You know the feeling. You are on a call, or reading an email, or filling out a form, and something is just slightly off. Nobody said anything wrong exactly. But your gut taps you on the shoulder and whispers, "this doesn't feel real."
That feeling has a name. It is called the uncanny valley, and it used to be a term for creepy CGI movie characters. Now it lives in your inbox, your chatbot window, and yes, your marketing forms.
I got to sit down with Kristen Habacht, Chief Revenue Officer at Typeform, and talk through exactly this problem. Not "is AI good or bad," because that conversation is tired and unhelpful. The real question is sharper than that. As B2B marketers add more tools, more automation, and more AI into the funnel, are we building experiences that feel like a person is on the other end, or are we quietly training our audience to expect less from us?
Let's dig into what Kristen taught me, and let's bring it fully into where things stand right now.
The moment you know something feels off
Kristen said something that stuck with me. The closer an interaction gets to feeling human, the more obvious it becomes when it is not. That is the uncanny valley in a sentence.
You have felt this. A subject line that uses your first name three times in two sentences. A sales email that mentions a press release about your company like that is a normal thing a human says out loud. An overly sincere, overly dramatic message that reads like it was trying too hard to sound like a person, and somehow proved the opposite.
Here is the important part. Inauthenticity is not really about using a tool. It is about using a tool without listening to how real people actually talk. People do not announce their own credibility. They do not repeat your name back to you five times in one paragraph. Real conversation has rhythm. Question, answer, question, answer. When your marketing skips that rhythm and just performs at people, they notice, even if they cannot explain exactly why.
Ask yourself this before your next campaign goes out: if a real person said this out loud to me, would it sound normal, or would I feel like I was being handled?
What human like interaction actually means
Kristen gave a definition I think every marketer should tape to their monitor. Human like interaction means the person on the other end can tell there is intelligence paying attention to them. Not artificial intelligence necessarily. Just attention.
Practically, that means a few things.
The conversation has a natural back and forth, not a monologue disguised as a form.
The brand remembers what it already knows about you. If someone already gave you their email once, do not make them type it again like the two of you have never met.
The tone matches how people actually talk to each other, not how a press release talks.
This is not complicated. It is also not automatic. Every tool you add either supports this rhythm or breaks it, and that is the lens you need for every decision going forward.
Three places your humanity quietly leaks out
Kristen pointed to a few specific spots where B2B teams lose the plot, and they are worth walking through one at a time.
AI generated content that reads like AI generated content. There is real value in using AI to help your team move faster. The mistake is asking AI to originate a piece from nothing and publishing it as is. You can usually tell. The structure feels templated, the voice feels flat, and nothing in it sounds like a person who has actually lived the problem they are describing. The smarter move, and the one Kristen described, is using AI to adapt something a real person already wrote. Let a human write the bones. Let the tool help you resize it for a different industry, a different use case, or a different channel. That is the difference between augmenting your team and replacing your voice.
This is not just an opinion anymore. Buyers are actively fatigued by content that all sounds the same, and brands are being told the same thing by their own data. AI is now considered table stakes rather than a differentiator, which means taste, judgment, and a real point of view are what actually separate you now. Greenough Agency HubSpot's own research into 2026 marketing found that more content is now generated by AI than by humans, and most of it is average at best, which is exactly why audiences are gravitating back toward content that clearly came from a real person. HubSpot There is even a documented backlash forming, with creators and brands leaning into a rougher, more obviously human style specifically because polished AI sameness has become so easy to spot. Digiday
Chat experiences pretending to be more than they are. You have lived this. You open a chat window expecting help and instead get fed FAQ answers in a loop. That is fine, as long as you are honest about it. The damage happens when a brand lets you believe a person is there, and then you realize nobody is home.
Segmentation that flattens people into buckets. "Fifty employees, this bucket" is not a strategy, it is a shortcut. Real segmentation asks what would actually resonate with this specific group of people, not just what field to filter by in your database.
The half mile problem
Here is my favorite metaphor from the entire conversation. Picture the buyer journey like a bucket brigade, water passed hand to hand toward a house on fire. Every time the bucket changes hands, a little water spills out unless someone is being careful.
That is your funnel. Someone watches your webinar, and now there is a "talk to us" form asking questions you already had the answer to from their registration. They tell a form what they want to discuss, and the sales rep who calls them never saw that note, so the first email says "I saw you attended our webinar, what can I help with," when they already answered that question twice.
Kristen called this a million little paper cuts. Each one alone feels minor. Together, they tell your buyer that your brand is not paying attention to them, and worse, that talking to you takes effort. That effort is what she calls buyer repellent, and I love that phrase enough to steal it permanently.
