How to Ask a Proper Question

Episode 93: How to Ask a Proper Question, with Jody Sutter

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How to Ask a Proper Question? Win business and elevate your communication skills with our guide on how to ask a proper question.

How to ask a proper question? As the great Tony Robbins once said, “If you want to change the trajectory of your life … ask better questions.” Here at Predictive, we’ve taken that philosophy to heart — especially when it comes to working with our clients.

Today, we’re turning the spotlight on the art of questioning and how it can be a game-changer for your agency. In this episode of Sell With Authority, we focus on how to raise the bar of excellence in the questions we ask clients and right-fit prospects.

You see, in the world of proposals and client interactions, it’s not just about the pitch; it’s about asking the right questions at the right time. How can we map out questions, rehearse scenarios, and fine-tune our approach to help clients not just get proposals accepted — but truly understand if an opportunity aligns with their agency?

Here’s a stat that will grab your attention — the typical proposal acceptance rate for an agency hovers around 25-30%. That means a lot of non-billable time is invested in opportunities with a low probability of success.

But, armed with the right questions and a sprinkle of Conceptual Agreement, your agency’s win rate can soar to an incredible 80%.

Asking good questions may be simple, but not always easy. That’s why I invited Jody Sutter for an encore episode so she could share her insights and wisdom about which questions we should ask — and when we should ask them.

Jody is the brilliant mind behind The Sutter Company, a consultancy specializing in advising small agencies and marketing services firms on growth strategies. Her expertise lies in how to ask a proper question, asking questions and the kind of questions that break the ice, engaging clients in the process, and ultimately facilitating decisions that benefit both parties.

If you apply the wisdom Jody imparts in this episode, you will change the trajectory of your agency for the better — so you roar through 2024!


What you will learn in this episode is about how to ask a proper question:

  • Why questions play a fundamental role in the power of the pitch
  • How to ask a proper question that are helpful, not confrontational
  • Why the second best answer to a “yes” is actually a “no”
  • Jody’s expertise around the nuance of when to ask the framework questions
  • A few basic preparation questions you should be sending in writing to right-fit prospects


Additional Resources:


How to Ask a Proper Question: Full Episode Transcript

Welcome to the Sell with Authority podcast. I’m Stephen Woessner, CEO of predictive ROI, and my team and I created this podcast specifically for you. So, if you’re an agency owner looking to fill your sales pipeline with a steady stream of right-fit prospects so you can sell more of what you do for a higher fee, well, then you’re in the right place. Do you want proven strategies for attracting a steady stream of well-prepared fit prospects into your sales pipeline? Yep. We’re gonna cover that. You wanna learn how to step away from the sea of competitors, so you actually stand out and own the ground you’re standing on. Yep. We’re gonna cover that too. Do you want to future-proof your business so you can navigate that next challenge that you know is going to come your way? Well, absolutely. We will help you there as well.

I promise you each episode of this podcast will contain valuable insights and tangible examples of best practices, never theory, from thought leaders, experts, and owners who have done exactly what you’re working hard to do. So, I want you to think practical and tactical. Never any fluff. Each of our guests has built a position of authority and then monetized that position by claiming the ground, growing their audience, nurturing leads, and, yes, converting sales. But all the while, they did it by being helpful. So every time someone from their audience turned around there, they were given a helpful answer to an important question. So their prospects never ever felt like they were a prospect. I also promise you every strategy that we discuss and every tool we recommend will be shared in full transparency in each episode. So you can plant your flag of authority, you can claim your ground, and fill your sales pipeline with a steady stream of right fit clients.

Okay. So, if you’re listening to this episode on the day that it went live, it’s January 10th, 2024, and you’re most likely knee-deep beginning the first quarter push of kicking off new work with clients after the renewals and the holiday break, and actively, openly, actively working on new business. Given that, when I thought about how we might be the most helpful to you and your team for where you’re at right now, I decided to focus our time and attention today on how to raise the bar of excellence in the questions we ask clients and prospects. So, Tony Robbins, a while back, once said, if you wanna change the trajectory of your life, and I’ll say also business here. If you want to change the trajectory of your life, ask better questions. And I will tell you, when we’re working alongside our clients here at Predictive, we often map out questions and then rehearse various scenarios in order to help our clients get proposals accepted or to help them collect and extract the information they need from a prospective client so they can better decide if an opportunity is actually the right fit for their agency.

Learn more about How to Ask a Proper Question by reading this article from Jody Sutter: Test the Strength of Your Agency’s Elevator Pitch

How to Ask a Proper Question: Jody Sutter Introduction

In my opinion, assessing fit is critically important because the typical proposal acceptance rate for an agency is 25 to 30%, which means an agency is investing a ton of non-billable time toward opportunities that, candidly, have a very low probability of winning. However, with the right questions mixed with conceptual agreement, your win rate increases a quick setting of expectations. Here you’ll also see a number of proposals or your number of proposals being submitted decrease, but you’ll only be providing proposals to write fit prospects. As a result, you’ll see your acceptance rate skyrocket to about 80% or more. Why? Because you took the time to ask better questions, and more specifically, you asked all the who, what, why, where, when, and how Questions. Asking good questions is indeed simple, but it’s not always easy. That’s why I invited Jody Sutter to come back to the podcast for this encore so she could share her insights and wisdom about which questions we should ask and when we should ask him.

