The Gray Cat Blog

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The Art of Problem Solving

Feb 09, 2026

When times are great, leadership can be straight forward.  Set stretch goals; inspire the team; give them the tools to succeed; and get out of their way.  A leader can have his team on cruise control and ensure that not only the work is being completed, but the team shares in the rewards.   In this scenario, sales can be a fantastic “cure all” for morale and productivity.

The flip side of leadership acumen is the ability to navigate through difficult situations.   Often, a leader’s mettle is measured by their ability to manage through problems more so than guiding the team through calm waters.  The challenge is two-fold:  1) solve the issue at hand; and 2) simultaneously maintaining the respect and commitment of the team.  A leader that can master that outcome stands to develop an extremely loyal following.

So, how does a leader master the art of problem solving?  First and foremost, they cannot be afraid to tackle the issue head on.  In my corporate days managing multiple divisions, it was a rare day when I didn’t have to tackle an issue – be it large or small.  For the larger, long-term issues, I would follow the steps below to ensure that we achieved the most optimal solution – notice I didn’t say complete solution.  In some cases, minimizing the damage was the most optimal outcome:

Define the Problem:  First on the list is to clearly articulate the issue you're facing.  Without a clear understanding of the issue at hand, developing solutions will be nearly impossible.  Gathering up all parties that have intimate knowledge of the issue is an excellent way of making sure “no stone is unturned” in scoping the issue.

Understand the Cause:   Understanding the problem is one thing.  Identifying what led to the problem can be a challenge all on its own.  This may involve retracing the steps that led up to the problem so not only can you solve the issue but prevent it from happening again in the future.  It is one-part reactionary and one-part precautionary.

Generate Solutions:  Brainstorming potential ways to address the issue can foster “no idea is a bad one” battle cries.  As I mentioned above, in some cases the only viable solutions are those that minimize the pain, not eliminate it.  The larger the issue, the harder it is to get every solution in a nice, neat box with a bow on it.  Sometimes, you must win just a few battles to mitigate losing the entire war.

Evaluate Options:  Once you have several solutions to choose from, assess the pros and cons of each option.  Game plan each option to fully grasp the ramifications (both intended and untended) of each to ensure it is a viable choice.  Ensure that everyone involved is aligned with the selection.  As a reminder, sometimes the best option is the least “worst” solution.

Make a Decision:  Once you have vetted every option, endorse the top one and run that through the wringer from an execution standpoint.  You may find that you must involve all the players that could impacted – legal, operations, marketing, etc.  to ensure that every “t” is crossed and every “i” is dotted.  Each of these areas has a stake in the problem solving.

Implement the Solution:  A clearly executed implementation plan not only solves the immediate issue but hopefully stems off further issues in the future.  I remember I had an issue in my corporate days that involved many different vendors.  Part of my execution plan was to physically visit thirty-seven (37) different vendors in seven (7) states.  The problem needed to be solved in a consistent fashion and having one person execute the plan mitigated the damages.

Evaluate Results:  Lastly, running this entire process through a post audit helps close the case on the issue at hand while providing the process for future problem-solving.  This is the step that is forgotten most of the time.  Have the discipline to document these steps with results or all too often, you will be chasing your tail on problem-solving.

Nobody ever wants problems to crop up but some are completely out of your control and must be dealt with.  Involving the key constituents in developing a go-forward strategy to address the issue is the only way to proactively mitigate further harm to the organization.

Want more ideas?  For more information on Gray Cat Learning Series, visit: https://www.graycatenterprises.com/gray-cat-learning-series

John Matthews, President & CEO, Gray Cat Enterprises, Inc.

John Matthews is the Founder and President of Gray Cat Enterprises, Inc. a Raleigh, NC-based management consulting company. Gray Cat specializes in strategic project management and consulting for multi-unit operations; interim executive management; and strategic planning. Mr. Matthews has over 30 years of senior-level executive experience in the retail industry, involving three dynamic multi-unit companies. Mr. Matthews experience includes President of Jimmy John's Gourmet Sandwiches; Vice President of Marketing, Merchandising, Corporate Communications, Facilities and Real Estate for Clark Retail Enterprises/White Hen Pantry; and National Marketing Director at Little Caesar's Pizza! Pizza!