Scott Armstrong — From A**hole to Ally: Why Ambitious Professionals Lose Trust and How to Get It Back
Becoming PreferredJuly 27, 2026x
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45:4236.62 MB

Scott Armstrong — From A**hole to Ally: Why Ambitious Professionals Lose Trust and How to Get It Back

SEASON: 7 EPISODE: 1

Episode Overview:

Welcome back to Becoming Preferred, the podcast designed to help ambitious business professionals and entrepreneurs build unshakeable client trust, scale their impact, and become preferred in the markets they serve.

If you run a professional services firm, an agency, or a consulting practice, you’ve likely fallen into a very common trap: you try to win clients by being the smartest person in the room. You show up to pitches armed with deep expertise and immediate answers, only to wonder why the client chose someone else.

Our guest today says that over-indexing on your own 'smartness' is the fastest way to kill a deal. Scott Armstrong is a marketing veteran, global agency founder who scaled his business to over twenty-two million dollars, and the mastermind behind Win The Question.

He is also a self-reformed 'expert' who learned how to build trust the hard way. His upcoming book, From Asshole to Ally, is a field manual on how highly qualified professionals accidentally lose trust and exactly how to get it back. Today, we’re unpacking how to stop relying on rare 'rainmakers,' how to coach trust as a tactical skill across your entire team, and how to shift from pitching answers to truly winning the question. Please join me for my conversation with Scott Armstrong.

Guest Bio:

R. "Scott" Armstrong has spent 38 years learning what most ambitious professionals figure out the hard way: it's not about you. Scott is the founder of Win The Question, where he teaches ambitious professionals how to build trust by reducing their natural self-orientation and working to win the question before the answer.

Scott's book "From Asshole to Ally: How Ambitious Professionals Lose Trust and How To Get It Back" is the field manual and it will be launch in the fall. He lives at the end of a dirt road in Creemore where he trusts his neighbors and his motorcycle.

Resource Links:


Insight Gold Timestamps:

02:20 I hadn't really learned yet how to build trust, I just learned how to hustle

04:27 Trust has a math to it, or professional services trust at least has a math to it

05:15 Trust is really the shift from about me to about you

07:31 Your upcoming book has a brilliantly provocative title, From Asshole to Ally

10:30 What does it mean to win the question in a high-stakes client meeting?

12:12 Stephen Covey's fifth habit, "Seek first to understand, then seek to be understood."

14:23 Often the managing partner or the leader of the firm doesn't even really know what skills they're using successfully to build trust

16:28 Ask before you answer

17:05 You should be learning from my mistakes rather than my successes

20:28 At the top of my page, I just put a little reminder, "Shut up," that's my first prep note

22:38 Using that methodology, we lost a $10 million account in a review, and won it all back and more 12 months later

25:08 Give me 45 minutes to come and have a conversation, and then we'll craft a perfect solution for you based on that conversation

27:52 He was better at asking questions than I was, and his big win question's a real simple one

31:30 One of the things I like about your podcast is how much research you all do

34:05 Bottom line is if you're putting deposits into that relationship bank account on an ongoing basis, they don't divorce you when the proverbial hits the fan

37:49 The tagline for that company is not go fast, don't die, it's really go fast, go far

39:47 You might have a weather forecast, but it can change

42:10 You can literally these days run Otter on a call or in the meeting itself... after the meeting is over, will tell you not only how often did you speak versus when your client spoke...

42:49 The book is From Asshole to Ally: Why Ambitious Professionals Lose Trust and How to Get It Back by Scott Armstrong. (available Q4)

43:33 Scott Armstrong at winthequestion.com

Connect Socially:

LinkedIn: https://www.linkedin.com/in/rscottarmstrong/

Email: scott@thewtq.com

Sponsors:

Rainmaker LeadGen Platform Demo: https://calendar.summit-learning.com/widget/booking/JKItVP7WErmCBjU2cCIx

Rainmaker Digital Solutions: https://www.rainmakerdigitalsolutions.com/

Speaker A

In 3, 2, 1.

Speaker B

Welcome back to Becoming Preferred, the podcast designed to help ambitious business professionals and entrepreneurs build unshakable client trust, scale their impact, and become preferred in the markets they serve.

Speaker B

If you run a professional services firm, an agency, or a consulting practice, you've likely fallen into a very common trap.

Speaker B

You try to win clients by being the smartest person in the room.

Speaker B

You show up to pitches armed with deep expertise, immediate answers, only to wonder why the client chose someone else.

Speaker B

Our guest today says that over indexing on your own smartness is the fastest way to kill a deal.

Speaker B

Scott Armstrong is a marketing veteran global agency founder who scaled his business to over $22 million and the mastermind behind Win the Question.

Speaker B

He is also a self reformed expert who learned how to build trust the hard way.

Speaker B

His upcoming book, From Asshole to Ally is a field manual on how highly qualified professionals lose trust and exactly how to get it back.

Speaker B

Today we're unpacking how to stop relying on rare rainmakers, how to coach trust as a tactical skill across your entire team, and how to shift from pitching answers to truly winning the question.

Speaker B

Please join me for my conversation with Scott Armstrong.

Speaker C

Well, hey Scott, welcome to the program.

Speaker C

We're delighted to have you.

Speaker D

Thanks for having me on, Michael.

Speaker C

I'm really intrigued about our topic today and what we're going to be talking about.

Speaker C

And we're going to talk about how you can start winning the question and how we can build trust.

Speaker C

And you've got a new book coming out, which I'm not sure if this gets, you know, blurbed out or not, but From Asshole to Ally.

Speaker C

So we're going to talk about that and why the title of the book, but hey, kind of makes sense to me.

Speaker C

But before we get started, Scott, let's go back.

Speaker C

You're in high school.

Speaker C

Where are you living?

Speaker C

What's Scott want to be when he grows up?

Speaker D

Sure, I was a nice, curious, small town kid who did well in school.

Speaker D

I did well and had a lot of fun in college.

Speaker D

And then I got into the ad business.

Speaker D

So I spent about 20 years working mad Men style and advertising and I had lots of success there, moving down to Chicago until I didn't.

