Do You Need Fancy Proposals?

hamyaw podcast episode title graphic for do you need fancy proposals.

One of the favorite titles I’ve given myself over the years, (and, by association, my esteemed colleague Margo Aaron), is “digital marketing heretic”.

It’s a cool way of summing up a truth that it took me a while to get comfortable with:

As a certified Easily Bored And Very Opinionated Human… I found a lot of “traditional” marketing how-to’s and requirements for being A Respected Business Person just didn’t work for me.

You Might Say I Like to Make a Statement…

Be professional in your emails and avoid swearing or sending a lot of ALL CAPS statements of support and enthusiasm? Meh.

Cover the stuff you “should” write about in your blog posts according to your profession before you allow yourself to write the fun stuff? Pass.

Wear business casual to conferences so people will take you seriously? How dare you disrespect my closet like that, those statement pieces deserve to see the light of industry day — take it back right now.

To me, most “srs business expectations” are a form of pageantry and buying into convention that I simply don’t find interesting, or necessary.

(This probably goes back to my public relations days, when I was told my pitches to media should be as stripped down and boring as possible…

The Proof Is in the (Stylish) Pudding

… And yet, the only time I saw responses to those pitches was when I was able to sneak a little style and story in there.


Marketing heretic-ism also means I’m generally used to blowback, and getting disagreed with — along with the general praise and relief others express when they realize that they, too, can flout expectations.

It’s part of the gig, and also helps me explore where I might be bending the rules for my own satisfaction… and where, on occasion, I miss the mark when it comes to why those expectations exist.

So I shouldn’t have been surprised when I tweeted about proposals a few months ago — and received almost perfectly equal numbers of “YES, THANK YOU,” and “Nooo, wait!” responses.

The Hot Take That Took Off

The tweet itself (which you’ll catch at the start of today’s #HAMYAW episode), was a quick-fire hot take on the reason why I believe most proposals that creative service providers send out are overkill.

In my estimation…

  • Most folks are just looking for a quick recap of what they’ll get and the price, anyway
  • Your selling should happen on the sales call — the proposal should never be seen as the way to “seal the deal”
  • Putting fancy proposals together can be a MEGA time suck that you don’t necessarily need to fret over

Naturally, my own experience has made me biased.

Who Really Needs a Fancy Proposal?

Over the course of my almost-10-year-career, I’ve put together mayyyybe 2-3 in-depth, PDF-style proposals.

Everything else has been in the body of an email… and with this strategy, I’ve sold hundreds of thousands of dollars worth of contracts over the years.


Shortly after I started this tweetstorm, my beloved co-heretic Margo slipped in to my iMessages (as she does) to tell me a very non-heretic thing:

Sometimes, that business pageantry stuff?

It IS necessary… in very specific contexts.

Because, even when YOU might not want to play by the rules, or, in fact, be way more interested in changing the game itself (hello!)…

… The fact is, other folks are still playing.

And sometimes? That means you gotta play along to get where you’re going.

Walking the Line Between Business Pageantry and Practicality

Where does that rule-following serve you… and promptly stop serving  you?

We get into all of this AND MORE in the latest episode of #HAMYAW.

Come for the twitter tea, stay for the Beyonce references — and let me know in the comments:

How do YOU feel about fancy, in-depth proposals?

Do you use ’em? Why or why not?

Did you ditch ’em?  What happened next?

We wanna hear all about it.

Now, get your fancy booty over there to subscribe, and catch today’s episode.

I can’t wait to hear what you think.

Write on,


Episode Transcript

Also hello Blue Memo.  

I know. I was like Ooh, we’re both wearing color today.  

All right.  

All right.  

Let’s get into it and see where we end up. Shall we? (upbeat music) 

Welcome back marketing nerds of the world. It’s time for another episode of HAMYAW, the blue episode. And today what we wanna talk about is pageantry and posturing in the online business space.

So, what we mean by that is there is a lot in the online space about what’s expected when you hand in proposals or whether you’re expected to look a certain way, or dress a certain way, or talk a certain way in order to be seen as professional and credible.

Now, a few weeks ago, I made a tweet that caught a little bit of fire in one corner.  

