--- title: "297 - Ask Before You Answer: The Client-Trust Habit with Scott Armstrong" description: Scott Armstrong explains how asking better questions, listening to learn, and reducing self-orientation help professionals earn lasting client trust. image: https://pod.allies4me.com/hubfs/Podcast/Episodes/Scott-Armstrong-LnL-R4.jpg --- [![Allies4me](https://pod.allies4me.com/hubfs/raw_assets/public/Allies4me_May2022/images/logo.svg "Allies4me")](https://allies4me.com/) Menu - [Home](https://allies4me.com/) - [Grow](https://allies4me.com/grow/) - [Financial Advisors](https://allies4me.com/grow/financial-advisors/) - [Foundations Courses](https://hub.allies4me.com/courses/course-signup/) - [Podcast](https://allies4me.com/podcast/) - [Have Craig Speak at Your Event](https://hub.allies4me.com/lp/speak/) - [Be a Guest](https://pod.allies4me.com/podcast-guest/) - [Get Started](https://allies4me.com/get-started/) - [Have Craig Speak at Your Event](https://hub.allies4me.com/lp/speak/) - [Community](https://allies4me.com/about/community/) - [Downloads](https://allies4me.com/downloads/) ## 297 - Ask Before You Answer: The Client-Trust Habit with Scott Armstrong October 29, 2026 by [Craig Andrews](https://pod.allies4me.com/podcast/author/craig-andrews) Scott Armstrong grew Brainrider to $22 million without making a profit, then rebuilt it as a $4.6 million agency with a 13% margin. That painful contrast challenged a common assumption about growth: adding revenue and smart people does not necessarily produce a stronger business. Scott found that client relationships depend less on continually demonstrating intelligence than on becoming someone clients trust. School and early careers train professionals to have the right answer, but that instinct can work against them in client conversations. Expertise becomes a liability when it causes someone to answer before understanding the real problem. Scott argues that better thinking begins with asking another question, listening to learn rather than listening to reload, and remaining curious about the practical, emotional, and career concerns beneath a client’s words. Those habits become especially important when a client rejects the work, challenges the budget, or threatens to walk away. Instead of reacting defensively, professionals can slow down, acknowledge that their understanding may be incomplete, and frame the problem collaboratively. Scott even suggests reviewing client calls and counting the follow-up questions: answering after fewer than two questions may mean the client’s concern is not yet fully understood. Trust, in Scott’s model, is shaped not only by credibility and reliability but also by self-orientation—how much the conversation revolves around the professional’s knowledge, process, or need to appear smart. One deceptively difficult way to reduce that self-focus is to let silence linger for five to seven seconds after a client finishes speaking. The pause may feel awkward, but it often gives the client room to reveal the deeper thought that changes the relationship. Want to learn more about Scott Armstrong's work? Check out his website at [http://winthequestion.com](http://winthequestion.com). Connect with Scott Armstrong on LinkedIn at [https://www.linkedin.com/in/rscottarmstrong/](https://www.linkedin.com/in/rscottarmstrong/). Think you'd be a great guest on the show? Apply at [https://podcast.allies4me.com/podcast-guest/](https://podcast.allies4me.com/podcast-guest/). Want to learn more about Craig Andrews' work at allies4me? Check out his website at [https://allies4me.com/](https://allies4me.com/). ## Key Points with Timestamps - **00:16:55** — Handle client frustration as an ally instead of blaming the client - **00:18:33** — Start by asking, not answering - **00:18:54** — Listen to learn instead of reloading the next smart point - **00:19:54** — Use trust framing to define the problem collaboratively - **00:25:52** — Replace the hunt for right answers with collaborative better thinking - **00:31:07** — Professional trust grows when self-orientation shrinks - **00:37:19** — Let an awkward silence invite the client’s deeper thought ## Transcript **\[00:00:00\]** I was in a coma for six weeks while the doctors told my wife I was going to die. **\[00:00:11\]** When I woke up, she told me the most fantastic story. **\[00:00:15\]** My team kept running the business without me. **\[00:00:19\]** Freelancers reached out to my team and said we will do whatever it takes as long as Craig's **\[00:00:24\]** in the hospital. **\[00:00:26\]** I consider that the greatest accomplishment in my career. **\[00:00:30\]** My name is Craig Andrews and this is the Leaders and Legacy podcast where we talk to leaders **\[00:00:36\]** creating an impact beyond themselves. **\[00:00:39\]** At the end of today's interview, I'll tell you how you can be the next leader featured **\[00:00:44\]** on this show. **\[00:00:51\]** Today I want to welcome Scott Armstrong. **\[00:00:54\]** He is the co-founder and CEO of BrainRider, a B2B marketing agency's run for over 17 years. **\[00:01:03\]** He's also founder of Win the Question, where he trains client facing professionals to build **\[00:01:09\]** trust in every conversation. **\[00:01:13\]** His book, which is coming out any day now, is From Asshole to Ally, why ambitious professionals **\[00:01:19\]** lose trust and how to get it back, it's coming out this fall from Trustcraft Press. **\[00:01:28\]** Scott grew BrainRider to $22 million with no profit and then rebuilt it as a $4.6 million **\[00:01:37\]** agency with 13% margin and learned the expensive way that firms don't grow because their people **\[00:01:44\]** got