Beyond Surface: Coaching Through Discomfort to Real Breakthroughs
Send us a text The moment you hesitate is often the moment that could change a client’s life. We dig into why coaches avoid hard questions—fear of making someone uncomfortable, worry about being intrusive—and how that hesitation keeps conversations on the surface. Then we model a different path: asking brave, compassionate questions that help clients face what actually moves the needle. We walk through a concrete example from relationships where most helpers jump into advice. Instead, we use...
The moment you hesitate is often the moment that could change a client’s life. We dig into why coaches avoid hard questions—fear of making someone uncomfortable, worry about being intrusive—and how that hesitation keeps conversations on the surface. Then we model a different path: asking brave, compassionate questions that help clients face what actually moves the needle.
We walk through a concrete example from relationships where most helpers jump into advice. Instead, we use ownership questions like “What part did you play?” and “What could you have done differently within your control?” That shift moves clients from venting to agency. You’ll hear how focusing on controllables—the way we think, speak, and act—turns stuck stories into forward motion without blame or shame. We also talk about timing: sensing the right moment, asking for permission when emotions rise, and holding space with steady silence so insights can land.
Across the conversation, we return to three anchors: brave questions reveal what matters most, surface questions keep change shallow, and discomfort is the price of a meaningful life. When coaches dare to “go there,” clients become braver too, and the standout breakthroughs at session’s end trace back to one clear, clean question asked at the right time. We close by linking this practice to our earlier deep dive on the power of silence and tee up what’s next: the essential step to take even before asking brave questions—removing yourself from the equation.
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00:00 - Why Coaches Avoid Hard Questions
00:40 - Why Brave Questions Create Breakthroughs
01:09 - Three Principles for Deeper Coaching
01:13 - The Quote: Brave Questions, Brave Clients
01:13 - Example: Relationship Ownership Questions
02:12 - When to Ask: Intuition and Permission
03:04 - Encouragement to Go There
03:40 - Recap and Tease for Episode Seven
0:00 Once coaches start practicing, we notice that sometimes they avoid asking the harder questions. Why is that? Because they're afraid of making their client feel uncomfortable. This includes even sometimes making yourself feel uncomfortable. What would they think about me if I asked that question? Is that too intrusive? Is that the wrong question to ask right now? But we've seen it time and time again is that when we show people how to ask those braver questions, it actually creates the real breakthroughs that your client has been looking for. Because most people are willing to ask those questions. As a coach, we are willing to ask those questions. So I want you to remember a couple things when you come upon this.
0:40 Remember that brave questions actually help your client explore what is most important and meaningful to them. Number two, is most surface level questions keep things on the surface, which means they won't have a deep emotional impact for your client. And number three, remember what we always say discomfort is the price for a meaningful life. So not only your discomfort, but sometimes your clients being willing to have that conversation can be the thing that will change their life forever. And that's why today's quote is brave questions create brave clients. What's an example of a brave question? That's such a great question. So when I think about relationships, I find that sometimes those are the deepest questions that I can ask.
1:23 And one of the things that I constantly bring up is the ownership piece, like taking control of the things you can control. So if somebody has a conversation with me or they're like, this is what I said to my kids, and this is how they responded and reacted, I'll ask them, what part did you play in that situation? Thinking about the things that you can control, what could you have done differently? And see, most of the time people would have like jumped in the pool and been like, oh, well, they shouldn't treat you like that, or just jump in giving it advice. But what I have found is as being a coach, helping them identify what they can control and taking ownership of it, I always ask them those questions. And you will see a total shift because they will start taking control of the things they can control, which is the way they think, the way they talk, and the way that they act.
2:06 They can't control those from the outside. And I make sure that they're aware of that. So they're spending their time and energy how best they can. How do you know when it's time to ask that question? Intuition. I'm gonna say like when you have a conversation, even with your friend, you're probably feeling it. It's probably something that's like, ah, should I go down that path? Should I ask this question? Now, the truth is, is we teach coaches how to ask it in a way that's kind of compassionate and it's not beating them up or shaming or guilting. So there is a process behind that. But at the same time, it's just being willing to go down that path. Now, the truth be told is like sometimes when I'm actually going down a path, I actually ask for permission when I'm coaching because I notice that some things create an emotional experience for someone. And I want them to know that I'm all in.
2:48 I'm all in with going down that path if they're willing to go down it with me. And so sometimes I will ask them for permission. Sometimes I'll ask it and see where we go. And there is some finesse around how we teach this, but it's really being willing to meet people where they are. What do you tell coaches that are afraid to go there? Oh, this is the greatest opportunity that you have. Most people aren't willing to go there and ask those questions. But that's why most people stay service level and don't help create the transformations their clients can really have. And so being willing to do that, not only does it make you brave, but it makes your clients brave too. And you'll be amazed that when you ask those questions, when you get to the end of a session, it will be the question that actually created the breakthrough for your client.
3:31 And then you can remind yourself of the next time. The next time that hard thing comes up, you're willing to talk about it because it's going to make an impact, not only in their lives, but in your lives too. Now, if you missed episode number five, go back and check that out. We talked about the power of silence, because that is also an uncomfortable situation, but it's actually your greatest opportunity. Today, we talked about how to ask those brave questions. The ones that you know that you need to ask, but you're a little uncomfortable with asking. But there's something very important that you need to do even before you start asking those brave questions. And that's what we're going to lean into in episode number seven. Because it's time to take yourself out of the equation.