If you’re meeting Jody for the first time, she’s the owner of the Sutter Company, a new business consultancy that advises small agencies and marketing service firms on how to organize and operationalize their growth strategy. She’s also the author of the book A Small Agency’s Guide to Winning New Business, eight Steps to Winning More of the Right Kind of Clients. Jody is brilliant at asking smart and insightful questions that break the ice with a client, help them lean into your process, and then share what you need so both you and your client can make good decisions going forward. I promise if you take and apply the golden nuggets that Jody shares with you during this episode, you will change the trajectory of your agency for the better so that you roar through 2024. Okay. So, without further ado, welcome back to The Sell with Authority podcast, Jody.

Thank you very much. It is really wonderful to be back, and, I’m excited to talk about this topic ’cause it’s something I feel really strongly about, and that agencies can do so much more to control the power of the pitch by asking good questions.

Learn more about How to Ask a Proper Question by tuning in to our tutorial: The “HOW” Framework

How to Ask a Proper Question: Taking Control for Success

How to ask a proper question? I love how you just said that. The power of the pitch. Okay. Okay. So, as I mentioned in the Green Room, since this is your second Yeah. Time on, on the podcast, the So With Authority podcast, I wasn’t gonna ask you to share a path of the journey our the audience can go back to episode 17 and get that. Uh, but take us behind the curtain yeah. And, set a little bit more foundation here around how questions play such a fundamental role in what you just said, the power of the pitch.

Yeah. Well, what, so what I find found historically, and I’m probably guilty of this as well when I was running business development for design firms and agencies, is, that agencies tend to err on the side of being solicitous maybe a little polite, when it comes to getting an RFP or a brief or a request to pitch from the client. And, I think there’s a sense that they feel like, well, the client’s got it all figured out, And so the client steps into this role of power over the pitch. They’ve got the money; they’re setting the terms, they’re setting the guardrails for how we’re gonna pitch, and agencies because we tend to be people pleasers. We also feel like, well, we don’t wanna rock the boat. We don’t wanna appear like we are I don’t know, troublemakers or that we aren’t willing to be like playing nice in the sandbox.

And I feel like I’ve just used about a thousand metaphors, and I know when I listen to this again, I’m like, oh my God, Jody, stop with the metaphors. but I do think that a pitch shouldn’t be a one-sided situation. It shouldn’t be a one-sided conversation. Yeah. To a certain extent, the clients do hold the purse strings. They do have a lot of power, because typically also, you’re not the only agency pitching for this business, but I think there’s so much more control that agencies can assert that will be beneficial for both the agency and the client in the end. You know, you said in your introduction, one of the things, one of your purposes and passion with predictive ROI is to help fill the pipeline, which is awesome, but once it’s filled, I sometimes watch really great leads come in, and then they leave because the agency isn’t taking control and saying, now I’m gonna shepherd this lead through to a good close.

Learn more about How to Ask a Proper Question by tuning in to our tutorial: The “HOW” Framework

How to Ask a Proper Question: From Confrontation to Collaboration

How to ask a proper question? Okay. So let’s take it before we get into the actual questions, like, like as you were talking about the client has it all figured out, and we’re people pleasers, by the way, I loved your metaphors, and you said it shouldn’t be a one-sided conversation. So as I literally wrote in my notes, that equals confrontational. Now. I don’t think that it has to be so, and it shouldn’t be. So would love to get your insights and wisdom around Yes. Asking questions is super important, and it doesn’t have to feel confrontational. So do you think that that is an apprehension that maybe, oh, gosh, I can’t ask that question. If I did, I’d be confrontational. I’d be asking them something that’s rude. They do have it all figured out when really they don’t, and the questions will help you kind of ferret that out. But confrontational might be a hurdle, right? Not wanting to seem confrontational.

Yeah. I think that can be a hurdle, and I think it’s more psychological than actual. and I think sometimes it also is a bit of a practicing of how you would do it. I think if anyone is worried about sounding confrontational, sometimes I take it like I suggest taking it out of the sales situation. Hmm. So, I don’t know if anyone, well, one of my favorite sales books is Spin Selling by Neil Rackham. I think it was written in the eighties. And it’s a classic. Everyone who sells services should read it. He talks about a situation where a neighbor was talking to him about buying a new car, a new lawnmower, or something, and the neighbor observed how this car was not serving the purpose of the owner as well. And was able to say, like, well, wouldn’t a new car help you do this?

