Today’s post is all about pushing your boundaries—through something as simple as a conversation that makes you uncomfortable. Sounds intriguing, right? Well, it’s time to dive in!
Whether you’re leading a team, managing your business, or just navigating the complexities of life, you’re bound to face uncomfortable conversations. But what if I told you that there’s a way to practice handling these tough conversations—with something as simple as your next coffee order?
Yes, you heard that right. So, grab your coffee, sit back, and let’s talk about how to build confidence in uncomfortable conversations… starting with coffee.
The Coffee Challenge
Next time you’re at your favourite café—yes, the one where the barista already knows your order—try this: ask for a discount on your coffee.
Now, I know what you’re thinking, ‘Why on earth would I ask for a discount at a coffee shop? Isn’t that awkward?’ Well, yes! That’s exactly the point. This exercise is designed to take you out of your comfort zone and get you used to managing discomfort. It’s a small step, but the ripple effects can be huge for leaders like you.
The worst thing that could happen? The barista gives you a puzzled look, and you walk out with your coffee at full price. Not so bad, right? But the best thing that could happen? You could score a discount—or even a free coffee. It’s happened to me before!
The goal here isn’t about saving money on your cappuccino, though that’s always nice—it’s about practicing how to have conversations that feel a little awkward. Because as leaders, we know that uncomfortable conversations are often the ones that matter most. And the more we practice navigating them, the better we get at handling tough discussions in the boardroom or with our teams.”
📖 Recommended read: Why coffee should be important in your relationship?
Levelling Up: Negotiating with Service Providers
If you’re feeling brave after your coffee challenge, it’s time to step up your game on embracing uncomfortable conversations. The next exercise is one that can actually save you real money.
Try calling up one of your service providers—maybe your mobile phone company, your internet service provider, or your cable company—and ask for a discount. The same rules apply: the worst thing that could happen is they say no. But you might be surprised—negotiating can often result in a lower bill, especially if you’ve been a loyal customer.
Here’s a simple framework to guide you through this conversation:
- Introduce Yourself as a Loyal Customer: Start by identifying yourself as a long-term, regular customer. Mention how long you’ve been with them—give the number in months to make it sound more impressive.
- Present Your ‘Why’: Explain that times are tough, and you’ve noticed other competitors offering more attractive deals. You don’t have to make this up—do some quick research, and find a competing offer that genuinely appeals to you.
- Ask for the Discount: Finish with something simple but effective, like: “I’m hoping you could do something special for a loyal customer like me—can’t you?” Ending with a question gives them the chance to step up and make an offer.
The goal here isn’t just to save a few bucks—it’s about refining your negotiation skills. Whether you’re negotiating contracts, discussing team performance, or trying to persuade others in a leadership setting, these small practice runs help you build confidence for more significant conversations down the line. Uncomfortable conversations become more natural and, well, more comfortable 🙂
📖 Recommended read: Never Split the Difference: Negotiating As If Your Life Depended On It
Why Leaders Must Embrace Discomfort
Now, you might be wondering, “Why should I, as a leader, practice uncomfortable conversations?” The answer is simple: leadership requires us to be comfortable with discomfort. Whether you’re negotiating a deal, discussing performance issues with a team member, or simply making a difficult decision, it’s all about mastering the art of navigating tough conversations with ease.
Think about it—when was the last time you had a conversation that made you nervous? Maybe it was asking for a raise or giving constructive feedback to a colleague. These moments are part of what it means to lead. The more we embrace them, the stronger we become as leaders.
And if you’re sitting there listening, with a cup of coffee in hand, thinking, “Well, I don’t know if I could ever ask for a discount at my local café…”, that’s exactly why you should try it. It’s a small exercise that can create big shifts in your confidence.
So next time you find yourself in line at the coffee shop, take a deep breath, smile, and ask for that discount. You might just surprise yourself.
Lessons learned from this coffee journey
At the end of the day, mastering uncomfortable conversations is about more than just coffee discounts and negotiating bills. It’s about being able to lead with confidence, even when the situation feels uncomfortable or uncertain. And like any skill, the more you practice, the better you get.
So, what’s your next move as a leader? Will you take on the coffee challenge? Will you make that call to your service provider? These small steps could be the key to mastering the bigger conversations in your leadership journey.
Useful links
- The Art of Digital Detox: Reclaiming Your Mind in a Hyperconnected World
- Why coffee should be important in your relationship?
- A short mental exercise that will help you how to think big
- How to Handle Difficult Conversations at Work
Thanks for reading!
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