Upskilling is the word a CEO reaches for when they know what to do about AI but not how to do it. Said on its own, with no plan behind it, it means one thing: we have no strategy. The work that actually matters comes first, and it is not upskilling. It is upculturing the whole organisation.
The tell is not in the press release, it is inside the building
When a leader announces that the company is upskilling its people on AI and offers nothing else, the interesting thing is what is missing. There is a fair rebuttal to sit with first: serious firms sometimes keep the playbook quiet as a competitive edge, and silence to the market can genuinely be strategy. So do not judge it by the announcement.
Look inside instead. Can your people describe the plan in their own words? Is there a cadence, a rhythm, time actually set aside to learn, workshops that genuinely happen? Silence to the market can be strategy. Silence to your own people is the absence of a plan. If the employees cannot tell you what the plan is, there is no plan. There is only a word.
Why this is the CEO’s job, not the CIO’s
AI has been treated as a technology problem, owned by the CIO or the CTO. It is not. It is a culture problem, and culture is the one thing a CEO cannot delegate. This is the argument I keep returning to in AI is Not a Technology Project. It is a Culture Project and in Cultural Innovation Before AI Investment.
Every CEO now says the company is AI-first. Being AI-first requires a plan to change how the company thinks and works, and that is a cultural undertaking, not a training module. When a leader can only offer the word upskilling, it is the CEO, not anyone below them, quietly admitting they do not yet know how to lead this.
Upculture before upskill
Here is the sequence. You upculture the company first, then you upskill it. Everyone knows you train people for a new task; that part is easy, and it is not the point. The point is preparing the organisation to want the change, to believe in it, to see what it does for their work and their lives.
So where are the announcements of the culture programme, the town halls, the honest examples, the day a week set aside to learn together? Invest not only in tokens and licences but in changing the culture. If a third of the company genuinely comes on board in the first round, that is a strong result; run a few rounds through the year. This is the honest reckoning I described in Shed the Skin First, and it matters most when a culture is already quietly splitting, which is the situation I set out in Your Calendar is Full. Your Culture is Splitting.
And it is never too late. AI is not going anywhere. The cost of starting late is real, but it is far smaller than the cost of never starting.
Upskilling teaches people to use a tool. Upculturing decides whether they will. Do the second first, or the first will not hold.
If you are leading your organisation through this, I work with a limited number of senior leaders each quarter. Get in touch at Anglero.com.
Thomas Anglero is a Strategic AI Advisor, keynote speaker and author of Intro to Artificial Intelligence. He has delivered over 450 keynotes across 30 countries for organisations including IBM, the WHO, the World Government Summit and the European Commission. He founded the IBM Watson AI Lab for Cancer at the Oslo Cancer Cluster and closed over $500 million in enterprise transformation deals as CTO and Chief Innovation Officer at Cognizant.
Frequently asked questions
What is the difference between upskilling and upculturing?
Upskilling teaches people to use AI tools. Upculturing prepares the organisation to want the change and to work differently. Culture comes first, because training people to use tools they do not believe in does not hold.
Why is only saying “upskilling” a warning sign?
Because on its own, with no plan behind it, it usually means there is no AI strategy. The honest tell is internal: employees cannot describe the plan, there is no cadence, and no time is set aside to learn.
Whose job is AI culture change?
The CEO’s. AI has too often been treated as a technology problem owned by the CIO or CTO, but it is a culture problem, and culture cannot be delegated.
Is it too late to start upculturing?
No. AI is not going anywhere, and the cost of starting late is smaller than the cost of never starting. If a third of the company comes on board in the first round, that is a strong result.