The Most Destructive Word

And the 5 words to use instead.

Words are, of course, the most powerful drug used by mankind.
— Rudyard Kipling

As a leader, your job probably includes thinking about the direction of your company, motivating your team to achieve success, and making critical strategic decisions about what your organization will focus on next. All of these tasks require words. Now, this may seem like a funny way to put it - but you can’t talk to yourself in deep thought, talk to your team to motivate, or describe the next steps your organization will take without words. Words have meaning.

The Jungle Book Author, Rudyard Kipling agreed, saying:
“Words are, of course, the most powerful drug used by mankind.”

Just like any drug, The right words used at the right time and in the right way can transform life. The wrong words, used carelessly, can destroy focus, obliterate productivity, and devastate a team. The beauty of words is that they, unlike controlled substances, are constitutionally mandated (at least in the US) to remain free. So it is up to us to inject self-control in between our cognition and use.

At the top of the list of the most devastating words that I have heard is Should.
I’ve seen team members and executives of all levels literally should all over each other, and it rarely ends well. Here are a few different uses with their corresponding effects:

Used to Declare Powerlessness

"What should I do?” A business leader says when he has decided he can’t or won’t make a decision. The problem with this sentence is that it declares victimhood. It sounds like “I can’t decide, make a decision for me.” There are always times when this is how we feel, but we always have to remember that we alone are responsible for our decisions and actions. We can always make great use of the advice of our mentors and colleagues, but not at the expense of our own agency.

Used to Avoid Empathy

"You should do it this way!” Declares a business leader who has already made up her mind. The problem here is that none of us have lived in another’s shoes. We can offer advice to each other. We can always tell direct-reports how we need something to be done. Invoking should goes a step further. It implies that we know better than they do. Maybe we do, but they’ll perform better without us treading on their free will.

Used to Reinforce a Limiting Belief

You should only do work on weekdays, businessmen should be men, your company should start working on an app, leaders should have MBAs, your company should advertise on Facebook, and the list goes on and on. Whoever is telling you this isn’t really talking about you. Should is a dead giveaway that they are talking about their own limiting belief. Thank them for the likely unsolicited advice and move on.

Used to Prescribe Right and Wrong

There are only very few times in our life where there is an absolute right or an absolute wrong and it usually involves someone’s death. Every other decision we make falls into this uncomfortable gray area where we can never be absolutely sure if we made the right decision. We can talk about philosophical balance later, but for now, resist the safety zone of should. It is easy to get indignant and declare that your action is exactly what you should have done. But no need. It was a tough call, maybe you were right maybe you were wrong. Only time will tell. Remember, great leaders make bad calls sometimes too.

I’ve used should in every one of these ways at one time or another. So have all of the leaders that I’ve ever met. However, the best leaders choose to learn about the nuance of their word choice and pick from these 5 replacements.


My go to replacement in self-talk is could. When I hear myself self-instruct using should, I quickly remind myself that I could do that - or I could focus on other options. Could implies choice, which is why I like it so much. There are endless coulds and each one is a door into a possible future. For big decisions, I follow a structured strategic planning process to decide which could is the right one. For small decisions, I try to decide quickly and move on, fully accepting that I might be right and I might be wrong.


"We would do that if…” is a great way to replace a should when working in a team. I hear groups make plans based on everything they think they should do. Would-if allows you to take all of your possibilities and filter them by available resources. "We would consider advertising on Facebook if we had an inbound marketing strategy.” Making decisions within the context of my available resources is the healthiest way to live my personal life and run my business.

What if?

The best way to crush a limiting belief is to ask the empowering questions of “what if?” or "why?” These are the foundation of every meaningful innovation our society has ever known. If you meet should with skepticism, then you can be empowered to make your next move. Early on in my career, a mentor taught me the game of 5 “Whys”. Take a belief, usually preceded by a should, and ask why 5 times. Sometimes you get to the kernel of a limiting belief and sometimes you reaffirm why that norm is in place.


In a sea of endless possibilities, it is often helpful to limit your choices. When you hear yourself or others apply a should, decide if it ought to be on a won’t list. A not-to-do-list is helpful for both an individual and a team to stay focused on the most valuable projects, steps, and actions that need to be focused on next.

Am Doing

If you struggle with too many shoulds, or if your incomplete coulds are matched with shame, there is one easy way to break the cycle. That is to return to the current moment. While the past can feel full of should-haves, and the future can feel full of uncertain shoulds, the present just contains your current action. Being in business today is too complicated for most of us to manage on our own. What are you doing? Focus on that for this moment because your current action is the only one that matters right now.

Words matter. They have meaning far deeper than their surface may indicate because they evoke meaning inside of the speaker and those who are spoken to. If you’re seeking to innovate and challenge the status quo in your business or industry, you could (see what I did there?) choose to first challenge the status quo within your own speech. Try it and let me know how it worked for you below!

P.S Another way that you can be more intentional with your words is to get intentional with your company’s purpose. Download our free Purpose Guide and start getting intentional with your purpose today.