
Jon Lester describes himself as being in the business of “technology-enabled transformation.” As IBM’s VP of HR Technology, Data & AI, and with a career spanning three decades, he has long grappled with the question of how to integrate new technologies into people management.
“Solving problems over the last 30 years has now been more and more about technology and people,” he affirms, discussing how his career progressed from working post-university as a software developer, to acting as a consultant for IBM from 2005. He assumed his current position at the tech company in 2022, and in recent years the rate of change at IBM has accelerated considerably.
“We used to write five-year roadmaps and strategies; we stopped doing that in 2016,” he explains. “ We then wrote three years; now we’re writing 18-month strategies and roadmaps, because by the time 18 months has gone, the whole world has changed again.”
But while technological shifts are accelerating, Lester explains that his role retains largely the same overarching goals it had at the start of his career. So regardless of the rapid development of AI, quantum computing and sovereign tech solutions at IBM, he will continue to be responsible for integrating new tools into HR processes, and for developing the skills necessary to make the most of them.
Removing a fear of failure
Up until 2016, Lester was an external consultant for IBM, overseeing and offering guidance on technological changes that the company was introducing within its HR teams. He was one of the first people with IBM to gain Workday certification during this period, yet he reports that the move to an internal position helped him to take a longer term and more informed view of the changes he was helping to implement.
We used to write five-year roadmaps and strategies. We stopped that in 2016
“With IBM being my employer for 11 years now, I get to ask what did we get right” he explains. “What did we get wrong? What can we learn? How can we do it better?”
Assuming an internal position also enhanced Lester’s ability to effect shifts in organisational attitudes and culture, including removing the fear of failure in relation to adopting new tools and practices. “Failure’s fine, because do you know what? If we fast forward to today with Gen AI, large language models, we don’t really know what we’re doing at times, because there’s nothing that says, ‘This is how you do it in this scenario.’”
In such situations, Lester encourages his team and his colleagues to experiment with new technologies and working methods. And while the preference is on failing quickly and cheaply, reducing the aversion to failures gives teams the freedom to “try stuff, learn stuff, and then figure out once you’re relatively confident this is the way to go, then go all in on it and really go for it.”
Connected to this more fearless mindset is an openness to continuous learning, which is something Lester has been keen to promote at IBM. “How do I as a payroll specialist, as a comp specialist, as a recruiter, how do I then change the way I have to work, and the skills I have to learn to enable me to get the best out of this new opportunity?” he says.
Hiring for skills, not just for people
Such an approach is necessary when new technologies are being introduced on an increasingly regular basis, as is happening at IBM. In turn, the rapid arrival of new tech has led to a greater emphasis on developing and hiring for particular skills, rather than simply focusing on the employee or on teams as a whole. “As we’ve gone through cloud, as we’ve then gone through traditional AI we even built skills, for example, as a big part of our whole model for talent management,” Lester reveals. “How do we get the right skills through people, through hiring? How do we develop the right skills through people learning?”
He adds that he and his team began paying special attention to skills while most other companies were still talking about jobs. IBM has even put skills at the centre of its reward structure, incentivising greater learning on the part of employees, while also providing greater expertise which the company’s clients and partners can harness. “If you kind of are really serious about developing your skills, we’ll make sure that you get rewarded for that,” he explains. “So, putting skills at the heart of this continuous learning culture, and making sure that we reward people for doing so, I think is another big building block within where we’ve got to today.”
AI in IBM’s HR department
It’s in such a fertile environment that IBM has been integrating AI into most of its operations, including in its HR department. Back in 2016, the company had 1.6 million HR support tickets and 890 HR systems, according to Lester. However, the integration of automated systems, LLMs and other technologies has helped simplify and streamline workflows. It now has only 89 HR systems, and has plans to whittle this down to 60, underlining how much more efficient and joined-up organisations can become if tech adoption is handled properly.
IBM has only 89 HR systems, and has plans to whittle this down to 60
“At the heart of everything, it’s still how do people then use this?” Lester says. “How do people in our HR support desk then change from answering phone calls to becoming what we call ‘conversation specialists,’ designing the conversation through AI, to prompt engineers, prompting an LLM to get you the right answer, to now contextual engineers, because LLMs are very good at responding to prompts, but they need the context.”
While there are clearly substantial gains to be had by adopting technology in a meaningful way, Lester also affirms that new tech can pose significant organisational and regulatory challenges, particularly for HR departments. Such departments have to comply with a multitude of different laws in different jurisdictions, including regulations on privacy, data protection, cybersecurity, and employment rights. Yet the peculiarities of LLMs and agentic AIs throw other challenges into the mix, which are making Lester’s job even more interesting than it already was.
“We’ve gone through cloud, RPA, we’ve gone through AI, we’ve gone through digital twins, digital assistants. We’re now at this concept of agentic and large language models,” he says. “And what is fascinating and slightly scary is you’re now passing control to an extent to an LLM to make up an answer to a legal HR question.”
In order to combat the risks of incorrect AI outputs, which you really do not want if you’re a HR professional dealing with legal matters, IBM has been undertaking work to render its tools more reliable, and to allow for different levels of ‘exactness’ or ‘creativity’ in different contexts. “Through experimentation, we figured out how to measure the probability of a response being a hallucination, and if that question is what’s the sickness benefit, 0% probability of being hallucination,” Lester reveals.
More AI, more quantum computing, more sovereign tech
But once implemented appropriately, AI has been making HR workers at IBM more informed and more able to arrive at sound decisions. Importantly, it has also been enabling them to operate at greater speed, something which Lester says is not always typical of HR departments, but which is essential if enterprises are to stay ahead of the curve. “Speed is probably the biggest lever to pull for any organisation in today’s world,” he says. “And traditional HR is not where you find speed.”
Speed is the biggest lever to pull, and traditional HR is not where you find speed
In terms of the future, Lester expects not only AI to become more prevalent, but also quantum computing and sovereign technology. He notes that IBM has recently announced that it has signed a Letter of Intent with the U.S. government to develop the next generation of quantum-ready chips, backed by $1bn in funding from the Department of Commerce. Similarly, it announced plans in June to invest $10bn in quantum technologies over the next five years, running from R&D to capital expenditure, partnerships, and acquisitions.
He says, “So, sovereign technology with AI, with quantum coming up, I think that’s really the hotspot of where we’re going.” But ultimately, Lester and his team will be pursuing the same fundamental outcome, which is solving HR and people-management problems with technology. The variables may change, and the pace may accelerate, but the same need to keep improving processes will remain.
“The problems keep changing and multiplying and getting different, but the speed of our response I think is also the next big thing that’s got to come into it — is where we used to do things in five years, then three years, it’s now 18 months,” he concludes. “And that’s the challenge for most organisations you cannot stand still.”
Jon Lester describes himself as being in the business of “technology-enabled transformation.” As IBM’s VP of HR Technology, Data & AI, and with a career spanning three decades, he has long grappled with the question of how to integrate new technologies into people management.
“Solving problems over the last 30 years has now been more and more about technology and people,” he affirms, discussing how his career progressed from working post-university as a software developer, to acting as a consultant for IBM from 2005. He assumed his current position at the tech company in 2022, and in recent years the rate of change at IBM has accelerated considerably.
“We used to write five-year roadmaps and strategies; we stopped doing that in 2016,” he explains. “ We then wrote three years; now we're writing 18-month strategies and roadmaps, because by the time 18 months has gone, the whole world has changed again.”




