Mastering Difficult Conversations: Expert Tips from Madeline Schwarz

Hi there. My name is Avil Beckford, and I'm the host of The One Problem podcast. There are tons of problems in the world, but we're tackling them one problem at a time. Why should we get overwhelmed? As has been the case with most of the guests on this podcast, I have some prior relationship with them. That's the case with this week's guest, Madeline Schwarz. I met her in 2019 when I went to a conference in New York City. She was speaking at the Ellevate Network event for the chapter leaders. At the time, I was co-president of the Toronto chapter. Over to you, Madeline.

Madeline Schwarz

Thank you. The problem that I want to talk about today is how to have a difficult conversation with someone on your team. Because I see so many people get tripped up when they are putting off or avoiding difficult conversations, when they are going into those conversations bracing for the worst, or when they are so wrapped up in their head that they forget to listen. And none of those things lead to having productive conversations and solving the problem.

So what I'm going to share with you today is five skills to help you prepare and show up for difficult conversations, feeling calm and clear. Skill number one is to be prepared. Plan out what you want to say in advance and practice that out loud. When I am working with leaders and managers in corporate and they are preparing to deliver their performance reviews, often the feedback can come out sounding like, “This is your final warning, and it's time to shape up.” When what they really want the message to be is, “I'd like to promote you, and these are the three things that need to change in order to make that happen.”

And taking the time to plan out that strategy ahead of time makes such a huge difference in easing anxiety, making the conversation more comfortable for both parties, and being really clear so that your feedback is kind and motivating.

The One Problem with Madeline Schwarz

Madeline Schwarz

Skill number two is to be direct. Delivering bad news doesn't land any easier by taking longer to get to the point. When you are having a difficult conversation, you want to be specific. You want to be straightforward, and you want to be succinct. And to give you an example. I was working with a client who's the beverage director of a big restaurant group. And she was having a really hard time saying no to vendor meetings. And what she realized was that by stringing people along, she wasn't doing anyone any favors. It wasn't a good use of her time. But it also wasn't a good use of the vendor's time.

And by just being upfront with the person, she realized it was the best way to preserve the relationships.

Have you read or watched?

1. Boost Your Productivity with Professor Margo Berman’s 5-Step Process
2. Overcoming the Gender Confidence Gap with Sheena Yap Chan
3. LaRae Quy, Author of Secrets of a Strong Mind
4. Laura Flessner, Innovation & Leadership Coach
5. Jennifer Regular, The Soul Illuminator
6. Judith Sherven, Executive Coaching for the Brightest and Best
7. Jackie Lyles, C Level Growth Strategies to Maximize Sales
8. Jackie Maclean, Energy Innovator and Clinical Hypnotherapist
9. Leslie Nydick, The Conflict Strategist, How to Lead Inclusive Conversations
10. Holly Jackson, TEDx Speaker, Holistic Leader
11. Kes Morton, President and CEO, Pisces Research Project Management
12. Kerry Wekelo, COO of Actualized Consulting
13. Dr Pauline Crawford, The Conversation Game Changer
14. Syya Yasotornrat, Podcast Strategist and Producer
15. Becky Wolfe, Works with Burned Out Teams
16. Dena Lefkowitz, Business and Career Coach for Lawyers
17. Lisa Rangel, Executive Resume Writer

Skill number three is to be curious. And there's a great Harvard Business Review article about the business case for curiosity and why it's so important for companies. And it really is this amazing skill because when you are preparing for difficult conversations, it can get you out of anxiety and into wonder. Curiosity helps you see different perspectives. It helps you respond less defensively, and it helps you ask better questions.

And when you ask better questions, you get better answers. And that allows you to come to these difficult conversations from a place of collaboration and be able to solve problems more creatively.

Madeline Schwarz

Skill number four is to be attentive. Once you get in that curious place and you ask curious questions, you want to actually pay attention and listen. I had this freelance job several years back where every time I had a one-on-one meeting with my boss, it involved me standing behind his desk and watching him file his email while we talked.

And granted, there were major space constraints. There wasn't an available conference room for us to meet in. But I never felt like I was being listened to. And thus it made it really hard for us to make this time productive. So remember, if you are planning your counter argument, if you are running through your to-do list or filing your emails, you are not really listening.

When I work with clients, I teach them a concept called listening with all of your senses to help them tune into all the cues and really listen on a deeper level.

Madeline Schwarz

And skill number five is to be empathetic. This is probably the most important skill in difficult conversations and also the most challenging for many people because we are so trained to listen for where we disagree and where we can justify our own position.

And being empathetic requires a tremendous amount of self-control, because what we need to do instead is to listen to other people and allow them to have their own thoughts about a situation and their own feelings. We don't need to change those. We just need to allow them to have it and acknowledge their position. When you get good at using empathy as a strategic tool, it takes all the wind out of the sails, so it can really deescalate high-pressure situations.

So those are the five skills. Be prepared, be direct, be curious, be attentive, and be empathetic. And if you want more help to implement these tools and learn how to use empathy and listening and curiosity, and be more prepared, grab my free resource for skills to master tricky conversations. You can find it on my website, www.madelineschwarzcoaching.com/4skills. Back to you, Avil.

Avil Beckford

Thank you so much. I like that five-step process and it's so easy to remember.

Next Steps

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