I’ve always found that breaking down professional work into planned steps and executing accordingly comes naturally, whether for a small initiative or a major program. Recently, however, when faced with significant, unexpected personal challenges, as complex as any professional crisis I’ve been called to manage, I was reminded just how foundational this instinct to plan truly is. Several people commented on my ability to move forward and not seem overwhelmed, and I realized the “secret” was simply applying a structured planning approach to the chaos.
You can’t always plan for every unexpected event. But when the unexpected does happen, your ability to quickly build a plan to deal with it can be the difference between being paralyzed by the challenge and navigating it effectively.
The First Step: Defining the Problem(s) Clearly
When facing a complex or overwhelming situation, be it a personal crisis, a sudden market shift for your Small or Medium-Sized Business (SMB), or an unexpected technology failure, the first step is to clearly define the problem or problems you face.
- Break it down: Focus on simple, core issues in a factual way.
- Be specific: Each problem statement should ideally be a single sentence identifying a distinct aspect of the overall challenge. A simple challenge might have one problem statement; a complex one will have several.
Next: Envisioning Success and Defining Outcomes
Once you have clarity on the problem(s), you can define what a successful outcome would look like for each. In fast-moving or highly challenging situations, it’s also wise to define a minimally acceptable outcome. Knowing what you ultimately want, and what you’d be willing to accept, helps structure the steps and potential trade-offs in your plan. As a fractional CIO, when an SMB faces an unexpected IT crisis, our first steps are always to clearly define the immediate problem and the desired state of resolution.

Building the Roadmap: From Outcomes to Actionable Steps
With a clear understanding of where you are (the problem) and where you want to get to (the outcomes), you can build the action plan.
- Choose your tools: This could be as simple as pen and paper, a digital to-do list, or more robust project planning tools.
- Group tasks logically.
- Assign completion dates: Make them reasonable but structured. Unrealistic dates are unhelpful, but no dates breeds procrastination, especially when tasks are difficult.
The Power of a Plan in Overcoming Overwhelm
Applying this planning discipline, even amidst emotional turmoil or the perceived magnitude of a challenge, brings stability and focus. It transforms what might feel like an unsolvable problem into a series of manageable tasks. It allows you to make progress, maintain a sense of control, and achieve more than you might have initially thought possible.
Planning: Not Just for the Predictable
We all know the adage: “Failing to plan is planning to fail”, typically applied to predictable projects and goals. But I contend that when we face unexpected challenges (even the big, hairy, audacious ones), failing to quickly build a plan to address the situation is akin to accepting the impossibility of overcoming it. Problems and challenges only feel impossible without a plan. With a plan, almost anything can be navigated and accomplished.
What’s Next
For SMB leaders, the ability to bring structure and create an actionable plan in the face of unforeseen market shifts, competitive threats, internal crises, or urgent technological demands is a critical leadership skill. It’s about quickly moving from reaction to focused, strategic action.
Is your SMB equipped to create and execute clear plans when faced with unexpected challenges or opportunities, especially in your technology landscape? If you’re looking for a strategic partner to help you navigate uncertainty, define actionable IT roadmaps, and bring structure to complex initiatives, let’s connect with Succeed Sooner Consulting.


Leave a Reply