The Shortlist Episode 85: The Short(er) List: Asking Strategic RFP Questions

Most firms treat RFP questions as a formality—a quick clarification before the real work begins. But what if the questions you ask (and how you ask them) could actually give you the answers you want?

In this episode of The Short(er) List, Becky and Melissa are back with their eagle eyes fixed on the details, cutting through the noise on one of the most underutilized tools in the AEC pursuit process: the RFP clarification question. We dig into strategic phrasing and considerations, air a few grievances, and talk about how to use questions to uncover hidden value and efficiencies. Did you even read the RFP? After this episode, there will never be any doubt.

Podcast Transcript

Welcome to The Shortlist. Hi, I am Becky Ellison from The Shortlist Podcast, and I am going rogue, because apparently some things are just too silly, weird or extra to fit into our regular Shortlist episodes.

So we are bringing those conversations and rants and other fun stuff that was too spicy for TV direct to you in bite-sized little podcast treats hosted by me and featuring all of your favorite Middle of Sixers.

Joining me today is Melissa Richie, and I also stole our producer, Kyle Davis too. Hello, Melissa. Hi, Kyle.

Someday I'm going to make him talk.

Hey, Becky.

Please give me a thumbs up. Not good enough, Kyle. Next time, we're recording you.

So excited to have you here, Melissa. You're one of my favorite people on Earth. We work together quite a lot and almost exclusively on proposals.

I want to say it's something we do. So I'm really jazzed to have you on this particular episode of The Shortlist because today we're getting into some dark psychology tricks.

We're looking at how to write questions in response to RFPs to influence procurement people and get what you want. Is that too salacious or do you feel like that is descriptive of what we're talking about?

I think that is quite descriptive. For some reason in this industry, we can't get an RFP that has everything clear, so there's always some level of interpretation or what do they mean by this.

So it's felt like a good little bite-sized topic to tackle.

Nice.

So your question philosophy, do you feel like you should always ask a question? Is that always in your best interest to just find something to ask about or no?

If I don't have to ask a question, I don't want to. They're busy people, they probably don't want to answer a bunch of questions, but unfortunately, a lot of RFPs do leave a lot to interpretation.

I feel like especially when we're working as a consultant, I don't want to guess, I want to know for sure. And I think sometimes the person that's actually submitting is the one, the company that's submitting is the one that's worried about it.

So that's a nice thing about Middle of Six is then it's coming from us and they don't know who's asking it.

So I guess there's one reason why working with a consultant can help you if you're concerned about your name being the one asking the question.

Ooh, so you're comfortable being the bad guy. We'll be the annoying question asker. You guys come out smelling like a rose.

So do you have some tips? What are the secret tricks to word the question, to get what you want? Like give us some hot question, ask and tip.

Well, the biggest over arching thing is think about the answer you want.

What do you want them to say and then ask the question to get that answer.

So if it's one of those murky things about the page count is, well, it's a 30 page limit, but they didn't talk about this form or the bonding letter, you can phrase it like a please confirm.

Please confirm that the bonding letter and the required forms are excluded from the 30 page limit. Easy for the procurement person to be like, confirmed, done, easy.

Sometimes though, it's not that easy, because you've got to look at all these different section numbers. So I always keep that in mind. What do I want the answer to be to get what I want out of this?

But then also being sure that I'm being extremely clear. I'm referencing the section, the number, the subsection.

So whoever's reading this question can go back to the RFP, see exactly where I'm talking about, be like, okay, I see how that was unclear, and then just write it that way. Pursue it to section, yada, yada, yada.

It is our understanding that X, Y, Z, please confirm, and they answer it. So it's just thinking about how do I get them to give me the answer I want. That is my overarching theory and strategy.

Melissa is our eagle eye.

She is always the expert on the RFP. She can quote it from memory. It's insane, but it works.

So you always reference the section in section number whatever, question number whatever, and then you just write the question that you want to see in the world and hope that they will just be like, yes, confirmed.

Do you have an example of like the best question writing success that you've ever had where you have gotten what you wanted?

Stumped me.

That's such a hard question.

I mean, I'm not thinking of a real specific instance, but I do feel like I have pretty good success of getting them to agree that whatever I'm pointing out, that they should go with what I said. So, I don't know.