smarter. **\[00:01:45\]** They grow because their people got trusted. **\[00:01:51\]** Scott, I don't know how we're going to cover all this. **\[00:01:54\]** There's so many points here. **\[00:01:56\]** I mean, you're talking about building an agency that grew a massive profit, but one making **\[00:02:03\]** money. **\[00:02:04\]** You don't have to be an agency. **\[00:02:05\]** There's so many businesses that fall into that trap. **\[00:02:11\]** But before we go there, I got to hear more about this. **\[00:02:16\]** You say that you ski and ride motorcycles in places where your insurance company would **\[00:02:21\]** rather you didn't. **\[00:02:25\]** I have got so many questions. **\[00:02:28\]** Where do you go? **\[00:02:30\]** Anywhere the road tries to end, so last December it was the biggest down to Kahlo Baja the **\[00:02:40\]** year before it was up to the Arctic Circle. **\[00:02:44\]** Just a couple of weeks ago, I was riding all around you. **\[00:02:46\]** I did the Gulf Coast from New Orleans, through Galveston, a real country into Austin. **\[00:02:53\]** What made that ride hard is that it was sweaty. **\[00:02:58\]** I bet. **\[00:03:02\]** What type of bike do you have? **\[00:03:05\]** If you're a real rider, the number of bikes you have is a formula. **\[00:03:09\]** It's M plus one. **\[00:03:12\]** Whatever bike you have today plus whatever bike you're listing at for tomorrow. **\[00:03:17\]** My two main ride, one is a big adventure bike that is really good for long distance trips **\[00:03:22\]** on and off-road, and then I ride a Kityami XC500 for real off-road trips when we're **\[00:03:29\]** not on pavement for days. **\[00:03:31\]** They're different horses for different courses, but what they do is they anchor my spirit in **\[00:03:38\]** adventure which recharges me from being in the client services business week to week. **\[00:03:45\]** Wow. **\[00:03:46\]** You know, Jesse James lives here in Austin. **\[00:03:50\]** I love all riders because there's just always a little bit of the outlaw in the rider culture, **\[00:03:57\]** and I'm an advertising agency guy which means that I'm part of the weirdo crowd, also means **\[00:04:04\]** I fit into Austin quite comfortably. **\[00:04:07\]** I don't care what you ride or who you are, there's just a little bit of community that **\[00:04:12\]** forms there with that kind of attitude. **\[00:04:16\]** Yeah, you know, I have a buddy who's, I think he calls it over landing, and it's these pickups **\[00:04:23\]** with campercabs, but it's not your average pickup and it's not your average camper cab. **\[00:04:28\]** Do you encounter those folks? **\[00:04:31\]** We sure do, and you can actually, over landing is a broad description, so what we do with **\[00:04:35\]** the bikes is also considered over landing. **\[00:04:38\]** I rode Buffalo to Lake Placid this spring, and we had maybe 10% pavement getting in between **\[00:04:45\]** them. **\[00:04:46\]** We had maybe 30% dirt roads. **\[00:04:48\]** The majority of it was just gorgeous trails through the mountains. **\[00:04:52\]** Yeah. **\[00:04:53\]** Yeah, he lives out in Utah, kind of in the middle of Utah, and, but he went from there **\[00:05:02\]** all the way up to the Arctic Circle, and I don't know if there's multiple paths. **\[00:05:07\]** Does that tend to normally be sort of a Western path, or are there other paths up to the Arctic **\[00:05:12\]** Circle? **\[00:05:13\]** Yeah, that's a great question. **\[00:05:14\]** You can go both sides, so you can go up to James Bay, which is a Hudson Bay, which is **\[00:05:18\]** not just south of the Arctic Circle. **\[00:05:21\]** You can go to Tufta Yuck Tuck, which is likely where he went, that's sort of the famous route **\[00:05:25\]** up to the Arctic Circle. **\[00:05:27\]** It's a challenging technical ride to get there, but it's doable. **\[00:05:31\]** And the beautiful part about that is it takes you right through or near Alaska, which is **\[00:05:36\]** some of the most beautiful country in the world. **\[00:05:39\]** Yeah, wow. **\[00:05:42\]** And I like what you said, and you know, there's something I used to be better at, and I've **\[00:05:48\]** gotten back to the point where I'm struggling with it about taking time to unplug. **\[00:05:55\]** And I know it's one of those things, I know it's critically important for my health, and **\[00:06:02\]** it's not just important for my health, but it's important for my creativity, that I feel **\[00:06:09\]** the pressure of deadlines and what have you. **\[00:06:14\]** And in some ways, I feel kind of like a drug addict, I know it's hurting me, and it's decreasing **\[00:06:21\]** my effectiveness, but I'm having trouble breaking free. **\[00:06:26\]** And I admire the fact that you do that, and obviously if you're up around the Arctic Circle, **\[00:06:33\]** not sure how many cell towers are up there, or how many hotspots. **\[00:06:40\]** Exactly. **\[00:06:41\]** Yeah, fully off the grid. **\[00:06:42\]** When you take that time off, what does it give you? **\[00:06:47\]** It cleanses my brain, it clears all the clutter that's preventing me from seeing the obvious, **\[00:06:59\]** and swept out, and it kind of relaxes, I mean, obviously I've had to do a lot of recovery, **\[00:07:10\]** and when I was in the hospital, and I had like 800 milliliters of lung capacity, and **\[00:07:19\]** they're saying, "Hey, slow down, slow down and breathe easy." **\[00:07:25\]** And I'm like, "If I could breathe a little bit more, I would choke you." **\[00:07:30\]** Just because I get it, that's great theory. **\[00:07:34\]** But I feel like I'm