Microsoft’s Copilot Rises From the Ashes of Bob and Clippy


As I observed the presentation, I couldn’t help but feel a sense of nostalgia wash over me, reminding me of the ambitious launch of Microsoft Bob and its accompanying digital assistant, Clippy, in the 1990s. Although these early endeavors fell short of their lofty expectations, the latest iteration of a digital assistant, Copilot, promises to deliver exponentially more than its predecessors could ever imagine. The impact of this technology, both within and beyond Microsoft, is truly remarkable.

Prior to the event, I had a meeting with a company named Reply, known for preparing businesses for Copilot and establishing performance measures to validate the advantages of the technology. Reply enthusiastically praised the increased productivity experienced by both themselves and their clients.

The Copilot technology, which was relatively new just eight months ago, recently became widely available to leading companies in various industries such as healthcare, agriculture, IT, transportation, finance, and oil. Surprisingly, 70% of users express a strong preference for having this feature and are reluctant to go without it.

I have worked in this industry for four decades, and I have never witnessed technology advancing so rapidly from a beta stage to its current state. Let’s discuss this topic throughout the week.

To end, I want to highlight the Fisker Ocean, an electric SUV that I recently purchased and believe is the top choice available until 2025. Currently, there are 62,000 orders placed for this vehicle, but with a production rate of only 2,000 per month, I will have to be patient for my delivery.

Microsoft’s innovative approach to computing is exemplified in Bob and Clippy, two pioneering technologies that recognized users’ desire for a streamlined, user-friendly experience. Bob’s avatar-based interface and Clippy’s AI-powered assistance, both aimed to simplify tasks by allowing users to communicate with their computers in natural language. By embracing this vision, Microsoft set a precedent for future innovations in human-computer interaction.

Bob was an enigma, eliciting both sorrow and amusement. Initially, it was designed with the elderly in mind, those who found Windows challenging or unappealing. And indeed, when surveyed, this demographic embraced Bob with open arms. However, a Microsoft insider had other plans, promoting it as the cutting-edge Windows iteration. This misfired, as existing Windows users were unimpressed, even hostile towards Bob.

Before the advent of artificial intelligence, computer programs like Clippy and Bob were limited to pre-defined commands and lacked true conversational capabilities. Despite their limitations, they still managed to create the illusion that humans could interact with their computers in a more natural way. However, when their abilities fell short of this promise, they ultimately failed to meet user expectations.

Conversational AI has the innate ability to accomplish what Bob and Clippy were unable to achieve, that is, permitting users to interact with their computers as if they were engaging in conversation with another person. This technology not only enhances the way you communicate with your computer but also has the capacity to learn your work patterns and perform recurring tasks, such as responding to emails, scheduling meetings, and even participating in team meetings on your behalf.

Resolving Steve Ballmer’s Dilemma

I was reminded of a meeting with my friend and former Microsoft CEO Steve Ballmer while watching a presentation. He had confided in me about his challenge in prioritizing customer requests. With a large number of significant customers, including national and multi-national companies, Steve was buried under a wealth of data that made it difficult for him to give customer feedback the attention it deserved. This made it hard for him to set priorities that would truly benefit his customers.

Ballmer’s intellect was remarkable, especially when it came to analyzing data, but the intricate nature of the challenge proved to be too much for him to handle.

Microsoft’s Ignite event showcased Copilot for Services, which leverages extensive real-time feedback from a diverse group of customers to generate a prioritized action plan based on user-defined criteria. This approach enables a customer-validated roadmap that aligns with the needs and expectations of a broader range of users.

Had Ballmer been able to utilize Copilot, his been significantly greater, and Microsoft’s products would have been much more appealing while he was in charge.

Ballmer’s challenge belonged to a category that was previously thought to be unsolvable without Copilot, since the sheer volume and rapid fluctuations of data rendered traditional analytical techniques impractical.

Currently, artificial intelligence operates rapidly, providing solutions much quicker than traditional approaches. This suggests that individuals in leadership roles who are only achieving moderate success could leverage AI to excel, while top-performing CEOs, who are rare, could use this technology to solidify their dominance.

It is a real game-changing innovation.

Prior to the conference, I had the opportunity to meet with Reply, who shared their experiences with customers who have been using the beta version of their product in production environments. Unfortunately, a recent update caused the product to malfunction, highlighting the inherent risks associated with deploying beta software in real-world settings.

You’d think people would be understanding since it’s still in beta, but instead, over 66% of users reported that they’ve become reliant on the product and can’t function without it. They’re desperate for a solution and they got it. I’ve never seen such urgency and dependence on a beta product before.

Preliminary responses indicate a potential rise in productivity ranging from 10% to 30%.

The improvement seen in the statistics is a result of Copilot handling repetitive and tedious administrative tasks that employees typically find unpleasant, such as email responses, note-taking during meetings, agenda creation, Excel manipulation, and pivot table operations. During its beta phase, Copilot was assisting users with these tasks, allowing them to become acquainted with the product. Wharton professor Ethan Mollick, an expert in generative AI, suggested that once users are comfortable with tools like Copilot, productivity gains could reach up to 80%, a remarkable achievement. While the initial statistics from Microsoft and Reply were promising, it is anticipated that by this time next year, the results could be truly astounding.

Employees utilizing this technology are expected to make significant progress, and the technology itself is projected to develop rapidly, surpassing any previous rates of advancement. The potential for improvement, exceeding 80%, takes into account not only the enhancements made by users but also the anticipated progress of the underlying AI technology.

Microsoft’s Momentum:
In the early days of my career, I witnessed two controversies. One was significant, while the other was relatively minor.

The initial incident occurred when a journalist found out that IBM, despite promoting the new technology as a way to boost productivity significantly, was not implementing it themselves. The then-CEO of IBM, Louis Gerstner, posed a question along the lines of whether IBM should focus on benefiting themselves or their customers, as if it were a choice that could not be both. This response did not receive a positive reception.

After a number of years had passed, I found myself in a meeting with representatives from Intel, who were advocating for the early adoption of their latest technology due to its impressive productivity enhancements. However, it seemed somewhat incongruous that the Intel team members present were all using laptops that were at least five years old, leading to the query, “If these machines are truly that effective, why aren’t your own people utilizing them?”

Ever since that time, whenever a vendor promotes a technology as greatly improving productivity, I always inquire about whether they are actually utilizing it. If they are not, I assume they are not being truthful.

Microsoft is thoroughly implementing Copilot, which will greatly enhance the proficiency of its employees in this technology compared to those of other companies. They will be able to showcase Copilot’s full capabilities and potential, making Microsoft employees significantly more valuable in the job market. Just as people used to be asked about their familiarity with Office, job applicants will now be questioned about their expertise in generative AI and Copilot. Possessing these skills will give candidates a competitive edge over others who have not developed them, making it a valuable asset for any organization that adopts this technology.

Organizations may need to reassess their employee retention strategies and provide adequate compensation for workers with expertise in Copilot to prevent them from being poached by other companies. Job seekers would be wise to familiarize themselves with Copilot and highlight their proficiency in it on their resume or CV to increase their employability.