Generous Conversations: Inspiring Hope, Collaboration and Action in Every Interaction

What sets apart a conversation with someone who helps others feel smart despite varying levels of experience and college degrees from a conversation that triggers defensiveness and feelings of inadequacy? The distinguishing factor is generosity.

I’ll be the first to admit that I have been selfish in conversations at times, especially when I feel insecure and am trying to prove my worth. Recognizing this area for growth in myself, I’ve studied generous conversationalists in my life. You know the type–those enchanting individuals who exude brilliance yet manage to make you feel inspired rather than intimidated in their presence? Being around them sparks hope and excitement about the limitless possibilities the future holds. Their fusion of intelligence with a generous spirit results in empowering conversations that instill a sense of capability to pursue one’s dreams.

Do you have a person like this in your life? If you do, cherish every moment spent with them, absorbing the subtleties of generosity in conversation and its profound impact. Chances are, you’ll notice them constantly saying things like:

  • “That’s an excellent point…”
  • “I see a connection to what you’re saying…”
  • “You might find this really interesting…”
  • “You possess a multitude of skills in this area…”

Generosity in conversations involves acknowledging that when we engage in dialogue, it transforms into a collective experience, shifting from “me” to “we.” Generous conversationalists extend invitations, even when sharing their expertise. They assume their counterparts possess a robust skill set and positive intentions, a sentiment they convey through their carefully chosen words.

At times, conversations can leave us feeling compelled to defend ourselves, a stark contrast to the spirit of generosity in dialogue. In the field of education, a common statement is, “I always make decisions based on what is best for students.” While often well-intentioned, this statement may not always be received as such. When someone claims to consistently prioritize students in decision-making, it can be construed as an implicit suggestion that others do not. This accusatory tone hinders collaborative problem-solving and hampers the potential for authentic conversation.

What if, instead, we phrased it as, “Let’s consider this topic from the student’s perspective—what might be best for them?” or perhaps, “We all benefit from a gentle reminder to prioritize students in our decision-making.” How might the conversation evolve from there? By refraining from defensiveness and the need to validate ourselves, we open the door to collaborative problem-solving.

Here are some tips to add generosity to conversations that I have learned from brilliant leaders in my life:

“Everything should be made as simple as possible, but not simpler.”

– Albert Einstein

Simplifying language enhances the chance of mutual understanding. It’s crucial to steer clear of using complex words or phrases that may sound sophisticated but lack widespread comprehension. In the field of education, we often employ acronyms, but from my experiences traveling across states, I’ve learned firsthand that they can create obstacles to effective communication. Ensure the information you convey is accessible to everyone involved in the conversation, minimizing the risk of misinterpretation and feelings of inferiority.

“The art of conversation lies in listening.”

– Malcolm Forbes

Perhaps the single most important part of being generous in conversations lies in what you hear rather than what you say. We’ve all encountered discussions where our words seemed negligible, as the other party was simply awaiting their chance to speak instead of genuinely listening. As deep listeners, we strive to understand, taking a moment after listening to reflect before responding, often posing thoughtful questions rather than making declarative statements. True generosity in conversations arises when we assist others in feeling comprehended and valued for their viewpoint.

“Give others the benefit of the doubt; assume positive intent until proven otherwise. It’s a powerful foundation for understanding and building trust in relationships.”

– Unknown

Embracing a mindset of positive intent opens the door to assuming knowledge and skill. Saying things like, “That is a terrific point,” exemplifies this dual acknowledgment of positive intent and expertise. When faced with challenging conversations, even if discomfort arises, we can welcome the exchange with the anticipation of reaching a shared understanding. This involves positively recognizing inquiries, responding with statements like, “That’s a fair question…”. In authentically generous conversations, all participants stand on an equitable playing field, each valued and included for their unique contributions and perspectives.

While writing this blog post and delving into the topic of generosity in conversations, I had the opportunity to engage in coaching discussions with new teachers and their mentors. During these sessions, I asked a colleague to give me feedback on my generosity level, with a specific focus on the types of questions I posed. I aimed to ensure that my questions assumed positive intent and showcased active listening. I also asked her to identify any spots where the conversation seemed to be stifled by my responses. Here are additional reflection questions for us to ponder as we strive to be generous conversationalists.

  • Where did I ask questions that opened doors to mutual understanding and problem-solving? Where did I ask questions or make statements that created barriers?
  • When did it appear that I was listening to reply instead of listening to comprehend?
  • What language did I use that was subject to interpretation or caused confusion?
  • Why did the participants feel included and valued? How did I show them?

You’ll notice that in this post I did not suggest any overly simple tips, such as avoiding the use of the word “I”. Engaging in generous conversations allows for the authentic sharing of perspectives and expertise, even if it involves using words like “me” and “I.” The essence of generosity in conversations hinges on an individual’s overarching intentions. If the goal is to assert personal value and worth, the spirit of generosity will be compromised. Conversely, when the intention is to embrace the diverse knowledge, skillsets, and perspectives of all participants, conversations become truly generous. Such conversations inspire and instill a sense of capability, fostering an environment where everyone feels motivated to achieve great things. In the current landscape of education, where inspiration, hope, and action are paramount, infusing our conversations with a generous spirit is not just beneficial but imperative.


Living life with a “Serendipity Mindset” does not mean pretending that everything is a happy accident. It means knowing that everything we go through, from our highest of highs to our lowest of lows, offers us beautiful gifts–IF we look for them. You can check out the #SerendipityEDU books out on Amazon by clicking HERE. Each book is filled with inspiration to help us discover the gifts in along life’s journey. My newest books, #LeadingTheWholeTeacher  and #LeadwithCollaboration are available now!!! Contact me at allysonapsey@gmail.com if you’d like to bring me to your school, district or event.

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