Breath of Clarity

Comment #2: Challenging Your Team

Original Post by Caleb Kiser:

Challenging your team is a crucial piece of overall team success. If your team does not feel challenged, they will never push boundaries, get out of their comfort zone, expand their knowledge, or grow the company. Unfortunately, challenging your team is not as easy as it sounds. Leaders cannot manipulate their employees to perform in specific ways at work. The first piece before you can challenge your team is the skill of observation, as Kathryn did in The Five Dysfunctions of a Team. Observation allows you to see how your team works together and how each individual is motivated and what they are good at and what they may need to develop more. Once observations are made, you can learn how to properly motivate and challenge your employees based on their personality, working style, and learning drive.

One way to challenge employees is to offer them new assignments that may interest them based on your observations and force them to learn a new skill. For example, my boss asked me to lead the complete redesign of our environmental web page on our internal company site. I have never done anything like this before. However, I am very interested in it due to the environmental aspect of connecting with other people and learning new coding skills. He knew this would appeal to me because I love challenging projects, and I learn the best by just going out and trying something learning from mistakes, and then trying again. Keeping that in mind when I attempt to help somebody learn a new skill, I do not just walk them through the steps; I get them to do hands-on learning as I vocally and visually guide them, but they are in control. Sometimes, this may be frustrating because some people need to see before they do, but they also need to learn that it is okay to make mistakes along the way and that not everything will be perfect every single time.


Lencioni, Patrick. 2002. The Five Dysfunctions of a Team. San Francisco: Jossey-Bass.

Manning, George. 2014. The Art of Leadership. New York: McGraw-Hill

My Comment:

Hi Caleb,

Great point that challenge is needed to grow. In the book The Five Dysfunctions of a Team, Kathryn expected the off-site retreat and company re-structuring to be challenging which helped her persevere. It is interesting to consider that, although a pursuit, such as saving a company, is challenging, it also requires the need for a leader to surrender control in the process. Kathryn prioritized generating group participation over following her agenda to a T. For example, the group decided without any interference from Kathryn that Nick was the best fit for Director of Sales after J.R. left. As this post mentioned, Kathryn did a great job in leading the way by observing the team’s strengths and areas for further development from the get go. By reiterating that her statements were derived from many moments of observations, she was able to gain the respect required for the members to initially start to buy-in. She would even start off each meeting recognizing that the team has some of the best talent in the industry and then emphasized there was room to develop further if only they were able to work as a team. Since she maintained a respectful attitude while doing so, the team started to model her tone to determine each person’s strengths and where they can be developed further. All of the members were then able to put their insight together to make great decisions aligned with the group goal.

Great example of challenging employees by offering them new assignments. That’s awesome that, even though the task was so unfamiliar, your boss set you up for success based on your interest and learning style. Also, I agree with the need to give someone a hands-on learning experience when you are training them to do something that is particularly challenging. Teaching the employee that it is okay to make mistakes along the way will support them in not entirely quitting the task once they face adversity.


Lencioni, Patrick. 2002. The Five Dysfunctions of a Team. San Francisco: Jossey-Bass.