And wouldn’t a new car help you do that? And wouldn’t it help you avoid these things? And so, of course, the neighbor wasn’t trying to sell him a new car, but it actually served to persuade Neil Rackham, the author, that I gotta buy a new car. So I think it’s more like that. It’s like, if you were, I even do this with my own sales calls, if I were this person’s friend or colleague, how might I be advising them for the best outcome for all? And they also think too, is like, just in terms of your, for your own, for your, for like protecting your own time and your own and your own agency’s, um resources, what kind of information do you need in order to get back the best proposal for that client? That’s also sometimes the way you can frame it as well, I wanna make sure that we are responding in the best way possible for you. Can you help me to understand a few things?

So then that tells me your point of view around questions is the right questions are actually helpful, not confrontational.

Yeah. Yes, absolutely. Yeah. A great way of putting it.

Learn more about How to Ask a Proper Question by tuning in to our tutorial: The “HOW” Framework

How to Ask a Proper Question: The Power of What and Why Questions

How to ask a proper question? Okay. Alright. So, how do we get to that point? Uh, like, what are the right questions to ask? And I know that some of that is situational based, I get it. Uh, but like, what are the right questions to ask? And then, and then how do we know when to ask the right questions?

Yeah, that’s two, two great questions. So I think you’re right, A lot of times, it is very situational, and as you learn how to ask the right questions, it’ll start to become innate and easier. But initially, if you’re not if you’re feeling a little bit uncertain, I offer a very simple framework to my to my clients and the people I work with. It is based on the journalistic framework of the five whys plus the H, the who, what, where, when, why, and how. and I’d be happy to walk you through those and some of the questions associated with each one. Yeah. And again, once you start doing this more, your instincts will start to take over. Okay. But so I always say, let’s start with the what I know that the Simon Sinek thing is to start with why, but I’m gonna start with what If your, if your client, if the client is, is taking responsibility for themselves for a cooperative pitch, and they are also good at writing briefs, a lot of these what’s will be answered.

But then what are often to do with the basic stuff, like what is, what is the scope, what is the budget? but sometimes also what is the problem that we’re, we’re trying to solve? And that’s not always in the brief. So a client may come to you and say we need a better website, or we need our social media to be more active. And when I’m confronted with those quests or those statements, I often say, well, like, well wait, well, what’s the real problem? Why, why, what, what’s, what’s the problem that a better website’s gonna solve? And again, I think sometimes, I push my clients with that as well, but sometimes it annoys them. But yeah, like, well, the what, what, what is the real business problem? So what’s the problem? What’s the budget?

What’s the timeline? a lot of those things that come with the basic questions that go along with bant, if you’re familiar with that acronym, budget, authority, needs timeline. Then after those questions are answered, I guess the trick is not to feel, I don’t know if complacent is the right word, but the, what questions, I think, then lead right into the opportunity to ask a lot of why questions. And I love why questions. So when they do, when you can get them to articulate as best as possible, what they think the problem is, why questions might be like, well, why is the problem a problem? what other why questions? Why are you interested in talking to us? , why now? And sometimes just, yeah, just let’s sort of the power, anything that this a statement followed up by an intelligent why question can reveal a lot.

Learn more about How to Ask a Proper Question by tuning in to our tutorial: The “HOW” Framework

How to Ask a Proper Question: The Five Whys Technique for Problem-Solving

How to ask a proper question? There’s a technique that I also like, and I use and recommend called the five whys technique. Are you familiar with that? No. It was called the Five Why’s. And it was, I’m not gonna remember the name of the person who developed it, but I think it was a Swiss or German psychologist, I don’t know, a number of years ago. And the idea is very simple. The idea is that it takes about five why-based questions to get to the root of the answer. And so by asking the why and continuing the probe, the why, it forces you or the person you’re in dialogue with to peel away the layers of the onion and really think about, well, what, what is the truth thing that I’m trying to solve? I’m trying to ask.

Okay. So let’s use that as, so let, let me give that back to you, and make sure I’m tracking with you. I think I am, but I just wanted to be sure. So when you say, what’s the problem we’re trying to solve, solve, they give the answer. Then you say, well, why is the problem the problem? , they give an answer, then. Well, why is that important? Yeah. and then they give you the answer. Oh, and then, and then why? And then why continue to?

And why has that been a problem for now? So it’s, I get, it’s a problem. Okay, why is that? Well, why didn’t you? Well, hasn’t your team been equipped to solve that? Well, why hasn’t your agency? Yeah. So it’s, yeah, that’s smart. Finally, they, yeah, it’s a great technique,

But it really, it really shows how engaged you are in the process, as opposed to, what’s the budget? $200,000. And the questions stop and cease. Oh, thank goodness we’re going to totally slam the fact that they have a budget. We’re gonna slam dunk this thing $200,000 check into the first quarter when for Pete’s sake, you’ve just begun. Right? Yeah.

