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The Shortlist Episode 24: Tackling Cover Letters

Middle of Six



Proposal cover letters are tricky. Sometimes they aren't scored, but more often than not, they impart a critical first impression. So why are they frequently approached as an obligatory, blasé introduction when the selection panel is looking to be inspired, entertained, and informed? In this episode, Allison Tivnon shares five key elements of effective cover letters that will distinguish your team from the competition.


CPSM CEU Credits: 0.5 | Domain: 4


Podcast Transcript


Welcome to The Shortlist.


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


I'm your host, Wendy Simmons, and each episode, I'll be joined by one of my team members from Middle of Six to answer your questions.


Today, we have Allison Tivnon back in the podcast hot seat to talk about the cover letter and why the first line matters most.


Hey, Allison.


Hey there, Wendy.


Before we get into the details of a cover letter, which is very, very important, what are the other areas of the proposal that matters?


I mean, obviously, we have to kind of forget about budget and schedule because that's a huge driver of the selection panel decision-making process.


But beyond that, what do you see as the most important parts of a proposal?


Yeah, I love the way that you phrase that, to begin with, of which parts of the proposal matter most.


And I think you have to finish that sentence of which of the proposal parts matter most to us or to the selection committees.


I think if we're really serious about trying to dial in our proposals so that they resonate with the people that score them, we have to figure out what their pet peeves are, the sections that they flip to first or scroll to first, and where we might be spinning our wheels and wasting our time and other areas where we might not be spending enough time.


And there's lots of great panels, webinars out there, different events that industry organizations like SNPS put on, and they'll invite agency personnel to sit around and talk about this very subject.


I've attended a lot of those over the years.


I'm sure you have too.


And routinely, there are two areas within the proposal that I hear talked about more than any others, and that's the cover letter and the understanding.


So I know we're diving into the cover letter today, but hopefully at some other point, we can also dig into the understanding as well.


Oh yeah, we definitely should.


Hey, the cover letter, I'm just thinking about this and how I feel like there's often two camps.


Curious what you think, but the people who don't read the cover letter at all, skip right past it.


I don't think that they lay eyes on it.


And then the folks who will score you based on the cover letter, they will look for a typo.


They want to know that you're really kind of focused on their project and you're bringing something different, a different voice, you know, it just doesn't feel like boilerplate.


Am I missing a whole middle group there that actually does kind of read it and appreciate it like other pieces of the proposal, or is there something to my theory?


No, I think you're right.


I think the ones that skip past it skip past it because they have seen way too many that start with the dreaded we sentence at the beginning of it.


We're excited to something and it starts to sound really canned and boilerplate-y, and they just think that the rest of the cover letter is going to follow suit.


And so they just skip right past it.


And then, like you said, there's others that kind of use that as the acid test.


They look to see, okay, are they going to nail it here?


Because if they don't, I'm going to be really dubious about the rest of this proposal.


And it's probably going to weight their scores down instead of up.


I do think that there might be a middle category, which is people that are newer to selection committees.


They aren't as jaded yet.


And it really is just the opener.


It's the person who comes out while the curtain is still down and says, thanks for attending today.


And it's kind of the warm up for what's to come.


You don't score it, but it matters.


And I think there's room for us to grab all three of those different groups and center their attention, get them ready, and maybe even start inspiring them from the very first line and onward from there.


Yeah.


If you're part of a firm that has a very heavy proposal load and you get stuck in the trap of wanting to use that standard cover letter, just remember that there are folks who are reading that and the generic cover letter really sticks out.


It doesn't feel like it's making a connection.


It's noticeable, so it is worth the extra effort.


Going back to your early point there, Allison, about where do you spend your time or where do you not invest as much of your resources in, the cover letter is a really great place to start.


So cover letters always seem so daunting, whether you're starting from boilerplate and you're a little bit stuck on what to modify or how to make it special, or maybe you just have a clean blank slate, white word document that you are starting from scratch.


