The Shortlist Episode 64: Proposal Submission Confessions

In Episode 64 of The Shortlist, Wendy Simmons is joined by Middle of Sixers Melissa Richey and Becky Ellison for a candid and comical discussion on proposal submission confessions.

Harkening back to Episode 46, Night of the Living Deadline, this conversation dives into the best, worst, and wildest submission experiences—crazy requests, impossible demands, and unpredictable personalities. From horror stories to hard-learned lessons, it’s all on the table.

Whether you’re managing a team or balancing company goals, workplace stress is inevitable—especially in a high-stakes industry with relentless deadlines. The pressure to succeed can take a serious toll, but by sharing our struggles, we can find camaraderie and maybe even some laughter along the way.

CPSM CEU Credits: 0.5 | Domain: 4

Podcast Transcript

Welcome to The Shortlist.

We're exploring all things AEC marketing to help your firm win The Shortlist.

I'm Wendy Simmons, and today we're talking with Melissa Richey and Becky Ellison to discuss Submission Confessions.

Hey, everybody.

Hi, Wendy.

Hey, hey.

Who is the brave soul who thought of Submission Confessions for a podcast episode?

Think the guilty party is on the mic.

Oh, me?

No.

No, I was like, this is not my idea.

This sounds scary, but I'm very excited to get into it with you all.

Before we dig into the topic, a little warm up question here.

I like to think about, you know, as we're going through our days, our weeks, our months, we win some things, we lose some things.

You win and you learn.

What have you two been learning recently or winning?

I don't know.

Wow, we win a lot, right?

What have you been winning or learning?

Well, my big win for the week was we gave a presentation to SMPS Seattle when Wendy and I were doing our wildcards workshop.

And so it was just fun to see everybody contributing and the hands-on activity seemed to go over really well.

So that was a nice win to join Wendy in presenting that.

Yay.

It feels good when you get up there in front of, especially that audience is, they are our friends, we know them so well, some new faces for sure, but to be able to present well in front of that group, it does feel like a win.

Yeah, that's right.

We're not too familiar.

You haven't heard us too many times.

That was really good.

And we're prepping for our PRC, SMPS Pacific Regional Conference presentation of the same topic.

And it's going to be a little shorter, so we're going to have to figure out what juicy bits to cut out of that.

Yeah, I think that was the learning of like, okay, now what we saw in reactions, where's the spot we can cut?

Not going to be easy tasks, but we'll figure it out.

We also learned or were reminded that when you have an activity and people need to think or brainstorm or, you know, go into their mind and start working on something, music helps.

We didn't have that in Seattle.

I was like, oh, putting that on the list for PRC.

Have a little music.

So if anyone's not using music for their brainstorm assist, do we have any data on that?

Or is that just anecdotal, like, that helps?

No one?

We don't know.

I mean, I'm aware that classical music specifically is supposed to increase brain activity by, like, you know, 30, 40 percent, something like that.

And I was always advised, like, put on, you know, Mozart or whatever, when you're trying to study, when you're trying to remember something because it activates your synapses or whatever.

But I mean, I'm sure that, you know, like trip hop or like indie rock or German rap would do just as good.

We'll be consulting you for a playlist for PRC, Becky.

Well, I can tell you that a quiet room is equal to a blank document, an in-design or word where the cursor is just like flashing at you.

It's very poetic.

Yes, that's what it can feel like.

But everyone did great and they had lots of good ideas.

And so maybe it's just the observers that it was a little quiet for.

All right.

Well, then, Becky, any wins or learns for you?

You know, this week, I've been working with a new client, working on branding a new company, which is very exciting.

And we just clicked with her, the owner of the company, so much.

And I feel like everything that we discussed and suggestions that I brought to the...

I think she even used the words, like, you read my mind, something like that.

So that was very exciting.

And it's very cool how pumped and stoked and engaged she is.