Learn more about How to Ask a Proper Question by tuning in to our tutorial: The “HOW” Framework

How to Ask a Proper Question: Navigating Client Conversations with Strategic Questions

Yeah. Now, I will also say that the other thing about questioning is that it helps people respond. Hmm. So, something with the what questions. Yeah. You ask the what questions. So you get the budget, and you get the timeline. You think, all right, I can go back to my team now and say, here’s what we gotta do. Of course, they, if they’re good, they come back with a lot of questions that you think, oh, I didn’t ask client that. The other thing about the why questions is that, ideally, they start some sort of a dialogue where you can then say, oh, well, listen, that’s really interesting. What you’re telling me is interesting, and I think it sounds like we might be really able to help if we were to focus here. Is that, is that correct? And to get them to validate things. So now what you’re starting to do in the pitch process is potentially carving out, a fast track, carving out a preferred partner track. ’cause you’re asking all the good questions, and you’re starting to develop in this conversation, your strategy for responding.

How to ask a proper question in navigating client conversations? I love how you just said a preferred partner track because you, through that process, might be pushing them or nudging them to think about things maybe they hadn’t even thought about before. And you’re really demonstrating that you deserve to own a strategic seat at that client’s table, right?

Absolutely. Yeah. And you and I are talking about this a little bit in our green room as well. So what happens if the client says A, actually no, that’s, that’s all wrong. We disagree that that’s not really right. Are you screwed? Like, is that when you go like, oh, man, I knew I shouldn’t be asking these questions, And I say, of course, no. Number one, if you really feel like if your, if your conviction is that they, they need to be, treating a problem in a certain way, then you’re probably not the right partner if they don’t wanna if they don’t wanna treat that problem the right way. Also, if they are that close to other expert suggestions, then they may not be the right client for you either. So it also serves to help you qualify early, whether this is a pitch you wanna invest in.

Was that the quote from Mark Duvall when you said, like, the second best answer to a yes is a no, I’m kind of butchering it.

Learn more about How to Ask a Proper Question by tuning in to our tutorial: The “HOW” Framework

How to Ask a Proper Question: Unleashing Agency Power

That may be butchering it too. It’s like, yeah, the second best answer to a yes is a no. Right? ’cause then now you can move on and start to nurture all the other potential leads that are cropping up because you’re doing all your marketing well and stuff like that. Yeah.

Amen to that. But I think it’s my guess, you’ve seen this a ton too, is that we as agencies tend to want to twist ourselves into a pretzel to make ourselves Yeah. The right fit for what the client needs, as opposed to what you had said at the beginning, like the power of the pitch, right? Like, I think we were talking about that right at the onset, the power of the pitch. And by twisting yourself in a pretzel to, to sort of make this work totally removes any sort of leverage or power or whatever that the agency actually has in the process, right?

Yeah. I’ll relate an interesting story, which actually, in some ways, illustrates the opposite. But we end up at the same point one of my clients is uh, an agency based in California, and they were trying to move it more into, packaged goods products. And they got a, they got an opportunity to pitch a, a new product that, that for all intents and purposes, was exactly fit, exactly fit their ideal client profile. So my client was really excited about this, and he talked to, the company, and they say, yeah, we wanna launch this new product, or we wanna go from launch to really get it out into the marketplace, expanding beyond the launch, and we have this much money to do so. And it was a minuscule amount. And so I’m having my coaching call with my client, one of the HD partners, and I think he was quite proud of himself.

He’s like, I’m just gonna say no because I know I shouldn’t pursue this ’cause there’s not enough money. And, and I said, well, that’s good that you know that you don’t want something that’s not gonna be profitable, but before you completely abandon this, why don’t you, before you completely say no, why don’t you go back and say, we cannot do this for the budget, but before we turn this down, can I ask you why is there, you wanna get from, from point A to point B, but the money that the budget that you have is not gonna do it for you? I say, I don’t care who you work with, whether it’s me or another agency, the money’s not gonna get you there. Why have you budgeted something so low? So that led to this conversation with the marketer saying, I’m so glad you asked that because, because I, so the, the marketer, she was long, seasoned resume worked for bigger companies, and she was actually trying to convince the CEO of this company who was a startup entrepreneur who didn’t really understand why you needed a lot of money to launch something.

Learn more about How to Ask a Proper Question by tuning in to our tutorial: The “HOW” Framework

How to Ask a Proper Question: The Power of Asking the Right Questions in Pitches

She’s like, I’m so glad you said that. I want you to sit down with us. Would you, would you be willing to sit down with me and the CEO and talk, just give us a little bit of a briefing on why, what a well-funded campaign like this looks like? And he is like, yeah, sure. And so long story short, or maybe it’s already a long story, he, they got the business, the budget was quintupled, and yeah, they got the business for, for about a year. And then I think the client did end, end up being a terrible client, end of firing them. But yeah, so that’s another example of, yes, where something seemed like it was a closed door. And by asking a few good questions, the door swung wide open for a fruitful relationship.

It takes courage at the moment to push and then, but not push in an offensive way, is asking good clarifying questions. So, oh, okay, we’ve gone through what, and we’ve gone through why did we finish.

