23 Questions Great Leaders Ask

Mountains, Leadership Peak

Photo Credit: Dragomir Vujnovic. Used by Permission.

This past week we’ve been reading Boundaries for Leaders by Dr. Henry Cloud. When I came across these list of questions for yourself, your team, your direct reports, the vision and strategy, and for the culture I knew I had to share it. I encourage you to even print it out and post it near your desk as questions to ask yourself on a periodically to keep yourself leading in the right direction for your team and organization.

“As we look further into the foundational role that leaders play in establishing boundaries, ask yourself these questions:

For Yourself: What do I do now to make sure that I am attending to what is most important? Have I defined it? What do I do to inhibit myself from getting pulled into what is not important? How do I keep what is important in front of me all the time? How do I create a “current river” of information, initiatives, and steps that keep what is important moving?

For Your Team: What structures and processes do I have in place to make sure my team is attending to what is crucial? Do they know what that is and are they aligned on it? In what areas is the team not inhibiting what should be inhibited, and what am I doing to eliminate toxins or distraction? How do I make sure the team is creating a flow of working memory with what they are trying to drive forward?

For Your Direct Reports: If I interviewed my direct reports, would they be able to say that I help them to attend to the things that drive the results that we have agreed on? Do I help keep distractions, conflicting goals, or destructive elements from interfering with their attention? Do I enhance or inhibit their ability to stay current on the important working memory?

For the Vision and Strategy: Is my vision and strategy clear and communicated in a way that allows everyone in my organization to attend, inhibit, and move toward it? Do they know what it is? Do they know what it isn’t? Can they take steps in the right direction? Do they know what activities belong to the vision and strategy and which do not? Do they know how what they control directly contributes to that vision and strategy?

For the Culture: Am I proactively deciding what the key elements of my culture are going to be? Do those elements directly drive the attainment of the vision? Are there ways that I keep them front and center so that they are attended to? What elements am I determined will not exist in the culture and what is in place to inhibit those from occurring? What exists right now in the culture that either slows down or prevents the vision from happening?”¹

As leaders we are responsible for creating good boundaries within these five spaces. They have a specific purpose, as Dr. Cloud says, “Good boundaries, both those that help us manage ourselves and lead others, always produce freedom, not control.”² Read Boundaries for Leaders with us along with more great books that will help you grow your leadership skills.

Join us in an amazing journey of transformation SUBSCRIBE HERE, because we love leaders like you!  

Sarah Jackson

Vigilant Poster Girl

Every week I talk about a book that we’re reading on leadership and self-development. You can follow along by going to the Book of the Week page at the top. And order a book (either kindle, audible, or paperback) by clicking on the photo of that book. When you do that, it also helps fund this site. 


  1. Cloud, Henry. Boundaries for Leaders (pp. 40-41). HarperBusiness. Kindle Edition.
  2. Cloud, Henry. Boundaries for Leaders (p. 44). HarperBusiness. Kindle Edition.


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