Speaker D

And it all kind of came crashing down because I thought I was the smartest guy in the room and I hadn't really learned yet how to build trust.

Speaker D

I just learned how to hustle.

Speaker D

So much so that the creative teams used to tease me and call me, I don't.

Speaker D

Hustle and jingle, I think is what they called me because they could Hear me running down the hallways to try to win business.

Speaker D

And that's a hard way to get to the next level.

Speaker D

So that's kind of why I crashed and burned.

Speaker C

It's interesting.

Speaker C

When did you discover that trust was really the secret formula and how we build trust?

Speaker C

Because a lot of people, they talk about it, hey, we got to have trust.

Speaker C

And I believe it's the foundation of all relationships.

Speaker C

Right?

Speaker C

You got to have trust.

Speaker C

Can we have a relationship without trust?

Speaker C

You can, but you lose to one where trust exists.

Speaker C

So where did you discover that?

Speaker C

And then what are some of the ways we can build trust quickly?

Speaker D

So I had this amazing president at Ynar Chicago, and I was trying to win Miller Brewing as an ad account.

Speaker D

Great account, pretty high stakes.

Speaker D

And so I was so focused on that, I was running around being the asshole myself in the title of the book or I was being a jerk.

Speaker D

If we want to use it, keep it clean.

Speaker D

And.

Speaker D

But she used the A word to describe me in her office when she said, no one's going to want to work for you or with you and clients are going to like you if you keep on this trajectory.

Speaker D

And I trusted her a lot then.

Speaker D

And so that hurt.

Speaker D

That really shook my whole world to get feedback like that.

Speaker D

And I don't know if in your career you've hit a moment where it just sort of shook your foundations, but it shook my foundations.

Speaker C

No, I think it's important.

Speaker C

Those are the catalysts.

Speaker C

Those are.

Speaker C

And once you realize it and go, you know what?

Speaker C

That's correct.

Speaker C

You know, I really love the byline on your website where it's field tested trust training for ambitious professionals smart enough to need it.

Speaker C

And in other words, it's an awareness issue.

Speaker C

They don't even understand that it's there.

Speaker C

And I'm curious about how you see the process because we try and get new clients.

Speaker C

You work with professional firms, and we haven't evolved like we should evolve with.

Speaker C

Technology's evolved, but we're still back there peddling services.

Speaker C

And how do we evolve it?

Speaker C

What's your state of the unit?

Speaker C

What are you saying?

Speaker C

Because I know you're right in the thick of it.

Speaker C

How would you define it?

Speaker D

Well, trust has a math to it.

Speaker D

Or professional services trust at least has a math to it.

Speaker D

So everything you bring to the table as an ambitious professional, you know, your credibility, your reliability, how much you know the client and the industry, all of that gets divided by how much you make the conversation about proving you know all that stuff as opposed to focusing on what you're learning about your client and how you can use all that expertise to help them.

Speaker D

So if you can reduce that denominator in that equation, you can build professional trust.

Speaker D

And getting through school in the early part of your career focuses on the top line.

Speaker D

It focuses on credibility and reliability and delivery.

Speaker D

And all those are table stakes.

Speaker D

Once you get to a certain point, trust is everything else.

Speaker D

And trust is really the shift from about me to about you.

Speaker C

If you look at most websites and it's all about them, and it's really about them, people are brochures.

Speaker C

Here's how great we are, here's how wonderful we are.

Speaker C

And I love the term, and I believe you're referencing it as self orientation.

Speaker C

You talked about math.

Speaker C

I love formulas.

Speaker C

And you have trust equals C plus R plus I divided by self orientation.

Speaker C

Can you unpack that for us?

Speaker D

Yeah, sure.

Speaker D

So the.

Speaker D

The C is the credibility, and R is reliability, and I is intimacy, or how much you know your client and how much your client is relying on your expertise.

Speaker D

But as soon as you turn that conversation back to proving what you know, you not only stop talking about your client in constructive way, but you often leave them behind.

Speaker D

You know, a great example is a doctor.

Speaker D

I don't know anything about medicine, and I usually.

Speaker D

I'm not all that certain when I go into a doctor's office.

Speaker D

That's why I'm there.

Speaker D

Like, I'm sick or there's something wrong or my case, I've broken a shoulder or an elbow or a wrist riding or skiing or all the stuff I do on the side.

Speaker D

And so when I show up with a doctor, I'm saying, hey, this is my situation.

Speaker D

These are my problems.

Speaker D

And what I first want to do is I want to be heard.

Speaker D

I want to make sure the doctor understands exactly what I'm saying is wrong with me.

Speaker D

Right.

Speaker D

I know.

Speaker D

For example, I was riding down in Mojave, the bike crashed.

Speaker D

I separated my shoulder.

Speaker D

I knew my shoulder was separated.

Speaker D

And it had been a month riding after that separation before I got back into the doctor's office.

Speaker D

I want the doctors slow down and really hear the whole story and get me as a part of the diagnosis before they jump to a solution that says, okay, you.

Speaker D

You need a cast or you need a pill or you need whatever else.

Speaker D

I mean, I'm already doing physio every day on my own.

Speaker D

What I really want is to work together on the solution because I know my body just like my clients know their business.

Speaker C

Yeah, you're collaborating.

Speaker C

Diagnosis before prescription is malpractice.

Speaker C

Or prescription before diagnosis.

Speaker C

So it's, you want to be properly diagnosed, and then what's the right solution for me to.

Speaker C

And my body customer.

Speaker C

And that works the same way for businesses as well.

Speaker C

I know you get that your upcoming book has a brilliantly provocative title, From Asshole to Ally.

Speaker C

You argue that the very path of becoming a highly qualified professional actually trains us to lose client trust.

Speaker C

Why is being the smartest person in the room often a massive liability in a business development?

Speaker D

Well, there's a couple of ways to look at that question.

Speaker D

I'd start with something they call the curse of knowledge.

Speaker D

And that is once you know something really well as an expert, it becomes really hard to understand it as someone who's not an expert.

Speaker C

Right.

Speaker D

And even harder to explain it and have some empathy around it.

Speaker D

And so when you're an expert, you jump to jargon and shortcuts.