So what is next in your process?

The next one is who? Be clear on the who. By that, I mean look at the individuals that are involved in this pitch. So if it’s a more organized pitch, you may get a brief, and it’ll probably tell you, here are the decision makers, here’s who, who are gonna be involved in the meetings. And usually, there’s a primary contact and a team behind that and really unfair, really opaque ones. You may just have the procurement person, and that’s a whole other reason, not to pursue that. And by the way, that’s a good way to question when you do talk to the procurement person if you can, why am I only dealing with you? Why are we not dealing with a team that’s gonna be actually doing this work? But anyway, we have to hear who, okay, so the who questions?

Learn more about How to Ask a Proper Question by tuning in to our tutorial: The “HOW” Framework

How to Ask a Proper Question: Mastering the Art of Uncovering Key Players in Pitches

Yeah. Who’s on the selection committee, who we’ll be meeting with, who are the stakeholders, and what are the roles in the pitch? That’s some of the questions. So, and as I these, these questions may sound like they’re the same kind of question, but they’re actually not. And one of the things I think we sometimes overlook is the importance of different roles on the client side. So you may think that the chief marketing officer, if they’re involved in this pitch, that’s a good thing, and that’s the person you need to build a relationship with. And on the surface, that might be true. But if this project is for a really specialized set of marketing services, like, I don’t know, TikTok marketing or campaigns on Amazon, and there’s a person involved who is more knowledgeable on the client side, digital head of digital marketing, the CMO may be making the decision, but it’s that digital marketer who’s actually really in charge of making the recommendation.

So you wanna be really smart about who, who has the control. And so you can ask those questions like, who’s gonna be deciding this and who, who, who are the stakeholders? And then you can look at it and interpret, and you can say, I mean, sometimes this also happens with big companies. If there is, um the board or public companies, if the board is involved for really big decisions or nonprofits, if the chairman, sometimes the chairman of the board is involved, and so you may be pitching like hell to the, the, the director of marketing. And without knowing that the chairman who’s gonna be weighing in at some point without knowing that she’s going to what’s important to her, then yeah, you’re actually pitching to the wrong person.

Okay. I’m gonna ask you to do a little bit of impromptu coaching here, Jody, because I, because I can feel sort of our audience bristling right here, right? It’s like, oh, for Pete’s sake, Jody, there’s no way I’m gonna ask who is in control, who’s making the decisions, da dah, dah, dah, dah. So I understand the importance of that. So, but, but take us by the hand, and yeah. And nudge us through this piece because my guess is our audience is putting up some resistors a little, or Yeah. Uh, whatever shields against asking those questions. Yeah.

Learn more about How to Ask a Proper Question by tuning in to our tutorial: The “HOW” Framework

How to Ask a Proper Question: Handling Decision-Makers Gracefully

Sure. So let’s say you are talking to the director of marketing. Okay. And she’s saying, like, I’m the one in charge. I’m organizing this. It’s my decision. Okay. The response might be something like, great, thank you. I understand. And we wanna make sure that we’re putting together the proposal that’s right for you. Now, we’re actually getting into a couple of other questions, but tell me a little bit about what happens. What do you need to do in order to decide on the agency? Is there anyone else that, and again, I dunno, it’s so much of this is situational, but, tell me a little bit about the process? Once all these proposals are submitted. Well, after that, we will all be going to the CEO, and we’ll be doing a big presentation to the CEO with our top recommendations. Like, oh, okay, so your CEO will be reviewing this. They need to somehow, you’re consulting, or they need to allow at least you to make the right decision. That’s great. Is there anything we can do? How can we help you prepare for that meeting? So it’s things like that listening, and again, going back to what we were saying before being helpful. 

Oh, I’m sorry. I didn’t mean to interrupt you.

Not at all. No, I’m done.

Okay. Just go back to like what we were talking about in the, in the green room, not asking questions because there’s a perception that it’s way or that it’s rude or pushy or whatever. So in that scenario, would it be rude, inappropriate, pushy, whatever, if the director of marketing says what you just said and then says, that’s awesome? Uh, we look forward to sharing our thoughts and ideas with you and the CEO at the same time. So how can somebody kind of orchestrate that in a, like that sort of situation, director of marketing and also the CEO? How can somebody orchestrate that in a way that doesn’t feel rude or pushy, or can they not? Do they just have to sort of respect kinda the chain of command and the hierarchy?

I think it depends on a little bit. So as an agency, I would also ma recommend that you have made decisions overall, about the criteria that you follow. So, one of your criteria might be that you do not enter a pitch unless you are really sure you’re talking to the decision-maker. Ah, and so you wouldn’t necessarily say that to that client, but it might be. Well, we have an opportunity to present to the CEO, and the answer might be no. Okay. interesting that, that’s, that’s, that’s unfortunate because we feel like we, and again, I’m sort of not necessarily saying the exact right words, but that’s unfortunate because we feel like we might be able to help you if we’re allowed to pitch. Or you might even say, well, that’s unfortunate because our policy is to pitch to the final decision maker. And so we respect your process, but we probably won’t be able to participate.