suffocating. **\[00:07:40\]** Yeah. **\[00:07:43\]** The ability to step away and get perspective, and the ability to step away and get understanding, **\[00:07:49\]** and for me, in my practice, which is all about being a recovering asshole, the ability to **\[00:07:55\]** sort of get that perspective, and lean into my trust strengths. **\[00:08:00\]** Because when I adventure, I never do it alone. **\[00:08:03\]** We're always a team, we're always making decisions about where people are feeling safe, and what's **\[00:08:09\]** too much. **\[00:08:10\]** That just happened for me two weeks ago. **\[00:08:12\]** We celebrate a no on an adventure, more than we celebrate a yes on adventure, because when **\[00:08:18\]** you're adventuring, saying no is really hard work, and usually, if you think you should **\[00:08:25\]** say no, it's the right decision. **\[00:08:29\]** When you talk about that perspective, what going away on an adventure does for me is **\[00:08:33\]** it just fires up those trust skills that I lean into professionally in a different context, **\[00:08:40\]** and I come back all fired up and ready to go. **\[00:08:45\]** And I usually am pretty good about doing a hard shutdown for two weeks over Christmas. **\[00:08:53\]** And the last week, I just have ideas flooding my brain, and I can't wait to get back and **\[00:09:01\]** start playing them to work. **\[00:09:03\]** I am pretty good about holding off, but that first week, two weeks after Christmas is probably **\[00:09:11\]** my most creative time of the year. **\[00:09:15\]** And everybody's got a world different. **\[00:09:18\]** Everybody's got to find the engines that drive them. **\[00:09:22\]** And for you, it sounds like that two week, well, first of all, breathing was a good start. **\[00:09:27\]** That kept driving you. **\[00:09:29\]** It's the secret to life is to continue to breathe. **\[00:09:33\]** But also, you're a creative passionate guy, and so that step down lets those ideas percolate, **\[00:09:38\]** so you come back all fired up. **\[00:09:40\]** I think that's amazing. **\[00:09:42\]** What's another period in your year where you feel that same fire? **\[00:09:54\]** At that level, that's the only time of the year. **\[00:09:56\]** I am trying to think if there's another ... When I take a proper vacation, and this has been **\[00:10:08\]** something that's been part of our culture for over a decade, we tell our clients when **\[00:10:14\]** we're on vacation, we're not checking emails, and we're not taking phone calls. **\[00:10:19\]** When I catch employees doing emails, checking emails, because I use HubSpot and it has all **\[00:10:28\]** the notifications. **\[00:10:29\]** I can tell if one of my employees opened an email, and if I get a notification, I send **\[00:10:34\]** them a text, and I say, "Quit checking email and do vacation." **\[00:10:44\]** That, it's when I completely unplug, I mean, I love what I do, and when I cut myself off **\[00:10:53\]** for a week, I start craving it and getting plugged back in, and as long as I'm disciplined, **\[00:11:01\]** when I come back, the first days after vacation, a lot of people come back from vacation and **\[00:11:09\]** they're dreading what's awaiting them. **\[00:11:14\]** I come back from vacation excited and energized and ready to dig in. **\[00:11:20\]** For you, it sounds like a business engine. **\[00:11:24\]** You're ready to dig in when you come back with new ideas and things to do. **\[00:11:28\]** Is that right? **\[00:11:29\]** Yeah. **\[00:11:32\]** It's almost like you could reframe your vacation as a business starter, or a start-up week, **\[00:11:39\]** or an ideation week, or something like that, where it's not a holiday, you're not stepping **\[00:11:44\]** away from the work. **\[00:11:45\]** You're recharging so you come back with the ideas you couldn't get through. **\[00:11:47\]** I love that idea for you. **\[00:11:51\]** The first time I remember, I spent six years in the Marines. **\[00:11:58\]** I would take, we call it leave, but vacation, when I would take vacation, it kind of looked **\[00:12:03\]** like general patents storming through Europe. **\[00:12:09\]** I remember this was right before I came back from my last deployment. **\[00:12:18\]** Right before I came back from my last deployment, I decided I'm going to take a vacation. **\[00:12:23\]** The rule of this vacation is I make no plans until the morning of that day. **\[00:12:31\]** I was living in Japan and I jumped in my little Daihatsu hi-jet, and I drove across the island **\[00:12:38\]** over to the Sea of Japan, which is lovely, but very isolated, and I checked into a youth **\[00:12:44\]** hostel and he said, "How long are you staying?" **\[00:12:50\]** I said, "I don't know." **\[00:12:51\]** He said, "Where are you going tomorrow?" **\[00:12:53\]** I said, "I don't know." **\[00:12:54\]** The next morning, I would check out the youth hostel and say, "Hey, I'm going to Daisen **\[00:12:59\]** or wherever." **\[00:13:00\]** He said, "Are you coming back?" **\[00:13:01\]** I said, "I don't know." **\[00:13:04\]** I ended up staying at that particular youth hostel pretty much the whole time because it **\[00:13:09\]** was kind of a good central location to go off and do different day trips. **\[00:13:16\]** I remember one of the best times of that was that youth hostel was right on a big lake, **\[00:13:24\]** and the Japanese have amazing bread and amazing produce. **\[00:13:27\]** I bought a loaf of bread, one of their giant tomatoes, and a squeezed bottle of mayonnaise, **\[00:13:34\]** and a bottle of Keating lemon. **\[00:13:37\]** Keating the beer company