Coffee Conversations Ep. 8: The Quagmire of Questions

January 27, 2021
  • David VanderMolen
  • David VanderMolen
    Learning Sensei

Is it possible to be too helpful to a friend or teammate in need?

Is the help we are trying to give sometimes counterproductive?

That is the question posed by our latest episode of Coffee Conversations. You can watch through the link above.

It seems helpful, caring and thoughtful to ask a friend a bunch of questions when you detect they’re experiencing a problem.

In general, it’s what we’ve been taught to do.

It’s what – we’ve been led to believe – considerate and compassionate people are supposed to do. It’s how we’ve learned to help per se. But it’s not as helpful as it would seem on the surface.

In life and in leadership, people have been trained to respond to the problems other people are experiencing with an “it’s my duty to solve their problem” mindset! In turn, most folks will fire off a series of questions to the one experiencing the problem to thoroughly understanding the problem, so they can go about solving the problem. But that’s a real problem! (Pun intended!)

Like the working-under-the-hood of the Jeep example in this episode of Coffee Conversations, asking one question after another (after another) to understand the situation or to solve the problem tends to exasperate, raise the emotional temperature, or potentially even rile-up the one experiencing the problem. He or she tends to interpret all the questions as criticism of their inability to solve the problem and receive the “I’m attempting to help you” intentions driving your questions.

Brew on this...

  • Asking questions pulls people out of their mental groove and puts them into your mental groove.
  • Asking questions erodes people’s sense of trust and security.
  • Asking questions shifts the ownership of the conversation from the one with the problem to the one asking questions.

Reflect on this...

  1. In my mind, do I think or believe it is “my duty” to solve other people’s problems?
  2. Do I tend to ask questions to understand the problem so I can solve the problem?
  3. Who in my span of care would benefit the most if I were to simply stop asking them questions when they are experiencing a problem?


David VanderMolen is a former professor in Barry-Wehmiller University and the host of Coffee Conversations.


Related Posts

Need help in applying principles of Truly Human Leadership in your organization? Chapman & Co. Leadership Institute is Barry-Wehmiller's leadership consulting firm that partners with other companies to create strategic visions, engage employees, improve corporate culture and develop outstanding leaders through leadership training, assessments and workshops.

Find out more at