Building a chatbot: The Conversational Specialist

Typically, an agile squad will contain all the skills required to achieve your mission or solve the problem you’ve been given. However, as I developed a chatbot, it became clear that as well as UX, CX, frontend developer and Tech Dev Lead roles, we would have to create some new roles.

  • Cognitive Engineer – fairly well known role in the big players in the AI market – IBM, Microsoft etc but outside of those environs, Cognitive Engineer, while sounding super cool is a new role to most organisations. I’ll write about the role in more details in coming weeks but the key thing here is that they provide the technical know-how of the platform you’re using – configuring, developing etc. Alongside the frontend dev, UX and tech dev lead, they’re a crucial element in bringing your ideas to live.
  • Conversation Specialist – these does already exist outside of the tech world, they’re called scriptwriters, playwrights etc! These are the folks that can handle the mechanics of a conversation but also create the language and dialogue that make a conversation work, in this case between your customers and the chatbot.

These two roles work hand in hand once your research has been done, the answers to the problem found and now the chatbot needs to be taught to understand how to have the conversation with customers to resolve the issue.

The study of conversation is an area lacking in depth and attention but I’ve a feeling that this will change quickly over the coming years. It’s a study space that will lift from other creative spheres – scriptwriting etc but bring it into the business space. Persona or brand will of course play a part, and those skill exist in many businesses but the application here goes well beyond training frontline staff in how to have a conversation and into the technical and documented world of AI.

In my, somewhat limited experience, frontline staff are the perfect starting point when you’re looking to hire a conversational specialist. Their conversational skills, understanding of the brand they work for as well ability to relate to the issues customers have and how to solve them, provide the perfect starting point. The technical skills of conversational design and build are easily taught/learned and also vary from platform to platform. However, instinctively having the voice of the customer in their head means that conversations they design and build will resonate and work with customers – they have in the past!

So, how to hire someone into that role? I believe it’s 90% gut reaction to that person in a face to face interview and 10% on the answers they give to the questions below. As with any interview questions, there are no right or wrong answers but they’re simply designed to draw out whether the person in front of you has the right mindset as well as the skills.

Questions you could ask

Please outline what you think makes a good conversation?

Keywords to listen out for here are empathy, listening or active listening, respect, fun, interesting, engaging. Essentially, is the person equally aware of the other person, listening and not simply waiting for their turn, demonstrating empathy for the other person – though important that this can’t be simply showing an empathetic expression as your chatbot, unless you’re building a virtual human, will be only using text.

Extra points or anyone who picks out couplings like greetings etc but especially check-ins i.e. do you understand/know what I mean? And, also for affirmative endings thanks for talking, anything else I can help with and so on.

Give me an example of a bad conversation

Perfect follow-up and gives the person the chance to fill in the gaps, if any, from the previous question.

If “X” were a person, what would they be like?

A chance to check-in on your interviewee’s understanding of the brand involved and also fun question to let them imagine/personify etc.

Demonstrate how a “X” conversation with a customer would go?

Similar as before, a chance for the person to fill in gaps with a more practical example. So, they may be lousy at creating a character but still know your brand really well and explain how a “branded” conversation could/should go. Key elements being the greeting, tone, ability to keep things moving along (value) and demonstrate some of the elements they probably previously mentioned i.e. empathy, listening and being engaging. Essentially, for a frontline person, show me what you do on a day-to-day basis. Their people leader will be able to support their performance here.

Speaking a conversation is natural but how would you go about writing/creating a conversation to solve this [example] problem?

To the meat now. As I mentioned, there are various 3rd party sources/examples of this but what we’re looking for here is the ability to take the softer skills from above questions and start to build something using logical points such as decision point, conversation branch into something that both addresses the customer/example problem mentioned and resolves it – answer (information), direct to action point (fill out this form), or direct to answer with context i.e. if your bot isn’t plugged into customer data, the bot takes the customer to the self-service tool that can – app/website etc.

We’re hoping to see that your interviewee can step back from the actual conversation to understand the skeleton or structure of it for example a conversation branch where options could take the customer off on a tangent (that also needs answering) or a decision point (shall I send you the link to the form?). Even if they understand the top (greeting) and tail (farewell) and know there’s “stuff” in the middle, they’re onto it.

Key outcome is how was the customer helped through the conversation – answered/solved the issue, redirected or even if no answer available, connected to someone who can.

Tell me who your favourite 3 fictional characters are and how would they have a conversation about being stuck and unable to move forwards?

Another looser, more fun question that should illuminate more about the person i.e. which characters they choose and also what the conversations might be like. Especially interesting if they pick a character who’s not know for speaking a lot i.e. Batman.

Looking to see that the person can demonstrate at least 3 different character types or voices and the difference between them.

Extra points for good impersonations!

Finally, if your prospective conversational specialist is from your company’s frontline, the show me your weakness question i.e. when something went wrong what did/would you do?

Tell me about a time a conversation with a customer started to go wrong and what did you do to bring it back on track?

Again, a little bit of all of the above plus showing the ability to “save” a conversation, which given the way people use Bots is quite likely to happen. Should show a lot from the above questions, empathy, on-brand, and self-reflective i.e. they realised where perhaps they set the customer off down the wrong path using jargon etc and of course, how they saved it.


Got any more you would suggest or feedback on the above? Would be glad to hear from you.


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