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The Steven Files Ep.2 – The Key Points Every CXO Must Look For in Their Conversational Chatbot Partner

Digital Transformation chart


The wind was particularly sharp that Friday night. However Roger Friedmont, the digital transformation lead was oblivious to the sudden gusts blasting from all sides; For you see, he was a man with a mission. His well thought out plan was finally being set in motion.

If you have missed reading the Episode 1, read the back story first – Steven Files Episode 1

Chapter 1 – Know thyself!

Understanding internal capabilities to not make a conversational AI project into a DIY fiasco

“It’s no use jogging that memory. Not right now.” Roger was mumbling to himself as he made his way toward home. Roger was a private man and more than that, he considered himself a minimalist. Something that his work and his condo on the 10th floor made sure to communicate with the world. Roger entered his apartment and somberly made his way toward the study. The bright lights of the study were a welcome gesture as opposed to the scantily lit lights inside One-eyed Mackey’s. The words were still ringing in his head “Monday, Roger. I’m counting on you.” He poured himself his favorite, a cup of Joe, and settled on his work table.

Roger sitting on a bean bag and using his laptopHe has been tasked with planning the entire digital transformation journey of his organization’s customer service process, and he drove home the idea of a conversational chatbot. However, he was clueless about how to start this entire exercise. This was not his first project, but this one can certainly be a dealbreaker for his future if he fails to deliver. And his entire plan depended on how he will be delivering this.

One point that he was clear throughout the entire idea was that he wasn’t going to build it, he was going to buy it. According to McKinsey, 70% of digital transformation projects failed and he wanted to make sure his project won’t feature as a major one in that statistic. The internal tech team even if they could develop a sophisticated chatbot, lacked three things.


The internal IT team members were not subject matter experts on the concept of conversational AI or deriving insights from it. They were not even aware of the subject, and introducing such a topic to them to learn can be disastrous given that they were already loaded with their day-to-day deliverables.

Turnaround Time

They were treacherous with their turnaround times. One project will stretch beyond 8 months to deliver, and frankly, Steve won’t be happy with an 8-month delivery riddled with bugs that should have been addressed in UAT itself.

Training Data

This is the most important point of the lot. Even if the IT team built expertise, and improved their turnaround time, they still lack the training data to train their bot. The experts in the field however would have built their own relevant AI use cases and their bot would have been trained in millions of rows of data.

Convincing the board to invest in a project headed by an external partner is going to be tough. He very well knew what would transpire when he brought in an external vendor. They will put out a steering committee and try to beat down the very idea under the pretext of culture and building internal expertise. “They are control freaks!” Roger shouted breaking the shrill silence of the night.

But then, he suddenly got his idea. The idea that will break the unwritten rule at his organization of not taking external tech partners.

Chapter 2 – An Unlikely Ally!

Getting buy-in from the right stakeholder at the right time

Mornings were something that Joseph “Joe” Nakamura, the CIO loved. He would get up from his bed, freshen up, and go downtown for his favorite run across the city’s acclaimed jogging track. Saturday mornings were the best of the week as the runners on the track would thin, it was the weekly off and he could hit the track leisurely.

However, this Saturday has been different. He mindlessly put on his track pants and running shoes because one question was running in his mind, back to back. “What did Roger want from me?”. It was a bit odd that he should drop an email at 1.00 in the morning, and it was safe to assume it was indeed urgent, specifically after the showdown in the office yesterday with Steve. The meeting was at the coffee shop at the end of the track.

The time was 8.00 AM, Joe came in ordered his favorite Latte with thick cream, and was sipping it with unmasked pleasure when Roger dropped in.

Joe and roger meeting casually “Hey Joe”

“Hey, Roger. I was pretty much worried about the mail I saw at 1 in the morning. Everything alright?”

“Nothing to worry about Joe. I just had a few questions about something. But let me set the context first. Steve liked the idea of Conversational AI-powered chatbots.

“Ooh, Nancy is not going to appreciate that,” said Joe.

“I Know. To top it off I’m stuck at the very first level. Honestly, I have no clue as to how to figure this out. I just wanted to rack your brain to get some insights.”

“ Alright. Anything that is within my power to help a friend” was Joe’s response.

“Thanks, I appreciate that. So tell me, Joe, in all probability, do you think our internal IT team is capable of delivering a project like Conversational AI chatbot.”

“Well you cut to the chase, no leading me into it huh?” laughed Joe. Then he continued “I am sure my team is more than capable of delivering such a project. We have data engineers in our team, who are technically qualified with efficient managers running many such projects.”

“That’s great. My next question is whether will they be able to deliver a mega project like a conversational chatbot for improving CX in a time as short as 3 months?”

“As the CIO, I will give a confident yes. However, the reality is we need to factor in the time for the team to understand the subject, put a plan together and in extreme cases, hire more senior data engineers if required. In all practicality, executing this in-house is a long-term commitment.”

“So, you also agree that we need to look for an external vendor” said Roger.


“So can I count on you to counter the board on Monday, when they definitely will reject the plan?”

Joe took a long breath and looked at Roger before nodding at him.

Chapter 3 – From the Horse’s Mouth!

Learning about what a CIO will  expect from his Digital Transformation Vendor

Now that Joe had been roped in to play a major role in Roger’s idea. He moved on with his questions to Joe.

“Joe, what do you think are the top things a CIO like you would expect from a vendor who is an expert in building and deploying conversational powered chatbots?”

“Well, you are a digital transformation lead and a conversational AI project for customer experience is also a digital transformation project. So I will try to relate it to the three pillars of digital transformation. People, Process, and Technology.

3 pillars of digital transformationPeople

Joe continued the conversation, “As CIOs, we expect that the best of talent resources be available for the project right from consultation to deployment and post-live support including training and change management. We also expect them to develop our in house resources and bring them up to speed so that the support communications can be seamless.


“CIOs want an agile and nimble execution of the project. To achieve Speed to value, out-of-box implementations should get precedence followed by relevant customizations. They understand that a data-driven approach to tracking implementations is required and they expect that from the vendor. Especially after a major consumer goods company was able to reduce its time to market by 15-20% after taking a data-driven approach. The fail fast, fix fast is what CIOs are expecting, so that the value for the implementation can be experienced at an early stage”


“CIOs nowadays are looking for convenience. They will be on the lookout for platform accelerators that makes integrations easy and most importantly they are looking for technologies that can learn itself, communicate with other systems, and ensure that digital silos are broken between systems, data, and technology. AI sits at the core of this. Maybe that’s why Deloitte quoted, “Investment in AI is forecasted to triple by 2023 to nearly $100 billion as the AI business-cases increase exponentially.” Therefore, CIOs would require strong use cases, especially in conversational AI from the vendor’s side to show their tech capabilities”

Chapter 4 – Parting Advice!

Things Roger needs to keep in mind before presenting to the board

Joe finished his discussion with Roger and stood up saying, “Now you do have an idea of what the IT heads expect out of a project where they’re part of the steering committee. I’ll back you up when you present to the board your findings on Monday. I do suggest that you be prepared by reading any specific use cases. I do have one with me, it’s about how a startup in the CAI space revolutionized the world of Insurance. I do understand it’s miles away from what we’re doing. Still, it might help you present your case to the board.

Roger nodded to Joe and looked at the long stretch of the jogger’s track. This was not apparently easy as it seemed. He had one day to prep himself and his team for the onslaught of questions that the board will ask. One thing was for sure. They will be ruthless with their questions, and he had to be ready.

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