It does sometimes I sit there and agonize and write it and read it and rewrite it and reread it, what seems like a silly amount of time. But I think that's part of the way to get the answer you want is to spend the time thinking about it.

So, I don't know. It takes a little time. But if it gets you an extra page or gets you out of some silly margin requirement that was from the 1980s when they scanned documents in.

Yeah.

You know they're just copying and pasting stuff from a thousand years ago. They don't know. Sometimes I feel like questions get asked and the question asker doesn't really know what the hell was being said in the RFP.

And it's very obvious from the answers that are put out that the people who made the RFP also have no idea what they were saying in the RFP.

So, I wonder, listeners, if you create RFPs, please take the time to go through those requirements and make sure they make sense. Just take a quick pass and remind yourself that it's 2026 and like, do we need one-inch margins?

I don't know, you know, look inwardly. So, do you, I'm sure you've seen some hilarious question asking fails, some failed attempts. Do any come to mind that were particularly amusing?

It's typically when they release all the Q&A as an addendum and then you get to read everybody else's.

And I often see examples of poorly written questions or just, you know, not clear, not specifying where they're looking at the RFP, that they want to know the answer to this question. So, just making it hard for the reviewer.

And then you can, I think there is a limit where maybe on really big RFPs, these procurement people get sick of answering questions because I thought of this really huge transit agency that had this behemoth of an RFP.

And I mean, we're reaching hundreds of questions. Like this was a billion dollar contract, so I get it.

But you could tell the procurement people's level of patience was running out because the further down the list of questions, the more they were like gonna disagree with whatever question was asked.

So I guess there's a law of diminishing returns on question asking. So get yours in early.

Yeah, because they'll just be like, no.

What you've just said is one of the most insanely idiotic things I have ever heard. At no point in your rambling, incoherent response were you even close to anything that could be considered a rational thought.

Everyone in this room is now dumber for having listened to it. I award you no points and may God have mercy on your soul.

Here's an example of when you could tell that maybe the procurement people were a little bit over it. Somebody asks, other than a current business license for the state of Washington, what licenses are required?

Response, the consultant is responsible for knowing which licenses are required.

Jam. Wow. Wow.

And the requirement of the RFQ was something very unclear, like provide copies of required licenses, and the services were a whole gamut of every possible engineering, construction management type of service you could provide.

So that was the one where I'm like, oh, these procurement people are like, I don't know, this is just my job. I don't know everything.

You should know what licenses you need, meh. That person was having a bad day, okay.

Yes, that was a good one.

That's fun. Yeah, I feel like I've seen some mean responses, but I can't remember. I like when they just like restate the question where somebody asks, can this be like excluded from the page limit or whatever?

And then they just literally copy and paste the exact requirement without changing any of the information. And you're just like, why are we doing this?

Yep, there's this particular RFP has a lot of those where they just kind of restate it or they started giving the same answer to questions that had little nuances about like the page size or the page orientation.

And they're like, per clarification, 42.8.

Per is aggressive. Per means F you. So this is coming from an actual example.

This is a blind item, listeners.

It is. It is.

Can we get any clues?

A very large transportation agency.

Interesting. Get your house in order, large transportation agencies, because we're watching your movies when we're judging you. Interesting.

So for the people listening, who may or may not be hands-on marketers, we might have people in leadership roles in their company. We've got people all over the place. Does it matter who asks the question?

I think that is less important.

I would say if it is a pursuit or they're going to have a pre-proposal meeting, it might be a good idea to have that question ready at the RFQ pre-submittal meeting Q&A session. They may not officially answer it.

But then you've kind of given them a tip that maybe there are some things that are unclear in the RFQ. So then maybe the client owner side will get together behind the seeds before they officially answer the question in an addendum.

So that would be a tip. I think anybody who's getting asked some questions might like to know what's the gist of that? Where are we going with this?

So they can feel prepared. It seems like most public agencies will give you the answers probably this in a proposal meeting and then follow up with the official answer. So I think having your ducks in a row before that date is really helpful.

Of course, as you dig into the RFP and start responding, laying out your InDesign, you're going to be looking at the RFP even more carefully. Maybe things reveal themselves.

But as much as possible, trying to have those questions ready before the pre-proposal meeting is a good best practice.

