The Secret to a Winning Proposal

| 25-min read

Want to know the secret to a winning proposal?

It’s all part of the Proposal Oreo Strategy from my Domestika course, Writing a Winning Proposal. (Watch the trailer!)

Of course it’s not quite as simple as that, as with anything of value. But there is something you can do to give yourself that leg up.

Actually, it’s not one thing – it’s a process, because it is the process that’s important.

I call that process, The Proposal Oreo Strategy. And in Episode #456 of the Marketing Mentor Podcast, I talked with web designer, Mary Maru, and content strategist and writer, Rebekah Mays, about what their proposal process involves and exactly how they do it most effectively for themselves. 

So if you want to take a baby step in the direction of winning more proposals, I suggest testing a real time proposal presentation on a practice prospect – or a real prospect, if you dare. I think you’ll find it to be surprisingly effective.

But first, listen here (or below) and scroll down to read the transcript.

 

And if you like what you hear, we’d love it if you write a review, subscribe on Apple Podcasts and sign up for Quick Tips from Marketing Mentor.

Read the transcript of "The Secret to a Winning Proposal" 

ilise benun

Hi there. This is ilise benun, your Marketing Mentor, and this is the podcast for you if and only if you are ready to leave the feast or famine syndrome behind. And I mean, for good. 

Want to know the secret to a winning proposal? Of course, it's not quite as simple as that, as with anything of value, but there is something you can do to give yourself that leg up. But it's not one thing, it's actually a process. Because it is the process that's important. And I call that process the ‘Proposal Oreo Strategy.’ And in today's episode, I talked with web designer Mary Maru and content strategy and writer Rebekah Mays about what their proposal process involves and exactly how they do it most effectively for themselves. So, listen and learn. 

Hello, Mary and Rebekah. Welcome to the podcast.

Mary Maru

Thank you.

Rebekah Mays

Thanks for having us.

ilise benun

Yes. All right, well let's start with Mary. I'm going to ask you both to introduce yourselves, and then I will share what we're doing and why I chose you for this podcast. So, Mary, tell us who you are, and what you do and for whom, and how long you've been in business.

Mary Maru

So I'm Mary Maru, and I work mostly with professional service firms like lawyers, architects, marketers, therapists, that sort of professional service business. And I create smart websites that are designed to attract and engage more of their ideal clients. I started my business in October of 2010, so I'm coming up on, if I'm counting right, my 12-year anniversary.

ilise benun

Awesome. Congratulations. You're doing something right, clearly.

Mary Maru

Something.

ilise benun

Something. We might talk about what exactly. And Rebekah, welcome, and introduce yourself, please.

Rebekah Mays

Yes. So, my name is Rebekah Mays and I help sustainable brands, mostly in the eCommerce space but also a little bit of B2B, and I help grow their leads in sales through SEO, content strategy and writing.

ilise benun

Excellent. And how long have you been in business?

Rebekah Mays

I've been in business for about two and a half years, but the sustainability focus and the SEO content strategy focus has only been in the past several months. So yeah, kind of looking forward to this next stage for my business.

ilise benun

Yes, constant evolution. I think we all have learned that, by now, whether you're two and a half years in or almost 12 years in, or for me, almost 34, maybe almost 35 years in … I've lost track at this point. But it is a constant evolution. 

And we are here as part of the Creative Freelance Summit to talk about the secret to a winning proposal. And we may even disagree on what exactly that secret is, and we haven't decided if we're going to reveal the secret here, but we might. So keep listening.

But I want to start with the Proposal Oreo Strategy, because both of you who have been working with me and using the Proposal Oreo Strategy—so I just want to lay it out so people know what it is, and then we'll talk a little bit about each of the elements. 

So, the elements are two cookies and the cream, right? I love Oreos. We all love Oreos. And so, cookie number one is qualifying prospects. It's basically the first conversation that you have to qualify a prospect. And the cream is the actual document, your proposal, that you may or may not decide to do after cookie number one. 