also makes something sort of like 7-up without the lime. **\[00:13:43\]** I just said on the edge of that lake, making tomato sandwiches, watching the sun go down. **\[00:13:48\]** It was wonderful when I came back, when I went back to base, as I'm pulling in the **\[00:13:54\]** park and the barracks, I had people running up to me, they're like, "Hey, Craig, you just **\[00:13:58\]** made sergeant." **\[00:13:59\]** I'm like, "Yeah, I know." **\[00:14:00\]** They're like, "How do you know?" **\[00:14:01\]** I was in a small field, and I was like, "Because Schwartz got out," and I was next. **\[00:14:06\]** As soon as he got out, I was, "But yeah, no, but it's been just in my early wiring. **\[00:14:19\]** It's been something I've had to be intentional about, to be deliberate about relaxing." **\[00:14:28\]** How do you teach that to your team, because you talked about interrupting them when they're **\[00:14:31\]** on HubSpot? **\[00:14:32\]** Like, what's the leadership cue you used to spread that? **\[00:14:36\]** Well, I just, I just told them straight up, I said, "I don't want you working during **\[00:14:42\]** your vacation. **\[00:14:44\]** You are more valuable to us. **\[00:14:47\]** You're more valuable to us when you have a proper vacation. **\[00:14:54\]** This is not adding value, this is taking away value, because you're going to react." **\[00:15:01\]** In the early days, they didn't believe me. **\[00:15:08\]** Kind of like it takes me time to train them to, "I didn't hire you to agree with what **\[00:15:13\]** I say." **\[00:15:14\]** If I'm saying something stupid, I hired you to say, "Hey, Craig, that's just dumb." **\[00:15:25\]** So it takes time for them to believe it, and something you mentioned in the green room **\[00:15:34\]** was employees have been trained to behave in certain ways, and most employees have been **\[00:15:41\]** trained that your job is to be a yes man or a yes woman, and like, "No, not here." **\[00:15:48\]** Yeah, every time I talk to people, I'm always curious about how they lead and how they get **\[00:15:57\]** their teams to be better, and my subject for sure is around communication and how communication **\[00:16:04\]** builds client trust. **\[00:16:06\]** Like, the thesis we were talking about in the green room is that school and college and **\[00:16:13\]** early career teach you to constantly prove you're smart. **\[00:16:18\]** Especially if you're a smart professional, where knowledge is the currency that you're **\[00:16:22\]** playing, but that's not creating much value for your client trying to prove you're smart **\[00:16:28\]** all the time, and the best way to be smart is actually to do what you just talked about **\[00:16:34\]** on your vacation, to slow down, to listen better, to work collaboratively with your client to **\[00:16:41\]** understand the problem and possible solutions, and then to handle the disasters that happen **\[00:16:47\]** in our business, because they happen all the time. **\[00:16:49\]** It's not an easy business to do marketing. **\[00:16:51\]** It's not an easy business to do advertising, and so there are always challenges to show **\[00:16:55\]** up, and to handle those as an ally, that whole process as an ally, it kills me when you hear **\[00:17:04\]** an agency complaining about their clients. **\[00:17:11\]** The really complaining about themselves at that point, they should either fire the client **\[00:17:15\]** or learn how to understand their client. **\[00:17:18\]** What are some of the typical complaints you hear people leveling? **\[00:17:25\]** The number one complaint in the agency business is bad briefs. **\[00:17:33\]** Clients don't give us good briefs, and clients will say that the number one thing that they **\[00:17:39\]** often want help with at the strategic process is building a better brief. **\[00:17:47\]** The journey, the road from bad brief to good brief, is not smarter people in the room. **\[00:17:54\]** Every agency and every client's already filled with very smart people. **\[00:17:58\]** It's really the communication that gets unlocked by trust within that relationship, so that **\[00:18:05\]** everybody is understanding each other, and listening to each other, and working together **\[00:18:11\]** to get to the good brief on the same agenda. **\[00:18:18\]** That's some bolts. **\[00:18:19\]** What's that look like? **\[00:18:21\]** How does that happen? **\[00:18:23\]** None of it's brain surgery, or lung surgery for that matter. **\[00:18:28\]** It is four key skills that are in the book. **\[00:18:33\]** The first one is start by asking, not answering. **\[00:18:38\]** If your client says something, don't immediately give them an answer, because they probably **\[00:18:43\]** don't fully understand what they told you. **\[00:18:46\]** You don't fully understand what they told you, and so if you jump to an answer, you're **\[00:18:50\]** not going to get the answer right. **\[00:18:54\]** Then the second skill is listen to learn, don't listen to reload your next smart point. **\[00:19:03\]** Be genuinely curious about what's happening in their client's business, what's happening **\[00:19:08\]** on the team, what's happening in their life, and understand the different conversations **\[00:19:11\]** they might be having. **\[00:19:12\]** They might be having a timeline practical conversation, but they might be having an emotional conversation **\[00:19:17\]** that's really about I'm scared about this project, or I'm scared about next quarter's **\[00:19:22\]** results, or I'm scared that we might be doing a riff and eliminating my role. **\[00:19:29\]** That takes you to the