How can you create an efficient process that takes the guesswork out of building that cover letter and results in something that's really good and feels special and it's going to resonate with the selection committee?


Well, I think that we overthink them too often.


There is a formula that you can follow to come up with really quality content.


And this goes to any type of writing.


We should have structure around what we write.


We learn that as early as like sixth grade with the five paragraph essay, cover letter should follow some kind of formula as well.


And once you get those steps down, then you can focus on making each component within it meaningful.


But I do think that at a minimum, and probably not much more than this, you should have five different things that are important, that are interrelated to each other, that stand out and that are going to capture their attention early on when they're just digging in to your proposal.


And that is why this project matters to you, why you care about it, that's got to be front and center.


The next is how you're qualified.


The third is that you have the right team.


And this is the right team ones are usually the bullets that you see in a cover letter.


And it's also where your value propositions can reside.


After that, I think it's always important to hit on DEI and go there on every single proposal that you put together.


What diversity, equity and inclusion looks like to you internally to your company as well as on your projects.


And then I think that you always got to round things out by talking about the schedule and the budget and that they're sacred.


If you can nail those five areas, you're going to be speaking to different kinds of concerns, wants and needs that each selection committee member is probably going to have somewhere in the back of their head as they're going through the rest of your proposal.


Oh, that's really interesting.


That feels comprehensive for sure.


And I think a lot of our proposals, yeah, I would say you would want to hit on all of those five items.


I've also seen some different strategies that maybe we could just kind of work through here and get our opinions on a really, really short cover letter.


Shockingly short.


I've seen a few of them that at first glance, I thought, did they do this?


Is there even a cover letter here?


But when I read the words, every word actually mattered.


It meant something to this project, and I was impressed.


I was like, whoa, okay.


Now that's a refreshing approach.


And as we move further and further away from having more words, and people want to just kind of get to the point sooner, having that kind of brevity was pretty impressive.


Do you think that the five points can be brought into that formula, or is that just like another special case?


You decide to use this super brief letter.


No, I think that cover letters should be brief.


And there's two things I always think of.


One is that quote by Mark Twain, if I'd had more time, I would have written a shorter story.


And then the second one is omit needless words, which was a poster I saw when I was in college, and the word needless had been struck out.


Oh, right.


Yeah.


You know, go back, revise, revise, revise.


Think of it as a sauce.


You know, reduce, reduce to get more flavor out of it.


You have to actually reduce the amount of stuff that's in the pan.


And that's kind of the same with the cover letter, is all of these different things are meaningful and they're real.


And you don't have to spend a whole lot of time explaining that because if it's meaningful and it's real, you can say it pretty quickly.


It's when you start to get into what I call the BS detector, the boilerplate sentence detector, that you start to get these really long winded statements that kind of take you nowhere.


Right.


Or at least nowhere authentically, you know?


I like to think of the cover letter as the exact same thing as when you're looking at folks that you're considering bringing on to your team.


So you put out an ad for a job for your team, and you get lots of different people that apply for it.


The very first thing that you look at is the cover letter that they send you before you look at their resume.


And if it's nothing but words about them, and like I saw that you had this position, and here's my qualifications, I think this about this, they don't mention once that they have looked you up online, that they know anything about your firm.


You know, you're just, you're not going to be as excited to look at their resume.


The one in the pile that has really turned it inside out and has focused that cover letter on you and your position, and thinking through why you need this role field and what types of talents and skills you're looking for, and that they have demonstrated that they're really thoughtfully thinking about how they would get incorporated into your firm, and that through that thought process, they decided to apply.


And they're confident that they had the right skills.


That doesn't have to take up a lot of space to say all of that.


But in the reading of it, you're probably going to mentally be in a much more receptive place when you turn the page to start reading through their resume.


Yeah, I totally agree that the, when you see something that's deeper than the surface, right?