So just being at the beginning of that brand design project is always an exciting time because you're just trying new things and throwing them out and everyone's excited.

And just pumped about that.

That felt like a felt like a win.

That's awesome.

I mean, I think that not only did you read her mind, but my recollection was she said, I had like a dream or a vision of this.

Like there was a real connection there.

So that's that's fun.

They can't all be like that.

That's not always going to happen, but embrace it when it does.

All right, let's get into this podcast.

The Submission Confessions.

This is scary.

This is vulnerable.

I don't know exactly where this is going to go, but none of us are perfect.

And we work with also imperfect teams.

It's just how it goes.

And I'm sure we have some, a few horror stories to share or near misses or whatever you want to call it.

Becky, Melissa, either one of you kind of want to tee it up.

Like, why we picked this topic and why we think it might be important to discuss.

Yeah, I mean, I think we've all been there.

Anybody who's worked under a deadline, who's had to submit a proposal, has had some absolutely wacky, horrifying.

I mean, you've experienced the whole range of human emotions getting this done, because we work in such a high stress, high pressure industry.

Like, you know, when you cannot miss the deadlines and there's millions of dollars at stake and people's jobs are on the line.

I mean, like in that intense of an environment, like you have to you have to kind of acknowledge the strange and funny things that happen.

We have to be able to joke around with each other.

We're like, we're like soldiers in the trenches singing during the First World War.

You know, like you have to.

So I think it's OK to talk about like our mistakes and our, you know, funny experiences and weird, you know, almost near misses, because we all have that in common and it makes you feel safe for the next time that something absolutely 100 percent will go wrong because you'll never, you know, you're never going to be perfect all the time.

And it's just, it's nice to be able to like blow off some steam and relate.

All right.

Well, we're going to, we're going to be very open and transparent here.

Becky, since you teed that up, do you have, you want to start us off with your first confession?

Sure, so, background.

I used to work in house at a construction management firm for a very long time.

Started off as a marketing assistant, worked my way up to marketing manager, but I was always doing hands-on proposals.

That's 99% of what I did.

So when I first started at this new job, and I had been trusted to run my very first proposal on my own, you know, for the first time, and I was under so much pressure, I was like shivering.

I put together this proposal, and I feel like I dotted every I, crossed every T, I was obsessively focused on accuracy, and like, oh my god, millions of dollars, everyone's looking at me.

And hit submit, sent it in, copied everybody, did it, everybody's so proud.

And then the project manager called me and said, hey, we have kind of a major problem here.

It looks like we left the budget out of the proposal.

So, yeah, we sent in a proposal for a job with no cost information in it.

And fortunately, the project manager was kind of buddy buddy with the client.

So he just called the client, was like, hey, explain the situation.

And we were able to send a corrected version.

But like, this is it, I'm about to get fired.

Grand opening, grand closing.

But no, everybody around me was kind of like, oh, that happens.

And then they started sharing their first time proposal mistakes and horror stories.

And that was kind of nice.

They didn't, they weren't too hard on me.

Were you really early in your career?

Is that why it felt so detrimental?

Or like, was it that sort of thing?

Or just because it was the first time ever for you?

I feel like it was days or weeks into my AEC marketing career.

I had never, I had only done other kinds of marketing before that.

So it wasn't like fresh out of school or anything, but like I was fresh into that job and at that company.

So I mean, yeah, it was pretty great.

And then I was fearless after that, though, because once you mess up that bad, you know, like it's it's all roses and sunshine from there.

I think back to your other podcast episodes where you're like, it is the marketer's job to know every bit of the RFP.

That is your job.

We know it.

And this is now it all makes a little more sense.

They're like, check that checklist ten times.

Yep.

Well, thank you for sharing.

That's a good starting point.

Melissa, you want to try to top Becky with a confession?

Well, my confession is also something from very early in my career.

And I've been in this industry for over 20 years now.

So this was a long time ago when things were still done in paper.