Speaker D

Like the example of the doctor is the same example I feel when I go see my business lawyer or my accountants or consultants or even the ad guys that I've worked with or the high performers on my team.

Speaker D

And so you really need to slow down those high performers and have them recognize when their knowledge is a curse as opposed to an advantage in building understanding and knowledge with your client.

Speaker C

Is it about the rapport?

Speaker C

Is it about the.

Speaker C

If I'm.

Speaker C

And we have to watch that even as speakers, like, we come in and the keys to be authentic, you know, when we're delivering from the stage, as you know, because you do what I do and we have to connect with that audience.

Speaker C

So we need to be relatable and then maybe tell them about our journey.

Speaker C

Hey, I've been where you've been.

Speaker C

Here are the questions I've asked.

Speaker C

Here's the solutions.

Speaker C

And we're kind of sharing that.

Speaker C

Is that kind of what you're referencing?

Speaker D

I think that's a lot.

Speaker D

But it's not about charm school.

Speaker D

Like the.

Speaker D

The ad folks in the world are the weirdos in the business conversation.

Speaker D

And I definitely sit in the iconoclastic zone of professionals.

Speaker D

I usually wear this baseball and usually wear this black shirt.

Speaker D

Doesn't matter what the meeting is.

Speaker C

The hat says go fast.

Speaker C

Don't die for those who are listening.

Speaker C

So.

Speaker D

Right.

Speaker B

Right.

Speaker D

Or something.

Speaker D

Something saucy.

Speaker D

Right.

Speaker D

That's part of my personality.

Speaker D

And it's going to show up as part of the conversation if I'm being authentic to myself.

Speaker D

So it's not about charm.

Speaker D

It's really the numbers prove it out.

Speaker D

So.

Speaker D

And they're super rude.

Speaker D

The top performers in Client conversations talk about 43% of the time and people who lose deals talk about 65% of the time in climbing.

Speaker D

Right.

Speaker D

So it's really how much am I making a client's briefing or a client talking about their situation or their need about me and what I know versus how much am I really trying to listen to better understand what they're telling me?

Speaker D

And then framing up my answer.

Speaker D

I call it trust framing.

Speaker D

So framing up my answers, my understanding of the problem in the language they gave me to prove that I was listening to them in the first place.

Speaker C

No, that makes sense.

Speaker C

You talk about a critical shift that every successful professional must make moving from trying to win the answer to winning the question.

Speaker C

What does it mean to win the question in a high stakes client meeting?

Speaker D

Yeah, I can tell you a little story.

Speaker D

So I was at Y and R Chicago.

Speaker D

We were pitching United Global Airline account.

Speaker D

And Y and R was a global business.

Speaker D

So I brought about 12, flew 12 people into Chicago to present our credentials and our capabilities and our thinking in this giant deck.

Speaker D

The binder was 2 inches wide.

Speaker D

And we were pitching against Fallon out of Minneapolis.

Speaker D

It was a small shop.

Speaker D

They didn't bring a big deck.

Speaker D

They brought three people into the meeting room.

Speaker D

We had a presentation.

Speaker D

Fallon had a conversation.

Speaker D

They didn't even have a global agency.

Speaker D

In fact, one of their promises was, if you give us the global business, we'll launch a global agency to support it.

Speaker D

My pitch was, we are the global agency.

Speaker D

You want to work with Fallon.

Speaker D

One interesting, right?

Speaker D

They walked in as the likable, listening, empathetic and really authentic team.

Speaker D

My team was introducing themselves to each other as we were walking in the room to pitch the client.

Speaker D

And the client clearly said, I want to work with the people who seem much more trustable and authentic than the people who seem like they've got lots of high powered credentials, but I'm not even sure those are going to be in the people in my business when the pitch is over.

Speaker C

No.

Speaker C

Yeah.

Speaker C

And you see that a lot.

Speaker C

There are people coming in there.

Speaker C

It's all about them.

Speaker C

And that's why I say I like the term you're using.

Speaker C

That or self orientation or it's about me where really it needs to be about them and ask the questions.

Speaker C

You know, I love the Stephen Covey's fifth habit.

Speaker C

Seek first to understand, then seek to be understood.

Speaker C

And I think that should be a tattoo for every professional is right on their forehead.

Speaker C

Seek first to understand before you prescribe.

Speaker C

And they've got to know, hey, we might not be a fit for you.

Speaker C

Thanks for doing this meeting, Scott.

Speaker C

Not sure we're a perfect fit.

Speaker C

That's why we have these meetings.

Speaker C

We prepared some questions which we'd love to ask you mind if I ask questions?

Speaker C

Then people don't mind answering those questions.

Speaker C

It's interesting.

Speaker C

I'll give you an example because I'd love your comment on this because you're a speaker like I am.

Speaker C

We get committees will phone us up and go, hey, we were interviewing three or four speakers and we'd like to interview you to see if you're right for our particular engagement.

Speaker C

So I'll come online, there'll be a zoom call with four or five people on the call and they'll say to me, why should we hire you?

Speaker C

We're looking at others, but why should we hire you?

Speaker C

And most people will jump in on this.

Speaker C

And I go, my now response is, you know, going through the.

Speaker C

Some things you talk about are you might not want to hire us, we might not be a perfect fit.

Speaker C

Mind if I ask you a few questions first which will help fine tune and tailor our 30 minutes together so that you have enough information to make the right choice.

Speaker C

And they're going, sure.

Speaker C

So then my next question is, I want you to imagine the event is over.

Speaker C

I want you imagine it's done.

Speaker C

They've had a great time, great location, they've been well fed, they've been educated.

Speaker C

You're interviewing your team on the way out the door.

Speaker C

What do you want them thinking about?

Speaker C

Do you want them doing?

Speaker C

What do you want them feeling?

Speaker C

And then I shut up.

Speaker C

They then start telling me all the outcomes that they're desiring for which I'm making little notes of, which go right into the presentation because they're actually telling me this is what the outcomes we're looking for.

Speaker C

So it's really about identifying those outcomes is that, I mean you can see where that just works.

Speaker C

So how are you finding that when it comes to teaching that within organization?

Speaker C

Because you go into organizations, you look at their existing processes.