Everyone can, you can look at a website, you can figure out what someone's values are, and you could feed that back to them.


And obviously, there's a lot that comes out of the RFP that might be valuable.


But going beyond that will spark that piece that makes the selection committee feel like, oh, actually, they kind of know us, or we haven't heard that from anyone else.


Right now, it's super competitive, and your proposal may be up against, I hope not, but, you know, 10 others.


And that's not the best, but that's where the world we live in at this moment.


And so when they all start the same, if you can find something that's special about your team in connection with this project or, you know, the goals of the community or whatever it might be, that just is that next level.


And you earn some trust in there.


And they're like, okay, what else you got?


Well, and I'm curious.


Oh, I was going to ask you a question.


Yeah, and I was going to ask you a question.


You want to go?


Sure.


You and I have been in this business for a very long time.


And one of the inside jokes for marketers is that we're pleased to submit our qualifications.


And we're constantly like ruler on the back of the hand, admonishing our technical staff, like, don't say that, don't say that.


But how many of us have found ourselves up against the clock?


The covered letter never really got done.


We're sitting there trying to write it ourselves.


And your very first instinct is to write.


We're excited to submit this proposal for your consideration.


Oh, guilty.


Because so many cover letters start with that dreaded statement.


Why do you think that is?


Why is that the first place that we go to in your experience?


Why do we do that?


I mean, I would guess that it's because we actually are pleased to submit our qualifications.


You know, I get a smile on my face.


I think I love this team.


I think they have the right experience.


We want to win.


We think it's important.


We've invested a lot of time and energy into this, but that's where it should stop.


I've written letters where that's a start, because I couldn't find that magic other thing to say.


But you should really be thinking about how to push beyond that, and it probably means some tips that we can share after this, about how to get to something more substantial.


So it's not wrong to say it, it's just that everyone says it, it's the go-to.


So we want to move beyond that, and you don't want in that first line that the people who are reviewing the proposal to turn off their brain and say, oh, okay, this is just, I'm not even going to read the next five lines, right?


It's the same, even though there might be something wonderful in line five or six.


But where I've been most successful in writing a great cover letter was at the end of the proposal process, we've gone through the war.


I know it might feel like you're tired and it feels last minute, but actually I think that's sometimes where inspiration can come.


You have learned through the process that, I don't know, the superintendent's children were born at that hospital, or you learn that the architect's grandfather designed the first student housing on the campus.


I mean, whatever it might be, you find out these things and they inspire you.


And as a marketer, I think we can be inspired by our teams.


So, grabbing on to either those little stories and then feeling brave enough to just write something from scratch to tell that story, I think is where you can come up with something pretty amazing.


Have you had any, I don't know, experiences with that kind of just, let's be totally creative here.


Throw out the formula, throw out the playbook for writing this letter and write something that's just going to go to another level.


Yes, and you bring up two points that I think are really funny, is that we always complain the cover letter gets left to the last minute, but you're in the best position to write a meaningful one as the last step in the proposal.


So maybe it's more about time management and making sure that you leave yourself a little bit of buffer towards the end of the whole long proposal process.


But the other part of it is, and this is going back to thinking about the papers that we write in school or in college, is a lot of times people write their conclusion first.


If you've ever written a research paper and your teacher tells you to come up with a thesis for it, and you start to write that down, it's really uncanny how by the time you get through the entire process of researching exhaustively and coming up with all of the different points that you want to make when you're defending your thesis, the very first paragraph that you wrote typically ends up being your conclusion.


And the very last thing that you write ends up being your introduction because you finally know how to truly open it up.


And it's similar.


And so as far as an experience that I had, I remember working on this proposal.


This was like probably nine or ten years ago.


And the person I was working on it with was pretty quiet.


He was 30 years into his career, really pleasant guy.


And it was a project that was in the inner southeast area of Portland around the, it's called OMSI.


It's the Oregon Museum of Science and Industry.


