How to Master Difficult Conversations with Bill Benjamin

December 03, 2025 00:14:38
How to Master Difficult Conversations with Bill Benjamin
Simple Wins
How to Master Difficult Conversations with Bill Benjamin

Dec 03 2025 | 00:14:38

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Show Notes

Are you a business owner struggling to have difficult conversations with your team, contractors, or clients? In this episode of Simple Wins, Bill Benjamin reveals a simple yet powerful framework to help you navigate these critical "last 8%" moments without avoiding them or making a mess. We dive deep into why mastering these interactions is essential for building a strong performance culture in your business.

We discuss:

Bill Benjamin, a partner at the Institute for Health and Human Potential, has worked with organizations like NASA, Amazon, and the US Marines on performance, culture, and leadership. His expertise gives you an actionable simple win you can implement today.

Make sure to go visit Bill at ihhp.com

If you enjoyed this episode, please consider leaving a 5-star rating.

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Episode Transcript

Adam O'Leary (00:01.044) If you're business owner struggling to have difficult conversations with your team or clients, then our guest, Bill Benjamin, is about to give you a simple win you can implement today. Bill is a partner at the Institute for Health and Human Potential, a global leader in delivering the last 8 % culture system. Bill has worked with the US Marines, NASA, Intel, Amazon, the Myoclip, and yes, even surgeons who call on him for his expertise in performance, culture, and leadership. Bill knows firsthand the importance of having to perform under pressure. He is a recovering mathematics major. He is a former sales and marketing executive in the IT industry and he has received direct feedback from his two teenage daughters that being smart is not enough to succeed at work or home. Bill, so excited to have you here. Looking forward to this. Bill (00:55.07) Awesome, great to be here. Thanks for having me. Adam O'Leary (00:57.204) Absolutely. So I've heard you discuss how many people either avoid difficult conversations or just handle them poorly leading to long-term regret. So why is it so crucial for business owners to master the skill of navigating these last 8 % moments effectively? Bill (01:13.346) Yeah, and let me just for your listeners who don't know what the last 8 % is, we came up with that concept about seven or eight years ago, we were coaching two executives at a large company and they weren't getting along like that ever happens. And they were coached to have a conversation with each other about the impact they were having on each other. So they go and they have the conversation, they come back from the conversation, their coaches individually ask them how did it go? And they both say, it went fine. Well, the coaches know better. So the coaches pushed it a little bit and said, yeah, but did you say everything we said you were going to say? And both of them essentially said, I got 85, 90, 95 % of the way there. And the other guy started reacting and I held back. I was impacted by that emotional response and I held back. I didn't really step in and say that last five or 10%. So we took that concept that most people have experienced and we did a study of 34,000 people and determined that on average, It's 7.56%, which we rounded up to 8%, that people feel they leave unsaid in a difficult conversation. So that's where the genesis of this concept of the last 8 % came from. Now the reason these conversations are so important, so now I'm actually going answer your question, is because of the cortisol effect. The cortisol effect is that when there's tension, when there's pressure, uncertainty, and conflict, cortisol gets released into our brains, which has a number of things, but one of the things it does is it causes memories to sear in. So people remember what you were doing and saying and how they impacted you in a difficult conversation in that last 8 % moment. They don't remember what you're doing in the 92 % of moments where everything was going well and everyone's getting along and the deadlines were being met. Those last 8 % moments are more memorable and they establish your reputation. They establish the culture of a team and they actually establish a personal relationship too. Adam O'Leary (03:03.531) So this 8 % is primarily focused on the difficult moments. That's correct, right? Bill (03:08.91) Yes, and in fact, we're going to talk mostly about conversations today, but as we workshopped it, people said, it isn't just about conversations. There's the difficult decisions I face. There's the easy ones where everyone's agreeing or I'm not taking a risk. But then there's those tough ones. And for many of your listeners or business owners, am I going to make this investment? Am I going to hire this person? Am I going to fire this person? Those decisions, those are tough ones. Again, it's the 92 % that are easy where everyone's going to be happy and you know it's going to work out. But those high risk ones. They also have an outsized influence. So yes, the last 8 % represents really any situation in which there's tension and pressure. Conversations for many people is one of the most relevant example of last 8 % situation. Adam O'Leary (03:50.388) And I like how you were talking about the fact that that's what people remember is the 8 % moments. And I think that's really fascinating because it's true, right? Like everything's going okay. You don't necessarily remember everything that went on your day. But if somebody's furious at you, you're going to remember that for weeks. Absolutely. Bill (03:58.86) Yes. Bill (04:08.269) Or if somebody