Speaker C

I'm assuming you map that out what they do, listen to the questions they are asking or what they're mostly telling about.

Speaker C

How do you solve the problem, how do you entrench that skill?

Speaker C

And then there's different levels of the skill within an organization.

Speaker D

Yeah, I keep it simpler than that.

Speaker D

So I'm sort of like a quick hit.

Speaker D

You've already got an ambitious high performing teams, you want to try to get them to the next level.

Speaker D

And often the managing partner or the leader of the firm doesn't even really know what skills they're using successfully to build trust and how they've changed their self orientation over time to win.

Speaker D

And so when I go in to work with a team, the first thing is having them discover they're self oriented in lots of these conversations.

Speaker D

And it's really easy to do.

Speaker D

You get them play acting, a client conversation, and you get everybody to watch this, this rehearsal or this play acting at the front of the room.

Speaker D

And usually by the third question they're asking their new client, they're turning it into what they know, or even worse, what they can do to solve that problem.

Speaker D

And then I just say, stop.

Speaker D

Look at how quickly we got there.

Speaker D

And then the second thing I point out is how eager the person playing the advisor was to interrupt and get their words into the conversation instead of slowing down and letting the client who's thinking on the spot about all these questions.

Speaker D

And it's not a professional in law or banking or advertising or whatever else, formulating their thoughts.

Speaker D

And I teach them, hey, count to five to seven seconds after they finish answering.

Speaker D

And more times than not, that client will keep talking and they'll tell you more at a deeper level than they did in their first answer.

Speaker C

Yeah, or tell me more about that.

Speaker C

Tell me more, tell me more.

Speaker C

Why is it important to you?

Speaker C

Why is that important to you?

Speaker D

100%.

Speaker D

And it's active.

Speaker D

You know the five whys of Toyota, right?

Speaker D

Just dive deeper and deeper.

Speaker D

But the mechanism they need to get there is to take that, that need to prove their credentials off their shoulder and say, you're already in the room.

Speaker D

You're in this conversation because you're qualified.

Speaker D

Now you need to create client value.

Speaker D

And I show them four skills they can use to do that.

Speaker D

The first is ask before you answer.

Speaker D

So really slow down the conversation.

Speaker D

Ask a lot of questions before you jump in with a solution.

Speaker D

Because your client might be having a practical conversation with you where they want to figure out where a project is or how much it'll cost or what timeline is.

Speaker D

But the more senior you get, the more those conversations become nuanced.

Speaker D

And your client might want to have an emotional conversation with you where they're sharing their worry about the project or their excitement about the project.

Speaker D

And if you jump in with budget, which I've done countless times to my discredit in client, I've done more mistakes like you should be learning from my mistakes rather than my successes.

Speaker D

To be honest, it took me 20 years to get good at this.

Speaker D

Right?

Speaker D

It's only the last 10 years that I've really become a better client whisperer.

Speaker D

So the first is ask, not answer.

Speaker D

The the second is listen to understand.

Speaker D

Yeah, I used to listen to reload so that I had my next answer ready.

Speaker D

If you're doing that, you're not listening.

Speaker C

Yeah.

Speaker D

And then the third, we talked a bit earlier.

Speaker D

Trust framing.

Speaker D

So frame up their problem with their words and have them do it as a draft.

Speaker D

Don't feel like you need to be perfect in a client conversation.

Speaker D

As a senior person, what you want to be is collaborative your word with your client and that means leaving room for them to correct you and depreciating the clarity that they provide.

Speaker D

And then the fourth is what to do when everything goes wrong.

Speaker D

What I call moments of trust building.

Speaker D

So those are the four skills.

Speaker D

But you can't get to those skills until the ambitious professionals go, oh my God, I am the person interrupting in this conversation.

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Speaker B

And now back to my conversation with Scott Armstrong.

Speaker C

Well, you know you talk about diagnosing our self orientation and building trust as a skill.

Speaker C

Self orientation or worrying more about how we look, how we pitch and perform.

Speaker C

What the client needs are is a natural.

Speaker C

It's a natural human instinct.

Speaker C

We do it.

Speaker C

But how can an ambitious professional spot their own self orientation in real time during a call before it actively damages a client relationship?

Speaker D

Yeah, it's real hard.

Speaker D

You know they really need to work with their boss to be coached doing it.

Speaker D

You're right.

Speaker D

And your whole practice kind of leans into this, right?

Speaker D

Like it's in us to be the center of attention.

Speaker D

And the smarter you are, the harder that habit is to break.

Speaker D

The more successful you are, the harder that habit is to break.

Speaker D

The second tip is to prepare for it in advance of the call.

Speaker D

So I do call notes.

Speaker D

All good sales professionals do call notes.

Speaker D

Good professionals should do call notes.

Speaker D

But they do it less often than you think.

Speaker D

And at the top of my page, I just put a little reminder.

Speaker D

Shut up.

Speaker D

That's my first prep note.

Speaker C

The point is, and you talked about percentages.

Speaker C

We have two ears, one mouth.

Speaker C

What's the old adage?

Speaker C

Listen twice as much as you speak.

Speaker C

There's your ratio.

Speaker C

But if they're talking, you're doing good things.

Speaker C

If you're talking, you're losing them and you're boring them.

Speaker C

Now, there's different questions.

Speaker C

And many leaders treat trust and business professionals treat trust like it's a mystical binary thing.

Speaker C

Either have chemistry with a client or you don't.

Speaker C

You treat trust as a teachable, coachable tactical skill.

Speaker C

What are the core repeatable mechanics of earning trust that a professional can actually practice?

Speaker D

Yeah, so it's really those listening skills from a professional lens, it is.

Speaker D

Understanding your value in your client relationship isn't always your answer.

Speaker D

And when you're dealing with more senior clients, chances are they know what the answer is.

Speaker D

They're looking for an ally to help them get the answer across the line or reduce their doubts, or help them manage risk and uncertainty.

Speaker D

And so jumping to the answer doesn't do that for them until they get all of those elements in place.

Speaker D

And then I think the biggest one, the moments of trust skill, is when your client says something that is an emergency.

Speaker D

So, for example, for us, you didn't win the pitch.

Speaker D

So I've now spent hundreds of thousands of dollars and months getting ready for this pitch.

