Engagement Coaching Questions 

Coaching, Engagement, Insights

Jessica Delaney

We do a lot of training and a lot of the questions we get towards the end of the training are around getting internal buy-in, making the case for engagement and helping to influence internal culture so there’s more focus on meaningful and authentic engagement.  

This is why Jessica and Kristi both became coaches in 2025. It was this recognition that culture sets the tone for engagement and building staff capacity is only one side of the internal engagement relationship. Leaders, decision makers and boards play a huge role in setting the tone and expectations for engagement.  

While there are no easy answers when it comes to culture, here are five powerful questions that we often ask. 

  1. If you could look back in three to five years and be really proud of the engagement work the organization has done, what would you want to see?  
  1. When you think about engagement and service, how do these intersect for you?  
  1. What motivates you to engage with the people in your organization? What energizes you and what depletes you?  
  1. What’s something you learned from a past engagement and collaborative process? How did it influence your leadership style since that time?  
  1. When you think about an organization you admire, what is it about them you admire most?  

These questions might not give you an exact blueprint for thinking about engagement, but they will help to elicit leadership’s values and gain a better understanding of how it views engagement. Meaningful and authentic engagement requires that organizations and groups share influence with those who are impacted by the decision, action or change and most of the time that comes down to leadership.  

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