Nearshore Americas

When Planning Becomes a Problem: Becoming Agile to Stay Focused on Long-Term Goals

We all know a detailed plan is crucial to the success of your team and your company, right? Perhaps not.

The answer is more complicated than you might think.

Planning is a task that we must be good at on multiple levels; as an individual, as a team and as a company, proper planning is key to our success. But only up to a point.

At each level of planning, we have to master the art of knowing when we have reached the point of a plan that is “good enough”. Over-planning leads to tunnel vision that prevents us from seeing other more valuable opportunities along the way. Or, even worse, over-planning pushes us to stubbornly rely on a plan that is no longer useful and will lead us directly to failure. “Working to the plan” can give us a false sense of progress and we can end up losing sight of the goals behind that plan.

Planning and goals are not the same thing, and knowing the difference is the foundation of knowing when you have planned enough.

Mike Tyson, former heavyweight boxing champion of the world, famously said that “everyone has a plan until they get punched in the mouth.” As soon as life or work punches you in the mouth, your plan no longer matters. Reeling from the punch, you may try to grasp onto your plan, but your situation has changed. Your goals have not changed however, and so we must build our plans according to a framework that not only allows for change, but invites it.

To consider how you can build a plan that thrives on change, let’s consider planning at the team and company level.

Use Agile Methodologies for Flexible Team Planning

At the team level, we are particularly guilty of following the wrong metrics. In the worst-case scenarios, we curse a project from the start by assigning unrealistic goals that fix the scope, budget, and timeline all at once. We build a fancy plan that shows every task we imagine performing between now and the deadline.

We leave no room for creativity in the team, and we don’t leave enough margin in the plan for unexpected delays and obstacles. We may even pride ourselves on a fancy Gantt chart, but that chart quickly becomes outdated and serves only as a monument to the hubris of our early project planning when we thought we had all the answers.

Planning and goals are not the same thing, and knowing the difference is the foundation of knowing when you have planned enough.

The framework for combating this at the team level is to follow an Agile methodology such as Scrum or Kanban. Agile teams set overall goals for a project, while allowing for flexibility in the budget, timeline, or scope necessary to meet those goals.

An agile team plan identifies the goals that our customers need to meet to have a successful outcome. Even more important, we prioritize those goals and work on the most important ones first.

We can still have a fixed budget, or a fixed timeline, as long as we are flexible with how much scope we can achieve for that fixed budget or timeline.

If there is a minimum set of the highest priority scope that must be completed before our customers will consider our work to be successful, then we must leave flexibility in how long it takes to complete that work, to what depth we complete the work, or in what budget we can complete the work.

The worst part of any plan is the up-front assumption that we already know everything we need to know about the problem we are trying to solve. Most likely that is not the case, and we will learn more about the problem as we go. By implementing an agile plan, we will have the flexibility to change the path we take to achieve the most effective solution.

Keep Company Goals Annual but Keep Planning Shorter

At the company level, we need to allow for the same flexibility in our annual planning. I recently stumbled across an old notebook in my files, and inside the opening pages I had listed my frustrations about how my company was operating at the time, and things I wanted to change to fix those problems. I had made specific assumptions in my business resolutions that year, which assumed which of our product efforts would be successful, and the distance we could go along that path to achieve the success I wanted.

The depressing part of finding this notebook from 2019 was how similar it was to things I would have written down at the beginning of 2021. The problems I described were identical nearly two years later, but none of the solutions I had imagined in the past had worked. Why was not a single one of those problems solved in the intervening two years?

“Everyone has a plan until they get punched in the mouth” — Mike Tyson

If you guessed “global pandemic” then give yourself a prize. Although it was not the sole reason that I didn’t solve my 2019 problems, the global Covid-19 pandemic that spread in 2020 completely upended my assumptions of how I could approach business challenges I was facing. I had made additional faulty assumptions in my plan, which the negative economic effects of the pandemic magnified and forced me to deal with drastically. In business survival mode, I quickly discovered how little those plans mattered and threw them away in the face of rapidly changing conditions. If I had stubbornly stuck to my prior plans, my business would not have survived.

At the beginning of 2021, I set out my company goals differently. Instead of prescribing to myself or my senior managers the specific paths for how we were going to solve those same problems from 2019, I focused on the outcomes I wanted as a business owner. We focused on goals of achieving certain amounts of stability and profitability, and delegating certain responsibilities in order to create more time to work on strategic items and be able to respond to unexpected change.

Instead of defining a detailed tactical plan for the year, assuming I knew how to reach my goals, we created a more strategic plan to identify the issues we were facing, and created the framework in our management team to better handle changes as they came our way. For example, I did not define a set number of employees we needed to have by the end of the year, instead we committed to following a management framework that helped us to communicate better as a team. We also agreed to constantly revise our plans throughout the year so we could adapt to what was necessary in order to meet our most important goals.

In business survival mode, I quickly discovered how little plans mattered

In our case, the management framework we implemented is the Entrepreneurial Operating System (EOS), which is defined in a book called Traction, by Gino Wickman.

As part of this framework, we set annual goals but we are not prescriptive or overly detailed about how we are going to reach those goals. Each quarter, we set new “Rocks” for each member of the management team, which are shorter term goals for things we need to accomplish that quarter in furtherance of the annual goals, or to solve other issues that come up along the way. The specifics of how to accomplish that Rock is still left up to the individual, but we meet regularly throughout the quarter to report on our progress to each other.

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In your case, a different framework might make more sense. For example, in a large corporation with many different agile software development teams, you may need a framework like SAFe, which helps you organize a portfolio of work across many teams, while still maintaining the flexibility in defining and implementing that work that traditional enterprise management methodologies do not allow for.

Today, we have made great strides in solving the problems I noted in 2019. The way we have done it is very different to the way I’d imagined previously, but that doesn’t matter. We have actually become a better and stronger company than we were prior to the pandemic. We not only learned some specific lessons from the struggles of the past, but more importantly, we now have a framework in place to help us better respond to the unanticipated problems our company will undoubtedly face in the future.

Preparation Over Detailed Planning

As usual, the only constant we can expect is change, and so we must learn not to fear it. Overly detailed planning will not help us stop change, it will only slow us down in responding to that change which we must confront. The key to success at any level, from the individual to the organization, is to follow a planning framework that encourages adapting to change. That is the sort of preparation that enables us not just to plan for change, but to plan for thriving because of the change.

Arin Sime

Arin Sime is the CEO and Founder of AgilityFeat, a boutique software development agency founded in 2010. The company is based in the US and Panama, but works with remote talent throughout Latin America. Arin is also founder of, a development agency specializing in building live video applications for web and mobile.

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