Last week someone asked me a simple question.
What was Steve Jobs actually like to work with?
The honest answer feels uncomfortable.
Demanding. Relentless. Extremely focused.
In 2003, Steve asked me to run a board search for Apple. On paper, it looked straightforward. He described the profile. I mapped the market. My team and I built a slate of world class executives.
Former CEOs. Aerospace leaders. People who matched the experience, geography and industry background he requested.
I flew to California with polished decks and carefully prepared arguments.
And every single time, he passed.
Meeting after meeting, Steve listened, asked sharp questions, explored edge cases, and then moved on. He gave no decision, no green light, and no clear direction that allowed us to adjust the search.
For a while, I believed the search had failed.
Then, in the middle of the process, Steve made a move that caught me by surprise.
He added Al Gore to Apple’s board.
No warning. No request for help. No formal short list.
I felt frustrated and convinced that months of work had vanished.
Only later did the real lesson become clear.
Gore did not join Apple to help with quarterly sales or short term branding. His presence prepared Apple for rising geopolitical risk, United States and China trade tension, environmental scrutiny and regulatory pressure that would shape the next decade of technology.
All of this happened before the iPhone launch.
Steve hired for a future most people around him could not yet see. I focused on the present. He spent his time three years ahead.
Apple then invited two of my candidates to the board.
Andrea Jung in 2008. Ron Sugar in 2010.
Both continue to serve on Apple’s board many years later. These became the final two board appointments that Steve touched.
The pattern remains consistent.
The leaders who treat every key hire as a three year decision build compounding advantage, especially in AI.
What Steve Jobs taught me about future focused hiring
That Apple search rewired the way I look at executive hiring.
Most companies describe roles through the lens of current pain.
Sales execution this quarter. Velocity of product releases. Structure of the next fundraising round. Fires that already feel hot.
Steve filtered candidates through a different lens.
He asked what the world would demand from Apple three years later.
He cared about how policy might evolve.
He cared about public trust, climate scrutiny and global supply chain exposure.
He cared about board chemistry and the kind of judgment his directors would exercise when something went very wrong.
The executives who thrived in that environment carried a long horizon in their head. They thought in systems, not only in functions. They guided the company through moments that did not yet have a playbook.
Why this matters for Chief AI Officer hiring
Right now, boards and CEOs feel intense pressure around AI.
They launch task forces, sponsor pilots, build small internal labs and interview Chief AI Officer candidates with impressive resumes.
Many of those conversations center around immediate issues.
Model selection
Vendor choices
Initial governance frameworks
Cost of compute
Experiment backlogs
These topics matter, yet they describe only the first chapter.
The real test for a Chief AI Officer arrives several years in.
Three years from now, your company will face a very different AI landscape.
You may need to handle:
• Regulatory regimes that treat AI systems more like financial instruments than simple software
• Public expectations around transparency, safety, and data use that feel as strict as healthcare privacy today
• Competitive pressure from rivals that deploy agentic systems across operations, logistics, customer support and product development
• Talent markets where true AI leadership remains scarce and shallow experience looks deceptively credible
A Chief AI Officer hired for today’s pilot programs can struggle in that world.
A Chief AI Officer hired for the 2027 environment guides your company through it.
The questions boards should ask before every senior AI hire
The Steve Jobs experience left me with a set of questions that I now encourage CEOs and boards to apply to every AI leadership search.
- Three year reality
- Imagine your company in 2027.
• How does AI touch revenue, cost structure, and product experience in that future state
• Which risks appear on board agendas every quarter
• Which regulators, partners, and watchdogs pay attention to your sector - Board and executive chemistry
• How will this AI leader change the way your board debates strategy
• Which current director will challenge this person in a productive way
• Which blind spots in your existing leadership group require a different kind of voice - System-level thinking
• Can this candidate connect infrastructure, data strategy, product, security, and talent into a single operating model
• Do they understand tradeoffs between speed, safety, and brand trust
• Can they explain these tradeoffs in language that directors, investors, and customers respect - Endgame for the role
• What will success for this leader look like three years from now
• Which decisions will they own at that point that other executives handle today• How will your organization feel different because this person joined
When boards slow down and work through these questions, the profile of the ideal Chief AI Officer changes. The search moves away from pure research credentials or shiny lab experience and toward leaders who combine technical depth, institutional judgment and long horizon thinking.
Hiring for the company you build, not the company you inherit
Steve Jobs did not approach board hiring as a compensation exercise or a networking exercise. He approached it as design.
He designed for the Apple what he wanted the world to experience years later.
AI leadership requires the same posture.
Every Chief AI Officer, VP AI, or Head of Machine Learning you hire today will hardwire habits, risk appetites, and cultural norms into your company.
a That influence grows with tme.
So the real question for any CEO or board chair becomes simple.
When you look at your AI leadership plans, do they serve the pressures and possibilities of the next three months, or the next three years?
The leaders who treat each hire as an investment in 2027 create space for transformation instead of reaction.
The ones who follow that path usually wake up in a future that looks much closer to the one they intended to build.