The good news is this exact friction point has gotten real attention industry wide. Conversational form design, the kind that asks one thing at a time and feels like a conversation instead of a filing cabinet, has gone from a Typeform specialty to a widely adopted standard across the whole industry. Jotform And the specific "why are you asking me this again" problem Kristen raised is being solved at the infrastructure level now. Typeform has built ScaleStack directly into its own product to enrich form data automatically, matching new contacts against existing records with a reported 92 percent match rate in under two and a half seconds, which means less redundant asking and a lot less spilled water in that bucket brigade. Scalestack
Walk your own funnel end to end this week. Every handoff point, ask one question. What does this next form, email, or call assume the person already told us, and did we actually pass that information along?
Busting the myth that AI alone makes you human
Here is the myth Kristen wanted gone for good. The idea that the path to human like interaction is simply using more AI. It is not. AI is a tool that can support a human centered approach. It cannot become the human centered approach by itself.
Humans are still the empathy engine. The creative judgment engine. There are still moments where a real person needs to be the one talking, and no amount of clever automation replaces that. The myth to actively fight against is thinking your team can be replaced wholesale by tooling, or that any tool will feel human enough on its own without a person actually shaping how it shows up.
There is a new wrinkle worth naming here, because it did not exist in quite this form a couple of years ago. B2B buyers now trust AI tools significantly more when researching vendors, with trust up nineteen points year over year, and a large share say AI genuinely makes it easier to find information. Corporate Visions At the same time, AI agents themselves are increasingly doing early stage research and evaluation before a human buyer ever looks at your brand. That means the clean, honest, well structured version of your story matters twice now, once for the human and once for whatever is reading on their behalf. Sloppy, inauthentic content does not just lose a person's trust anymore. It can get you filtered out before a person ever sees you.
Where to automate, and where to show up as a human
Kristen's practical advice was refreshingly simple. Automate the parts where the human touch adds the least value, and free your people up for the parts where it adds the most.
- Automate data collection, lead scoring, and routine follow up sequences that do not need a personal voice behind them yet.
- Keep a human on the phone call, the complex question, and any moment where empathy actually changes the outcome.
- Build templates the way you would build a Mad Libs page. Keep the proven structure, change what genuinely needs to change for this audience, and stop rebuilding everything from a blank page every single time.
- If your sales team's follow up sequence could have been written by marketing, that is a sign the human moment got automated by mistake. Save the human for the conversation only a human can actually have.
This is also where the classic B2B buyer frustration data still holds up. A large majority of B2B buyers report friction in their buying experience, and most say they would switch to a vendor who removes that friction. Sana Commerce Every hour you save your team on the low value automatable work is an hour they can spend removing exactly that kind of friction somewhere it actually matters.
What success actually looks like
Here is where Kristen said something I want every marketer reading this to sit with. She called delight a legitimate success metric. Not a nice to have. A real signal.
Beyond delight, she pointed to a few honest markers.
People are engaging and buying, which is the most direct signal there is.
Your NPS reflects how people feel about the brand, not only the product.
You are seeing genuine referrals and virality, and virality is a harder bar than it sounds. Recommending a vendor is personal. If your friend has a bad experience after you send them your way, it reflects on you. People only recommend brands that will not embarrass them, which means every friction point you remove is also removing a reason someone hesitates to send a colleague your way.
Words of wisdom
Kristen closed with a line worth ending on here too. It does not matter what size your company is. You can still create thoughtful, meaningful engagement without a giant budget. Small teams tell themselves they are too small or too resource strapped to invest in this, and that is simply not true. Delight shows up in small moments. A rep who did five extra minutes of research. A form that only asks what it actually needs to ask. A follow up that remembers what you already said.
Treat the person on the other end of that email or that phone call like an actual human, because they are one. People buy from brands, and people, they like. So be the likable one in the room. That advice works in marketing, and honestly, it works in life too.
Where Sidekick Strategies comes in
This is exactly the kind of gap we help HubSpot users and B2B marketing teams close. Not by telling you to rip out your automation, but by walking your actual funnel with you, form by form, email by email, handoff by handoff, and finding where the water is spilling out of the bucket.
If you have a feeling your forms, your lifecycle emails, or your handoff between marketing and sales are quietly repelling the exact buyers you worked so hard to attract, that feeling is worth listening to. Reach out to Sidekick Strategies and let's map your funnel together, and find the half mile where you are losing people before they ever get the chance to say yes.
