do we fix the problem?
Who/what/where did the ball get dropped?
These are necessary questions, but they are not a complete set. In order to truly understand the problem, you need to understand the conditions that lead to the problem in the first place. This is especially true for those persistent problems that seem to be sticky and un-solvable!
Such questions touch on the late Chris Agryris' work on Double Loop Learning (see his seminal work Action Science for more in-depth analysis).
Examples of deeper questions include:
What assumptions lead to us to make these decisions?
Who or what are might we be protecting by doing things this way?
Who benefits from keeping things they way they currently are?
These better questions are a perfect on-ramp to the next important element in solving those sticky recurring problems.
Understand The System
Even if you ask the right questions and spend time processing them, the solution may not be adequately informed if you do not take a systemic look at the problem. If you end up diving in too early, you end up with only a fraction of the data necessary to make the meaningful change needed. I could go on and on about systems thinking for problem analysis. But here's the key point that should be taken from this article: Your solution is only as good as the conditions of the system allow it to be. I feel that when Deming wrote/said "a bad system will beat a good person everytime", he could have just as easily been talking about a good solution. To paraphrase James Clear, "you don't rise to the level of your [solutions]; you fall to the level of your systems" (actual quote uses the word "goals", and can be found in his book Atomic Habits"
Double loop learning questions help build a systemic muscle to understand what is truly going on in your system (be it an organization or government body, or even an entire community). Behavior in your system may form observable patterns, but are guided by invisible elements like assumptions, values, and loyalties. This goes far beyond habits and behaviors of the system. It goes to the heart of what makes these things happen in your system.
Therefore, if you do not have the "conditions" for doing the work your solution calls for - be it explicit tangible or implicit intangible work - you will find your soultions faltering again and again. Final Thoughts
Solutions informed by better questions and better system knowledge are that much closer to making meaningful progress on the challenges and problems your organization faces. At Well•Led, we help organizations better understand the problem they are trying to solve. Through our consulting work, we use tools like system mapping and experiential learning to help clients build their own capacity to diagnose and solve the challenges they know so intimately well. Part of that capacity is to think systemically, and ask better questions before diving into problem-solving mode.
To learn more, schedule a call with us!



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