637- What Happens When AI Search Builds the Wrong Picture of You?
Jens Heitland explores what happens when a CEO's online presence no longer reflects who they are.
Drawing on a direct experience with a senior leader, this piece looks at how AI search tools are reshaping first impressions in business, why digital identity gaps are a leadership risk, and what it takes to close the distance between who you are and what the internet says about you.
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What Happens When AI Search Builds the Wrong Picture of You?
There is a moment in many sales conversations that nobody names directly. The other person has already looked you up. Before you have said a word, before you have made an argument or built rapport, they have formed a picture. The question is whether that picture is accurate.
In my experience working with senior leaders, this is rarely something they think about until it becomes a problem. And by the time it becomes a problem, the conversation has already started on the wrong foot.
What tends to happen is this. A CEO prepares carefully for a high-stakes meeting. They know the business case. They know the relationship dynamics. They walk in confidently. What they do not know is what the other person found when they searched their name the night before. In most cases, neither does anyone else.
I was working with a CEO who was preparing for exactly this kind of moment. We were reviewing how he showed up across different channels, thinking about consistency, about alignment between who he is and how he is perceived at a distance. At some point, we did what most people do not deliberately think to do. We searched him. Not just on Google, which most leaders have at least glanced at, but also using AI-powered search tools, which are increasingly where first impressions are formed.
What we found was not him. Or rather, it was partly him, and partly someone else. Another person with the exact same name. The AI had drawn from sources across the internet and assembled a composite, a professional identity that blended two different people into one incoherent picture. Wrong company associations. Wrong context. A version of him that no one who knew him would recognize.
This is not an isolated case. It is a pattern. The issue is not that AI search tools are unreliable, though they can be. The issue is that most leaders have no active relationship with their presence in digital environments. They assume that because they have a LinkedIn profile, or a company bio, or have been quoted in a few articles, the picture is coherent. Often it is not. And in a world where AI is increasingly the first layer of research, the gap between who you are and what is findable about you is becoming a real business risk.
At scale, this matters in ways that go beyond individual meetings. When a board evaluates a potential partner. When an investor does preliminary research. When a journalist looks for background. In each of these cases, what they find is not filtered through a conversation you control. It is assembled from fragments you may not even know exist.
What we concluded in that session was straightforward. Before the next important conversation, there was work to do. Not on the pitch. Not on the narrative. On the foundation underneath all of it. On the signal that goes out before anyone picks up the phone.
That work is not glamorous. It is not about personal branding in the way that term is usually used, which is to say, as a form of self-promotion. It is about accuracy. About making sure that the version of you that exists in public corresponds closely enough to the version of you that walks into the room.
When that alignment is missing, the other person arrives at the meeting carrying a picture that is already wrong. They may not know it. You may not know it. But the distance between their expectation and your reality is already shaping the conversation before it begins.
What is worth examining is not just what exists about you online, but what is missing, what is outdated, and what has been inadvertently mixed with someone else entirely. The digital environment does not update itself to reflect who you have become. It holds on to what was true, or what looked true, at the moment it was captured.
In complex organizations, leaders invest significant resources in how they show up in a room. The preparation, the presence, the positioning. What is often overlooked is the preparation that happens before the room, in the searches that form the first impression, before any of that effort begins.
Highlights:
00:00 First Impressions Online
00:24 AI Search Surprise
00:41 Name Mix-Up Problem
00:49 Fixing Digital Presence
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Transcript :
One of the things that I learned while having the discussions with the CEO was that in the end, when you go into a sales conversation, the other person had looked you up and the tricky thing is that if you don't focus on how you show up in the internet as a whole, then they might form an opinion about you, which is not truly you. So the thing was, when we discussed that, that we did a Google search, and then we said, "Okay, Google is the old school. Well, let's do an AI search and look you up." And then we looked him up, and what we found out that in the end, what was written in AI was super old.
It was conflicting with another person that was having the exact same name as, as the CEO had. So it was a mix of him and the other person, so it would be completely wrong picture and what we then concluded was we need to work on how he shows up in the whole internet, and to fix that was one of the main priorities we agreed on