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How to Have Hard Conversations: Tips For Getting Started

Think of the last difficult conversation you were part of, and try not to shudder. It's a naturally dreadful topic, as difficult conversations are typically associated with personal failings (if you're being approached) or the instigation of conflict (if you must approach someone). The last few weeks of the Inner MBA have been all about how to have better, more productive hard conversations.

Examples of hard conversations 

It might help to start by thinking through the realm of possible hard conversation topics in your life. For me, they often look like:

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  • At work:

    • Performance convos

    • Compensation & promotion questions

    • Addressing burnout or overwhelm

  • At home:

    • Shared use of space

    • Cleanliness preferences

    • Perception of inequality

  • In my relationships:

    • Feeling neglected or rejected

    • Seeking distance

    • Strong difference of opinions

Start with the right mindset 

As always with the Inner MBA, there are a few important words to define & understand before diving into a topic. I was moved by the following definitions of two words I use frequently and without much thought:

  • Wisdom: A sense of knowing what the right thing to do is

  • Compassion: The intention to be of benefit to others

Being mindful of the etymology of the words - or the way in which their meanings change over time - is just another aspect of care we can bring to how we think and communicate. In this case, understanding these definitions can help you approach a difficult conversation with the right mindset. More musings from my Inner MBA coursework here. a

Understand what’s getting in your way 

Having the right mindset will help, but if it were that easy, aspiring leaders wouldn't need a whole educational module on the topic. Let's explore the three major states that tend to get in the way of conversations that are both hard but productive:

  • Empathy. When you lead with too much empathy, you run the risk of letting your emotional identification with someone prevent you from doing what you know is the right thing for your relationship, organization, etc.

  • Busyness. If you're too busy to be aware of opportunities for hard conversations, let alone sit down to deliver or receive one, you are unlikely to experience necessary growth in yourself, relationships or organization. You'll operate in a space of ineffectiveness or indifference. This can manifest as lacking curiosity in the listening process, whether in conversations with your romantic partner or employees at work - what is busyness preventing you from asking and ultimately hearing about the state of your shared reality?

  • Ego. Your ego might tell you to put results or your self-image before the wellbeing of the people around you. At work, that could look like asking your team to work late to meet a deadline. At home, it could look like a sour attitude toward your partner when they don't clean the kitchen how you like. Ego identification can represent a troubling absence of humility, meaning you've come to think too highly of yourself. If you want to effectively relate to others, remaining humble is critical.

Be the hero of your own story 

I was reminded in my studies that the lead character in any story is often the one asked to do hard things. The most celebrated of these characters usually rise to the occasion with a mix of integrity and grace. To be the hero in your own story, consider what hard things you might be avoiding talking about with the people around you and whether empathy, busyness or ego might be getting in the way. Where a difficult conversation is needed, approach it with a mix of wisdom & compassion: do what you know is the right thing with an intention to be of benefit to the other person.

I'm already excited to read your next chapter. 

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Up Next: What I Learned From "The Science of Happiness," Part 1