And cookie number two, if you did the proposal, is on presenting the proposal in real time, which more and more these days is seeming very, very necessary. 

Let's talk about cookie number one. How do you qualify prospects? Mary, would you tell us first a little bit, right? A distillation of what is your process for qualifying prospects.

Mary Maru

Sure. Well, first of all, I have to start with how prospects usually come to me. I mostly get referrals from people I know because I do a lot of relationship development as part of my marketing strategy. And so they'll either come to me—which is actually the best kind of lead, or maybe I've met someone at an event or online like on LinkedIn. And there'll be some kind of initial communication whether a conversation, email, face to face. And it's during that initial communication when I'll discover that person needs help that maybe I can provide or not.

So the way I qualify whether or not I want to take the next step with them, which would be to do a one-to-one call to discuss what they need, I try to ask a couple of questions. Basically, try to find out what kind of problem they're trying to solve. And if they articulate something that seems like a match for me, and we seem to have a little bit of rapport, then we go to the next step. 

If they need something that is completely out of my expertise, I will most likely let them know that that's not something that I do. But sometimes I want to talk to them anyway, because if what they say sounds like something someone I know specializes in, it's just a great reason to send this prospective client over to someone in my network. So that's basically what my process is.

ilise benun

And one of the things I hear in what you've just described is that when someone comes to you—maybe in response to some marketing that you've done or as a referral, word of mouth—your reaction is not: "Oh my God, they want me," as much as "Hmm, that's interesting. Let's have a conversation to see if it's a good fit." Is that accurate?

Mary Maru

Exactly.

ilise benun

And I think that's important and I want to highlight it, because most people, especially when you're just starting out, think to themselves: "Oh my God, they want me. What do I have to do? How do I have to perform? How am I going to get them to choose me?" 

And the whole premise of the Proposal Oreo Strategy—and actually of being self-employed, from my point of view—is that you get to choose who you work with. And therefore, it's really important to have a process by which and through which you qualify your prospects to decide: 

  • Can I help them?
  • Do I want to help them? 
  • Is it a good fit based on all the different criteria that are specific and unique to you?

So that's not really a question, but feel free to respond.

Mary Maru

I love the way you just summarized that. And I want to add to that. That when having those initial conversations, its' not even really about me. I mean, they may have questions for me, but it's really about giving that person the time and space to express themselves and who they are and what their problems are. Because people just really love to talk about themselves. And if I take up a lot of air space trying to put my marketing and selling cap on from the get-go, I run the risk of alienating the other person and making them feel like they're not being heard. So I try really hard just to keep my mouth shut as much as I possibly can and absorb whatever it is that this other person is trying to say to me.

ilise benun

I love that. Rebekah, talk to us about your process and how you qualify prospects, or how you think maybe differently about what we're talking about here.

Rebekah Mays

Well, first of all, I love everything Mary just said. I think it's so true that we have to get them talking as much as possible and make it about them more than it is about us. 

But I'm at a little bit of a different phase in my business, so I don't have lots of referrals yet. So a lot of the people that I'm talking to are people that I have reached out to. And so, what's kind of cool about that is that I've already qualified them to some extent because I'm not reaching out to just random people. I'm reaching out to businesses that are maybe in business networks that I'm a part of. I look at their niche, their location. So I'm trying to see if the time zones will work because I'm based in Europe. I'm looking at how big of a team they have because that can also play a role in how well we're going to work together. And those are the initial things that I'm looking at when I reach out to people. And then, of course at any time, I'm also just trying to get the general vibe of how we are. If we do talk, then I can learn a lot about them from that and just see, is it also a personality fit?

ilise benun

And I know also that both of you have questionnaires that you … I'm going to choose my words carefully here … ‘invite’ prospects to fill out or perhaps require prospects to fill out. 

Rebekah, how do you deal with and handle the questionnaire and what are you looking for on your questionnaire?

