Purge Ruthlessly Every Six Months—A Conversation with Proposal Champion Kathryn Bennett

Chris Gillespie | July 8, 2022

Kathryn works in the niche world of requests for proposals, or RFPs—those big reports large companies request from vendors to say, “Show us what you got.” They’re something of a public figure in that area, and a topic expert for writers who cover this field. (Including us at Fenwick. See them profiled here and here.)

Kathryn has a bit of a unique vantage, straddling proposals and content marketing. The similarities are many—in both, people solve problems with words—but the differences in operational efficiency are vast. Proposal management follows strict conventions while content marketing tends toward scarcely mitigated chaos. That makes Kathryn a particularly qualified commentator for our series on content ops.

The question we explore is, what can writers, designers, and marketers learn from the much more scientific field of proposals? Lots, it ends up. And while applying this advice might be painful, it will be productive.

Kathryn Bennett is a polymath. They co-founded Outlaw Proposals and the podcast “No Really, Everything’s Fine.” They’re also the owner of the strength training brand Warmaiden Fitness and author of Productive Pain. They were also Senior Manager of Proposal Operations at the 500-person healthcare provider Maven Clinic. This conversation has been lightly edited.

Everyone creates. But how many think about maintenance?

Kathryn: The reason I reached out to you is because I think a lot of people understand the principles of creating and distributing good content, but not the ways in which they maintain their library. Something like 60 percent of marketing material never gets used, so how you store, reuse, and update it is really important.

In proposals, there are some rather aggressive philosophies and methodologies for that which translate perfectly into marketing. I think it’s an important, missing angle, so I’d love to share.

Rule number one: Ruthlessly delete anything not used

Kathryn: If you don’t dispose of outdated stuff, it will rot your system. And that makes a nice acronym: If it’s ROTten—redundant, outdated, or trivial—get rid of it. And by get rid of, I mean delete.

To understand why this is necessary, it’s helpful to think about why you’re managing content in the first place. We all want our team or customer to be able to stroll into our virtual library, walk to the right stack, pick up a book, and put their finger on the thing. Right? It’s the same whether it’s proposals or ebooks. And if you take that perspective, anything that is not supporting them is getting in their way.

"We're not archiving it. We're not storing it. We are deleting it because it's no longer relevant."

There’s another framework that’s helpful for thinking about this called knowledge-centered service, or KCS. (Credit to Anthony Rossi at MX for showing me this.) It’s an IT help desk philosophy that your content should be four things: valuable, trustworthy, demand-driven, and abundant. As marketing teams, we usually nail abundance, right? We've got a ton of good content. But what we don't have is an understanding of how often that content is used by our team and which pieces, consequently, we should keep around. So we tend to fail at being demand-driven. We keep it all, and it becomes a hoarded mess.

At my last company, we’d hold a ruthless purge every six months. If an answer hadn’t been used in any of the last 70 proposals, it was not important. We got rid of it. The thinking was, “We're not archiving it. We're not storing it. We’re deleting it because it's no longer relevant.”

Archiving is not an option. It only creates a psychic burden

Kathryn: Archiving makes you feel safer, right? But it’s like keeping a closetful of clutter in your house. You’re always aware of it in the back of your mind. And the temptation for your C-suite is always to go back and say, “Well, we wrote something about this before.” But what you wrote in 2017 isn’t applicable today. Things have changed. Particularly in tech. You can’t go rummaging in that old closet and expect to find something valuable because there’s a reason you hid it all in that closet.

And then, how much effort does it take to retool something that’s out of date, when you could just create something fresh? It’s actually more work to go back, especially if it didn’t help you win the first time. And what if someone else on your team finds it and thinks, “Oh, this is how we explain what we do,” and copies it?

What it comes down to is risk mitigation and energy savings. It feels terrifying to get rid of content, but I guarantee you won’t miss it. Just like you won’t miss the closetful of garbage. You have to overcome your attachment and see it for the psychic burden that it is.

"It feels terrifying to get rid of content, but I guarantee you won’t miss it."

But actually. Delete it. It allows your winningest content to expand

Kathryn: I know people will object to all this decluttering, but what is that fear based in? What are you going to lose? I’d rather have two or three kickass pieces of content that I can slice and repurpose in a dozen different ways. Give me one great report and I can do a webinar, a blog post, a podcast, a video, and more.

If the thing you’re struggling to delete was at the bottom of the list, it was at the bottom of the list for a reason. It’s no good. Clean house and take your winningest content and throw it in the permutation factory where it gets used over and over.

Honestly, bad content is worse than no content and we have to get over our squeamishness of getting rid of old things that don’t serve us. If nobody’s reading it or it doesn’t convert, it needs to die.

"If nobody’s reading it or it doesn’t convert, it needs to die."

To know what to delete, test, and measure with minimal rigidity

Kathryn: When we first start out, we’re all just operating from our opinions about the content. But you have to graduate to measuring how it performs because you can’t achieve what you can’t measure.

There’s two parts to that. There’s talking to your audience daily, and measuring the results. You have to test a lot of different things. When writing about best practices for proposals, I was surprised that people were actually interested in hearing about career stuff, which is how I dug into that. I would not have known what direction to take. And you need data, if only to make the case internally. Otherwise, you’re just going to wind up talking about what your CMO wants.

I’d also like to see us break out of just looking at clicks and conversions. We need less rigidity. We need to acknowledge all the diverse experiences people are having with our content and its emotional impact. I’m on social media all the time and I have to think of that success as multidimensional and about more than just likes. I once had some webinars that didn’t get any traction. Like 50 people showed up. But I knew the topic was meaningful. So I just continued to beat the drum, reinforcing it, pairing it with different things, and asking people to share. In the end, I forced it to be successful and people told me they appreciated it. I would never have known to do that based on its initial reception.

Never adopt software unless you have a philosophy of work

Kathryn: Managing lots of content in a decentralized way can create a big, big organizational problem. Your biggest ally in that fight is technology. But you have to be fluent in that technology and have a preexisting philosophy of work. That philosophy is what gets encoded in the system and makes it productive. Lots of people will say, “Oh, just bring [the sales content storage tool] HighSpot on,” and they end up with a beautiful pile of crap. Because everything tends toward chaos, right? It gets out of control.

The way I create boundaries is through administrative and environmental controls. People’s opinions are great, but the machine is going to do what it’s going to do, and I can let it do the dirty work for me. Someone’s really attached to an outdated white paper and I can blame the machine. Like, “Oh, well, the machine is designed to get rid of things after six months because that’s the best practice, and it’s what we all agreed upon. Right?” So you encode that philosophy and then let the machine do its work.

"The machine is going to do what it’s going to do, and I can let it do the dirty work for me."

An ideal marketing library is searchable, democratic, controlled, AND abundant

Kathryn: Whatever system you create to store content should be searchable by keyword, with metadata and tags, which by the way, you can employ in Google Drive. And it should be democratic so as many people can contribute as possible, but it also needs administrative controls to ensure that content is used in the right way.

And of course, there’s abundance. That library should be able to store lots of different types of file formats, and there shouldn’t be a limitation that prevents some types of content from being included.

Stop working yourself to death

If I could put up a billboard it’d say “Stop working yourself to death over this stuff. Make the machine do it for you.” That’s what I would want everyone to know. If you create a system, your life gets a lot better.