Are there questions that people should be asking that they don't realize they can or should ask? What is everything on the table? Are there secrets in regards to specifically what you are asking about that people should know?

I like to know the full procurement schedule.

So if there's a date for interviews or when they're going to shortlist, especially if you've got people on your team, you're like, maybe it's the summer and you know there's some vacations.

Maybe the city or county hasn't thought about that, but that might be something you want to ask about so that you can better prepare your team.

And then if you know everyone's going to be out on vacation, maybe that gives you a chance to put in your cover letter that you would like to request a certain interview date that they propose because that's when your team's available.

I mean, there's some kind of strategic things that thinking through the next step after you submit your proposal that you might want to ask about. And then, you know, there are definitely people who just don't want to ask anything.

I mean, they don't want to give anything away. There's so many ways to skin this cat, but I'd rather have a little bit more information. I don't think it's a big trade secret when the interviews are.

It's just helping us all be a little more prepared.

Sure. I wonder if sometimes it's better to assume strategically because, like, we've had a lot of internal discussions as to, like, what does this mean? Everybody read, you know, this line of the RFP and what's your interpretation?

And we sometimes will have different ones. And sometimes I think, you know, we guess we could ask the question and get the clarification.

Or do we take the gamble that our interpretation is better than the answer they would give us and go with our interpretation? If it seems vague, do you have an opinion on that?

I think you bring up a great point. That's the other side of the coin of why you wouldn't ask a question, is you want to assume this is how we're interpreting it. We're going to run with this.

And maybe that will then kind of convince the client that that was the right way to go and someone else might go a different way. And that doesn't go in their favor.

Have you ever been disqualified?

And have you actually have you ever worked on a proposal that was disqualified and for what?

No.

Oh, aren't you great? I have.

What happened?

Well, when I worked in house at a large general contractor firm, we very often proposed on a client's proposals who had the same requirements copy pasted for 100 years never changed.

And we weren't 100 percent in adherence to the font size requirements. But the thing is, is we had proposed 100,000 times before, and nobody ever said anything.

But then one time somebody complained, I guess, and we got disqualified for font size violation, though we had gotten away with it a million times before. So it was not a call that I made.

We were just doing the same thing over and over again that we had always done. So I don't lose sleep at night, but I thought that was petty on their part.

It hardens my resolve of always following the font size requirement.

It is. It's a tough one. The font size will get you every time.

They're limiting the content. Sometimes it makes sense, other times it just hurts. But yeah, I mean, you could probably always ask about stuff like that.

Font sizes, page limits, margins. I mean, I think we care a lot about that, but the people on the other side of the RFP probably are more malleable about that than any other thing.

Although, to be honest, I have definitely seen people get shut down quite a lot, but it's worth a try, right? It's always worth a try to ask. You're not going to like, they're not going to be mad at you.

Well, yeah, I think that font size one is a good one where you can ask in the way you want the answer.

Please confirm that the 12 point font limit does not apply to tables, charts and org charts due to the fact that a smaller font size enhances readability or something like that, where you're like pointing out to them.

You actually don't want 12 point font on all these charts because then they're actually less legible. So that's one.

Oh, yeah. Good point. Like explain why this is beneficial to you.

Then you're not just complaining. You're saying, listen, this is what you're going to get. You don't want that.

Like, yeah, that's wonderful.

Those are Zs. They look like ours to me. That's not fair.

Rarudo is not a word. He's a baseball player. You're cheating.

All right.

Well, thank you so much for being on this fun little psychological tricks episode. I don't know. This is I said it was dark psychology.

It's really not. It's just smart question writing. But like, you know, clickbait.

So I appreciate your wisdom. It's always nice chatting with you. Remember to rate, subscribe and share the love.

Make a friend. Recommend the podcast to another AEC marketer who wants to feel seen out there because we see you. We love you.

We are you and we are always here for you here at Middle of Six. See you next time where we will probably give you more secret hot tips on how to get ahead in this world or even just in pursuits. Melissa, so nice to see you.

Kyle, thanks again. Everybody out there. Have a great day.

Have a great week. Do something for yourself today. I hope you're sleeping well.

I can keep doing this all day long. We'll see you next time.

Thanks, Becky. Thanks, Kyle.

So you see the puppy was like industry in that they were both lost in the woods. And nobody, especially the little boy, society, knew where to find them.

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.