avoided and didn't step in and support you or isn't giving feedback to a peer who's underperforming. So it's also the avoidance. And in our research, 68 % of people faced with a last 8 % conversation, they avoid. They either avoid the conversation altogether or they don't really say that last 10 % the part that really needs to be said. That's 68 % of people. There are 32%, and I fall into this category sometimes, I'm in that difficult conversation. The other person starts getting defensive. Instead of avoiding, I step in, but I come on too strong, and now I'm making a mess of it. So we talk about people either being avoiders or making messers. Adam O'Leary (04:49.045) So how do we get people to not avoid a situation then? Bill (04:52.717) Yeah, I mean, it starts number one with understanding the importance and recognizing when you're avoiding. And we all feel that anxiety and that discomfort. And it's really about recognizing the need to push through that anxiety and discomfort. Because by doing that, you're trading that off for long-term regret. Because we all know when we're not having the conversation we should have, we all know we didn't really say what we should have. In fact, we talk about the last 8 % really being the gap. between the risk we know we should take and the risk we are taking. So number one, it's recognizing the importance of pushing through that discomfort and stepping in, but stepping in skillfully so you don't make a mess, that middle ground. So number one is that recognition. Number two is being aware of what is it that causes us to avoid a difficult conversation or the last 8%. And it all comes down to emotion and fear. And here's how I know this, Adam. If I told you a difficult conversation you have to have, I could guarantee you that it was gonna go well, that the other person was gonna thank you and take your feedback. Would you avoid it? No, you'd be like, okay, I can do this. So it's the fear and the uncertainty that it might not go well, they might get upset, it might have a negative consequence. So it's all about managing the emotions and fear that cause us to avoid. Adam O'Leary (06:16.151) Absolutely, and as a business owner, if we need to go into a tough, difficult conversation, whether it be with a contractor or an employee, how can a business owner be able to prepare themselves mentally for that conversation? Bill (06:28.621) Yeah. By the way, it could also be saying no to a client. That's something that a lot of business owners, I mean, when you need every penny of revenue you can get, to actually say no to a client, not like completely no, but no to something they're asking for, or no to a way they want to do things, or no to a discount they're asking for. So that's the last 8 % moment too, but certainly managing performance of employees, dealing with contractors. It's number one, learning to manage emotions. Because no matter how skillful your words are, if you step into one of those conversations and you're tense, you're anxious, we all have mirror neurons, emotions are infectious. The other person's gonna sense those emotions and they're gonna get triggered and so your words aren't gonna be as effective. So number one, you need to learn to manage emotions. Number two, there are some very specific skills, approaches you can use to increase the likelihood that the other person won't get triggered emotionally, that the other person will be able to hear what you have to say. So it's that combination of managing emotions and then learning some skills to be more effective at different conversations. Adam O'Leary (07:38.999) So let's talk about one of those. I've heard you mention the SOS method before. Do you mind kind of going into that? Bill (07:44.399) Yeah, and by the way, this works in any situation where you're feeling under pressure. If you're about to give a big presentation or whatever the situation is, or you're just nervous watching your teenager in a sport, you can use this in any situation, but certainly heading into a different conversation. We originally developed the SOS strategy over 25 years ago with the US Navy. By the way, the Navy has a great quote, which I love, which is, Ships are safe in the harbor, but that's not what ships are for. So this is all about getting outside of our comfort zone. This is all about doing hard things because that will make us better. So we developed it with the US Navy and we intentionally use the SOS metaphor because it's kind of like we're sinking underwater and we need something to get us above water. So the first S is stop. That's disconnect from the trigger, not as an avoidance strategy, but as a way to manage ourselves so we can step in more skillfully. And there's a couple different things you can do. When you are alone, stand up, stretch, go for a walk, do something that gives you some calm. Because you're kind of triggered emotionally and you're overthinking things. We stay up at night thinking about these things. We kind of overthink. So you want to calm yourself down. The draft folder was designed for emotional intelligence. Write the email you want to write. Don't put it in the to list just in case. Put it in the draft folder. Go for a walk, come back. I've done this many times. Never once have I looked at that email that I wrote in a triggered state and thought, yeah, that's the email I should send. That's me at my best. So some way to disconnect from the trigger. Now, if you are already in the conversation, either virtually or in person, what can you do then if you're feeling a bit triggered? Well, did you know you can't cry and drink water at the same time? Maybe not so useful in business. Pretty useful though if you have young kids or nieces and nephews or grandkids. If you can get the four-year-old who's crying