The answer to “Why?” is not as easy as a simple logical explanation. Leaders must work at accepting the question “Why?” and developing the skill of proactively explaining the why of an assignment as it relates to the big picture. Many Gen X and Baby Boomer leaders have a different connotation for the word why and different emotional response to being asked “Why?” This is not an easy thing to turn off and on. No easy task, but a 21st-century superpower.

The newer worker, not understanding the situation, may hear defensiveness, closed-mindedness, and the lack of any innovative thinking from older leaders’ responses. The conclusion that might be drawn is that this organization is closed-minded and not looking to grow and develop. After asking, “Why do we do this?”, someone might interpret the response as, “Because we have always done it that way,” or, “Because I say so.” Unfortunately, this communication breakdown could drive a younger worker out of the organization. After all, who wants to work for a closed-minded organization?

To put the situation into further context, think of the ages of each generation during major 21st-century events. To use an example: In the Great Recession of 2008, the youngest Traditionalist was 62, the youngest Baby Boomer was 43, and the youngest Gen X was 28. In contrast, the youngest Gen Y was 7 and Gen Z was not even born yet.

It is not so hard to understand that a 62-year-old might understand the why of certain decisions far better than a 7-year-old. Certainly far better than someone who was not even born yet! It is critical for leaders to develop this leadership superpower and understand that context is needed, and many times, that only comes from experience and perspective.

What a 62-year-old may take for granted in any situation would be dramatically different than the view of a 7-year-old.


21st-century leaders need to understand this communication issue and the evolution of the question “Why?” It is not intended to be disrespectful or question authority. It is intended to tap into an experienced worker’s wisdom.

One of the first things a 21st-century leader can do to begin changing this dynamic is to hear the question differently. Instead of hearing it through any generational filters, listen to the question and be flattered by it, not frustrated. When someone is looking to tap into your experience and wisdom, that shows a great deal of respect. You should be flattered to receive this kind of respect.

Reframing the way we hear the question is a great start to developing this 21st-century superpower. The next step is to learn how to proactively explain the why when giving out an assignment. One of the reasons leaders do not do this is that they are unconsciously competent. Since they clearly understand, deep down, the why of every assignment, there is a tendency to think everyone else does as well. That is simply not true.

Another reason may be that they aren’t great leaders. They “manage” tasks but don’t set and convey a vision for the organization.

21st-century leaders need to explain things in these ways:

  • Let me tell you why this is critical.
  • Let me put this in context and explain why we do it this way.
  • Let me share with you why this is the process.

When Solutions 21 coaches next-generation leaders, specifically Millennials and Gen Z, we explain the evolution of the question. We suggest that instead of simply asking “Why?” that they try to rephrase it and use something like “Help me understand” or “I want to understand the context.”

As discussed, this is often a two-way street. Twenty-first century leaders need to learn to explain the why, and staff need to learn how to rephrase the question. If all generations understand the evolution of this question and its intended meaning, then both sides can adapt either their answer or the way the question is posed.

Better communication. Win-win.

Adapted from our best-selling book, The Leadership Decade: A Playbook for an Extraordinary Era. For more information, check out