Learn more about How to Ask a Proper Question by tuning in to our tutorial: The “HOW” Framework

How to Ask a Proper Question: Asking the ‘How’ Questions in Client Relationships

Yeah. I like it. I like it because it puts all the cards out on the table in full transparency. And if they, and if the client says, Nah, no, and now sort of like a gatekeeper, that kind of stuff, I think that’s a red flag to what type of client they might be.

Yeah. Yes, exactly.

Challenge, challenging to work with. Okay. So we’ve gone through what we’ve gone through.

You may also be a little, like, empathetic with ’em. Like Yeah, we totally get it. It was probably really frustrating to have to allow, to have, to get your CEO to buy into this decision that you really have full autonomy over. We get it. How can we help you?

That was brilliant. That was really smart. That I think that that was a great way to so, so going back to when you were talking about spin selling, right? Yeah. and you mentioned that book from the eighties when you mentioned if I were this person’s friend. I think you just did. I think you demonstrated it brilliantly right there.

Really smart. So we went through, yeah, 100%. So, we went through what, why, and who. Yeah. So what’s next?

The next one is how or as I call it, know-how. So, like the why questions, the how questions tend to offer you an opportunity to dig a little deeper and get a broader or more nuanced understanding of the client’s level of commitment and how well they’re gonna perform as a partner. So a few of the how questions that I like are more about how, how, how they operate. So one might be, how will we know if we’re successful? How will you measure success if you get the business? Okay? how do you typically work with and manage your agency partners? What’s the internal process like? How will your team be willing to adapt their roles or their methods if we come back to you with a more effective approach? So yeah. Are you gonna be one? Is it a one-sided relationship, or are they willing to, to do, to adapt as well? So it also, I think, helps you sort of suss out dysfunctions amongst the client team as well. and again, raise red flags that, as I say, will help you understand whether are they gonna be a great partner. Are they gonna be desperate or are they even gonna be the types of people who just never return your calls?

Learn more about How to Ask a Proper Question by tuning in to our tutorial: The “HOW” Framework

How to Ask a Proper Question: Setting the Standards

And I love the fact that, so each of these questions that may be digging into, to each one here, when you said how you’ll measure success, I love that from the standpoint of, like, what are the criteria, the, the vital metrics that both the client and the agency are going to use to prove that their work together is actually moving the needle. And that it’s not subjective, that it’s not ambiguous, that there are actually clear metrics that both teams or the collective team can use to be able to celebrate the wins and make adjustments when it’s not going so great. But I feel like when that’s all out on the table in full transparency from the beginning, then it’s not a, oh geez, we’ve been working together for four months now. The client’s not happy, but we’re not really sure why. Right?

Yeah. Or like an unpleasant surprise, like, oh, what do, what do you mean? It was about generating a certain amount of revenue. We just thought it was about generating a higher level of awareness. That’s probably really broad, and I hope that that situation is exceedingly rare. Yeah. But probably does happen.

Well, and then, and then your next question in, in the how category, how do you typically manage agency partners? Yeah. I think that’s brilliant because, that exposes or potentially exposes like, again, are they going to be the right fit? Like, oh, we meet every six months, as opposed to on a weekly basis or whatever the answer is to that. But, like, asking that question takes courage, but the answer to that question is gonna be really important.

Yeah. I mean, they’re asking you that question: How do you manage us? That’s a standard set of questions in RFPs. And so yeah, I want to allow you or encourage you to flip the switch a little bit, flip the script a little bit, and ask them the same things.

Learn more about How to Ask a Proper Question by tuning in to our tutorial: The “HOW” Framework

How to Ask a Proper Question: Navigating the Where and When in Client Relationships

And then your third question, how will your team adapt if we come back with a better approach, a better solution, a better strategy? Again, I think that that is a really smart question, too, because essentially what it says is, are you gonna treat us like a vendor, or are we actually a strategic partner?

Yeah. And I actually, that question I adapted, I guess I started asking it of my own clients since a lot of what I do is coaching and offering different frameworks, different approaches and I probably took it from one of my coaches, but it’s this notion that if someone is, for instance, in my case, and probably in your case too, if someone is hiring us, then the only way they’re going to get out of it what they put into it. And so we wanna be suc you, and I wanna be successful with our clients. And so that’s become a really important question from, from the beginning to say, if I show you that you’re doing something wrong and I can give you a better way of doing it, but you don’t change your habits, then that’s really up to you. That’s not necessarily saying that my approach is ineffective. And so that also helps me keep people accountable, and I think that agencies can adapt that question as well.

Oh, this is so great. So we’ve covered what, why, who, yeah. And how, is there anything else in your question framework that you think we should we should tackle?