And it's this really wonderful place that's right along the Willamette River.


And it's absolutely surrounded by old industrial buildings and not really utilize as much anymore.


And it was kind of poised for redevelopment, but no one can really get their heads wrapped around exactly how to do it.


And this was an early project just to look at the transportation grid and look at the movement of cars.


And if there was going to be any kind of development in the area, how would that impact traffic?


What kinds of investments would need to be made in a bike and ped and potentially street car or extensions of other types of transit?


So we put the whole proposal together.


It was interesting and frankly fascinating.


It's not often that you get to dream about something like that.


But then towards the end of the project, he starts to tell me that this has been something that has been thrown around by administration after administration, both at OMSI, as well as with the city of Portland, as well as with TriMet, as well as with the, I think it was the inner Southeast Industrial District Coalition or something like that.


Everyone had their eyes on this.


And he had first heard about it at the very beginning of his career and had a chance to work on a few little pilot projects, met all these people in the process.


So this wasn't just an RFP to him.


This was like the culmination of three decades of experience thinking about this site.


And it was really, really cool.


And so I'm like, this is the opener.


He was going to be our project manager on it.


He was going to be the one leading the work.


If they could just know that this had been something that he had been personally thinking about and pondering for the length of his entire career, that would probably catch my attention if I was on the selection committee.


So we did go that route and it did capture their attention.


Yeah, it's like, tell me more.


OK, now you've got a story to tell.


I'm really excited because we ultimately everyone's hiring people, humans, right?


It's not just not just computers or whatever to do the work.


So that personal story behind it is going to bleed through throughout the project.


It's pretty awesome.


It's experiential.


It's the human part of it.


And you're right, we can be excited.


And we should probably throw that in there somewhere.


Maybe not the first line, maybe the last line.


Yeah, that's a great thing to close on.


We're excited to talk to you further about this.


Yeah.


Hey, can we talk a little bit about scored cover letters versus non-scored?


You know, sometimes they are worth zero points, and I think it could be tempting to be like, well, that's not worth anything.


It's not going to hold us back.


Or sometimes they'll provide some direction that says, you know, use the space to cover things not presented in your proposal.


So there's a couple strategic elements there as a marketer and a proposal strategist.


How do you handle that?


Yeah, I've even seen ones that say, do not cover anything that is not covered in the proposal.


And it makes you feel like, oh my gosh, this is so redundant.


A lot of people treat it as the executive summary.


And I get it, but that's again, it's so redundant.


They're not going to spend a ton of time on the cover letter.


And it's really rare that it's going to amount to any points.


But what it can do is people are always on a bubble when they're ranking things.


You know, it's like if you've ever taken one of those tests where it's a never, sometimes, always, it depends on your mood.


You know, if you're feeling in a really optimistic mood when you take some kind of ranked survey, you are probably going to lean up.


If you are not in a great mood that day, you might lean down.


And the cover letter to me is a mood adjustment opportunity.


It's to get them into a positive state of mind and oriented in a way that is thinking about you closely assigned to this particular pursuit.


And in a way that starts to feel resonant from the very first line.


And if you can get them into that frame of mind, if they do come across a typo later on, they're probably going to be in a more forgiving mood than if you've given them something super generic that's just, it's trying too hard, it's super long.


There's no bullets, there's no bolded text, there's nothing to help guide their eye.


You are going to make them grumpy on that first page, and they're not going to be as forgiving when they get in.


And one other note is they're also, they're just, they're not going to be looking for ways to score you up.


And at the end of the day, the rank system, that's exactly what they have the power to do, is to lean into it or to pull back.


As much as you can be pre-positioned, whether it's having some existing relationships at kind of any level with the selection committee or just understanding the project pretty well is going to help buy you some grace in the cover letter, right?


They're reading something that's from a familiar person or from a familiar voice that'll help you out.


We are always championing being pre-positioned for work.