And I worked for a firm.

We were a sub-consultant to architects quite a bit.

And there were two firms that were an acronym, like so many are in this industry.

They were across the street from one another.

And I had to go deliver materials.

Like they had asked the landscape architect to make a rendering.

And it was a hand-drawn rendering.

So I went to the firm.

I had the envelope.

I handed it to them.

They're like, thanks.

I left.

And then I got a phone call later saying, this was addressed to the other firm.

Why did you give them this rendering?

I was like, um, because that's what they asked for.

Sorry about that.

So that was really awkward.

Oh, man.

Yeah.

So that was great.

So then I had to go to the landscape architect, tell them what happened, tell them now that firm wants a drawing of some sort.

And from that, I now always quadruple check that whatever is going inside the envelope matches.

What's on there?

Double check.

Am I going into the right building?

So yeah, that was a tough lesson.

That was really embarrassing.

Yeah.

I mean, I'm so glad I asked that question about we win or we learn at the beginning.

This makes a lot of sense.

We never make the same mistake twice.

Nope.

When you learn it the hard way, it scars you and I guess you're just never going to let that happen again.

It's translated to e-mail, so now it's like double checking the e-mail address 5,000 times.

So I'm not putting it in the mail or hand delivery, and it's double checking all that.

I think we've all e-mailed the wrong person at one time or another though, because you start typing in the name and then you end up e-mailing Tiffany at ex-company versus Tiffany at the company here, and then like, oh, god.

Fortunately, that's never happened to the point where we were in trouble, but I've done that a few times.

It makes me very nervous.

Like, did I get that right?

You don't want to send.

Oh, I think of the number of clients that we work with now.

You know, I think when I was in house, it was a little more streamlined.

It was pretty much all internal.

Maybe you got the wrong Ryan or Bob or something like that.

But now it could be a pretty big deal.

So, good to slow down, slow down to go fast, right?

There you go.

I didn't make that up.

Someone told me that yesterday.

So, I'm like, keep that top of mind.

Go slow to go fast.

Yeah, I actually worked with an engineer.

You used to always say that.

Yeah, that's a good tip.

All right, what else you got?

These are my confessions.

Oh, man.

I mean, so many things happen when you're doing this kind of work.

I mean, like, I feel like there's always some kind of emergency or, you know, last second, like MacGyver situation where you have to make the impossible happen.

I remember I was working on a proposal at that same company where we just, for whatever reason, it went up until just the last minute.

They were still like the whole team.

What happened is everybody would start coming down to the marketing office.

Like I'd be there, you know, going on the computer, doing my thing like the other marketing person be doing their thing.

And then the PM had come in.

Hey, you guys need anything?

Like, what do I need to do?

Where are we?

And then the superintendent would come in.

You got the schedule?

I sent the new schedule.

And then the estimator would come down.

We just got like and we had to start like kicking people out.

But so on one of these occasions, we had half the team in there and we're down to the minute and people are freaking out.

Everybody's pacing around like and it just came.

It came so far down to the wire that like we all gathered around as the project manager sent the email and we looked at the confirmation and he had sent the the submission email at literally the exact second.

It was the second of the deadline and we were all like, you've got to be kidding me.

But I think we won that job.

So it worked out.

You need to have nerves of steel in this business.

I don't have confessions related to this, but I remember, you know, at a previous job, every once in a while, I needed to be the person that was going to run the bid in.

And they, I don't know, the estimating director or whatever, said, we think you can do this.

You have the right personality.

I'm like, are you sure?

Do you know me well enough?

But that feeling of going and dropping off the bid paperwork and handwriting and the price at the last minute, I mean, my hands were shaking.

And then I also learned that we don't need to spell out, numbers need to be round when you're writing them out in long form.

We don't need to write, you know, $1,237,652.97.

Like that takes a long time, just rounded up.

