Every Leader Is Pretending to Know More Than They Do
Victoria Canham • 06 May 2026 • 4 min read
May Leadership Series · Part 1 of 4
AI is moving faster than any leader can genuinely track. The ones handling it well are the ones who stopped pretending they know the most.
Meetings are happening in organisations everywhere right now, based solely on an agenda of AI. Around the table are senior people who have been briefed, who have read the reports, who have sat through the presentations from the consultants and the enthusiasts and the cautious voices from legal.
Most of them do not know what this means for their business. They have a position and a working familiarity with the broad contours of the debate. What they do not have is genuine clarity about what AI will do to their specific organisation, their specific market, their specific people, over the next three years.
What is Actually Happening in the Meetings
The dynamic is familiar to anyone who has been in senior leadership long enough. When a topic arrives that carries both urgency and genuine complexity, the SLT manages the uncertainty collectively and without fully or extensively acknowledging it. Everyone takes their cues from everyone else. Questions are asked that signal engagement rather than confusion. Positions are staked that are defensible rather than honest. The meeting ends with a plan that nobody is fully confident in, yet everybody is prepared to own publicly.
It is a social and professional adaptation to the expectation that senior leaders should have all the answers. That expectation has been there for the whole of most people’s careers. It is embedded in the culture of most organisations as a given.
The problem with AI specifically is that the expectation of the all-knowing fount has collided with a technological reality in which expertise has a shelf life of months. The people who knew the most eighteen months ago may know relatively less now, and the honest answer to most strategic questions is still genuinely open.
The Identity Strain Happening Beneath
For many senior leaders, particularly founders and executives who built their authority on accumulated knowledge and sound judgement, AI has introduced a challenge that goes beyond the practical.
The confidence to lead, to make decisions, to set direction, to hold a room when things are uncertain, rests on a foundation. For most experienced leaders, that foundation includes a belief in their own judgement, built over years of decisions that mostly worked out. That judgement was developed in a context that is now shifting faster than ever before.
The result is uncertainty about not being sure whether your own judgement is well-calibrated for the path you are now on. That is a harder thing to admit and a harder place to lead from.
Most leaders manage it by redoubling their confidence, because a lack of confidence here feels like the wrong move.
What Redoubling Costs
When leaders project certainty when they are anything but, a few things follow.
The people around them pick it up and become less likely to raise the awkward question, flag the troubling data, or challenge the direction, because the signal from the top is that the direction is settled. The organisation starts making decisions from a position of perceived certainty rather than actual clarity.
It also costs the leader. Maintaining a position you are not sure you believe in closes off the conversations that would actually help. Conversations with peers, with advisors, with the people inside the business who are closer to the operational reality. The leader becomes progressively more isolated from the intelligence that would improve their judgement, because they have signalled that their judgement is not to be questioned.
What Honest Uncertainty Looks Like in Practice
Saying you do not know is a different skill from admitting weakness. The distinction matters, and it is worth being precise about.
Admitting weakness is personal. It is about capacity or character, and it invites reassurance or rescue, but that is not what is being described here.
Stating what you do not know is situational, and about the current state of available information. It requires a good level of confidence to do well because you need the confidence to hold the floor in a state of genuine uncertainty without the team losing faith in your ability to lead through it. That is a more advanced leadership skill than projecting certainty, and it produces better decisions.
In practice, it sounds like: here is what we know, here is what we do not know yet, here is how we are going to make decisions in the meantime, and here is what would change our direction. That is a leadable position, which does not require pretending.
The Leaders Who are Handling It Well
Leaders who handle this well are not necessarily the most technically fluent. Some of them know relatively little about how the technology works at any level of detail.
What they have is a clear-eyed account of their own current knowledge, an honest assessment of where the genuine uncertainty lies, and a rigorous process for making decisions within that uncertainty. They ask better questions than their peers because they are not defending a position of knowing it all. They gather better intelligence because the people around them are not managing upwards to protect them from unwanted information.
They lead from where they actually are, in an environment moving this fast, that is the only position worth leading from.
This is Part 1 of a four-part May series: Leading From Where You Actually Are.
Next: The Gap Between the Culture Deck and Monday Morning.
♦️ Hi, I'm Victoria Canham. I work with senior leaders, executives, founders and organisations when performance, pressure and people dynamics reach a point where the usual tools stop working.
My work sits at the intersection of leadership psychology, organisational performance and culture reality. I help executive teams navigate strained relationships, cultural brittleness, emotional fatigue, and the quiet erosion of trust that most businesses prefer not to acknowledge.
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Victoria Canham - Performance and People Strategic Consultant
Victoria Canham works with executive leaders and organisations when performance, culture and emotional pressure collide.
She is a Change Leader with over 25 years of experience, an ICF-accredited Professional Coach and founder of Victoria Canham Consultancy. Her practice focuses on strengthening leadership capability and organisational performance in the real world, not just on paper.
With twenty-five years in talent development, behavioural insight and large-scale change, she supports senior leaders navigating strained relationships, brittle cultures and high-pressure decision-making. Her work helps leadership teams stabilise, rebuild trust and operate with greater clarity and authority.
She is brought in when organisations cannot safely hold difficult conversations internally—when executive teams have stopped saying what needs saying, when founders need to step back, when high-performing individuals are costing more than they deliver. She creates the conditions where those conversations can actually happen, and where organisations can move forward from them.
The result is leadership that functions under pressure, cultures that hold up in practice, and teams equipped to perform sustainably.
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