As entrepreneurs, we’re frequently required to navigate the challenges that come with a dynamic and often unpredictable business world.

We create forecasts and budgets for the upcoming year, strategies and goals, and metrics to measure it all.

But as the year marches along, we need to stay on top of this roller coaster of highs and lows.

We can better prepare for this journey by implementing a few strategies that allow for adaptability and resilience over a rolling twelve months.

So what are some key considerations for leaders when planning on a rolling twelve months?

Hold a Quarterly Review

One of the most important aspects of planning is to hold regular reviews. Because if it's a plan that you never review, it will very quickly become out of date.

Doing a quarterly review means that we get to adapt our annual plan for the next 12 months, and so that's how we end up with that rolling 12 months. An annual plan, of course, is an important idea, and I still do the annual plan at...

Phil Knight, the creator of Nike, once said: “History is one long processional of crazy ideas. The things I loved most – books, sports, democracy, free enterprise – started as crazy ideas.”

Let's face it. Entrepreneurs are usually known for having a ton of ideas. They're idea-making machines. And it might be tempting, as a small business owner who's looking to grow, to try all these ideas. That infamous shiny object syndrome. “This is exciting, let's try this.” “That is exciting. Let's try that.”

But what quick framework could you use to begin evaluating whether you should explore pursuing your latest “crazy idea”?

Is there a market for it?

The very first thing to consider: is their market for it? Are there people with access to money who will be willing to part with their hard-earned cash for what you're offering? Because if you're targeting a group that can't afford what you're offering, that's problematic.

Of course, if...

Have you ever been in a position where you had to revisit a past decision that you made, but when you started reviewing the available information, you couldn't remember why and how you came to that decision?

Yeah, that happens to me too.

As leaders, we have so much going on, so many decisions to make day in, day out. At some point some of the details will escape us.

So how can we help guard against losing too many valuable decision making details?

Leave explanatory notes

Whether it's when creating a budget, collecting metrics, or analyzing information, taking a moment to record your thought process could help yourself and other reviewers better understand what they are looking at and what was my thought process.

It doesn’t need to be long. Adding brief notes, a short comment, a thought, is sufficient.

This also helps provide an overview of some of the history, because that tends to get lost as well. If a team member suddenly leaves, that is a loss of history. This is a way to...

It's great when we get lots of time to dig into a problem before having to choose a solution to implement.

I love it when that happens!

Except that, in my experience, it rarely ever happens. In fact, in my experience, leaders usually have to make decisions essentially while still processing incoming information.

More than once, I have found myself having to stop and refocus because my mind was wandering off in “analysis land” in the middle of a meeting.

So, what process could we follow if we wanted to do a rapid risk forecast?

Ask yourself four simple questions

The first thing we could do is ask ourselves for simple questions:

• What could go wrong?
• What is the likelihood of this happening?
• What would be the consequences if this were to happen?
• What is the level of impact of these consequences?

Write it all out.

If you have something that is likely to happen and the consequences are low, consider whether it is something that is extremely risky that you need to address...

Nintendo started out producing handmade playing cards. Netflix was selling and renting DVDs by mail. Starbucks used to only sell high-quality coffee beans and equipment (no brewed coffee or delicious handcrafted espresso drinks!).

As different as their businesses were – and still are – they all managed to pivot/strengthen, expand and thrive. Even without firsthand knowledge on the details of how they went about these changes, it’s not hard to imagine that experimentation and a desire to constantly improve was somehow involved.

Anyone who has spent any amount of time visiting the Corgibytes website (where I am COO), reading the blog or listening to our podcast (Legacy Code Rocks!) knows that we’re constantly talking about reducing technical debt to make codebases stable, scaleable and secure.

What you likely don’t know is that we also apply those same concepts to our operations.

Just like we do code health checks, we do operational health checks....