E418 | How to Get Better at Having Hard Conversations

For myself and a lot of other people, it seems like folks are getting more and more unprofessional. Not just individuals — organizations too.    People hide behind screens. They don’t want to have real conversations, and it chews up time and wastes energy.   You’ve got to find a way to get past that in today’s world.   So today we do a broad ranging Q&A on how to be assertive when you need to be — whether you’re dealing with a lazy contractor, a business that didn’t deliver, or just trying to get out of your own head.    How to frame conversations whether they’re over email or in person, so you decrease the likelihood of things escalating. How to take the governor off, say what you need to say with a clear, assertive message, and maintain your composure in the process.   What You’ll Learn:   ∙ How to say the hard thing without over-explaining, apologizing for it, or walking it back   ∙ Why most people mistake conflict avoidance for kindness — and what it's actually costing them in their relationships, career and credibility   ∙ How to deal with people who are unprofessional or hide behind screens instead of having a real conversation   ∙ How to stop overthinking   ____________________     Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

In this episode, Brett breaks down many of the themes that rarely get addressed in modern leadership conversations. He talks about power dynamics, internal and external conflict, and what it actually looks like to lead when the situation isn’t clean or clear. That includes navigating manipulative behavior, managing seemingly no-win situations, and making decisions that can carry real personal and professional ramifications. The situations faced can tempt you to soften your standards or drift into people-pleasing just to keep external stakeholders satisfied. Brett explores how to avoid that trap, how to read the room more accurately, and how to assess what’s really going on beneath the surface — not just in others, but in yourself. He also shares an update on his upcoming book with Penguin Random House, which releases December 1, and explains why he chose to focus on the morally gray, psychologically demanding side of influence and leadership. Preorders are live at artofcoaching.com/book.   What You’ll Learn:   ∙ The morally gray decisions that challenge your assumptions and beliefs   ∙ How internal conflict can be more destabilizing than external opposition   ∙ The subtle ways leaders drift into people-pleasing to satisfy stakeholders   ∙ Navigating manipulative behavior and seemingly no-win environments   ____________________     Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

Most people can name a great coach or leader. Far fewer can explain what actually makes one. In this episode, Brett breaks down what separates truly elite coaches and leaders from everyone else—and it's not what most people expect. From the role of self-awareness to the uncomfortable truth about dark triad personalities who win, Brett challenges the romanticized version of coaching and replaces it with a more honest, battle-tested one. If you work with people in any capacity—athletes, executives, teams—this episode will sharpen how you see the craft and yourself.   What You’ll Learn:   ∙ The specific traits that separate elite coaches from effective ones   ∙ Why measuring success by wins alone misses the full picture   ∙ Common arguments people make to defend toxic coaching—and why they fall short   ∙ How self-awareness directly impacts a coach's ceiling and longevity   ____________________     Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

In this episode, I break down the legitimate number one tip you need to understand if you want to present your ideas more effectively — in a way that actually connects with people. There are a lot of folks out there who’ll tell you how to be a better speaker, then hand you something obvious you probably already knew. And to be clear, I’m not here to demean that kind of advice — some of it is helpful. But this is different. From a big-picture strategic lens, this is the one thing that, if you get it wrong, puts you in a bad spot immediately. And if you get it right, it upgrades everything: your clarity, your presence, and how well people actually track with what you’re saying. For more tips, techniques, and resources to help you communicate more clearly and connect more effectively, go to artofcoaching.com/speaker.   What You’ll Learn:   ∙ The questions to ask before you present so you actually understand your audience and their real pain points   ∙ How to use this insight in team meetings, tough conversations, and everyday leadership moments   ∙ Some of my favorite strategies for getting out of your own head   ∙ A simple framework to tailor your message and make it more concise   ____________________     Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

Ever notice someone’s withdrawn, quiet, or clearly bothered—but when you ask “what’s wrong?” they shut down even more? You’re not alone. Most people approach these moments with good intentions but terrible execution, and it backfires every time.   In this episode, Brett breaks down why the classic “what’s wrong?” or “are you okay?” almost never works—and what to do instead. You’ll learn how to frame your approach so people actually feel safe opening up, rather than defensive or interrogated.   What You’ll Learn:   ∙ Why asking “what’s wrong?” triggers defensiveness and makes people clam up   ∙ The psychological principle behind why people withdraw when confronted directly   ∙ How to lead with intent so your concern lands as care, not criticism   ∙ Specific language frameworks to use with a spouse, colleague, or team member who seems off   ____________________     Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

