One of the most helpful tools for coaches is the ability to ask powerful questions that draw out an individual’s best thinking. Whether you are an internal coach, external coach or a manager using coaching to support your team, combining Cloverleaf data along with powerful questions can act as an effective tool for leadership development conversations.
From CEO’s to middle managers, finding one’s leadership identity can be shaped by honest reflection. One of our favorite tools on the Cloverleaf dashboard is the Insights section.
Insights provides overarching statements that refer to the following areas: Work Style, Communication Style, Change, Conflict Triggers, Development, Leadership, Motivation, and Persuasion.
While every coach has their own signature approach, it's often best to allow the coachee to set the agenda. Even if you have been directed internally to coach someone in a specific area, these powerful coaching questions can forward leadership development in a way that begins to ignite behavior change.
These conscious behavior changes challenge the leader to grow while also serving their teams. Below are examples of powerful questions that touch on some of the insight categories and apply them to different levels of leadership.
Coaching Preparation
Consider using some of these questions while also curating some of your own. Spend 10-15 minutes prior to a coaching session or 1-1 meeting to review the coachee or team member’s insights, and design questions that may be even more targeted to the individual.
Within a coaching conversation, you might ask a question about their workstyle and listen, and then ask to “say more about that” or use other clarifying questions.
For the purpose of this list, you’ll notice we start with identification of a workstyle and follow-up with why that answer was given. In the context of a more organic coaching conversation, use the former approach to leverage active listening.
*Insights can be viewed by others, so I usually share my screen when coaching virtually.
For Executives & Senior Leaders
Workstyle
Which workstyle supports you most in leading your organization and why?
Which workstyle creates obstacles to the success of your organization and why?
Communication Style
Which communication style insight has produced the most success within your organization? Share an example of this.
Which communication style insight is one you could leverage right now to handle a current situation or challenge? Share why and how.
Change
How do your insights on your relationship to change support you in creating organizational health? How do they hinder you?
Development
Review your development insights. Share a development action you can take that would most benefit your organization right now.
What development practices could you create from these insights that would evolve your leadership to the next level?
For Middle Managers
Workstyle
Which workstyle supports your team’s success the most and why?
Which workstyle, if any, creates obstacles to your team’s success and how?
Which workstyle could you leverage more to motivate your team?
Communication Style
Give an example of how one of your communication styles was successful with a team member.
Think of all of the people on your team and consider all of your communication style insights. Which team member struggles the most with how you communicate and why?
How would you like to be communicating with your team that isn’t currently reflected in these insights?
Conflict Triggers
Review your conflict trigger insights and reflect on your current team. Which insight have you had to leverage in the past and why?
Which insight will you most need to strengthen for your team’s future success?
Development
Review your development insights. Share a development action you can take that would most benefit your team right now.
What development practices could you create from these insights that would evolve your leadership to the next level?
For New Managers
Workstyle
Now that you are a manager, which of your workstyle insights will be most effective in leading others?
Which workstyle, if any, has caused any challenges or obstacles to leading effectively and why?
Communication Style
Which insight has helped you the most to communicate effectively and why?
Give an example of how one of your insights led to a productive conversation with a team member.
Motivation
On a scale of 1-5 (1 being not present at all and 5 being very present), rate how each of your motivational insights are present in your new leadership position and share the reason for each rating using examples.
Change
Which insight could you leverage the most to support change in the future and why?