Little bit.  

A very specific corner over marketing Twitter. So I’m gonna show you guys that tweet. We’re gonna talk about it briefly. And then we’re gonna get into this idea of pageantry and posturing.

How much pageantry is necessary in the online space to seem credible? Is it necessary at all? Do we need any of it? Are we past this point especially in the era of Covid where everyone’s working from home anyway and no one’s wearing pants. How does this all work?

Before I screen-share, Margo do you have anything you wanna add to this piece of the conversation around pageantry?  

Like a peacock (indistinct) (laughs)  

It’s why we are in blue today. (laughs)  

No, show it. Let’s go.  

Okay. This is the tweet that launched 121 likes, 15 quote tweets and 16 retreats. oh, ah, ah, ah. Viral baby. No, I’m just kidding. This isn’t viral. But, it was nice to be recognized. So this topic was about

Happy to be nominated. (laughs)  

It’s an honor. Things I do not care about in proposal: PDF format. Email body is fine. Fancy graphics, bio, testimonials I’ve already read.

Your detailed step by step process I’ve already read. A brief summary will do.

Things I do care about in a proposal: What I get and price point. I would also like to add that there were a couple of caveats further down the thread.

(Margo chuckles) Just sort of saying you know, I respect pride in fancy proposals, but I skipped to the end every time. 

You know even if it’s for high-end, I’ve sold 20, 30K contracts with a few bullet points in an email. Put the 20 page PDF away. And I would like to sort of gaze upon this one more time before making it go away because I am always proud when I take a stand about something even if I have to caveat it because Margo and I ended up arguing for 15 minutes (laughs)

So before I get into my caveats, if any, let’s see Margo, talk to me about how you felt about this tweet.  

So I will caveat first with, this is how I read proposals (Hillary laughs) But, my point was it depends.  


And it depends because if you were working with conservative clients in fields that are really really buttoned up or fancy themselves fancy, you do have to have a fair amount of pageantry and play the game to make them feel comfortable.

Because a big part of what you’re communicating in those proposals has nothing to do with what they’re reading. It’s just the fact that it exists because you need to make them feel safe about spending money with you.  


And they feel like you’re a more established organization and firm when you can say, here’s all the things that I did, here’s my established process, here are all the people I did it for.

Like when you repeat over and over again and you emphasize those credibility indicators, then they jump to what you can do for them. They’re like, oh, that’s seasoned professional.

But it also depends like, real talk? Real talk on those big ticket items, those consulting firms. Sometimes they just want someone who they can show their boss.

You might’ve given it to the decision maker but they still have someone else to give it to. And so they need something fancy to take and show and be like, no, no, no, she’s legit. I promise you she’s legit. You know. (laughs)  

You know. And I think that was sort of the conclusion that I came to.  


So here’s something I wanna stress is that for a little bit of context, a lot of people who do the big propossibles, our propossibles, Whatever.


Propossible is so creative.  

There’s a new proposal platform for you.

We have Proposify, we have Better Proposals and now we have Proposible.

(speaks gibberish)

Anyway, million dollar idea. Hashtag trademark pending, hashtag don’t steal it, I’ll know. We have a date stamp on this, anyway.

Even though I’m anti-proposal, where am I going with this joke? Okay. So I’m not from the agency world and a lot of people who value proposals and see it as an essential part of the process are. Which I respect and understand.

But I’m a freelance, digital business native. You know I started my business at 21. And though over the years I don’t think I sent out a proposal in PDF format since I was working with a designer as a business partner which was back in like 2012.

So for me, you know even as my rates have gone higher and as my average contract has increased in size and scope, I’ve always only sent proposals in the body of an email with a breakdown about you know, short bullet points recapping the process. When we’re gonna have calls. What the deliverables are.  


What they can expect and the price point. And it wasn’t until I got a little bit deeper into you know hiring subcontractors, working with other creatives in the space that I realized how detailed people’s proposals were, and in my opinion for a number of my students how much time they were wasting.  


You know putting together these huge elaborate 20 page proposals for someone who is, you know, a solopreneur like me, who’s just going to be like, “Okay how much is it going to cost me?”

