A few months back, I had a crappy case study interview.

It was awkward from the jump: I assumed the customer had sufficient context about the call’s participants and purpose from the emails we’d exchanged previously, so I dove in with my first question. But instead of responding, he said, “Shouldn’t we do intros first?” 

D’oh! Yes. I was talking to another human, so perhaps politely acknowledging our first face-to-face interaction might have been in order before I started interrogating him about his business and the ways in which it was failing before my client’s software saved it. Anyway, intros completed, we kept going, and we kept running into speed bumps. He was obviously uncomfortable—concerned about how his company was going to come off, hesitant to share details he didn’t want exposed. I tried my best to ease him through and assuage his concerns, but I was already on the back foot. 

Things didn’t get better once the draft was in his hands for review. I got the sense he was uncomfortable with the whole premise of a case study, and while on one hand, this happens — sometimes a case study falls through because a company doesn’t like being positioned as having needed help — I had a sense that if I had just handled the interview more empathetically, with more attention to his concerns from the get-go, we might have had a smoother process. 

Empathy in Content (Not the Pain Points Kind)

To that end, I’ve been thinking a lot lately about empathy in content. Not in terms of your audience (that’s kind of a given, right?), but in terms of the people you encounter in the process of creating content. 

Being a marketer of any stripe involves a lot of collaboration. To get something done, you’re engaging with SMEs, execs, legal, product, and other marketers (or marketing-adjacent types, like comms/PR). And it’s easy to approach these engagements as battles — to brace yourself for what fresh hell legal is going to wreak upon your copy this time around, or to grudgingly send your draft to product, knowing they’re going to have a bunch of irrelevant comments you’ll have to politely wave away. 

But what if instead of girding for battle, we tried to position ourselves for shared success by approaching our collaborators with a sense of empathy—with concern for their concerns?

I riffed on this on LinkedIn a while back in terms of how marketers tend to engage with legal, but realized as I was gritting my teeth through this recent case study that I ought to have applied my own advice more broadly. 

Empathetic Questions for Better Content

Specifically, I want to start embarking on collaborative conversations in the content process with two questions in mind: 

1. What does the person I’m collaborating with (be they a customer I’m interviewing for a case study, an editor, a lawyer, etc.) need to know in order for them to help me?
   
   For example, I might have (after greeting the customer I was interviewing like a human being) explained to the customer that I was going to ask them a lot of detailed questions to get the context I needed to tell a thorough story, but that I would use my judgment and any limits they shared to keep any sensitive information private.
   
   Or, if I were engaging with Product on a white paper, I might tell them that I only need them to fact-check specifics on product features, and that the structure of the white paper had been agreed upon already and didn’t need any further feedback.
   
   
2. What else can I tell them, or how can I frame it, in a way that makes them feel bought in and supportive?
   
   In my case study interview, I might have started out by telling the customer that the goal was to tell a story of how his organization grew and improved by using my client’s software, in a way that was flattering to both parties.
   
   In the Product/white paper example, I might explain to Product that the white paper is intended to showcase the new feature they released to customers who haven’t made great use of it yet. 

Content is never not going to be a battleground. You’re always going to have pedantic product people trying to insert ten paragraphs of feature descriptions into your infographic, and lawyers asking if you can append three disclaimers at the bottom. (And you will always be, to them, that marketing person who doesn’t understand the nuances of their product or the law, yada yada.) 

And I don’t know that, even if we had started the case study interview with ten minutes of chitchat about the weather and our childhoods, this customer would have reacted better to the draft. But at least I would have demonstrated to them that I understood them at a human level and was prepared to engage and respond to their concerns, and I think that would have set us up for a smoother process than the one we went through. 

Ultimately, we can all only spend so much time on content, and the more we spend having constructive conversations rather than arguing about points we could have resolved proactively, the better. ■

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Dana is a freelance content writer and editor based in Brooklyn. Previously, she served as global head of content for an S&P500 software company and head of marketing for a seed-stage startup.