Speaker D

I pitched it, I didn't win.

Speaker D

It's natural human physiology, right?

Speaker D

Your amygdala jumps and suddenly you want to fight or flight.

Speaker D

You either want to run out of that room or you want to try to convince that client that their reasonable process oriented decision is wrong.

Speaker D

And you lose the future relationship if you do either of those.

Speaker D

And so moments of trust are where you can actually say, look, you're a smart client.

Speaker D

Clearly this is the right decision for you to take right now.

Speaker D

What can I do to help make this decision come to life for you?

Speaker D

Because we are best partners and we want to continue to be best partners.

Speaker D

And using that methodology, we lost a $10 million account in a review and won it all back and more 12 months later.

Speaker C

A hard lesson to learn.

Speaker C

It's a scary one to learn it that way.

Speaker D

Right?

Speaker D

It was about 90% of our firm revenue at that time, Michael.

Speaker D

And I won't lie, when we lost that, we kicked and screamed and drank a little whiskey that night and really railed against procurement and the process and everything else.

Speaker D

The morning we woke up and said, wait, you know, they've been an amazing client for 10 years.

Speaker D

We've learned so much.

Speaker D

We really like them.

Speaker D

What can we do that is best partner?

Speaker D

What can we do that will build trust?

Speaker C

Well, we have this dysfunctional selling process which has created a dysfunctional buying process.

Speaker C

And so the key is to interrupt it.

Speaker C

And how do we interrupt it?

Speaker C

And I think it's done.

Speaker C

I think it's done through good questions.

Speaker C

You know, I get a lot of questions companies will ask me about the rfp.

Speaker C

They're in the RFP world.

Speaker C

So I'll say, first question I ask is, well, how many are you winning out of 10?

Speaker C

They go one or two.

Speaker C

And my answer back to him is, you know, an RFP is a train leaving the station.

Speaker C

You don't have a ticket.

Speaker C

So unless you're One of the three Cs, the committee that created it, the competitor or the consultant, you are missing the boat.

Speaker C

So what I.

Speaker C

And this is the advice I gave, but it kind of worked in this scenario.

Speaker C

They said, hey, can you do an rfp?

Speaker C

And I was so frustrated with when we started our career that with these RFPs, because they're just.

Speaker C

I wasn't getting the conversations.

Speaker C

They were in control.

Speaker C

So it's like going to the doctor with the prescription in hand and going, this is the pill that I'm wanting.

Speaker C

And versus actually meeting with an expert.

Speaker C

So I said out of frustration one day, I said, please take your.

Speaker C

Thank you for giving us an opportunity to respond to the proposal.

Speaker C

Please take your highest bid, add 10% and let that reflect my bid.

Speaker C

Well, yeah, you get.

Speaker C

So I think I was the asshole on that one, actually.

Speaker C

And to ally.

Speaker C

Well, VP phones me up all pissed off in the afternoon, and he goes, you know, basically, you arrogant buggers, what are you doing?

Speaker C

And he actually used the term arrogant asshole.

Speaker C

Why are you guys think you're so wonderful?

Speaker C

And I said, well, you've got a major problem with your rfp.

Speaker C

I said, who created it?

Speaker C

The committee, the consultant, or a competitor?

Speaker C

And I go, what are you talking?

Speaker C

I said, you want us to guess on a perfect solution for you?

Speaker C

I said, at our Company.

Speaker C

We built our reputation on perfect solutions.

Speaker C

And these are, somebody's prescribed this.

Speaker C

And I said, can you really afford to have an imperfect solution or were you more interested in a perfect one?

Speaker C

And I said, give me 45 minutes to come and have a conversation and then we'll craft a perfect solution for you based on that conversation.

Speaker C

And he comes, but that wouldn't be fair to everyone else.

Speaker C

I said, has anyone else even asked for it?

Speaker C

And he goes, no.

Speaker C

And I said, that ought to be a big red flag right there.

Speaker C

And I said, so I changed the game all by asking questions, and then again went to outcome based thinking and we ended up winning that deal.

Speaker C

So we became an ally, you know, to borrow the title of your book from asshole to ally and work.

Speaker C

And so that became, once you win a few of those, it's easy to, hey, I'm staying with, I'm gonna dance with the girl that I brought to the dance here.

Speaker C

It's a great way to do it.

Speaker C

Let me ask you about the quality of questions, because I get asked this a lot.

Speaker C

I believe when we meet with a client at any level, there's what we call a mutual value line.

Speaker C

There's a line and then we have low value questions which bore the hell out of them.

Speaker C

And then we have the high value questions.

Speaker C

So to your point, you talk about your meeting notes.

Speaker C

I call it pre flight planning.

Speaker C

I've been a pilot for 40 years.

Speaker C

I do flight planning.

Speaker C

So I want to know anything that I should know.

Speaker C

I need to know that ahead.

Speaker C

And I call that being one up or one ahead as well.

Speaker C

So I've got to be one ahead of you.

Speaker C

Except if I come in there and going, you know, asking a question that I could find out on the web or anything that's in public information, I'm boring.

Speaker C

The daylights up of you and you're going, hey, you obviously didn't do your homework.

Speaker C

I want to ask you.

Speaker C

So I have what I call status questions.

Speaker C

Hey, you guys have nine locations.

Speaker C

Is that boring?

Speaker C

Then we have issue questions which we're moving up that value, but then we got across into the value line where it's in my mind, they're implication type questions.

Speaker C

What if we don't do something?

Speaker C

What if we say status quo and then move into solution type questions like what would be the outcomes if we were to do this or do that?

Speaker C

So, and the key is you're moving up and down throughout the whole questioning process in my mind.

Speaker C

But.

Speaker C

So you have to ask some of those.

Speaker C

But learn as much as you can.

Speaker C

And I think people are just lazy.

Speaker C

And professional rainmakers, true rainmakers are good at doing their homework.

Speaker C

And you're going to go do an hour prep, two hours of prep, or before the pitch, as you say, back with your agency days where you're doing your homework.

Speaker C

What do you see out there?

Speaker C

Is that, is that what you're seeing when you work with some of these organizations as well?