to drink water, it'll actually stop the crying. It's actually a great strategy and it really works right up until they figure out that that's your strategy. No daddy, I won't drink water. But it demonstrates the soothing effect that water has on our physiology. So you can stop in any meeting and stop and take a drink of water. I just did for the listeners who can't see me. And a couple other things, your fingers will start to curl. Bill (10:09.077) Even if you're just a little triggered, now you're fully triggered, you're make a fist, but you can open your palms. If you're sitting, you can rest them on your lap. If you are feeling like you're in a void, you're gonna avoid, you're gonna be leaning back and making yourself smaller. Lean forward and open yourself up. In the reverse, if you're in make a mess mode, you're gonna be doing the opposite, you're gonna be leaning forward, just lean back. That little pattern interrupt helps create that space between your emotional system and your cognitive system. Writing something down in the middle of a meeting, you know that requires cognitive thought that can give you a break So there's a lot of little things we can do to stop To disconnect from the trigger now six seconds is the amount of time between when your brain processes the stimulus your emotional brain Which gets triggered and the neocortex catches up your cognitive brain Most of us are doing things where it's okay to pause for six seconds whether you pause for six seconds, six minutes, six hours, or six days, you want to oxygenate. So that's the O. So the first S is stop, the O in SOS is oxygenate. The intake of a large amount of oxygen has the physiological effect of minimizing the chemicals that your emotional system is released. So it starts to dissipate that cortisol, the adrenaline starts to calm you down. So I want all your listeners, let your breath out, take a deep conscious breath. If you do nothing else, but the next time you're either in a difficult conversation or you're about to have one, stop and take that deep breath, you'll be amazed at how much of your better self you'll get back. Now, notice at this point, we haven't done any cognitive thinking. We've drank water, we opened our palms, we've leaned back, we've taken a deep breath. Now you have a little bit of kind of your thinking, your working memory back. So the final S is seek information. And we start by seeking information of ourselves. So often, we're amplifying the negative. We're taking a little bit of, oh, they said something, they're attacking me, they're criticizing me. We assume the worst. So you want to check your thinking. We call it a wind or tiger. Because if you're in the jungle and you know there's a tiger that could scratch you, and you hear wind rustling in the bushes, what do you assume the wind is? We have to assume it's a tiger. Well, there's two tigers. The real one and the one you imagine. So you want to check. I mean, am I reacting to wind? Bill (12:35.757) And so often we are. So we can sort of check our thinking, seek information. We can ask ourselves, what would my best self, what would I be, what would I do in this case if I was my best self? Well, I wouldn't send that email and type reply to all and add three people. I'd stop, I'd reach out, know, connect with the person virtually or, you know, I would do something different. So, and then finally in the seek information, we can start thinking about what's going on for the other person, some empathy, some curiosity. What might be the things that are concerning for them? Why might they be acting the way they're acting? How could I say this in a way that's, you know, more sensitive to their needs so we can start thinking about other people? So that's the SOS strategy. Stop, oxygenate, seek information. Adam O'Leary (13:19.934) Absolutely, and what sort of results have you seen from people who have implemented this process? Bill (13:25.837) Well, can speak for myself. get way less triggered. I can be a bit of a make-a-messer and sometimes I'll interrupt people. You asked me in a calm moment, should I interrupt people? Is that a good leadership style? Is that a good way to motivate and inspire people? Is that a good way to get along with my teenage daughters? Of course not. But get me a little triggered, get me feeling like I'm right, get me feeling like, I start interrupting. Taking my deep breath has allowed me to... be way better at listening. I still interrupt sometimes when people who know me have really noticed a difference. I also talk to a lot of people who are more avoiders and that deep breath has kind of just given them a little bit of confidence, a little bit of courage to say, okay, I need to step in and have this conversation or I need to give this person this feedback or hold this person accountable or say no, take my deep breath, step in, I know this is the right thing to do. So yes, we get lots of great feedback from people on how effective the SOS is at helping them overcome either their avoidance or their make-a-mess behaviors. Adam O'Leary (14:34.686) I love that. And where can people go to learn more about you? Bill (14:38.222) They can go to LinkedIn, Bill Benjamin on LinkedIn, or they can go to my company's website, IHHP.com, Institute for Health and Human Potential. Adam O'Leary (14:48.424) Amazing. Well, Bill, thank you, thank you, thank you so much for your time. This was super informative. mean, I literally felt myself leaning back and drinking water on this. Bill (14:56.013) It'll make a big difference. Thanks Adam and I wish all the best to your listeners. Adam O'Leary (15:00.777) Absolutely, well thank you guys for listening and I will see you on the next episode of Simple Wins.

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