third conversation, which is really an identity or a career conversation. **\[00:19:34\]** When you're a senior enough guy for a long time, you have lots of clients that talk to **\[00:19:39\]** you about things that have nothing to do with the projects that they're working on. **\[00:19:43\]** Their boss, their team, their company, their next step. **\[00:19:47\]** Listening to learn is really opening yourself up to all the relationship conversations in **\[00:19:52\]** the client. **\[00:19:54\]** The third skill is I call trust framing. **\[00:19:59\]** It's framing up the problem. **\[00:20:01\]** We're in the problem solving business, so understanding the problem always makes sense. **\[00:20:05\]** Trust framing is collaboratively framing it up with your client. **\[00:20:09\]** By starting out with the vulnerable statement of, I'm not sure this is the right understanding **\[00:20:15\]** of what you just said or the problem we're talking about, why don't I give you a hypothesis **\[00:20:20\]** of what I think we're working on, and then you can help me make it better. **\[00:20:28\]** The last one is what to do and shit hits the fan. **\[00:20:32\]** How do you react to that emotion when a client says, "I'm unhappy with the budget," or, "I **\[00:20:37\]** don't like the work," or even the biggest line, "You're fired." **\[00:20:47\]** Do you want to do a little role play? **\[00:20:50\]** Sure. **\[00:20:51\]** Do you have time? **\[00:20:53\]** We have time. **\[00:20:54\]** I was thinking of a, well, when you said, "Let me throw this out and we'll do a role play," **\[00:20:59\]** but when you said that they're not ready for the uncomfortable conversation, so I used to **\[00:21:04\]** do marketing and semiconductors. **\[00:21:07\]** I was up in Libertyville, which you probably know is just north of Chicago, and back when **\[00:21:12\]** Motorola made mobile phones, they had a group there I called the Think Tank. **\[00:21:17\]** If you were going to get into Motorola phone, you had to go through this screen. **\[00:21:20\]** They thought very highly of themselves. **\[00:21:28\]** It wasn't my meeting. **\[00:21:29\]** I'd been asked to tag along on this meeting, and we're sitting there with one of the co-founders **\[00:21:34\]** of our company and a couple other people, including the person who's meeting it was. **\[00:21:42\]** He gets up and he gives a presentation, and there's this just turd of an individual sitting **\[00:21:49\]** at the end of the table who just says, "Wow, I can see you've wasted our time." **\[00:21:56\]** This says nothing that we want. **\[00:21:58\]** This is addressing nothing that we ask for. **\[00:22:02\]** I'm sitting there waiting. **\[00:22:03\]** It's not my meeting. **\[00:22:04\]** I've got the co-founder sitting immediately to my left. **\[00:22:07\]** I'm just sitting on my hands. **\[00:22:09\]** I'm looking at the guy given the presentation, and his jaw is sitting on the table. **\[00:22:14\]** The co-founder's saying nothing, and I'm like, "Have these guys ever been kicked in the **\[00:22:19\]** balls before?" **\[00:22:21\]** I finally speak up, I look at the guy at the end of the table, I said, "Look, the last **\[00:22:26\]** thing we wouldn't do is waste your time." **\[00:22:29\]** We have the right people here to address whatever agenda you want. **\[00:22:33\]** Let's rework this agenda right now to make it exactly what you're looking for. **\[00:22:39\]** This says in a waste of your time. **\[00:22:43\]** Ended up, we went with the same agenda. **\[00:22:45\]** He was just kicking us in the nuts, but I was like, "Seriously, guys, you've never been **\[00:22:51\]** kicked in the nuts like this before?" **\[00:22:55\]** And often that's a great story. **\[00:22:56\]** We almost don't need to do a roleplay because you just told the story that anchors client **\[00:23:01\]** trust communication, which is instead of reacting emotionally to that moment, you slow down and **\[00:23:08\]** just asked another question. **\[00:23:10\]** You said, "Okay, if I'm not on the red agenda, what is the red agenda? **\[00:23:14\]** And let's see what we can do there." **\[00:23:17\]** And often that kick in the nuts is just trust testing, right? **\[00:23:21\]** They're just kicking the tires of the machine to see how you react and to sometimes to assert **\[00:23:28\]** dominance, but often they don't even have an evil agenda. **\[00:23:32\]** It's just their style is to be provocative. **\[00:23:36\]** What they really want to know is, are they willing to slow down and work with me or work **\[00:23:40\]** on my side? **\[00:23:42\]** And how did the rest of that go? **\[00:23:43\]** Did your founder recognize you as the brilliant young kid that was in the room who actually **\[00:23:49\]** asked a question? **\[00:23:50\]** I don't know. **\[00:23:51\]** I don't think he really liked me, but I think he saw that it's hard when you're talking **\[00:24:01\]** to one of the top mobile phone makers in the world and you're talking to the gateway and **\[00:24:06\]** to have a meeting rescued, it's hard to ignore that. **\[00:24:09\]** Right. **\[00:24:10\]** That's what I'm trying to teach founders and teams because I'm a Gen Xer. **\[00:24:16\]** In my generation, a lot of leaders spend time complaining about millennials and Gen Y because **\[00:24:23\]** they're very smart, they're very educated, they're very outspoken, they can sometimes **\[00:24:29\]** be sound entitled, I don't think they are entitled, but we often interpret them as entitled. **\[00:24:35\]** But what they also are is fearless. **\[00:24:38\]** If you teach them how to be fearless