In all of the strategic planning sessions I have been involved with (either as a facilitator or participant), this chart seems to be the most difficult one to address. It's so simple but these four boxes are a doozy!

The emphasis of the exercise here is on what we "stop doing" or "do less of". What we "start doing" or "do more of" is pretty easy and gets a lot of excitement and support. In our world of abundance, where more is better, layering on stuff just feels so darn good. What is really, really hard is figuring out what we stop doing. We experience loss when we have to “give something away” we invested in.

There are three reasons we mourn when we have to give something up:

Sunk cost: Sunk cost basically says that we’ve already put so much time or investment into something, the idea of abandoning it conjures up feelings of failure or reflecting poorly on our initial decision making.
Losses hurt 2x as much as gain: The idea of losing $10 is a lot more painful than the prospect of getting $10 (or even $20). This idea is borne out of behavioral economics around a theory called Prospect Theory (only click if you're really interested in the equation for it).
Endowment Effect: The Endowment Effect says that we value something much more highly when we own it. Letting go of something you have built or invested in is difficult if you’ve already “assumed ownership”.

So let’s break through this once and for all. Let’s run toward either stopping outright or doing less of things. If we take these actions with the right strategic filter on the business (or life), we free up more time to focus on the things that will really move the needle and give us happiness, results, and achievements. But you have to be ruthless and a bit unemotional about it. Here are five filters to use when figuring out what goes in the “stop” and “less” buckets:

Follow Your Instinct: When was the last time that you decided to stop something and regretted it? Exactly! As Greg McKeown writes in Essentialism, if you’re gut isn’t saying, “Hell Yes”, say “No”!
Time as a Variable: Think beyond the near term and would you want to be sitting here a year from now still plugging away on this project or effort?
Data as Support: Do I have data to support continuing? If the data doesn’t support it, kill it. If you don’t have the data in the first place, then you really didn’t set up your expectations which are fundamental to making trade-offs in the first place. Challenge yourself and team to define what is being measured and what success targets look like.
Opportunity Cost: What are you not going to be able to pursue because your can’t let go of this one project or investment? Yes, the future is uncertain but the future can be really, really bright. Remember that by not making a decision to stop doing something, a decision was, in fact, made.
Clear Your Personal Filter: Often we hold on to projects because of the story we tell ourselves. Examples might be, “I don’t want my investor to see I failed.”, or “If we stop this project then I might be out of a job.”, or “What are we going to tell the employees?” Check your personal storytelling at the door and it may help clear your lens.

"Stopping" or doing "less of" is an essential muscle for an entrepreneur and a company. It has to be done or you will fail. It is so hard because it often creeps up in a time of crisis and then it feels really stressful. If you use this simple grid more regularly as part of your ongoing strategic decision making, the natural angst associated with loss will be much less. Good luck!

What Will You Stop Doing?