And if you find yourself going for work that you're not as well pre-positioned, then you better make that cover letter work really hard for you.


Because it's going to be that first introduction.


Hey, we have a listener question that I think is pretty great and could fit in right here.


You ready for it, Allison?


Oh, yeah.


Hit me with it.


All right.


I'm often asked to take the first stab at writing a cover letter, but I always feel lost in doing that.


Isn't that the project manager or principal in charge the best person to draft this since they know the most about the project?


Yeah, I have felt this one.


I have heard this one.


Starting out when you're at the beginning of your career, you feel really intimidated and just not set up for success.


If someone's like, write this cover letter for me.


As you go on in your career, you start thinking, this is not my job.


Especially if someone's like, we're going to go after this and I really want this project.


It's like, well, demonstrate it.


You know, you should be writing this cover letter.


It's your proposal.


I have felt that myself and I have seen staff I've worked with get a little resentful that the person that's name is going to be on that cover letter, palms it off and doesn't want to work on it, or doesn't have time to do it.


But I've also found that a lot of times it's because they are not natural writers.


They have writer's block or they really don't have time to sit down and think through how to articulate how badly they want this proposal to win.


And they always do.


I don't think that it comes from a place of my time is more important than yours.


I really don't.


And I think that's where a lot of marketers do have this resentment kind of bubble up, is that that's what it feels like.


I do think it comes down to we're probably in a better position to write those cover letters because most marketers are communicators and most communicators can write.


It can be daunting when you have so many other things that you have to work on in pulling a proposal together.


But there are tips and tricks to make it a fairly painless process to get it written.


One in which you can get to a good draft quickly and end up with a really wonderful strong declarative opening statement that says something of substance and that the person who's going to be writing their name on the bottom of it, when they read that first draft, it's going to get their creative juices flowing.


They're going to think of other things they want to say and they're going to put their spin on it.


And by the end of it, they're going to not only feel really good about the content of the cover letter, they're going to feel really good about the relationship with you and that you can work together as a team on things like this.


It's not only a chance to write a good cover letter, it's a chance to bond yourself with a very important player at your firm who you're no doubt going to be partnering with again on future proposals.


I would just add to that the other piece that makes it work well for marketing to write cover letters is that we actually get to see the big picture.


We have access to firm data.


We know people's resumes in a way that a lot of principals or project executives, they don't know those details.


And if you've been working on the proposal, you're privy to these little anecdotes that came out as you were writing a case study that maybe that detail didn't get put in there, but it's fantastic.


You actually do know the full story.


So give yourself some credit.


You can tell a great story in the cover letter.


You have a lot of tools at your disposal.


And I do think the executive team is very happy to have that help if they've asked for it, right?


We've also met plenty of leaders who say, no, no, I want to do the cover letter.


It's mine.


I can't wait.


They are natural writers.


They just need some time to sit down on a weekend and make it happen.


But, you know, if that's not the case, then I'd say, I'd say embrace it and say it's a place that you can you can do some writing that isn't connected to a dreaded RFP question.


It's free.


Well, and even the the ones that are excited to write it themselves, how often do they send it back in that first line says, thank you for this opportunity to submit.


And then you write back, you know what, I think I want to take my own spin at this first opening line.


And yeah, but to the point about being the one to write it, if if you do find yourself in that position, you know, we haven't been the ones typically tracking the project, and we have learned a lot in the process of putting the proposal together.


But it still can be like, you know, you put your hands on the keyboard, you've got this blank piece of paper in front of you.


It can be hard to know where to start.


And one of the things that can really, really help is to set a meeting with the project manager, the principal, who has that information in their head and just grab 30 minutes and ask them questions and take a bulleted list of their responses and use that to guide your writing.


So basically, you're transcribing what's in their head and you're the one that's making sense of it on the page.


And then when you turn it around to them to review, what they're seeing written there is pretty much along the lines of what they were already envisioning in the first place.


