Guest Post by  Matthew L. Olmstead

Last week my family and I were taking a bike ride. Along our path was a young couple taking their wedding photos in front of a beautiful waterfall background. My son who is 5-years old promptly asked, “Are you getting married?” They responded with a slight giggle “yes, we are”. My son then quickly asked “Are you going to have babies?” Everyone started laughing and the young couple said “not right now”. My son, who was adamant about getting an answer said “What about next week?”

My guess is that they will never forget that moment. A young boy, 5-years old, made a permanent impression on a young couple’s life. A 5-year old boy who doesn’t understand much more than what is happening right now and one who certainly doesn’t understand what leadership is about. However, he did understand that if he wanted to know the answer he was yearning for, he needed to ask a question, and then another if necessary. This made me think. What if, as leaders, we weren’t afraid to ask the tough questions, especially those questions that we are afraid to hear the answers to?

As leaders, we must realize that most of all that we know about our companies or organizations is not because we have experienced it ourselves. It’s because others have. Those individuals who have the loudest voice are often those who are never asked to speak. To truly develop organizations, leaders must ask their employees these questions:

1)   How do you feel valued in this organization?

Don’t simply ask them if they feel valued, but ask them how. Value is subjective, not objective. Just because a supervisor or leader believes that their employees should feel valued, doesn’t mean they do. Keep this question open-ended. However, be ready for the awkwardness associated with the question. My guess is that most employees are never asked this question. Typically as soon as leaders ask this question, it is obvious whether employees feel valued. Valued employees show it. Employees who do not feel valued find it hard to hide it. This question encourages open communication and collaboration about what the supervisor or organization can do to bring employees together and make them a part of the team. Supervisors must be open to different perceptions and views of employee fulfillment. Also, let’s face it, supervisors and leaders cannot be everywhere at one time. There may be things going on in areas that we are not aware of. Employees may bring up their perception of favoritism in the office or lack of adequate work distribution. More than anything, a better understanding of the employee or how the employee feels he or she fits into the culture is often a product of the question.

2)   When is the last time you had fun at work?

Don’t get me wrong, I’m not expecting the work environment to be an amusement park, but employees want, need, to have some fun at work. Nothing is worse than having an environment that is allergic to laughter and fun. As a supervisor or leader, it’s important to understand that importance of having fun with prolonged productivity. This will also allow leaders to have a good outside look at the culture of the organization. As a supervisor, it’s easy to have fun. Who is going to get onto a supervisor for taking a prolonged lunch or taking a morning with a client to play golf? It’s easy to create an environment for yourself that is fun, different and ever-changing. Unfortunately, not all employees get that option and may feel like they are “stuck in a rut”. Be sure to get all employees involved in the process of having fun at work. I’ve been known to send out funny cartoons about leadership or management to my employees to loosen things up a bit. There is no one best way to do this, but find out what is needed for your organization to incorporate fun. Happier employees help the bottom line.

3)   How am I doing…seriously?

This question is the hardest. We are used to giving annual performance evaluations to let our employees know how they are doing, what they can do to grow in their job or just to give feedback. As leaders we need to be able to receive criticism as well as we want others to take it. I’m not saying that the employee needs to give you an evaluation. In fact, I would highly discourage that. However, I recommend keeping it informal by simply asking “Is there anything you think I could be doing differently to help you”? Letting the employee know beforehand that this question is coming will give him/her some time to give you an honest answer. The key is to let the employee know that you are asking so that you can continually monitor his/her needs and to continually improve yourself. If you have not already built a good rapport with employees, you probably will not get an honest answer, regardless of how long you give them to ‘think about it’. Expect that this answer will change, and have varying degrees of honesty each time you ask it. Employees need to know why you are asking it. Unless we know how people perceive our leadership ability, what we do is meaningless. Most all of us want to do the right thing. However, it’s how we do it that make all the difference. Leadership is about making a difference. If we are not making a difference in the lives of others, our leadership actions are futile.

Asking the tough questions is not easy. However, sometimes we may need to think like a 5 year old.  If we want to truly get the answers we are yearning for, don’t assume, but ask.

MatthrewOlmstead Headshot2Matthew L. Olmstead is an Executive Business and Operations Administrator in the Higher Education Field who resides in The Woodlands, TX.  With a background in Organizational Management and Leadership Development, he works with various small group organizations with leadership development and adapting to change.  You can follow Matt on his blog:  You can contact him at


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