Speaker D

Yeah, I mean, I was guilty a lot of that when I was an ad guy pitching.

Speaker D

And it's really hard in professional services because you're not selling anything tangible.

Speaker D

It's really hard to show the specs or the product.

Speaker D

You're sort of, you're selling something that's ultimately going to be a deliverable in the future.

Speaker D

Now, my business partner for last 20 years at Brainwriter, my marketing firm, is the best question asker I've ever met.

Speaker D

He was originally my client and I convinced him to come over and join me starting Brainwriter because he was better at asking questions than I was.

Speaker D

And his big win questions, a real simple one.

Speaker D

I don't think I've been in a conversation where he hasn't asked it.

Speaker D

And it's a two parter.

Speaker D

The first is what's the objective?

Speaker D

Help me understand in your words, what we should be focused on, what's the win?

Speaker D

And then he follows it up with what does success look like?

Speaker D

What's the win?

Speaker D

And there's not always the same pieces.

Speaker D

There might be success for the project, success for the firm.

Speaker D

Ultimately, if you're in a trusted rainmaker relationship, there's success for the person who is contracting you.

Speaker D

Now, rainmakers do that naturally.

Speaker D

The challenge is when you want to grow your firm.

Speaker D

You're not always in those relationships or in those conversations when the opportunity to ask those questions and get that learning is in place.

Speaker D

So it's one thing to win RFPs when the managing partner is in charge of the relationships, but once your size of your firm scales beyond your own ability, you really have to start getting those ambitious professionals to start acting the same way you do, which is really asking high yield questions.

Speaker D

And I think they would do well by reading your book and listening to the podcast because you cover all this ground really well, Michael.

Speaker C

Well, and I think you do.

Speaker C

The way you've identified it, it's like when you're scaling client facing teams and building bench strength.

Speaker C

You know, a massive pain point for agencies, consulting firms, law firms, is that rainmaker trap relying entirely on one or two founders to bring in all the revenue.

Speaker C

How does shifting a Team's focus from selling harder to mastering trust skills help a larger scale business development across the entire bench.

Speaker D

Yeah, the senior person's not in every conversation, right?

Speaker D

You know, I'll tell you a story.

Speaker D

I had a really smart account lead on a piece of business that I was running.

Speaker D

They were a rideshare app and we were doing lots of the creative execution for them.

Speaker D

It was high pressure, high growth, really fun client.

Speaker D

The business was changing every six months.

Speaker D

It was really hard to stay on top of.

Speaker D

I loved working on that business, I loved the challenge of that business.

Speaker D

But our business was growing.

Speaker D

So once it was established, it was a few years in, I handed off the reins and the report that I would get is, everything's great or we had a few problems, but it's okay, we fixed them.

Speaker D

And what that masks is that the relationship was eroding at the other end.

Speaker D

We were having problems.

Speaker D

The account lead was saying, okay, it's okay, I'll fix it and we'll make it better.

Speaker D

And it wasn't earning the trust that I used to earn by slowing down and listening to the concern and understanding the concern as opposed to just duct taping over whatever was going wrong.

Speaker D

And ultimately, when the business walked over the door, it was too late for me to save it.

Speaker D

Client really liked me, but said, look, we've had too many misses and I just need to move in another direction right now.

Speaker D

And that happens all the time in professional services when you have to hand the reins off to someone else to lead the assignment.

Speaker C

No, that makes sense.

Speaker C

Let's talk about managing friction, because when you're handing it off, sometimes they're not going to look after it or you're getting how to navigate an adverse moment.

Speaker C

So basically, how do we turn a mistake into a deep relationship, ally or loyalty?

Speaker C

And so every long term client relationship will eventually hit a rough patch.

Speaker C

A missed deadline, budget overrun, strategic disagreement.

Speaker C

How does an ally handle a high friction crisis differently from an asshole trying to protect their position?

Speaker D

You know, one of the things I like about I'm going to go sideways on you for a second.

Speaker D

One of the things I like about your podcast is how much research you all do.

Speaker D

I feel like you just quoted me right out of the in in that scenario because it's a really big challenge for all sales situations.

Speaker D

But it's definitely a big challenge for professional services because you hire a professional because the work is complicated or risky or very specialized.

Speaker D

And so I always tell my teams, by definition, they hire an advertising agency because we're going to get it wrong, something is going to go wrong along the way.

Speaker D

And if you look at the agreement you have with your law firm or your accountants or your consultant, your ad agency, the fine, like the, the legalese at the end of the agreement basically says, we, the accounting firm will be able to blame you for anything that goes wrong because ultimately you're the person who's going to sign off on all the statements that are submitted.

Speaker D

That's an asshole move.

Speaker D

And I've used that move when I was a younger ad guy.

Speaker D

You know, I blown budgets or timelines that were off or campaigns that didn't work.

Speaker D

And I was a master at blaming the client in those situations, as opposed to remembering the key is to be an ally.

Speaker D

You don't have to take the blame because your client's not usually looking for an apology.

Speaker D

What they really want is, we're here, I need to be there.

Speaker D

It's gone wrong.

Speaker D

What can we do to fix it?

Speaker D

And if you can get to.

Speaker D

I hear you on the problem.

Speaker D

I see why this problem is important.

Speaker D

I'm not going to minimize it.

Speaker D

I'm not going to say contract says it's not a problem or I'm not responsible for you.

Speaker D

This is a big problem.

Speaker D

Therefore, for me, this is a big problem.

Speaker D

And I can see a couple of things that we can do to move forward.

Speaker D

Let's work together to figure out the right next step.

Speaker D

Have you, like, what do you do in that situation?

Speaker D

I'd love to learn from you.

Speaker C

Yeah, no, it's a good approach.

Speaker C

I think it's just own it whether it's yours or not.

Speaker C

And it's accountability.

Speaker C

And so I tell my clients, hey, if you're losing sleep over it, we're going to lose.

Speaker C

I said, when you have a problem, it's a Rubik's Cube.

Speaker C

To me, it's a puzzle.

Speaker C

I said, I love to bring come to those problems, even if it's not, if we're not billing for it, if we're not, please, please talk to us about it.

Speaker C

Because I want to know.

