Sheila Long
3 min readNov 25, 2021

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Tricky Conversations Around the Table

Photo from Canva

As we prepare to have long awaited holiday gatherings with loved ones, we may be a bit nervous about having conversations with those whose opinions differ from ours. As we strive to offer a supportive network to our loved ones, we must work towards building a network which celebrates those vested in creating structural change. To be effective, we must learn how to listen, especially to representatives of communities whose needs are not being addressed.

Photo from Canva

Progress will only happen if we have difficult but honest conversations with cultures not typically represented. By conducting effective listening sessions with all, we can truly hear those who come from communities that may not feel truly welcome. Ideally, we leave our time together giving our loved ones an open ear and the knowledge they will receive our support should they want to continue the conversation at a later date.

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As a business owner, I learned how to host and moderate honest conversations through effective listening sessions when trained for an initiative called On the Table, put on by the Greater Milwaukee Foundation. (Source: 235 “Home,” On the Table, accessed January 31, 2021) (Source: “Home,” Greater Milwaukee Foundation, accessed January 31, 2021).

Part of my learning included how to be an effective table leader, which meant I had to be well-versed in managing groups through effective listening sessions. The initiative’s goal was to bridge the divide on issues that mattered to our community.

I selected the table topic of mentorship for women business owners of different cultural backgrounds, knowing it would lead to challenging issues surfacing which attendees would have to navigate. As my business prepared to host tables, we delved into the key drivers of business ownership and prepared to train attendees on the different types of entrepreneurs: sideprenuer, necessity, flexibility, and opportunity.

During the event, the attendees discussed the reasoning behind each type of business owner. After our discussions and through effective listening, we better understood the microaggressions stemming from cultural, race, and network power inherent in many women’s situations and why many women must own their own path as a business owner. The importance of building a strong and supportive network for women to thrive in spite of gender inequality and betrayal was apparent. We left there having made inroads.

Good luck with your conversations across the table from loved ones this weekend. More resources on how Powerful Networks Pave the Way can be found in Chapter Nine of my book, Surrounded by Awesome Women: Unlocking a New Model of Women’s Success in Business and Entrepreneurship for the Next Decade by Sheila Long and published by New Degree Press.

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Sheila Long

Sheila celebrates women who own their courage and empowers them to take on a life they love.