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Most CHROs I speak with tell me the same thing: the hardest challenges they face aren’t being solved inside traditional HR forums.
That’s why I created Future of Work Leaders—a private, invite-only community for Chief Human Resources and Chief People Officers who want to think beyond policies and programs and focus on what’s actually shaping the future of work and employee experience. Members include CHROs and CPOs from companies like Tractor Supply, Novartis, LEGO, Norfolk Southern, Saks Global, PwC, Northrop Grumman, and more. We come together monthly in small virtual sessions and once a year in person to tackle the conversations most organizations aren’t having yet.
If you want to move beyond traditional HR to focus on the future of work, then apply to join the Future of Work Leaders Group.
As a CHRO, how often do you think about the immense, almost crushing, pressure of C-suite succession planning? Getting it right can define an organization’s future for the next decade; getting it wrong can cause irreparable damage. It’s one of the highest-stakes responsibilities in the corporate world, yet the process is often shrouded in mystery.
In a recent podcast conversation, I spoke with Debbie Pickle, the Senior Vice President and Chief Human Resource Officer at Williams, a Fortune 500 energy infrastructure company. Our discussion pulled back the curtain on what it truly takes to select and onboard a new CEO, especially when replacing a leader who had been with the company for 40 years and in the CEO seat for 14. It revealed a surprisingly deliberate, multi-year process—a hidden architecture of strategic planning, deep vetting, and proactive coaching that goes far beyond a typical executive search.
Here are the most impactful takeaways from that conversation, offering a rare glimpse into how leadership change is meticulously designed at the highest level.
Listen to the episode here on Apple Podcast & leave a review!
It’s a Marathon, Not a Sprint: The Two-Year Journey to a New CEO
When we think of hiring, we often picture a timeline of weeks, maybe a couple of months. But at Williams, the CEO succession journey began a full two years before the former CEO’s retirement was even announced.
What’s striking was how Williams reframes time not as a period of passive deliberation, but as an active observation window. After the process started, it took 12 to 18 months just to select the final candidate. Debbie explained this was a strategic choice designed to test a candidate’s most critical leadership attribute: their capacity for growth.
This extended timeline allowed the board to give internal candidates detailed feedback from rigorous assessments and then, as Debbie noted, “see how they respond to that feedback, and to see how they’re working on their development plan…that wasn’t something we were going to know in three months.”
It transforms the selection process from a snapshot judgment into a real-world test of a candidate’s coachability and commitment.
The CHRO as Architect, Not Just Administrator
In this high-stakes transition, the CHRO’s role extends far beyond facilitation. Debbie and her team acted as strategic architects, actively guiding the new CEO to ensure his success from day one. A key tool they developed was a comprehensive “CEO resource guide.”
This wasn’t just a welcome packet; it was a strategic tool for focus. Debbie described the new CEO as having “a lot of energy and a lot of ideas,” a powerful asset that could also lead to distraction.
The guide, which included thought-provoking questions and a structured 30-60-90 day plan, was designed to “help him hone in on those” and “prioritize that focus.” It was a mechanism for channeling a high-energy leader’s enthusiasm into impactful action, preventing resource drain on initiatives that could wait. As Debbie put it:
“I would say for CHROs, who may be listening, your role is very key to this, and giving that honest feedback and becoming that strategic business partner for the CEO and for your other peers are really key.”
Beyond the Interview: The Deep Science of Vetting Candidates
The vetting process at Williams was a scientific, data-driven evaluation designed to remove subjectivity. It began by building a “CEO profile” with the board and a third-party firm, outlining the specific capabilities required to lead the company’s future strategy.
Internal candidates were then subjected to a “battery of assessments” to measure their fit. These tools included:
- Personality assessments like the Hogan, to understand core drivers and potential derailers under pressure.
- Cognitive tests, to evaluate critical thinking and complex problem-solving abilities.
- A longitudinal 360-degree feedback process, which was far more than a one-time survey. It involved intensive, in-person interviews conducted by a third party, followed by “pulse texts like six months later,” and another full 360-degree review a year after that.
This sustained, multi-year feedback loop is a powerful case study in evidence-based leadership development. It ensures the board can confidently tell investors they went through a diligent process and selected the best person based on a forward-looking rubric, not just a gut feeling.
Listen to the episode here on Apple Podcast & leave a review!
The “Rip the Bandaid Off” Imperative for New Leaders
One of the most powerful insights Debbie shared was counter-intuitive advice for new leaders. To prepare her incoming CEO, she interviewed other current and former CEOs, and a consistent theme emerged. New leaders are often hesitant to make changes to their team because, as Debbie said, “they’re like, I don’t want to rock the boat…they’re almost too cautious.”
Yet, the feedback from seasoned executives was unanimous in the other direction.
“No one ever said, ‘Man, I wish I would have waited longer.’ All of them said, I wish I would have done it sooner. I wish I would have just ripped off the band aid. It became harder, not easier.”
This is one of those insights that seems simple on the surface, but it’s a profound lesson in leadership momentum. While caution can feel safe, this feedback suggests that decisiveness in shaping your team builds clarity and stability far more effectively than a prolonged period of uncertainty.
The Surprising Reason New Leaders Fail: A Lack of Humility
When a new, high-level leadership placement fails, it’s rarely due to a lack of skill or experience. According to Debbie, one of the single biggest reasons a new leader doesn’t succeed is a “lack of humility.”
This failure point manifests as an unwillingness to adapt. It’s the leader who comes into a new environment believing their past success is a plug-and-play formula. They aren’t willing to say, “Okay, this is not the same as my previous organization. I have to approach things differently.” They fail to listen, to “recognize I don’t know all the answers,” and to accept that they need to go through a learning curve.
Debbie described the mindset of a leader destined to struggle:
“…they think ‘I’m smarter, I got the job. Many of you applied for it. You didn’t get it.’ That’s where I often see this lack of humility, of going through that learning curve.”
Success isn’t about proving you’re the smartest person in the room; it’s about having the humility to learn from the people already there.
Leadership Succession as Strategic Design
The conversation with Debbie Pickle makes one thing abundantly clear: top-tier leadership succession is not a hiring function. It is a complex, long-term strategic process of organizational design.
This meticulous architecture reveals a powerful truth: the time invested upfront (the two-year marathon) creates the space for the data (the deep, longitudinal vetting). It is the CHRO’s strategic partnership that translates that data into a successful onboarding, equipping a humble and decisive leader to secure the organization’s future. The entire process is an interconnected system designed to produce a specific outcome.
As you look at your own succession plans, where is your greatest opportunity to move from a reactive process to one of deliberate, strategic architecture?
Don’t miss the complete conversation to learn the intricate steps required for smooth, swift, and successful leadership transitions at the highest level—check out the full episode below.