Speaker C

I want to know what's going on with them and they appreciate that.

Speaker C

It's really about, you're going to screw up.

Speaker C

I call it the relationship bank account.

Speaker C

Bottom line is, if you're putting deposits into that relationship bank account on an ongoing basis, they don't divorce you when the proverbial hits the fan.

Speaker C

Right?

Speaker C

They'll forgive you, but you can't just be keeping it.

Speaker C

If it's transactional, they're going to dump you and move on.

Speaker C

If you're actually building a relationship, and they know that your carrier, being empathetic with them, helping with issues, then it makes a difference.

Speaker C

So that's how we would approach it.

Speaker C

So, hey, hey.

Speaker C

I won't say it's outside our scope.

Speaker C

I just say, if you're dealing with this, let's help you with that.

Speaker C

And it could be on a personal level.

Speaker C

It could be on a professional level.

Speaker C

It could be whatever the case is,.

Speaker D

You know, penny's in the jar and pennies out of the jar.

Speaker D

Right?

Speaker C

That's really what it is.

Speaker C

And success in life and love is in the details.

Speaker C

And so we always look at those details.

Speaker C

So I'm going to know your birthdays, your anniversary, maybe I landed your new client.

Speaker C

It was July 6th.

Speaker C

And your new client, one year later, I'm going to send you an anniversary acknowledgement.

Speaker C

Hey, happy anniversary.

Speaker C

It's been one year since we've been working together.

Speaker C

I'm going to know your special occasions.

Speaker C

I'm going to know the anniversary of your company.

Speaker C

I'm going to.

Speaker C

I'm going to be looking for touch points where I can go outside the scope of service and level up those touch points to where, you know, I'm thinking about you when there's no transaction in play.

Speaker C

And I think that becomes.

Speaker C

That's our motto.

Speaker C

That's how we work with it.

Speaker D

I love that in my context, in professional services, the senior people that you work with as clients are often quite.

Speaker C

Lonely at the top.

Speaker C

Lonely.

Speaker D

They're at the top.

Speaker D

It's a pyramid, and there's only one or two or three of them at the top.

Speaker D

And it's often quite political and competitive at the top, 100%.

Speaker C

I get asked by major corporations and they'll ask me.

Speaker C

They'll go, what do you think of this?

Speaker C

And I just tell them the truth.

Speaker C

And they go, why won't my own people tell me that?

Speaker C

And it's just because they're protecting their butts or silos.

Speaker C

They don't want to lock in.

Speaker C

And it is political.

Speaker C

So one of the advantages of having a third party or an outsider is paid to tell the truth and just say, hey, you know, yeah, here's your problem.

Speaker C

Fire hr, whatever it is, and.

Speaker C

Or HR is your outsource it, whatever the case is, and get to it.

Speaker C

Let's talk about that because it's.

Speaker C

I wanted to focus on a little bit on extreme environments and the first step.

Speaker C

Time moves fast here on these shows, and I love the conversation.

Speaker C

So we want to pull some wisdom from your background and Give some value to the audience this way.

Speaker C

But.

Speaker C

So in addition to your corporate and academic life, you're an adventure motorcyclist.

Speaker C

I'm a motorcyclist myself.

Speaker C

You're an extreme skier, lives at the end of a dirt road.

Speaker C

What has navigating high risk terrain taught you about rapid trust building, building and situational awareness that applies to a boardroom.

Speaker D

Okay, I love that question, but let me slow down and ask you what you ride.

Speaker C

So I was motocross guy for, for years.

Speaker C

So road motocross.

Speaker C

And then I was motocrossing with my son.

Speaker C

Then I used to come off the bike every once in a while, so my Last one was 400 and I'd hit the berm and roll and then as I got older and bigger, I'd hit the berm and not roll.

Speaker C

So I've got a street glide now.

Speaker C

And so my wife and I both enjoy riding and feel awesome riding.

Speaker C

How about yourself?

Speaker D

I'm in, I'm in physio, I think more often than I'm not in physio.

Speaker D

Thankfully.

Speaker D

I was not a motocross guy, but I do enjoy.

Speaker D

I like long rides.

Speaker D

So yeah, we did Vegas down to Cabo and back in December we did Edmonton up to Tuktuktuk, the September the year before that.

Speaker D

And I've ridden my KTM 500 exc in Baja 4 times now.

Speaker C

Beautiful.

Speaker D

I'm not racing, I'm adventuring.

Speaker D

So I have a little adventure company on the side.

Speaker D

The entrepreneur thing is a problem sometimes.

Speaker D

And the tagline for that company is not go fast, don't die.

Speaker D

It's really go fast, go far.

Speaker D

How do you take that racing thing you had when you were 20 and combine it with the wisdom?

Speaker D

I'm now 58 and still stay on the bike in a way that is enjoyable and still tickling my need for speed.

Speaker C

Yeah, and I love that feeling on the face.

Speaker C

And like I said, for me it's about mitigating and the lesson I've learned from it.

Speaker C

So for me I was airplanes and motorbikes and I'm always mitigating.

Speaker C

So I pre flight.

Speaker C

So I use my pre flight, which I'm checking.

Speaker C

I'll spend an hour pre flighting a flight that's half an hour.

Speaker C

I'll spend two hours pre flight and flight.

Speaker C

So I preflight my sales calls.

Speaker C

I preflight.

Speaker C

What questions am I going to ask?

Speaker C

I don't.

Speaker C

I'm not attached to asking them all.

Speaker C

But I ask the same questions when I'm looking at a motorcycle or I'M looking at an airplane.

Speaker C

What's this was my tire pressure.

Speaker C

You know, my wife and I'll go out tonight after dinner, we'll go for a nice ride.

Speaker C

It's beautiful summer night.

Speaker C

And I'll check everything.

Speaker C

I'll have all my systems check.

Speaker C

And I'm asking the questions, all right?

Speaker C

So I have my awareness and my situational awareness.

Speaker C

That's what keeps me safe.

Speaker C

So people say, are you scared of risk?

Speaker C

Yes, always.

Speaker C

I'm not scared of it because I'm risk adverse, but I look at my situational awareness and I think we have to bring that into the boardrooms and into our audiences and in front of our audience.