Rebekah Mays

So my questionnaire is on my Calendly scheduler. So when people are booking a call, they have to fill out the 10 questions or whatever it is to book the call. I have had a couple of people be a bit lazy about filling it out and not giving a full answer. And at this point, I'm not too much of a stickler for, "Oh, you have to do this." Because I'm more just interested in having the conversation, and if they're not filling it out, there may be a reason for that that I want to dig into in the call. 

For me, it's really a way to prepare for the conversation, because I am pretty early in my business and I want to know what kind of project are they interested in, and the more info I can get from them, then the more I can prepare for it and hopefully have some good answers for them.

ilise benun

And so do you ever have people either refuse to fill it out or say, "No, just give me your price," or something like that, since you're the one reaching out to them, they're not coming with a need necessarily?

Rebekah Mays

I know I do have a lot of people who just want a price and they don't understand why they would need to talk to me. And in that case, I just explain a little bit about a couple sentences about why I have that process in place. And if they're not ready to move forward on it and have a conversation with me, then that's fine. But they're not the best fit for me at this point, so I don't worry about it when they don't go along with it, but I'm not going to work with them.

ilise benun

So it's information. It's a red flag. And it's just one of the things you're looking for, it sounds like, to determine who is, in fact, of all the people you've chosen, who is or [who] kind of graduates to a better fit for you.

Rebekah Mays

Right. And then the conversation, the ‘discovery call’ as I call it, is really what's going to help me decide: “Okay, is this a good fit? Do I want to keep moving forward?” 

And what's cool about this process, is that at any point I can say, "You know what? It doesn't look like we're on the same page about this." And I can walk away. And they can also walk away if they don't see that it's a good fit.

ilise benun

That's so interesting also, because often I find people imagine that if they're the one doing the outreach, then they're almost obligated to follow all the way through if the client says “yes” all along the way, as opposed to what I hear you saying, which is: “I'm still qualifying someone, whether I reached out to them in the first place or not.” And at any point, you can say: "You know what? Turns out, probably not a good fit."

Rebekah Mays

Um hmm. Yeah. And I think since I've realized that, I've actually softened my language a little bit in my initial outreach. So I'm not trying to act like I want to marry them in that first email, but it's more like, "Hey, should we have a conversation? Would it make sense to talk about some project together?" 

And that gives me at least the feeling like I have more flexibility to do whatever I need to do with it.

ilise benun

An out, as it were. Interesting. 

All right. Mary, what about you and your questionnaire?

Mary Maru

Well, I ask about the same number of questions that Rebekah does and …

ilise benun

Which is how many?

Mary Maru

10-ish. I haven't counted them lately, but I would say that it's about that amount. 

Some of them are really easy fill-in questions to start with. It seems very rudimentary, but I do ask whether someone wants to talk by Zoom or phone, because I have been on the receiving end of someone else's process where they don't straighten those details out in the beginning, and then the time for the call comes, and I'm just sitting there waiting, expecting the person trying to sell to me to take control of the situation and reach out. So I think it's really important to get that detail squared away right up front.

ilise benun

And I would just add, it seems like a simple detail, but I think it actually reflects in a very broad way on how organized you are, how professional you are, how much you think things through, how you've done this more than once. And it's one of the many ways to demonstrate your value.

Mary Maru

Absolutely. I couldn't agree more, and especially as a website designer, with the kind of work that I do, there are so many moving parts that if I can't demonstrate that sort of trait—my ability to project manage—from the very beginning, then I'm in trouble. 

But I do also ask a few open-ended questions. And another one that seems really basic but can be really telling for me is having the person explain to me a little bit about their business. And I leave it very broad and open to see what they come back with. 

Sometimes I'll get one very articulate sentence back about someone's business, which tells me: “Oh, this person has already done some marketing and positioning work, or they've worked with a professional to get there.”

Other times I may get some really long-winded explanation that doesn't quite really identify a specific focus for the business, which triggers me into thinking, "Hmm. I'm not sure if this person is really ready to work with me on a website." 