in the right ways. **\[00:24:42\]** And so they have the permission to ask the dumb question in the room more than anyone **\[00:24:46\]** else. **\[00:24:47\]** And it's the dumb questions, the vulnerable questions, the conversations like you and I **\[00:24:52\]** are having that unlock new client value in those conversations and often more trust. **\[00:24:58\]** So I am on a world changing mission one workshop at a time to try to get people to unlock **\[00:25:07\]** what you did naturally. **\[00:25:09\]** And it sounds like your founder didn't value in what year was that event? **\[00:25:14\]** Yeah, that was, yeah, well, yeah, we, there was a conversation where I asked a question **\[00:25:19\]** that he didn't appreciate and, and, oh, well, you know, and, you know, that sometimes that **\[00:25:28\]** sticks with you and he obviously, he obviously let me come on that trip. **\[00:25:37\]** So when you asked me before the podcast, are there any questions that are off limits? **\[00:25:42\]** Is there any time? **\[00:25:43\]** And I said, no, in my world, the hardest question should provoke a second or third question **\[00:25:50\]** to learn even more. **\[00:25:52\]** And that discomfort that you feel is natural and school teaches you to have the right answer. **\[00:25:58\]** We don't live in the world of right answers. **\[00:26:00\]** We live in the world of better thinking. **\[00:26:03\]** And often that's collaborative, better thinking. **\[00:26:06\]** And so if you can get your mindset and more importantly, if you could help your team get **\[00:26:11\]** into a mindset where they're not trying to prove they know the answer, they're trying **\[00:26:15\]** to, the name of my company is called when the question, they're really trying to win **\[00:26:19\]** the question to win the business, they open everything up. **\[00:26:22\]** I mean, I tell you, I would have loved working with you back then. **\[00:26:29\]** Yeah. **\[00:26:30\]** And so for me, I mean, I thrive in those kinds of environments, you know, I used to go to **\[00:26:33\]** Asia a lot. **\[00:26:35\]** And one of the things I loved, you walk into a meeting and you'd never know what to expect. **\[00:26:40\]** You think you're showing up to one agenda and they change the agenda on you. **\[00:26:45\]** And you can, for me, that was just part of the adventure. **\[00:26:53\]** That just made me better. **\[00:26:57\]** And I should bring you in one of these trips with me because that's why adventure fuels **\[00:27:00\]** the thinking for me, right? **\[00:27:03\]** The predictable is the less valuable in my world and the adventure is terrific. **\[00:27:10\]** What skills or resiliency do you think you built up by having to live in that, that you're **\[00:27:14\]** now applying in Austin because it's a very different world? **\[00:27:19\]** Yeah, I think to your point that there's not a conversation I'm afraid of and I'm not **\[00:27:28\]** afraid to say, I'm not afraid to say, hey, look, I don't know your industry that well, **\[00:27:35\]** I'm going to ask some questions. **\[00:27:37\]** They may sound dumb, but is there a case I asked these questions? **\[00:27:42\]** Now deep down, I know that the gold is hidden under assumptions. **\[00:27:49\]** Yes, it's not. **\[00:27:53\]** And my shortcut is when I find a deeply, you know, an assumption or a deeply held belief **\[00:27:59\]** that sounds like, hey, that's not how it's done in our industry. **\[00:28:03\]** I know there's gold in those hills. **\[00:28:06\]** All we have to do is lift that rock and there would be a big chunk of gold. **\[00:28:11\]** Yeah. **\[00:28:13\]** And so, you know, I would, you know, I think some of that was just experience, but I also **\[00:28:22\]** think some of that's just kind of a mindset. **\[00:28:25\]** Some people were kind of born with that mindset. **\[00:28:27\]** I think anybody can develop it. **\[00:28:30\]** But the, you know, the idea of, you know, the idea that there's no problem. **\[00:28:39\]** It's so great that you can't overcome if you just, if you approach it thoughtfully. **\[00:28:46\]** If you do ask the questions, I mean, and so here's the kind of the, and again, I want **\[00:28:54\]** this to be about you, but not, and not me, but probably I would say the one time in my **\[00:28:59\]** life that the unknown and the uncertain that I navigated that the best was when I woke up **\[00:29:06\]** from my coma, your brain scrambled, right? **\[00:29:09\]** And I had a bunch of dreams in my coma, which for me were reality, those. **\[00:29:16\]** And I started noticing that people around me went and say something. **\[00:29:19\]** They would look at me weird and I realized they had different views of what was real **\[00:29:23\]** than I had. **\[00:29:24\]** And my brother was visiting me in the hospital and he said something about his last visit **\[00:29:29\]** to my house. **\[00:29:30\]** In my world, he had never been to my house. **\[00:29:32\]** And I was like, you can't say that. **\[00:29:34\]** You can't tell them that because they're going to realize you've lost your mind. **\[00:29:38\]** And if they realize you've lost your mind, they're going to take away privileges. **\[00:29:45\]** And so I asked him, I said, well, Brent, when was the last time you were at my house? **\[00:29:51\]** He said, last month when you were on the ventilator, well, Brent, tell me about your visit. **\[00:29:58\]** What'd you do? **\[00:30:00\]** As he started talking, I started remembering my house. **\[00:30:05\]** In my world, I lived in a different house, a fictitious house that doesn't