But that shaking feeling and that deadline and hitting send at the last minute, that can just, it makes you want to collapse afterwards.

And kind of makes you want to quit, actually.

I can only do so many of those.

But proud to have helped out the company.

That's a good sign, though, like, you need that sense of urgency.

That actually reminds me of another little tale that was told to me.

This was even before my time at my last company.

But they said there was a project engineer who was sent to deliver a proposal.

And he just stopped off to have lunch before delivering the proposals, which is a big no-no.

You deliver the proposals first before you do anything.

But he popped off to have lunch and then something got stuck in traffic or there was like a crash or something and missed the deadline.

And they just told him, don't come back, you're done.

A tip, never get lunch before you deliver the proposals.

What are you thinking?

Gosh.

That man's name was Kenny.

No, it wasn't.

What?

It might have been.

I don't know his name.

For those of you who have not listened to Night of the Living Deadline, the Shortlist special, we've all been there.

It's Deadline Day.

And as the saying goes, anything that can go wrong will go wrong.

Oops.

If you broke that coil, the next one is going through your ears.

Kenny, go to the door on the right.

What?

The door on the right.

The appendix.

We need an appendix tab.

Oh dear God.

Lisa, we might actually miss this deadline.

Night of the Living Deadline.

Episode, I don't know which episode number it is.

Probably edit that in.

Episode 46.

Producer Kyle's throwing a number there, but go and listen to it because you are going to hear all of Becky's nightmares in the story form.

It's so good.

It is a little stressful, but it's worth it.

Based on true stories.

All true stories.

Yeah, you all talking about that like last second deadline, shaking reminded me of a story and.

I remember a day when Bluebeam didn't exist and the only people who had control of PDFs were marketing.

And then that changed.

Shocker, Adobe and Bluebeam don't necessarily play real well together in PDF land.

And so I had everything ready to upload into the bidding system.

And the project manager estimator, whomever was still working on their fee.

And I get this email.

It's there.

I'm like, cool.

OK.

I'm opening it in Acrobat and it's blank.

There's nothing there.

I'm like, oh, my gosh.

I call the office.

Oh, no, he's at lunch.

I was like, what?

And they didn't want to give me a cell phone number.

And I was like, I'm trying to upload this bid and the information is missing off the PDF.

And the person at the front desk wasn't helpful.

So I called the president of the company and he helped me out.

But I was literally redrawing things in the PDF in Acrobat and had that same thing where exporting, waiting for it all to come up.

And I was uploading it in the bid system in the last minute and just watching the bar upload and like, oh, please to go on, please go in.

And I made it.

But yeah, that was, that was a real stressful situation that I would like to not experience again.

And that is why we now like have a 24-hour buffer, you know, because we can kind of control that as consultants.

And we, it's true when we say, it's because we're not in your office, we can't run down to the president's office and be like, I need you to sign this right now.

We don't, can't have any fire drills or they're not very effective.

But honestly, it's for our own sanity.

Yeah, I can remember that was like in the pandemic days where I'm like working in my attic office.

Like, yeah, it was, it was a special time.

Yeah.

Yeah.

Oh, man.

Well, I remember sitting at my desk one time since we're on this like deadline stress and we're trying to upload it.

And I think I'm like, I don't know, doing all of these things and that shaking hand part.

And I literally like looked up to my team who's they weren't like leaning over me, but you know, open cubicles.

And I'm like, I don't think we're gonna make it.

Just having that panic.

And then everyone steps up like, what can I do?

And I'm like, I don't know, this needs to happen faster.

And you just feel so helpless.

So or the FedEx guys at the front desk and the receptionist is getting them to wait because you're like trying to print and bind.

And you're like, just have them wait one more second.

And if we can't, then you're like, what's the last second?

I can take it to the FedEx drop off.

Everybody wants to know how they can help.

And it's like, get out.

The best thing you can do right now is leave the office and let me work.

Yeah.