In this episode, I give a real-time update on a few things I’ve been working on and thinking through lately — including the Non-Superficial Bullshit Conference, progress on my next book, and some hard-earned reminders for anyone building something of their own. I get a bit passionate in this one so be ready! More than anything, it’s a grounded conversation for people who are in the middle of it — business owners, leaders, parents, and anyone betting on themselves and trying not to crash and burn in the process. We touch on topics that are relatable for any coach, teacher, leader, entrepreneur and anyone else who puts skin in the game. Please send to a friend and kindly consider giving us a 5-star review in Spotify, Apple Music or wherever you get your podcasts.   ____________________     Here’s what you’ll learn in this episode:     •  The strategies I've used when I went through some really rough times over the past five years     •  The critical business questions every entrepreneur needs to ask themselves if they want to protect their blindspots     •  An overview of what my next book is about and what you can expect from it     ____________________       Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

Let’s just say it: some of you are losing time, sleep, and opportunities because you’re afraid to speak up. Not because you don’t know what you want to say — but because you’re scared of saying it wrong. So you sit on it. You rehearse the conversation 20 times in your head. You rework the email draft. You “wait for the right time.” But the truth is, you’re not waiting for the right time — you’re avoiding the discomfort of being misunderstood, disagreed with, or making things awkward. This episode is for the person who’s tired of overthinking every sentence. Tired of holding it in, sugarcoating things, or walking away thinking, I should’ve said something. We’re not going to “boost your confidence.” We’re going to dismantle the lie that if you just say it the right way, conflict will magically disappear. I’ll walk you through where this fear actually comes from, what it costs you over time, and how to build real reps in communication that actually works — even if it’s messy, uncomfortable, or imperfect.   ____________________   Here’s what you’ll learn in this episode:   •The real reason you’re scared to say the wrong thing   •What to say when someone gets frustrated so you don’t shut down or spiral   •How to stop overthinking every email, post, or tough conversation     ____________________       Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

Most people have a bunch of notes, voice memos, and half-baked thoughts scattered across their phone, laptop, or random legal pads. They tell themselves, “One day I’ll organize this…” but that day rarely comes. In this episode, I break down a skill that’s helped me think more clearly, communicate more effectively, and actually build the stuff I kept talking about. The tips in this episode will help you stress test your ideas, sharpen your thinking, and turn loose thoughts into something useful—whether that’s a resource for your staff, a framework for your clients, or just a clearer head.   ____________________   Here’s what you’ll learn in this episode:   • A simple skill that helps you unload mental clutter and finally do something with all the knowledge and experience you’ve been sitting on   • How to better document what you’ve learned and structure it in a way so the people you lead—or help—can actually benefit from what you know   • Tips that helped me write my previous best-selling book and my upcoming one   ____________________     Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

This is a short, personal episode about a few things I’m intentionally doing more of in 2025—not because they sound impressive or productive, but because they’ve genuinely made my life calmer, healthier, and more grounded.   Rather than focusing on goals or systems, I talk through a handful of changes that have come from experience, reflection, and paying attention to what actually drains me versus what gives something back.   I share why I’m continuing to make my circle smaller without becoming closed off or cynical, why I’m done feeling uncomfortable asking for support, how I’m trying to be more mindful of how my excitement lands with different people, and why I’m working on not giving away my power just because I’m comfortable with conflict or ambiguity.   This episode isn’t about cutting people off or becoming harder. It’s about becoming more honest with myself—and more intentional with my time, energy, and relationships.   My hope is that as you listen, you reflect on where you might need to make similar adjustments in your own life.   What You’ll Learn in This Episode   •How I’m continuing to make my circle smaller without becoming closed off — and the criteria I use to decide which relationships are worth maintaining   •What helped me stop feeling guilty about asking for support (especially for big projects like my book) and how to ask in a way that doesn’t feel weird or needy   •How I’m getting better at reading how my excitement lands with different people so I don’t come on too strong when I don’t mean to   •How I’m working on not giving away power through over-accommodation — giving benefit of the doubt, deferring too much, and being “too nice” longer than someone’s earned   ⸻   Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb

I get asked about books constantly—what I’m reading, what actually stuck, and what shaped the way I think about leadership, communication, and the world over the past year.   In this episode, I walk through some of my favorite books of 2025—a mix of fiction and nonfiction—and talk about why they mattered to me, not just what they were about.   Some influenced how I think about people and power. Some sharpened how I see leadership and decision-making. Some didn’t fit neatly into a category but stayed with me long after I finished them.   This isn’t a “you should read these because everyone else is” list. It’s a look at the books that genuinely helped me learn, reflect, and see things differently—and why pulling from a wide range of material (not just leadership or business books) makes you sharper overall.   You can find a full, continually updated reading list at: www.artofcoaching.com/reading-list   And if you want the complete list of books mentioned in this episode, you can get it by subscribing to our newsletter at: www.artofcoaching.com/begin   ⸻   What You’ll Learn in This Episode   •Which books actually stood out to me in 2025—and why they stuck   •How fiction has influenced the way I think about people, conflict, and leadership more than some “business” books   •Why reading outside your field makes you more interesting and more effective   •How I decide whether a book is worth my time (and when I abandon one)   ⸻   Follow Us: Website: ArtofCoaching.com Instagram: @coach_brettb X: @coach_brettb