Speaker C

So to me, there's a direct correlation.

Speaker D

100% Agree with you.

Speaker D

And I really like that you noted that you have your pre flight questions.

Speaker D

You don't feel like you have to ask them all.

Speaker C

No.

Speaker D

You're trying to make sure that it stays situational to your need.

Speaker D

But I've done avalanche training.

Speaker D

So in avalanche training, they talk about three factors.

Speaker D

They talk about the weather, they talk about the team or the personalities you're with, and then they talk about the terrain.

Speaker D

But for safe backcountry skiing, the only decision you can actually control is what terrain you're going after.

Speaker D

You might have a weather forecast, but it can change.

Speaker D

Yeah, you might think you know your team well, but somebody could lose it along the way or be having something going on in their life that just makes them either not ready for risk or even worse, too ready for risk.

Speaker D

And so when you're doing your pre flight from a flying term, or when you're doing your avalanche sort of checklist in advance, or if you're doing a client engagement engagement checklist, you really want to make sure you're focused on what are those things that are within my control and let's be ready on those.

Speaker D

And then I'm here because I'm smart.

Speaker D

I'm here because I'm qualified.

Speaker D

I'm here because I'm good.

Speaker D

I can handle the rest of it.

Speaker D

If I stay relaxed and in the moment and I focus on first backcountry skiing or riding a great adventure or in a meeting, a successful outcome for the client.

Speaker C

Yeah, no, it's well, and you, you've nailed it.

Speaker B

Really.

Speaker C

It's in the moment, it's being present.

Speaker C

So when you're riding a motorcycle and you're going to spay or you're in a terrain that's rough terrain or a dangerous terrain, extreme terrain, it's about being present when you're flying an airplane, you have to be present when you're fly fishing, you have to be present when you're skating.

Speaker C

So in your meetings, be present, listen, you know, listen to what they're saying, listen to what they're feeling, listen to what they need.

Speaker C

All right?

Speaker C

And listen from those perspectives and evolve when we can all evolve.

Speaker C

And I think, and actually my last question.

Speaker C

If a professional services leader or entrepreneur or business professional is listening right now and realizes that their team is losing deals at the pitch stage because they're over indexing on smartness, what is one tactical exercise they can run in their next team meeting to start fixing it?

Speaker C

And I'd highly recommend they can engage with you and come in because I know you can do that virtually or in person as well.

Speaker C

But what could they take and do that to actually start building that muscle, if you will?

Speaker D

Yeah, I would look at how quickly the team is jumping in with the next question and even worse, their next answer and focus on that.

Speaker D

43% Of successful professionals, sorry, successful professionals are speaking 43% or less of the time in the meeting.

Speaker D

And you can literally these days run otter on a call or in the meeting itself.

Speaker D

And after the AI recorder after the meeting is over, will tell you not only how often do you speak versus when your client spoke, but it can identify how often you jumped into the conversation while the client was still hesitating to provide something else.

Speaker D

Because their ums or their pauses are not an invitation to jump in.

Speaker D

They're actually an invitation to just slow down, count to five, and let them say the next even higher yield thing that's on the tip of their tongue.

Speaker C

Fantastic.

Speaker C

The book is from To Ally why Ambitious Professionals Lose Trust and How to Get It Back by Scott Armstrong.

Speaker C

The book will be available when it should be available.

Speaker D

Q4 this is my first book.

Speaker D

So the publishing adventure is almost like a dirt bike adventure in its complexity.

Speaker D

I'm learning lots along the road.

Speaker D

That one.

Speaker D

Yeah, but it should, it should be Q4.

Speaker D

It's into copy editing now and it'll, it'll make its way through.

Speaker D

But if people connect with me on LinkedIn, I'm happy to give away all of the thinking.

Speaker D

The book's not about making money.

Speaker D

It's really about making sure that the next time I chat with a lawyer or an accountant or a doctor, they do a better job as a professional.

Speaker D

I'd love to change the world.

Speaker A

World.

Speaker C

Scott Armstrong@winthequestion.com they can go visit their great website.

Speaker C

Lots of good information.

Speaker C

Lots of good insights and value bumps for our audience.

Speaker C

Scott, thanks so much for being our guest today.

Speaker D

I could stay on this conversation with you, Michael, for another hour.

Speaker D

I really enjoyed it.

Speaker B

As you are listening to this episode, what is one idea that you've heard that's caught your attention and why does it matter so much to you?

Speaker B

And who is one person who you can share that with, either sharing this episode or just sharing that insight that occurred to you while you were listening?

Speaker B

Perhaps it is that building professional trust requires a critical shift away from proving your own expertise and toward winning the question.

Speaker B

Or maybe it is that the most successful professionals speak less than 43% of the time, using intentional pauses to allow the client to share deeper insights.

Speaker B

Thank you for listening, for learning, and for investing in yourself so that you can become the best version of you.

Speaker B

If you found value in this episode, please write a review on Apple Podcasts.

Speaker B

If you haven't subscribed yet, please do so so you can get a new episode and start your week off right every Monday.

Speaker B

Until next time.

Speaker B

As you are listening to this episode, what is one idea that you've heard that's caught your attention and why does it matter so much to you?

Speaker B

And who is one person who you can share that with, either sharing this episode or just sharing that insight that occurred to you while you were listening?

Speaker B

Perhaps it is that building professional trust requires a critical shift away from proving your own expertise and toward winning the question.

Speaker B

Or maybe it is that the most successful professionals speak less than 43% of the time, using intentional pauses to allow the client to share deeper insights.

Speaker B

Thank you for listening, for learning, and for investing in yourself so that you can become the best version of you.

Speaker B

If you found value in this episode, please write a review on Apple Podcasts.

Speaker B

If you haven't subscribed yet, please do so so you can get a new episode and start your week off right every Monday.

Speaker B

Until next time.

Speaker B

This podcast is created and associated with Summit Media.

Speaker B

My Executive producer is Beth Smith and Director of Research Tori Smith.

Speaker B

The fee for the show is that.

Speaker C

You share it with friends when you.

Speaker B

Find something useful or interesting.

Speaker B

This podcast is subject to copyright by Summit Media.

Speaker D

Goodbye.