And if you're going to call for help, desperately do it before in the last two minutes.

Like, I don't think that made anybody feel better about the situation.

Well, the time you could have helped was like four days ago when you should have been giving me the content that I just got an hour ago.

And also, I've been up since 1 a.m.

that feeling where I'm not even really thinking straight.

Oh, I don't live in those days so much anymore.

Feels like we've gotten to having that buffer zone, you know, demanding a little bit more from the teams.

Maybe that comes with the experience, right?

None of us are, this is not our first proposal rodeo in any way.

So we push back a little bit harder when, hey, that didn't come, so we'll clean it up and we'll get it in there, but there's not going to be that beautiful graphic you envision because we just found out about it 30 minutes ago, you know, that kind of thing.

Yeah, I also am like, no, I'm not uploading it for you.

That's your responsibility.

Like I'm like, no, I'm not doing that anymore.

I learned my lesson, another lesson learned.

No, I do not upload it to the bidding system for you.

You do that, client.

Yeah, same thing with like, I'm like, I'm not responsible for the numbers.

Honestly, it's too important.

It's like I can't handle it.

I mean, I hate to leave you hang in, but you can make sure that that is all in there perfectly because a small typo could be a big deal.

Yeah.

Unless we have those early and someone signs off on them, but that last minute putting in the numbers like, give me a scan, throw it in there.

Great.

Becky, you mentioned MacGyver, a story or two ago.

You have more MacGyver stories you want to share?

Oh, man, I've been MacGyver for a long time.

The proposal's due in 10 minutes, wake me up in nine.

I've done a lot of last-minute, bizarre stuff to get the proposal across the Deadline.

I remember I've definitely hand-punched holes through paper when the puncher didn't work, stabbing them with pens and pencils and binding them up.

Oh, my God.

I've printed an entire proposal of screenshots from InDesign because it wouldn't export to Adobe PDF.

Because Adobe crashes at the absolute worst time every single time.

It only crashes right before the Deadline.

So I was just in an absolute desperate panic, just a flop sweat.

I was like, okay, I'm just going to screenshot every page.

And I did that and I printed that and I got it done.

I sent a PE to the store to get binder clips because we were required.

Because some proposals would say like, you can't bind it or whatever it has to be clipped or something like that.

And we didn't have anything that conformed to what they wanted.

So we sent a PE to the store and FaceTimed with him to make sure that he was getting the right thing.

That was very exciting.

Brilliant on the FaceTime.

Well, you got to check.

I mean, if he had got the wrong clips, we'd have been in trouble.

Buy them all, all the sizes, everything they have.

Yeah, get them all.

I've recruited everybody on the floor to come help.

At times, I'll just run up and grab the receptionist or the IT people.

I've conscripted a lot of people whose jobs we're not marketing to come in and help assemble.

It's usually with printed proposals that's always the problem, because that's when you're having to make tabs that weren't there.

Oh, no, we need an appendix tab.

We better get one of our old tabs from another response and strip it, change it, label it over.

I've hand cut out tabs that weren't there.

I mean, it's always something when you're trying to print, and the printer always jams, and then you have to yank somebody in who knows how to work the printer, and they're taking the printer apart while you're dead.

I don't know.

Honestly, that adrenaline rush used to be exciting.

I'm glad that I'm not in that much pressure anymore, but there was nothing like solving an impossible problem, and just go, yeah, high-five and all that.

Then you're like, and now I'm going home.

My watch has ended.

Goodbye forever.

Yeah, we're done.

I had told my boss in the past, it's like after the proposal, we should have the rest of the day off.

That is the intensity.

How come that can't happen, but we all have to clean up the files and think about interview prep or what's the next meeting, but it should be mandatory half day off.

We did that when I was the marketing manager in my office.

You did?

We sure did.

Yeah.

It was like my one time I put my foot down.

I'm like, that's it.

I'm out.

Mic drop.