If they can't really explain what they're doing in the world for their customers, how are we going to get through content development and designing this marketing piece? It just is a red flag. So that's probably one of my favorite questions on my questionnaire.

ilise benun

That's really interesting too, because again, it's not like you're judging, "Oh, they're stupid because they don't know how to describe their business. Or they're smart because they do." But it's just information about whether or not they're ready for you and whether or not you're going to be able to help them of that. 

All right. Anything else about your questionnaire?

Mary Maru

Well, I do also have a dropdown multiple-choice question asking when someone may be ready to work with me. Starting with ‘right now’ or ‘in a month from now’ or ‘sometime this year.’ And based on what I've got cooking on my work schedule, if someone says that they want to start working right now and it's a big complex project, that may not be a fit for me. 

I may not want to send them away right away because if it's a big project, I might want that anyway. So it'll just help me to think in advance before a call with that prospect, how can I either massage what I've got going on my plate to make some availability for this project, or how can I discuss with them the pre-work that they need to do on their end before I actually become very actively involved in supporting them with their project. So it just gives me something to think about and to be prepared on before having that first more in-depth, as Rebekah calls it, ‘discovery conversation.’

ilise benun

And one last question before we move on to cookie number two, which is about money. In this qualifying process, Mary, how do you find out if they can afford you?

Mary Maru

Well, in another multiple-choice dropdown question, I provide a bunch of budget ranges, and it starts at “$10,000 or below” and then increases in $10,000-approximate increments up until 50,000 and above. 

It can be a helpful question, but to be honest, most people choose “$10,000 or below,” whether they have a bigger budget or not, because people just don't want to tell me, right up front without having that first conversation, how much money they have. 

So is it helpful? I'm not quite sure. I actually eliminated the question from my questionnaire for a while, and it didn't seem to make a huge difference in the quality of those initial discovery calls with prospects. However, somewhat recently, I had a call with someone who had a really big budget, so I knew this in advance. I cranked my numbers up a bit to accommodate that person, and they did check off the box for one of the higher budget amounts. So that was a really helpful piece of information to have.

ilise benun

Interesting. And I personally think it's an important question, whether they answer it in an appropriate or accurate way anyway, because it shows that you're not afraid to bring it up, and you know that there's money involved, and you're going to be professional about it, and you're asking from the get-go. I like that. 

All right. Rebekah, what about you? How do you find out if they can afford you?

Rebekah Mays

Yeah, I'm in a similar position as Mary where I'll ask it, and often I'll ask the money question on the questionnaire, and a lot of times they don't want to respond. But the times that people have responded have been really eye opening, and it just gives me a little bit of a heads up on how the conversation might go. 

Most of the time, I have to bring it up in the conversation and basically give them a few options. So ilise's favorite question is, “Are you thinking $500, 5,000, 50,000?” And often that gets a response and they'll give me a rough number, and then we can work from there.

ilise benun

Awesome. All right. We actually don't have a lot more time, but I do want to get to cookie number two, at least briefly, so we don't keep everyone in suspense, to talk about presenting the proposal—which I think is the secret or one of the secrets to winning a proposal. 

So let's see if we all agree or disagree or where we disagree. Mary, let me start with you. I happen to know that you do usually present your proposal in real time. So tell us how you get someone on a call and is it helpful? What is it about that, that you find helpful?

Mary Maru

Well, I love cookie number two.

ilise benun

Me too.

Mary Maru

It's fun and it's easy. And the way I get a prospect on a call is I'll make sure that I've gotten myself to a point with their proposal where I'm really comfortable, almost ready to send it out to them, but I don't, obviously.

So when I'm feeling really good about it, I just send a one- or two-sentence email saying something to the effect of: “Tying up loose ends,” or “Dotting i's on your proposal. Can we hop on a quick call tomorrow at 10 o'clock to go over it? Let me know.”

Nine times out of 10, I'll get a response back, right away, from that person saying “sounds good” or they'll offer an alternate time. 

On the rare occasion when somebody pushes back, I'll reply to their email and just explain that this is just part of the process and almost everyone finds this really helpful because it gives them the opportunity to ask questions on the spot. 

