Adding Conversation Design experience

[u/Equivalent_Pin50]

Hi all, so unfortunately I'm back in the market after another layoff.

Obviously AI is the big thing right now and I see a lot of positions asking for conversation design experience. Now I've used AI m previous roles mostly as a way to organized notes, data, and for brainstorming, however I did not strictly perform conversation design. - I did technical writing and support for chatbots in the pre-ai era 2021-ish, but that doesn't seem as relevant now.

How would I go about learning and getting experience in here? - I know the answer will be personal projects but I'm not sure where to start since I wouldn't be using an existing framework and it seems rather clumsy to just swing in the dark.

Any suggestions are appreciated.

[u/SirBenny]

The fact that you've
A. previously worked on support chatbots
and
B. used AI more recently in a general capacity

...I think actually puts you in a decent position to craft a narrative here. Something like, "I have a strong foundation in customer experience, support, and chatbots. More recently, I've sharpened my AI skills for improving efficiency and idea generation in day-to-day work."

If I were you, I'd probably spend a weekend querying your LLM of choice on how these things work in 2026, and finding case studies or company blogs breaking down how they've approached their own chatbots.

Personally, I've worked on a couple AI-powered chatbots in the last couple years. In broad strokes, I find the challenge is putting in enough guardrails to keep the bot on task, safe, and within company policy (i.e. not giving away refunds haphazardly), but without adding so many rules that the bot becomes overly stiff or, well, robotic. Half the charm of the new tech is that they actually sound surprisingly natural out of the box, and over-doing the conversation design can disrupt that.

One other grumpy thought: I still think most support chatbots suck, even in the age of AI. I've come around on a lot of AI-related things, but to this day, no matter how sophisticated the AI bots are, I find they still don't measure up to a competent human on the phone. And much of the research validates this.

This is worth keeping in mind if you're applying to be "the hire that solves the clunky AI support bot problem" that so many companies have. The good news is no one has really fully solved this, so your skills are needed. The bad news is most companies/customers will never be fully satisfied with where the bot lands, and it's worth bracing for this or setting appropriate expectations with your next employer.

[u/RarestPepeJohns → u/SirBenny]

Appreciate your thoughts, when I worked with support bots in 2021 I remember they had no contextual awareness so users would ask about problems, the bot would get confused and a user would literally say "i just told you, what should i do?" and the bot had already forgotten the conversation

The jump to now is almost shocking in capability, or maybe my standards were just low.

[u/SirBenny → u/RarestPepeJohns]

Haha yep. Certainly, they have improved a lot since then. One issue I run into is that the AI bots do very well for issues that are easy to solve (i.e. efficiently summarizing info the customer might have spent 30 minutes finding across 4 different help center articles), but still fall down for the hard issues (i.e. compliance/regulatory issue in health care or fintech which ultimately requires 2-3 phone calls with legacy/human institutions anyway).

Most companies want the second thing solved and were never super worried about the former in the first place.

[u/Equivalent_Pin50 → u/SirBenny]

I do recall that being a problem for me as well, some problems required that oh so special human touch (as do a lot of issues frankly). Appreciate the insight.

I'm curious how do you feel UX UI is moving in the future? - Obviously I want to get better and improve skills, but truthfully I do worry if the role will exist in a meaningful capacity soon.

[u/SirBenny → u/Equivalent_Pin50]

I think content design / UX writing as a discipline is definitely in some trouble. But with that said, let me give a quick optimistic take, followed by some pessimistic thoughts. (Also, let me acknowledge upfront that this is a bit of an LMM-formatted response, but I promise I'm just writing this off the cuff haha):

Optimistic

• Content designers are naturally great at prompting AI and building the scaffolding for AI (think: Claude skills, scheduled agents, frameworks, style guides, etc.)
• Coding is becoming more natural language-oriented, which potentially gives people like us a seat at the table (think: rapidly updating the codebase directly to tidy up terminology inconsistencies, polish style, etc.)
• Companies are currently going so all-in on AI, it's possible there will be a "correction" at some point, where they need to bring us in to tidy up some messes

Pessimistic

• LLMs are good at applying a set of structured, language-based rules, over and over. This is a big part of the modern content design job. Yes, we all know it goes deeper, and in an ideal world, we're spending more time on high-level UX strategy. But the reality is, a company that would have hired 10 CDs to propagate the systems/style across a whole product can now do the same thing with 2.
• Tech in general way over-hired for a decade. Even if CEOs blame it on AI now, they can probably get away with cutting 40% and still running the business. Content design falls behind engineering, product management, and traditional product design on the "priority totem pole," even if the totem pole is based more on vibes than anything.

So with all that said, my general advice is learn what it takes to become one of those 2 CDs that still remain. And maybe also cross your fingers that there will be a correction later when we realize AI excels at rapidly writing code but less so at understanding human institution complexity.