By Trevor Lee

We love family vacations, and we’ve learned the hard way how they work best for our family. One of our first vacations was planned out almost minute by minute. We knew exactly what we were doing and when we were doing it. As the trip went along we had some unexpected issues arise, but because we had spent some much time planning we didn’t want to deviate from the plan. In the end that approach made us frustrated and irritable. We placed the plan over the purpose of enjoying a vacation together.

On a recent vacation we did pretty much the opposite. We went to a beach resort with no plan whatsoever, thinking it would be nice to just relax. By the end of the first day everyone was a little bored and we found ourselves being on edge with each other. We had no plan and we missed out on some great opportunities to make memories together as a family.

Having no plan was a bad idea. Being so tied to the plan that we wouldn’t adjust was a bad idea too. It’s the same in business. Planning is essential, but so is the ability to pivot when necessary. You need to consistently plan, assess, and pivot.


If you want your business to succeed you have to have a plan. I know, that’s obvious. But it can’t just be any plan. Your plan needs to be clear, achievable, and measurable.

Whether you’re an entrepreneur with sole responsibility for the plan or you lead a large organization and develop a plan with a team, it’s wise to share your plan with a couple people who weren’t part of the process to see if they think it’s clear. If the plan is muddy, execution will be problematic. So make sure you have a clear plan.

Second, the plan needs to be achievable, but that doesn’t mean it should be easy. It should push you. It should represent a vision for where your business can go. But if the plan is so outlandish that there’s literally no chance of achieving the results you lay out it will be demotivating. I once worked with a company who had set goals that were so astronomical that it became quickly apparent to everyone that we wouldn’t even come close to meeting them, no matter how hard we worked. It made people want to give up because we couldn’t be successful. So lay out a plan that will challenge you and is achievable with a lot of hard work.

Finally, your plan has to be measurable. It’s incredibly frustrating to put in hours, weeks, or months of hard work and then have no idea if you’ve been successful. It also makes is nearly impossible to do the next thing–assess how your plan has worked.

In short, you need to have a plan to be successful, and that plan has to be clear, achievable, and measurable to motivate people to move the ball forward.


Once you have a plan that is clear, achievable, and measurable you have set yourself up to be able to do meaningful assessment of your progress. This involves asking three questions: Where did we succeed and why? Where did we fall short and why? Are we headed in the right direction?

Where did we succeed and why? It could be easy to note the places where goals were met and move on quickly to the places you fell short, but there’s wisdom in taking some time to dissect your successes. The places where your plans succeed can tell you a lot. Who was involved in the successes? Are there ways they can be leveraged to create more success? What kind of momentum has been created? How can you build on that? Did anything out of the ordinary happen to cause the success? Take the time to really ask questions of the success so you can build on them.

Where did we fall short and why? This question is more obvious. When goals aren’t met you need to figure out what happened so changes can be made. Were the right people on these assignments? Was the goal too aggressive? Were there unusual circumstances that made it more difficult than normal to succeed? The autopsy of unmet goals is essential for the next step, but before we get to that there’s one more question worth asking.

Are we headed in the right direction?
There are times when unmet goals don’t signal a need for drastic changes. Maybe unforeseen circumstances required less attention be given to a particular goal. Maybe there was a key employee who moved on, temporarily stalling progress. Maybe the goal was bigger than you thought and more time is needed to meet it. Pivoting isn’t always the answer. If you are confident you’re headed in the right direction, then the right move right now is to stay the course.


After assessing the successes and failures of a plan that is clear, attainable, and measurable, it is time to pivot. As a leader you cannot become so tied to your plans that you are unwilling to make necessary changes. Some leaders have an easy time pivoting in necessary ways while others become overly attached to the plans they’ve created and are unwilling to budge. Being successful requires the humility to admit where plans need to be adjusted and then making those adjustments. Remember, success is fulfilling your mission, not a specific plan. The plans are just a tool to help you get at your mission.

When you pivot, you go back to the beginning of this process. Make sure your new plans are clear, attainable, and measurable. Part of having clarity is communicating to employees, investors, and customers the reasons for the changes. People generally resist change, especially when they don’t understand why it is being made. So make sure you communicate clearly and consistently about the reason for changes and the importance of the pivot.