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The danger of "should" in leadership

Updated: Jul 18, 2022

There are words that over time we learn have an impact - both in how they are communicated and what message that they send to the person. Sometimes we don’t even realize the message we might be sending to someone.

Recently, while reading Julia Galef's book Scout and David McRaney's book How Minds Change, I was reminded of the danger of "should." Reflecting on this, I started with definitions. Reviewing various dictionaries, "should" was defined in various ways, but all of them included words like duty, obligation, or propriety. So when we think someone "should" do something a certain way or react a certain way, as leaders (and humans) we are layering on our own expectation and perception - and that may make the person feel as if the leader's "should" is the only way to do something and that they do not have agency, or choice, in the way forward. (NOTE: There are aspects of being part of an organization and society that may be bound by duty, obligation, and/or propriety - organizational policies, treating others with dignity and respect, etc; though I would classify those under acting with integrity in terms of leadership behaviors.)

As I think about the various ways that "should" can show up as a leader, rarely is it within the context that there is only one way, rarely is it actually an obligation or duty, even more rarely is it the message I would intend to send to someone.

  • The implied direction "should": let's say you are problem solving with members of your team or an individual. You, as the leader, do not actually have a specific way you imagine the solution, but you move to a "should," which then can send those listening in to the idea that what you said "should" be done is now a duty or an obligation, not an addition to the conversation. If you feel strongly about the solution, avoid "should" and seek to communicate with clarity and/or confirm with the individual or team the future. At times, I will catch myself "should"ing in a problem solving situation, and I strive to notice it, pause and ask if I really want to be giving direction, and then if not, I will add something along the lines of "this isn't a direction but an idea. I trust your approach. Let me know how I can support you."

  • The "if I take your advice, it will work "should" or if you take my advice, your path will be like mine"... This “should” is when a leader or mentor gives someone a specific task or way forward, and it does not work. The use of should in these conversations could lead to an unmet expectation of success. Brené Brown reminded me in her book Atlas of the Heart that, "Disappointment is unmet expectations." (p. 43). So, as leaders in our moments of advice giving, be aware that you may be setting someone else for disappointment, when their path to success could look or wind differently.

  • The "hindsight should"... this one can be both personal (I should have ...) but more dangerous is the judgment of others in the should. "This person should have done this ..." This should is often the opposite of the first and/or is the Monday morning quarterbacking of a situation. The “should” that is either because expectations were not set or the “should” of considering a situation after the fact and layering on judgment while not having been in it. This use of should links closely to what Brown (2021) defined in her book; the feeling of disappointment (or possibly anger or frustration) that something was not done the way of a (possibly unstated) expectation.

The danger of the "should" in some situations of leadership is that it both limits the opportunity to enable creative and innovative ideas because of a sense of obligation to follow a leader's direction. Another potential danger is that it fails to account for the beautiful complexity of individuals and what they bring to the table without the "should."

One word. So many opportunities for miscommunication.

So, what might you say instead...

  • What are you considering doing?

  • You might consider .... (problem solving)

  • The questions I would ask myself in this situation are ... (mentoring conversation)

  • Our next steps will be ... (shared direction)

A final note is to consider when you hear or think a "should" in your language or thoughts, pause and consider ... what am I trying to communicate right now? What expectation was not met, and how can I, as the leader, be more clear in the future?


  • Brown, B. Atlas of the Heart

  • Galef, J. The Scout Mindset.

  • McRaney, D. How Minds Change.

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