Yeah, so then there are the where and the when questions. Okay. And these tend to be, more logistical, but still, they’re important, especially if you are an agency that is involved with sort of multi-layered pitches that go on for weeks or months with different deliverables. so some of them are pretty obvious, like, and sometimes the brief will answer these questions, like, when do we need to submit our proposal? Uh, where this is now that we’re actually going back to a few more live meetings, but okay, where will we be making our final presentation? when will we have the opportunity to interact with you and your team during this process? Okay. Um sometimes also these questions will provide opportunities for more why questions. So questions like, yeah, what, how, when, yeah, when and where are we going to be?

Learn more about How to Ask a Proper Question by tuning in to our tutorial: The “HOW” Framework

How to Ask a Proper Question: Strategic Pitch Logistics for Success

Are we gonna be meeting with you may elicit information that is not ideal. so one of the examples that I use are things like, sometimes, the seemingly unreasonable restrictions that clients can put around a pitch, like you’ve only got 15 minutes to summarize the last three months of pitch work, or, and this actually happened, this is what a real, real client, they had they were a Canadian agency. They were pitching a tourism authority. They had eight slides for their final presentation. Okay. Unfortunately, I met with them after they made their presentation, and I knew right away exactly why they were only allowed eight slides because I’d seen it, and I’d seen so many similar situations. They were only allowed eight slides because I thought that eight; that client has sat through so many endless 120-slide presentations that went on and on and on.

And the last 10 minutes, we’re like, oh, we’ll get through the last 70 slides really fast. And it was a terrible presentation. So, I mean, I didn’t know, like that was my assumption, and it did turn out to be right. And I remember seeing, but what they did is they, rather than saying to themselves as the agency, how can we alleviate their fear that this is gonna be an endless, boring, overly detailed presentation? What they did is they said, how can we stuff everything into eight slides? And, it was a terrible presentation. They didn’t get the business. Yeah. So, that is where, the where, and the win the logistics will also illustrate, some issues that you probably want to probe into a bit further. Sometimes. Not always, but

Yeah. Well, when you shared that, it made me think of a lot of people who have been attributed to this quote, but Mark Twain is one of them. When he said, yes I would’ve written a shorter letter, but I didn’t have the time.

Right. But, it’s true. Like, like what you just illustrated right there the client wants eight slides or whatever the framework is, but that doesn’t mean cram 70 into eight.

Learn more about How to Ask a Proper Question by tuning in to our tutorial: The “HOW” Framework

How to Ask a Proper Question: When to Ask the Right Questions

And it’s still, and yeah, I think one of the great things about that Mark Twain quote is it says to take the time and edit. But I think there’s also a bigger thing, which is sometimes what they’re asking for isn’t what they’re asking for, right? So, the explicit request was to keep it to eight slides. The implicit request was, please put your pitch into a format that is easy for us to interact with digest, and understand.

Amen to that. So the,

Oh my gosh. Wow. So we’d love to get your advice on, so you’ve given this framework of amazing questions that will absolutely help us change the trajectory like we were talking about at the onset of our conversation. But we’d love to get your advice around when, like, are these in, one meeting. Are these in multiple meetings? And I know that some of that is situationally based. It’s like, oh, we’re gonna have clarifying q and A call-in for all the RFP recipients. I get that. So would love to get your expertise around the nuance of when do we ask all these questions.

Yeah. So I think that why questions, the what, and the why are Ty Well, why questions I think are always in season, but I think initially you want to, I think it’s always, it ties back to what is your objective. Hmm. So, at the early stages of a pitch, your objective is multi-fold. One is to qualify this client and this opportunity enough so that you can go back, brief your team, and put together a really good pitch. so you probably, may not wanna get bogged down with some of the where-in-one questions if that’s just gonna get in the way of having a really, quality conversation as you get closer. And then then the other thing that may also, that it may, well, I don’t know. You know, I think I was just thinking about the who questions as well, and I think those are actually pretty important to answer early on as well. So it’s not so much which questions to ask at which stages, but it’s almost more like you want to keep all those questions in mind, and as you move through the stages, you get a little bit deeper into the nuances.

Learn more about How to Ask a Proper Question by tuning in to our tutorial: The “HOW” Framework

How to Ask a Proper Question: Balancing the Framework

Okay. So I think what I’m hearing you say is hey everyone, you should take these questions, put them into like a toolbox, put them into a framework. Put like literally printed. And, so that when you and your team are going back and forth with a prospective client, you can sort of have a cheat sheet, of recognizing having, having the skill sort of expertise of recognizing what stage in the process we’re at and what is the next right question. But if we’re winging it and we don’t actually have them in writing, we’re gonna miss something. and then we’re gonna maybe pay for it later with a lot of non-billable time, and we don’t get the win. Right.

