Careers are more non-linear than they’ve ever been. This trend puts workers who can flex with the times, moving fluidly across roles and departments, in high demand. This is true not only among early-career workers finding their way, but at every level of the organization.
At the top, companies are expanding the responsibilities of executives and adding new seats to the C-suite. Traditional paths to the top are being overwritten by “squiggly” careers. Take, for instance, the role of chief financial officer. Fewer CFOs are coming from purely finance backgrounds, with operational resumes becoming a popular pedigree. Some executives are pulling double duty. Salesforce appointed its first dual CFO-COO in 2025, as did PayPal and outdoor-apparel company Cotopaxi. Chief financial officer is now officially a route to the CEO’s job.
As careers become more circuitous than straight, succession planning gets harder. Old paradigms are less relevant. It’s now the skills that matter—and the assessment of them.
Workforce demographics further complicate succession planning. During the span of 2024-27, more than 11,200 Americans will turn 65 every day. Retiring Baby Boomers are vacating a record number of senior positions. Identifying and preparing the next generation of leaders is a key exercise for HR.
Artificial intelligence may be the answer. Overloaded HR teams are already employing generative AI agents to write the first draft of job descriptions and benefits newsletters, but the tasks AI can complete for HR are getting increasingly complex, like identifying attrition risks. Why not succession planning?
Succession Planning for a Skills-Based Workforce
Artificial intelligence is a promising solution because it helps identify employees who have the skills necessary for the role, not only the right career history. HR is already using artificial intelligence to identify skills within an organization, typically to match current employees to open roles or new projects, but “you could easily extend that to succession planning,” says Chris Pinc, the director of product management at consulting firm WTW.
Firms like WTW and other industry experts are spinning up their own AI-backed agents. For instance, the Josh Bersin Company launched its new AI platform for HR, called Galileo, in 2024. It looks a lot like ChatGPT; users type a query into a search bar and the tool returns an answer. Galileo can suggest prompts or help you find specific content related to HR expertise.
WTW released its own AI assistant, Expert, last month, while HR tech firm Visier has Vee, an AI agent specifically for people analytics. Google is working on its own AI-powered instance for its HR team. Like Bersin’s Galileo, the interfaces of Expert and Vee will be familiar to anyone who has used a generative AI tool.
Why use tools like Galileo or Expert instead of ChatGPT? First, these platforms are closed environments, which means that the information employers enter about their workforce stays only within their ecosystem; it doesn’t feed the larger corpus underlying the tool.
And second, these platforms are trained on data, research, and thought leadership from respected HR firms. Galileo pulls from the Bersin company’s own collection plus others, like research from Heidrick & Struggles. WTW’s Expert is similarly constructed, with the entirety of the WTW library backing the tool. Users can load in their own proprietary resources, like survey results, skills assessments, projects, plans, frameworks, processes, and original research. Amy Farner, Bersin’s SVP of product and member experience, said, “We’re not letting it go out there and troll the web.” These companies tell the AI what content to trust.
Where AI Can Supercharge Succession Planning
Let’s say it’s time to start looking for a successor to your chief marketing officer, who’s likely to retire in the next three years. Let’s use generative AI to find a good fit.
You might ask your tool: I need to find employees who have taken on several major, client-facing projects in the last year. Ideally, with the marketing team. They need to score high on our leadership assessment for innovation and creativity. They also need eight to 10 years of people-management experience.
The tool returns a list of leaders matching the criteria. You’re surprised to see Kelly Kapoor, a senior manager from business development, on the list. You learn that last year she worked on a successful product launch and still attends regular meetings with the tech and marketing teams. Not only that, Kelly’s name appears on several proposals for new product features and she has created detailed presentations on original competitive research. Plus, her performance reviews are excellent.
It looks like she might be a promising candidate, but under the company’s traditional framework, she never would have crossed your radar. So you load the CMO job description into the AI tool and tell it to map a three-year development plan to prep Kelly for the seat. You learn that she hasn’t yet completed a few key leadership-training courses, and she has very little experience working with creative teams. Plus, she’s had only two or three direct reports at a time. Looks like Kelly has a ways to go before she’s ready, but now you have a new candidate and a plan.
What Other Talent Have We Been Overlooking?
This is a fictional example, but there’s real-world precedent. Pinc has seen it happen. Recently, one of his colleagues in IT was promoted to a senior finance role. “She took on a special project to evaluate the cost-effectiveness of our overall software-development function,” he said. “She learned a lot about finance, then became a logical person to be the finance director for the IT function. She understood the finance work from that project and she understood the IT from her previous role.”
Use AI to fill a role like this, and it can be scaled for an entire organization. The success of so many nonlinear careers raises the question: What other great talent have employers been overlooking?
AI can lower the cost of succession planning too, said Pinc, who worked closely on the creation of Expert. Companies have long used leadership assessments for succession planning to find people who are capable of climbing the ladder, but it’s expensive to interpret the results, present them to leadership, then work with HR to write development plans. “That’s human time that I think will be able to be taken over by AI,” he said.
AI is still relatively new to HR professionals. This is due, in part, to privacy concerns. Companies can’t just throw employee data into a gen-AI chatbot, even if it is a closed system.
And HR is not historically a tech-forward department, but that’s changing. For now, HR is primarily using AI for time-saving, says Farner, but that will expand over time. Organizations are beginning to move past tapping AI as an assistant completing admin tasks to tapping AI as a consultant that operates like a colleague.
Emily McCrary-Ruiz-Esparza is an independent journalist and From Day One contributing editor who writes about business and the world of work. Her work has appeared in the Economist, the BBC, The Washington Post, Inc., and Business Insider, among others. She is the recipient of a Virginia Press Association award for business and financial journalism.
(Featured illustration by Photoman/iStock by Getty Images)
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