But I think that when you take some of the busy work out of business it’s often helpful and frees you up to do other things. So that’s part of why I made the tweet. But it’s also because I’m not from a school of business owner that values that. You know

No, I get it. I’m like this is where the conflict is because I exist in your world and I also think about me.  

My world, eh? (laughs) It’s mine.  

Our world that we’re creating.  

No, no. Mine.  

Of course.  

Taurus versus Leo here on HAMYAW.  

No. But like I agree with that. Like there’s nothing more annoying to me than the posturing that is necessary.

Like right now, I have a friend applying for a job. And the amount of PDFs he’s putting together that say nothing. I mean they absolutely say nothing. And the hiring manager is like, this is fantastic. Thank you so much.

It’s like the hiring manager’s posturing and he’s posturing and then they meet in the middle. They both kind of agree this is bullshit they were doing to move to the next stage. It’s like a complicit understanding.

I was of the opinion when Hillary and I were fighting at this that you do have to play the game. Hillary’s of the opinion, gotta change the fucking game. And honestly, I agree with her.  


I just think that it really does depend on your stage of business. When you were at a level where you can say fuck the rules, I think that you have to know what that level is.

So some degree of posturing I think it’s also important for yourself. Like you take yourself more seriously when you have documents that you’re proud of. Now,  


This is not to say it’s okay to get carried away in minutia. It doesn’t matter if it’s fuchsia or magenta or blue, or like whatever. Like those little details like fine you want to create a brand expression your assets should match.

Of course. There is something to be said for that.

But I do think like I know that I’ve had bigger ticket items that have sold in two page documents. But it’s because I was working with someone who was in our world.  


I don’t think that that’s possible in the corporate world.  

I’ve done work with agencies in the past and it hasn’t been a problem. But in terms of like big corporations with multiple stakeholders you know, gigantic teams, you know, while I have worked within those organizations it’s not been something where that’s required a proposal of that you know stature and weight.

But I think also there’s a lot to be said about having the information packet being floated around.

Because there’s multiple stakeholders, they’re going up the ladder and that I get. But I think for me, it was a lot of frustration about like why I had left the agency world in the first place. It’s that I hated the bullshit.

And like naturally I gravitate to things that are simpler and straight forward ‘cause I have an extremely short attention span. So we talk about this in the context of posturing and pageantry, right.  


And I think that the online space is essentially, you know anti-pageantry in a lot of ways because, you know we don’t worry about wearing suits and ties to conferences.

There’s nothing that benefits us keeping it formal. Because there’s no one upholding those old, tiny, just the way we do things systems. We’re going through things and kind of creating everything on our own.

But I think pageantry shows up in different ways in the online space as well. And this is something that I’ve fallen for in the past.

So, we were talking on another episode about my course. The Wordshops and how I spent $10,000 launching that course. I haven’t had to spend $10,000 to launch a course since.

But the reason why I did it at the time, was because I thought I had to. I wanted everything to be the highest production value so people would take me seriously.

I wanted the fancy graphics, the fancy video. But at the same time, I have made more money on launches that have been out of a Google doc and a simple email.  

Yeah. Yeah.  

And so I think there’s also that disconnect. Is that there’s a form of pageantry we get tired of in the online business space as well.

We all wanna be polished. We all wanna be shiny. But at the end of the day what makes the sale?

It’s us. And it’s our skillset. And it’s what people know of us previously. It’s the sales call where you should be doing most of your sale.  

And the relationship.  

Yeah. And the relationship.

So I think that’s another reason why I can be a stick in the mud about proposals needing to be shorter and more to the point. But I think there’s pageantry everywhere when we have to figure out what we want to buy into.

Because I love great branding. There are people who are like, I don’t even need a website. Branding is for idiots. Spending is the touchy feely side of marketing. And that’s also not entirely true.

So, I would like to add that was where I finally rested with the proposal thing. (Margo coughs) Is that it’s not necessarily for me, it’s not something I think a lot of people in our world necessarily need to do or worry about. But there’s a time and place for it.  

You were fighting me so much harder. Like

Oh yeah. (laughs)  

I was gonna come (laughs)  

I was right motherfucker. (laughs)  

We were having such a debate y’all. I think we say this every time we finally get to the show, we’ve like resolved the conflict.  