Especially if you are fairly new to the pitch. You know, if you’re either a more junior team member who’s been asked to run business development, but even sometimes for agency owners who maybe have spent a few decades. Doing great work for bigger agencies and now they’re starting their own agency, and they just need to start building some of those basic skills that someone else handled in the big agencies. yeah. Really smart, smart. I think I will end up with something okay, though. A little bit, maybe paradoxical or hypocritical. I think having these questions, having the framework is helpful, writing them down, anticipating, what you wanna ask. By the way, that’s something else that’s really handy in the spin-selling book. They give you a framework for coming up with at least four why questions. And it’s much better. I’m not gonna, I don’t wanna ruin it because this, they explain it better in the book, but it’s really useful to prepare even if, even if they don’t come up, it gets, you start to think about being inquisitive. But here’s the downside of having a questioning strategy. Okay. What I sometimes see is people people may feel they will overcompensate. So I also want to say that don’t question at the expense of listening and responding.

Love that.

So yeah, if you find that you’re asking all the questions, ’cause your checklist says, well, I gotta ask these 15 questions, and you’re not attuned to the fact that the client’s like, I wanna move on, then it’s, it could potentially backfire.

100%. I love it. It’s like having a framework that is flexible, not a cage. Oh, I just asked Jody question one. Okay, she’s done. Great. Question two, Jody. Right? Because then, that just shows you are probably not a seasoned business person. Yeah. But, but then, but then having these mapped out and then being able to pick and choose with flexibility so that we can listen and then respond like you just said. Yeah. So that we’re flexible with that also, then it reminds me of a miss that I just recently made. Like, I’ve been doing this for a while, right? Like, I would like to think that I ask the right questions. The other day had a meeting with a prospective client, and then I looped back to Hannah on our team Hannah Roth, who’s our math scientist and strategist here at Predictive.

Learn more about How to Ask a Proper Question by tuning in to our tutorial: The “HOW” Framework

How to Ask a Proper Question: Smart Questions for Successful Client Meetings

And she runs what we call Right Fit Clients University. And so I loop back to Hannah, I said, I think we have somebody to talk to about Raffa clients University. She goes, okay, great. where do they currently get their clients from? And I’m like, that’s funny. I don’t, I don’t know. I didn’t ask. She’s like, okay, great. How niched are they? Yeah, I missed that one too. And so, then she started asking me these questions, and I’m like, oh my gosh, when in the world did we talk about, you know? So it’s like it’s, I think what you’ve given us here is a brilliant set of questions that if we actually have the courage to ask or if we are courageous, but then also having them top of mind, which was my issue a few weeks ago, having the questions top of mind so we don’t have any gaps that then gives us the opportunity to have a really good at-bat with a prospective client. Right?

Yeah. You know, some things, I’m not sure how often you really have an opportunity to do this, but also what I found in my success in my business is to also have a few questions that you send in writing to the client initially. Now, sometimes, again, for really bespoke things, if you’re responding to an RFP that you might not have the opportunity, but if someone, especially if someone is coming to you in a, um an, an un unsolicited way, so they’re reacting to a blog post or a book or, and they’re like, Hey, I’ve heard a lot about you. I wanna have a meeting, and you’re great so that we can be as prepared as possible and really focus on your issues. Would you be willing to ask a few ques answer a few questions? Like Yeah. And some of those basics, like, do you have a niche? Where do you currently get your clients? That kind of stuff.

Oh, it’s fantastic. Really great. I know we’ve covered a lot, but before we go, before we close out and say goodbye, brilliant, Encore, do. Is there anything you think we might have missed? Uh, any final recommendations? And then please do share with our audience, Jody, the best way to connect with you.

Yeah, well, I think we probably did miss some things, but I think you’re right. I think it was pretty comprehensive, and I’m also a big believer in not overloading people all at once. So hopefully everyone will be okay with it, but I would say, I’m sure you’re, you probably have a very active audience. I’m sure if they’ve got questions, they’ll let us know. and you feel free also to forward any of those to me or connect with me directly. So you can reach me at Jody. And that’s JODY, [email protected]. I’m also on LinkedIn at Jody Sutter. I do offer a complimentary 45-minute consultation if there is anything that you would like to talk about or just explore working together, I’m always happy to talk to now almost any agency owner or agency leader.

Okay. Everyone, no matter how many notes you took and fully bananas, like took, I took a bunch. Uh, Jody, I think you gave me eight pages of notes. Wow. I’m, I’m not joking. Yeah. Eight pages of notes. No, but no matter how many notes you took or how often you go back and re-listen to Jody’s words of wisdom, which I sure hope that you do. You have to take it and apply it. Put these questions in this framework into practice because when you do, you will change the trajectory of your agency. And Jody, we all have the same 86,400 seconds in a day, and I’m grateful that you said yes for a second time to come on to the show to be our mentoring guide. Thank you so much, my friend. 

Thank You. I’m very grateful to be asked. Thank you, Stephen.

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Sell with Authority Podcast

The Sell with Authority Podcast is for agency owners, business coaches, and strategic consultants who are looking to grow a thriving, profitable business that can weather the constant change that seems to be our world’s reality.

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