So you can get from rough draft to final draft, usually a lot quicker that way.


Having a conversation and letting them talk and let it, you know, just kind of flow from them.


I think it makes the writing on our side so much easier and you can take a whole bunch of notes and cut it down.


But you've got the seeds of all of the great stories there and the good messages.


And I also think we're pretty good at polishing that stuff up efficiently and almost better to own that piece than have to wordsmith and rewrite someone else's stuff all the time.


So good to have that balance.


So I guess we're saying, it's okay.


Embrace it.


It's going to happen a lot, probably a lot more often than we want.


And, you know, we're at the stage of the cover letter.


If you're doing it towards the end of the proposal, you may feel like you're also hurting all the other cats and trying to get all of the other missing pieces into place.


It feels like a lot.


But the cover letter is really important.


And I think we've covered a few reasons why it's super important and a few tips for how to make it painless on the marketing side of things.


Allison, do you want to add anything to this conversation before we wrap it up?


The one thing that helps me in every single way, shape and form, when I'm putting a proposal together, is to imagine myself on the other end of it.


The one that is picking it up with fresh eyes and sitting down to read it.


And I always try and imagine this person.


And at some other point, I know we're gonna dig into selection committee psychology, which I love.


It's one of my favorite topics.


But I try and have this person in my brain of someone who has just put in a really, really long day at the office.


They are tired.


They are weary.


They want to be done with work.


And they have a stack of proposals that just came in the door that they have to get through and they've got a score.


And there's a deadline in front of them to get those scores submitted.


This is not uncommon.


This plays out all the time for people that serve on selection committees because that work is above and beyond their day job.


So they do end up doing it in the evenings and on the weekends.


And when you sit down to look through all of these different proposals, and you're right, each pursuit, we're seeing larger numbers of people responding to them.


So there's just more to grade.


They want to be entertained.


They want to be inspired.


They want it to go quickly.


And they want to be able to get the information they need to score it as quickly as possible.


And our job is to give them that information in a manner that allows them to score us as quickly as possible and as high as possible.


And the cover letter is a really great place to start by letting them know that their time is valuable.


And we understand that.


So we're going to get right to the point and right to the heart of what that pursuit is all about.


If you can keep your eye on that ball, it allows you to avoid the BS, the boilerplate sentences that can just worm their way in, whether it's the cover letter or any other page of the proposal.


So just always imagine that you're on the other side of that looking glass.


And what kind of proposal would you like to read in addition to the 15 others that came in the door for that particular pursuit?


And if you can ground yourself in that, you'll probably end up with something that feels really authentic and probably is a lot easier to write.


Yeah, I got that sense when you said, think about the proposal you would want to read.


I'm like, well, there's some magic that we need to put on a sticky note above our computers.


Like, you know, what do I want to read?


What will make this entertaining and interesting and, you know, create that connection?


That's a good tip.


Thanks, Allison.


And thanks for this whole topic.


I love it.


We read and write a ton of cover letters.


I know all of our fellow marketers are doing that too.


So hopefully there's some good little takeaways they can grab from this.


And if we need to revisit it because you sent us a question and we missed a point, you know, let us know.


We're happy to answer those questions.


But for now, thanks, Allison.


Yeah, thank you.


Always love being on The Shortlist.


The Shortlist is presented by Middle of Six and hosted by me, Wendy Simmons, Principal Marketing Strategist.


Our producer is Kyle Davis, with digital marketing and graphic design by the team at Middle of Six.


We want to hear from you.


If you have a question or a topic you'd like us to discuss, send an email or voice memo to theshortlistatmiddleofsix.com.


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


You can follow us on LinkedIn and Instagram at middleofsix.


Thanks so much for listening.


We hope you'll tell your friends and colleagues about the show, and be sure to subscribe so you don't miss any of our upcoming episodes.


Until next time, keep on hustling.


Bye.


Bye.


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.

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