Where I feel conflicted is I sit here along with I think many people where we want to invent the future of work.  


And we want to create it and we want to promote it and then we will behave in ways that are inconsistent with it. Like you said, with over-performance, over-execution.  


Let’s say something about brand. And here’s where I’ll draw the line. A natural expression of who you are and what you stand for is not posturing.

So, if you are a lux brand. If you are verbose. If you know like, all of these things that they wrap in and the same is true on the other side. Like I get a lot of shit for my sales pages being like way too bare bones. I don’t care. They convert. And…

Are your sales pages too bare bones? I feel like there’s a lot of words on your sales pages.  

Oh, no. They’re all words. They’re formatted like a blog post. Like’s there’s nothing.  

All right.  

The next section headers and it’s nothing really, really fancy. I’m not doing much like sometimes the buttons are a hyperlink coz I’m lazy if testing.  

It’s all pageantry folks. All pageantry. (chuckles)  

But like, that’s the other side of the spectrum. I probably should care a little more. But I think that it comes down to if you are actually professional, there isn’t any pageantry you have to do. You do need to know the rules of your game so you can break them.  


At the appropriate times. So you decide like if you’re going fishing, where are you putting that fishing pole? Like is it a pond? Is it a river?  


Is it the ocean? Like, you’re gonna need a different rod. You’re gonna need a different bait. And I think that’s where you can start matching things. But I think in the beginning especially we get buried.

It’s like people worried about their domain names and getting distracted with like what color the business card is gonna be. I think this goes in that category.  


Because I will stay on the other side of the spectrum like when I was doing…I’ll use numbers here, like bigger ticket, over $40,000 to $90,000 contracts,  


I would not feel comfortable with a two page. Well, that’s not true today. Let me talk out of both sides of it. Because when I was starting it definitely made a difference to present myself.

I also look really young and I definitely looked young 10 years. So I think that I needed a way for people to trust me and I think it made me take myself seriously so I think that grew.

Today would I do it that way? I’m so out of that world cos I’ve been coaching.

That world sucks. (chuckles)  

I know. I would say the last big contract they did was like a Google doc I turned into a PDF. (laughs)  

So I was right all along. I fucking knew it. Anyway, but no, I think sorry, I don’t wanna interrupt you.  

But consultancy.  


I mean, that’s not my brand, right? Like you know me at this point.  

Yes. And this is the point that we raised when we were originally arguing. Which is I swear to God a thing we do. But apparently we’re bad at doing it on camera. The point that you made that I was like, okay, point taken, you know after three hours of  

It wasn’t long.  

But I was right. Is the idea that you’re like, well you can do the body of the email because people know you and you have the reputation.  


If Beyoncé is sending you a proposal she could write it on a napkin and you’d be like (claps) Done, sold. Like you’re worth every penny. But for folks who are a little newer for folks who are you know building their place in this world, I understand the desire to go in that direction.

But at the same time, I had someone in the replies to this tweet be like, oh yeah, I was using one of those, I won’t name the platform ‘cause that would be rude. But I was using one of these fancy proposal platforms and it took me so much longer and zero of them converted. Which I thought was really interesting.

It may not have been anything to do with the platform and everything to do with product market fit or whatever. But, I was like, isn’t that interesting? How there are some people who will tell you, you know you need the proposal for a proposal to look credible.

And honestly, if you do a good job on your sales call, you kinda don’t. Again that’s been my experience within the range of clients that I’ve had. Let’s say, you know proposals going upwards of 50K.  

Well let’s talk about the first principle here. I mean, your proposal should never be the thing that’s about to close the deal.  


Like, that is actually what we’re talking about here. Is that if you are waiting and unsure the proposal is sent after you got a yes, and it’s just paperwork. That it’s basically your contract in long form. It justifies the sale that’s already been made. If you have not made a sale yet, do not write that proposal. (snaps fingers) (laughs)  


Don’t spend that time. Like all of that time does go into having another sales call. All of the content that people need to consume prior to ever speaking to you that makes you credible to them. You know like all of the things. The relationship building over the six months beforehand. I have never had the proposal be the thing that sealed the deal. Also no one reads them. (Hillary chuckles)  

That’s the other thing.  