So that usually is enough to encourage someone who might be a little bit hesitant about the potential for a ‘sales call,’ which honestly, I don't really do. I'm not a salesperson; I'm a designer. So I just really love seeing that process happen because typically it is such an easy thing. And then we get on the call the next day or whenever and run through the proposal together.

ilise benun

And Rebekah, how do you handle this part of presenting the proposal in real time?

Rebekah Mays

Yeah, I usually actually try to schedule the call during the discovery call. So at the end, if we agree that we want to move forward, I just find it sometimes easier to already get a time on the calendar, maybe a week from now or whatever. 

But otherwise, it's similar and I have my document that I've created, maybe I'll send that to them just a little bit before the call so that they can quickly look at it. But really, I want to go through it with them, share my Zoom screen, and basically make sure they have a chance to understand what I'm proposing; ask questions. 

And I really love this actually, because I've actually had really good responses and people will give me encouragement, and you'll get the validation that you're on the right track. And people appreciate the time that I've taken to make it customized for them. And so if I just email that to them, I wouldn't probably get all of that feedback. And so I think it's a really brilliant way of doing it.

ilise benun

You love cookie number two, too.

Rebekah Mays

I do.

ilise benun

And I happen to know that of the four proposals that you've presented in real time, you've won all four, right, or is the number higher by now?

Rebekah Mays

No, that is correct. Yeah, it's worked really well for me.

ilise benun

And so would you say, this is the secret to a winning proposal, or something else?

Rebekah Mays

I think it is part of the secret, but for me, it's also this underlying principle that I think is why this process works—which is, at least for me, I am qualifying, really carefully, those who enter it, and I'm sure for Mary as well. 

So I'm only doing proposals for projects that I really want, for the prospects that are ready to move forward, and for projects that I think I have a really good chance of getting. And because of that, then, I want to give them the best experience I can in this process and give them a high-touch experience. And this is, I think, one way to give them that experience. I don't know of a better way, but I think that's, from my perspective, the thinking behind it.

ilise benun

Awesome. All right. Well, we're going to have to wrap it up here, but y'all have shared so much really interesting, helpful, specific information. That's what I love about what you're both doing and also what I'm trying to elicit from people on the podcast. So thank you so much. 

And Mary, would you tell people where they can find you online?

Mary Maru

Sure thing, ilise. I am at marymaru.com (and on LinkedIn too)

ilise benun

Very easy to remember. And Rebekah, how about you?

Rebekah Mays

Yes, my business is called Thrive Copywriting, so you can find me at thrivecopywriting.com or, of course, on LinkedIn, as well. Just with my name, Rebekah Mays.

ilise benun

With a K, not a C.

Rebekah Mays

Yes, correct.

ilise benun

Excellent. All right. Well, again, thank you both for this and for what you're going to share on the Creative Freelance Summit, which will complement this beautifully. I've designed it that way, and I will see you both very soon.

Mary Maru

Thanks so much.

Rebekah Mays

Thank you.

ilise benun

I just love the way they're implementing cookie number two and the fact that they love it as much as I do. As for a baby step, I suggest testing this real-time proposal presentation on a practice prospect, or a real prospect if you dare. I think you'll find it to be surprisingly effective and you may even enjoy it. 

So did you learn a little something? I hope so, because that's how this works, one baby step at a time. Before you know it, you'll have better clients with bigger budgets. Speaking of better clients, they're probably not going into fall in your lap. That's why I keep hawking my Simplest Marketing Plan. If you want to build a thriving business on your own terms, it's never too late to start.

The Simplest Marketing Plan 4.0 has six case studies and six lessons about how to use the three most effective marketing tools. You also get three different planners, plus access to the free monthly Office Hours group coaching session where you'll meet other creative pros who are practicing what I preach and taking control over their business and their life. Find it all in the Marketing-Mentor shop at marketing-mentor.com. I'll be back soon with more conversations with creative professionals who are doing what it takes to ditch the feast or famine syndrome. Until next time.

 

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