Leadership Conversations

Posted on Saturday, September 6th, 2014

A client asked me to develop a series of leadership conversations that she can hold with her management team for the purpose of developing and nurturing their shared leadership practice. They want to be better leaders, in their organization and in their community. The design we are experimenting with is a “one-pager” that could be used at the beginning of a regular staff meeting. I am going develop “scripts” in four main areas:

  • Inquiry
  • Systems intelligence
  • Measurement
  • Better meetings.

I have in mind a variety of specific topics within each of these larger areas of practice.

Here’s an example:


“Open and Clean Questions”

(Based on the work of Don Swartz, founder of the Organization Systems Renewal (OSR) program)


A leader must know how to shift a conversation in an organization or team. Teams or groups, especially leadership teams, can get stuck in a conversation about “what’s not working” or what someone else is doing to block or blame us. A better conversation is about possibilities, or learning, or gaining a deeper understanding of some challenge. Leaders can begin by asking better questions. The practice of asking open and clean questions during meetings and other complex interactions is a powerful way to begin to shift the current conversation.

An open question can’t be answered with a simple yes or no or some other word or phrase that ends the conversation.

A clean question is open and flows from a genuine intention to learn or help.

Questions that are not clean (“dirty”, or unhelpful questions) seek instead to lead, to tie or bind, to imply or suggest, or to give advice. “Why do you always…?” implies guilt and is a dirty question. “Why is that important to you?” expresses the asker’s intent to learn more, and is a better question. Other unhelpful questions include: “When are you going to stop…?”, “Don’t you believe…?” or “Don’t you think…?”, and “Don’t you think it would be a good idea if…?”

Questions that bind...

Questions that bind…

Examples of clean questions include: “What do you mean?” and “What is it that you value about our current approach?” as well as, “Why is that important to you?”

Genuine intent to learn or help...

Questions that express a genuine intent to learn or help…

Context and tone are important, which is why this is a practice rather than a recipe. A leader must be fully present to get it right!


Individually, write down at least two unhelpful questions you have asked someone in your work situation. Then, write down two unhelpful questions you have been asked by someone in your work situation. No attribution is necessary!

When everyone has done this, go around the room first to hear what unhelpful questions people have asked, and then around again for questions they have been asked. Consider why these questions are unhelpful, and how they might be improved. How could one ask something in a more open and clean way? Which of the unhelpful questions are beyond remediation? What do you notice about context?


Meetings, one-on-one conversations, performance evaluations, conversations with teenagers and spouses/partners.

What to notice

Conversations generated by genuine questions should be less defensive, help strengthen relationships, promote transparency, and help a group avoid cycles of blame. Such conversations might seem to take longer at first, then they will be seen to be more effective. Individuals and teams may find they are more creative and more productive.

[End of example]

My question to you is whether you would find such a conversational exercise useful. What other ways would you use this material? What would you change? What would you like to talk about with your team? What questions do you have? Call me if you would like to have a conversation about leadership.