exist. **\[00:30:09\]** Yeah. **\[00:30:10\]** And I'd forgotten my house of 17 years. **\[00:30:15\]** And as he talked, I started remembering that house. **\[00:30:21\]** I also realized, oh crap, I need a way of figuring out what's real and what's not. **\[00:30:28\]** But it's back to what you're talking about is just ask questions. **\[00:30:33\]** And people love answering-- generally, people love answering questions at feeds or ego, and **\[00:30:39\]** they're happy to do it. **\[00:30:42\]** So we don't need to do a demonstration today at all, because your stories are 100% illuminating **\[00:30:48\]** what I would do through a demo. **\[00:30:49\]** I often do a demo in a workshop, because it gets people in the room to go, aha. **\[00:30:54\]** I couldn't do a better demo than the story that you just told, because you've got your **\[00:30:59\]** way out of that by not making it about yourself and by asking questions. **\[00:31:05\]** And there's math behind that. **\[00:31:07\]** Like the math of professional trust or earning client trust is that everything that you bring, **\[00:31:14\]** your credibility, your reliability, and what you know, end up being table stakes in the **\[00:31:22\]** professional services game. **\[00:31:24\]** Like the next agency, the next law firm, the next accounting firm, they are all smart **\[00:31:28\]** people who know lots of stuff. **\[00:31:32\]** The differentiator is in that equation, you've got reliability and credibility and knowledge **\[00:31:39\]** are all divided by self-orientation. **\[00:31:43\]** How much you make the process about you, your magic process, what you know, how smart our **\[00:31:48\]** work is instead of slowing down and doing what you did when you woke up into a new reality, **\[00:31:54\]** which is instead of saying, "I have an old reality that I understand and I'm smart about," **\[00:31:59\]** you said, "Help me understand. **\[00:32:04\]** When was the last time you were at my house? **\[00:32:06\]** What was it like at my house?" **\[00:32:08\]** And you built trust with your brother instead of the other direction where you said in your **\[00:32:14\]** example, they would have reduced your privileges, a great marine framework, right, because you **\[00:32:20\]** were going crazy. **\[00:32:22\]** Yeah. **\[00:32:23\]** That is the math of professional trust that I want more and more people that I work with **\[00:32:32\]** to know about because it motivates what you're so good at, which is asking better questions, **\[00:32:40\]** listening better, framing up problems better, and even handling that conflict moment of, **\[00:32:46\]** "Why are you wasting my time in this conversation?" **\[00:32:49\]** Yeah. **\[00:32:50\]** You're the summary of what's in the book, your summary of what's in my workshops, and **\[00:32:57\]** if anybody listening is thinking, "I wonder if how self-oriented I am, I have a professional **\[00:33:04\]** services trust skills quiz, you can take a mic site," it's a big provocative. **\[00:33:10\]** So the quiz is titled, "Are You An Asshole?" **\[00:33:15\]** And no one who's going to take it is, none of us are. **\[00:33:18\]** We're all smart people trying our best, but our self-orientation shows. **\[00:33:22\]** So go to winthequestion.com and take the trust quiz and then just email me. **\[00:33:28\]** I love chatting with people who are thinking about how to do a better job as a professional, **\[00:33:32\]** how to help their team, and I'd love to know the results that you get out of that. **\[00:33:37\]** I don't see them unless you share them with me. **\[00:33:39\]** So if you are an asshole, you don't have to tell anyone, but it will point out which **\[00:33:45\]** of those four skills I was talking about might give you the most leverage in your next client **\[00:33:50\]** conversation. **\[00:33:51\]** So where do we, I want to take this, where do I find it? **\[00:33:55\]** So go to winthequestion.com and then just click on the menu item that says, "Trust **\[00:34:01\]** quiz," and it's all set up right there. **\[00:34:04\]** That's awesome, yeah. **\[00:34:08\]** And it's interesting, let me ask this, before we wrap up, who are the people that are scared **\[00:34:14\]** to take that quiz and what's going on under the hood? **\[00:34:22\]** So you're an under the hood man, so you get it, right? **\[00:34:25\]** Which is the quiz really isn't about your trust rating at the end. **\[00:34:29\]** It's thinking about what are you learning by taking the quiz, by even asking and answering **\[00:34:34\]** the nine questions that are in the quiz, and by the skill that it's indicating you should **\[00:34:40\]** be thinking about. **\[00:34:42\]** This is a practice. **\[00:34:43\]** It's not a yes/no, it's not something that you memorize and go forward with. **\[00:34:49\]** Building trust in professional relationships has huge payoffs. **\[00:34:53\]** It improves referrals, it improves client retention, it grows projects and revenue. **\[00:34:59\]** It does everything that we as agency leaders want to do with our business. **\[00:35:05\]** When we're not in the room, and it does it by helping our team who hasn't yet been given **\[00:35:12\]** the permission that Young Craig needed to ask that question in that meeting, because you **\[00:35:19\]** really were the smartest guy in that meeting, if you want my opinion, and so those skills **\[00:35:24\]** haven't been taught, leaders aren't necessarily asking that of their teams, none of its brain **\[00:35:29\]** surgery. **\[00:35:30\]** It takes literally a two-hour session with me, and maybe a three coaching sessions over **\[00:35:36\]** the