Bye.

You're right about Adobe always crashing.

It's like there's a limit.

You can export four PDFs before noon, and the fifth one is going to crash.

You don't know which page it is that's causing the error.

You have to export in chunks.

Here's a hot tip.

If you're trying to export to PDF and it keeps crashing and you don't know why, export the first five pages.

See if that works.

Then go pages six through ten.

Then you can pick exactly which page has the object on it that's causing the error and maybe go address it or export all the other ones around and screenshot that one page.

If you're desperate, that's a hot tip from the trenches.

Yeah, that's painful.

I was working on a proposal once where we had to submit in binders.

I'm kind of glad those binders are over.

But we thought we were in good shape and we had a nice, it was a big proposal, two-inch binder.

Everything had been looking good until the day we went to print.

Then we put in our nice proposal paper, which is thicker than the other paper, and then did not fit in the binders.

So we had to create a second part of the binder, like scrounging up, oh, 10 more binders that were clean enough and sort of look like they matched and new covers and make that the appendix.

Oh, God, I can remember running around the office and pulling engineering reports off the shelf and being like, I need this binder.

Cleaning them up, like, is this one clean enough?

It's white, so I look scuffed on the bottom.

It'll be fine.

We'll put that at the bottom of the box.

Oh, well, yeah.

Lots of MacGyvering, for sure, to make it happen.

But that just goes to show you the commitment, you know, the enthusiasm from your marketing team.

We will do anything to get this done.

And that's why we need the afternoon off afterward.

Have you guys ever missed a deadline in your marketing careers?

I have not.

I haven't either.

Never.

Good for us.

Shaky fingers and all.

Never resulted in that.

Yeah, scary.

But I have cried over washes before in my early days.

Yeah.

I usually cry before the submission.

Yeah, probably during.

I was crying after like when we don't get it, you know, goes in, we do the interview and then we, I know, it seems, I can't actually even imagine myself doing that now.

But yeah, having tears over like, I thought we were the right team.

We put so much into it.

And someone that I was working with was like, oh, we got to be more like baseball.

Yeah, you got to, you got to take the highs and the lows and just even, even it out.

Just go in the middle.

We can't go up and down all the time.

There's no crying in baseball.

No crying in baseball.

Are you crying?

No.

Are you crying?

Are you crying?

There's no crying.

There's no crying in baseball.

He didn't say that, but I'm like, I get it, I get it.

You have some wins and you have some losses, but you can't go up and down emotionally with all of it.

And also a lesson as a marketer, you can't get too starry-eyed about your own team and not see their, maybe it's not flaws so much, but like the gaps in how their team could be put together or whatever.

You can't just be obsessed that your team is the only answer.

It'll make you more subjective as you're coaching and stuff.

But yeah, I don't cry anymore over that stuff.

Other things.

It is okay to cry, listeners.

That's right.

Cry it out.

That's right.

Just don't waste your tears on the things that do not matter or that you had no control over.

There it is.

Well, thank you for sharing and being vulnerable and letting our listeners know they're not alone in this.

We have all gone through it.

The tough parts and the inventive parts.

And it makes you better and stronger for the next one.

So thanks for sharing.

Great to see you both.

You as well.

Thanks for having us.

Thanks, Becky.

Thanks, Wendy.

The Shortlist is presented by Middle of Six.

Our producer is Kyle Davis with digital marketing support by the team at Middle of Six.

If you're looking for past episodes or more info, check out our podcast page at middleofsix.com/theshortlist.

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Be sure to subscribe so you don't miss an episode.

Until next time, keep on hustling.

The Shortlist is a podcast that explores all things AEC marketing. Hosted by Middle of Six Principal, Wendy Simmons, each episode features members of the MOS team, where we take a deep dive on a wide range of topics related to AEC marketing including: proposal development, strategy, team building, business development, branding, digital marketing, and more. You can listen to our full archive of episodes here.