I’ve never heard someone go through and go like, oh, on this page you said (Hillary chuckles) And basically they’ve heard the opposite. Where four months later they’re like wait, I thought you did this. I’m like, you signed the contract, I did not do that.  

You initialed it. Yeah. And it’s like you just…  

Your initials page is right here.  

You’re just flipping through pages and you are like, okay, that’s the price, yes. So that was sort of my logic. And people also love you for giving them the information that they need and nothing more. You know anticipating needs. So I think that’s another point in favor of simplicity.

‘Cause it’s like, all right what does the client actually need to know?  


Like do they need to see your bio again? Do they need to see like 10 testimonials? Do they need to see like large paragraph chunks about your process? Probably not if it’s on your sales page if we talked about it on the sales page.

So just think about if you want to do proposals, what information you wanna rehash and how in a way it’s gonna be approachable to the client. And that’s probably gonna look like reducing some of the information and maybe it’s worth a shot. I don’t know your life.  

Also being really clear. I would say still include those things.  


But be very clear, like even when you email them or when you write it like, page turn, all you need. (Hillary chuckles) Without it it’s got the items. Because that’s the other place where people are (indistinct) a lot.

And I used to see this because clients would hand me all of their proposals from marketers past and marketers future. Even past clients now are like, “Can you reuse this?”. And I will look at them and I’m like, I know I’m supposed to know a lot about marketing but I don’t know what the fuck is in this thing.

Like this is not, I don’t know what they’re doing for you in here. Are they building you a website? Are they making you a logo? Like I’m not clear at all.  


And it’s like, you will be handholding complex solutions to interesting problems along your growth journey. And I’m like (laughs) Yeah. Strategic advisory.  



Well, fiduciary got that. I’m already sold. Design so credible, truly. Truly, where do I sign?  

All right. So, here are our takeaways from this. There is an element of posturing and performance necessary with specific types of old school clients.  


You enter into those contracts knowing that it might be a little difficult and you’re playing a game.  


They know you’re playing, you know you’re playing. And when you get to a level that you’re big enough like Beyoncé, you can opt out.  


Until then, sometimes you gotta play the game. But, consider your audience and what they need. So if your audience is someone like Hillary or me do not waste our time.

Our most important asset is our time. And so if you’re making us read through 25 hours of stuff, like it’s not happening. We’re not reading it. We’re going straight to the price. We’re going straight to the deliverable. Which is what most people are doing. So,  


We are inventing the future of work here.  


Helps us make proposals better. Help us end the posturing. How can we make Ooh, honest proposals is another good one. (laughs)  

Honest proposal is (speaking gibberish) Perfect.  

But yeah, tell us about what it’s been like to write proposals for you. What has worked, what hasn’t. And remember, focusing on those first principles. So the proposal is not the meat.

The meat is your relationship with the buyer, with the client, with the person who is the decision maker. It’s the relationship you build over time. It’s the reputation you build for yourself online and through word of mouth.

All of those things you are working on during that sales call, you’re getting a yes, before you ever send them the proposal. The proposal is just paperwork that cements a deal that has already been set. And one last review because I can’t help myself. There are two rules of selling.  


One of them, is that we make decisions emotionally.  


And second one is that we justify those emotional decisions with rational reasons. So this is in my (clears throat) marketing master class on Skillshare. But

[indistinct] Skillshare. (Margo laughs)  

But that’s where proposals matter. It’s that they help you justify the decision that’s already been made. And they justifiy the sale. So, let them do that, and so there’s some performance that’s necessary but beyond that, don’t waste your time in the minutia.  

Keep it simple y’all. Keep it simple.  


All right, tell us everything about your proposal process wins, losses, what you’ve done right, where you wasted so much time in the comments below. If you liked this episode, please like it below. Share it with your friends, comment and tell us what you thought. I am Margo Aaron.  

And I’m Hillary Weiss.  

We’ll see you all in two weeks. Thanks for watching.  

Ciao for now. ♪ Hey ♪ (dramatic music) 

Photo by Juliet Clare Warren

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