next 90 days just to lock those habits in. **\[00:35:39\]** To get a dramatic shift, one of the things I get people to do is listen in on a teammates **\[00:35:47\]** conversation with a client, and a more complex conversation, and count the number of questions **\[00:35:55\]** they ask after a client says something. **\[00:36:01\]** If they jump into answering the client's question and under two questions, they probably don't **\[00:36:06\]** actually understand the client's question fully yet. **\[00:36:10\]** You have a really easy metric to do on yourself if you record your calls, and I'm addicted **\[00:36:18\]** to transcripts now. **\[00:36:20\]** It's even easier to do to try to coach your team, hey, you could have learned more, and **\[00:36:27\]** your client would actually appreciate you better if you slowed down a little bit and **\[00:36:34\]** asked a few more questions as you go through the process, and you're just one, two, three. **\[00:36:39\]** You know, I'm reminded of Mel Brooks' film Men in Tights, where they run in the Friar **\[00:36:46\]** of Tucker Men, and he's offering a circumcision, and he's like, "Oh, they're popular with **\[00:36:51\]** the ladies," and they're like, "Oh, I'll take one, I'll take two." **\[00:36:54\]** Yeah, and so they're jumping in, answering the question before they really understand, **\[00:37:00\]** and when he shows them what's involved, they're like, "Oh, never mind." **\[00:37:05\]** The next time you hear yourself interrupt someone in a client conversation, think of **\[00:37:10\]** yourself as a man in Tights. **\[00:37:12\]** Yeah. **\[00:37:13\]** You jumped right in, you didn't even let the client finish what they were saying, and **\[00:37:19\]** I actually lean into awkward silences. **\[00:37:22\]** Not only do I let the client finish, I then count to five or seven in my head. **\[00:37:31\]** It's a very awkward silence, and your client will often fill that awkward silence with **\[00:37:36\]** their next deeper thought. **\[00:37:38\]** Yeah. **\[00:37:39\]** That's what you are a ball to chat with. **\[00:37:44\]** I really think you get it, the ally process. **\[00:37:48\]** I mean, it's all over who you are and what you do, but you said before we got on screen **\[00:37:53\]** that this was going to be an enjoyable conversation, and I want to end. **\[00:37:59\]** You want it to end? **\[00:38:00\]** I don't want it to end. **\[00:38:01\]** Okay. **\[00:38:02\]** I'm learning lots of stuff in this conversation, and I understand why you're on a mission really **\[00:38:09\]** around leaders and legacies, around better thinking and organizations and teams. **\[00:38:15\]** It's powerful. **\[00:38:17\]** Scott, this has been an absolutely amazing conversation, and I also don't want, and we **\[00:38:22\]** could go a lot longer. **\[00:38:24\]** Maybe we'll do another one, but for everybody else, how can they reach you? **\[00:38:30\]** Go to winthequestion.com. **\[00:38:31\]** I've got a knee book version of the book you can get. **\[00:38:34\]** You can take the trust skills quiz. **\[00:38:37\]** You can learn lots of more about the thinking, and I have ways to help you if you think that **\[00:38:41\]** it would be helpful for your team, but my biggest mission is to get the book out there **\[00:38:46\]** and so that people can, so that I have to deal with people who do a better job of listening **\[00:38:51\]** in terms of the lawyers and the accountants and the bankers and everybody else that I deal **\[00:38:55\]** with as professionals within my lines. **\[00:38:58\]** I think getting the doctors there will be a stretch, but I'd love to change the medical **\[00:39:03\]** community too. **\[00:39:05\]** And the book is from Asshole to Ally, and it's coming out in the fall of 2026. **\[00:39:10\]** Yeah, it slid to the end of this year, so it should be out by December at the latest. **\[00:39:15\]** Excellent. **\[00:39:16\]** Well, thanks. **\[00:39:17\]** You can get a free version of that if you go to the site, because I'm really not trying **\[00:39:20\]** to make money off the book. **\[00:39:21\]** I'm trying to change the world. **\[00:39:24\]** Well thanks again for coming on leaders and legacies. **\[00:39:27\]** Thanks for having me. **\[00:39:35\]** This is Craig Andrews. **\[00:39:36\]** I want to thank you for listening to the Leaders and Legacies podcast. **\[00:39:40\]** We're looking for leaders to share how they're making an impact beyond themselves. **\[00:39:46\]** If that's you, please go to alliesforme.com/guest and sign up there. **\[00:39:54\]** If you got something out of this interview, we would love you to share this episode on **\[00:39:58\]** social media. **\[00:39:59\]** Just do a quick screenshot with your phone and text it to a friend or post it on the **\[00:40:04\]** socials. **\[00:40:05\]** If you know someone who would be a great guest, tag them on social media and let them know **\[00:40:08\]** about the show, including the hashtag leaders and legacies. **\[00:40:13\]** I love seeing your posts and suggestions. **\[00:40:16\]** We are regularly putting out new episodes and content. **\[00:40:20\]** Just make sure you don't miss anything, please go ahead and subscribe. **\[00:40:24\]** Your thumbs up, ratings and reviews go a long way to help promote the show. **\[00:40:29\]** It means a lot to me. **\[00:40:31\]** It means a lot to my team. **\[00:40:32\]** If you want to know more, please go to alliesforme.com or follow me on LinkedIn. **\[00:40:39\]** Thanks for listening. **\[00:40:40\]** We'll see you next time. ## Listen 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