Why Leadership Problems Are Often Personal: What 120 Hours of AI Coaching Revealed

An analysis of 63 AI Ben users confirms what I have seen throughout my years as an executive coach: business problems often have a personal layer

AI Ben was developed to help people with questions about entrepreneurship, strategy, leadership, difficult conversations and personal development. Users were free to ask virtually anything.

That is precisely why one thing stood out.

When CEOs and leaders were given the freedom to discuss any subject, most did not begin with their strategy, employees or company. They went straight to what was affecting them personally.

Not because their work had nothing to do with it. Quite the opposite. Their personal questions were often closely connected to how they led, made decisions and functioned professionally.

I recognise this from my work as an executive coach. What presents itself as a business problem almost always has a personal layer as well.

What the First 63 Users Discussed

Over a period of two and a half months, 63 people used AI Ben. Together, they spent approximately 120 hours talking to it. That is an average of almost two hours per user, although actual usage varied considerably. Some people stopped after about eight minutes. Others spoke with AI Ben for up to three and a half hours, spread across two to five sessions.

The group consisted of both people I knew and spontaneous visitors to the website:

• approximately 60 percent were CEOs or leaders;

• approximately 30 percent were employees;

• approximately 10 percent used AI Ben as private individuals.

An estimated 90 percent of the CEOs and leaders spoke exclusively about personal subjects. These subjects could be related to their work, but they were not introduced as business cases involving strategy, dismissal, performance or an employee.

The leaders went directly to what was affecting them personally.

Private individuals also used AI Ben primarily for personal questions. Their subjects included insecurity, feeling invisible or wanting to be seen, finding a sense of purpose in life and preparing for a difficult conversation.

I do not know exactly what was said during these conversations. I did not read the conversations or examine any transcripts. The data is anonymous. I could only see the broad subject categories under which the conversations fell.

This is therefore neither scientific nor representative research. It is an exploratory analysis of how the first 63 users naturally chose to use AI Ben. The pattern is nevertheless interesting, particularly because it corresponds with what I have encountered throughout my years of real-life executive coaching.

Business Problems Are Rarely Just Business Problems

We often behave as though there is a clear boundary between the professional and the person.

At work, you are the CEO, entrepreneur or leader. At home, you are a partner, parent, friend or simply yourself. In reality, we take our beliefs, fears, needs and insecurities everywhere we go.

Someone may believe they struggle to delegate when, in reality, they are afraid of losing control or no longer being seen as valuable. A conflict with an employee may be intensified by conflict avoidance. Indecisiveness may be connected to a fear of rejection or loss. Working continuously may be driven by ambition, but also by the question of who you are when you are no longer performing.

This does not mean that every business problem should be psychologised. Sometimes a bad strategy is simply a bad strategy. Sometimes an employee genuinely is not performing well. But even then, the way a leader observes, decides and communicates is partly determined by who they are as a person.

Scientific research into the relationship between work and private life supports the idea that these worlds are not psychologically separate. Stress, emotions, time pressure and behaviour can spill over from work into private life and vice versa. Research into work-family spillover, for example, shows that changes in autonomy, working hours and workplace support can affect tensions between work and family life. Kelly and her colleagues examined this relationship through a large-scale workplace intervention.

Personal development does not, therefore, happen alongside leadership. It changes the way leadership is practised.

The Visible Question Is Often Not the Real Question

Executive coaching conversations regularly begin with a visible problem.

An entrepreneur is uncertain about the future of the company. A CEO is in conflict with a fellow director. A leader cannot get the team moving. Someone is considering stepping down but does not know whether it would be the right decision.

That is usually the point of entry. When we look more closely, there is often more going on.

What would stepping down mean for my identity?

Do I dare admit that I no longer know what to do?

Am I making this decision because it is right or because I am afraid?

Why does this person’s behaviour affect me so strongly?

Am I remaining loyal to my responsibilities or merely to other people’s expectations of me?

The business question does not disappear as a result. It becomes easier to understand.

That is what struck me about the way people used AI Ben. Many leaders did not appear to need the business problem as their point of entry. As far as the available topic classifications show, they went directly to the personal layer.

Perhaps they already recognised the connection. Perhaps they did not need more management knowledge, but a space where they could think aloud about what was truly influencing their decisions.

The Higher the Position, the Harder It Can Be to Speak Freely

Leaders are usually surrounded by people. That does not automatically mean they can discuss everything with those people.

A CEO must consider employees, shareholders, clients and co-owners. Some information is confidential. Expressing doubt can create uncertainty. A personal struggle may be interpreted differently when it comes from the person who is expected to provide direction.

This does not mean that every leader is lonely. It does mean that the position can create situations in which speaking freely becomes complicated.

An exploratory study involving fourteen Norwegian CEOs examined how they experienced loneliness in their work. All fourteen identified decision-making as a situation in which they could feel alone. Every participant also mentioned the importance of having a trusted sparring partner: someone with whom they could test their thinking, express doubts or simply share what was on their mind. Read the study on loneliness among CEOs.

The AI Ben data does not prove that the participating leaders were lonely. It does, however, fit a broader pattern: the greater the responsibility, the less obvious it can become where someone can think aloud without consequences.

Does AI Lower the Barrier to Discussing Something Personal?

One possible explanation is that talking to AI carries less immediate social risk.

AI Ben has no position within the company, does not become disappointed and does not tell a colleague what was discussed. The user does not have to consider loyalty, reputation or the other person’s reaction. AI Ben is also always available, and the user decides when the conversation begins and ends.

That may make it easier to ask the first question.

Research into self-disclosure with chatbots does not, however, provide a simple answer. In an experiment involving 286 participants, people experienced less fear of being judged when speaking to a chatbot. Yet they did not share demonstrably more intimate information with the chatbot than with a human conversation partner. Perceived anonymity appeared to matter more than whether the other party was a human or a machine. Croes and her colleagues studied self-disclosure with humans and chatbots.

Longer-term research into relationships between humans and chatbots presents an equally mixed picture. Some users begin disclosing personal information relatively quickly, partly because they want to process troubling thoughts or experiences. At the same time, this varies considerably between individuals, and openness may decline when a chatbot responds inadequately or loses the user’s trust. A longitudinal study describes these different patterns.

We cannot therefore conclude that leaders opened up to AI Ben because AI inherently feels safer. We do not know their reasons.

What we can establish is that a substantial proportion of the leaders chose to discuss the personal layer with AI Ben.

Not Everyone Wants to Talk to an AI Coach

Responses to AI Ben varied.

Four users personally told me that they did not like it. Three other people did not even want to try it. By contrast, two users said that, after only a few minutes, it felt as though they were actually sitting at the table with me.

These reactions do not prove anything about the effectiveness of AI coaching, but they do demonstrate how personal the experience is.

What feels natural, accessible and familiar to one person may feel artificial or uncomfortable to someone else. A human voice, appearance and way of responding can reduce the perceived distance between the user and the technology, but they may also provoke resistance.

AI Ben does not need to work for everyone. Human coaching does not work for everyone either.

The relevant question is not whether everyone wants to talk to an AI coach. The question is whether this format gives some people an opening that would not otherwise be available to them at that particular moment.

A Starting Point, Not a Replacement

AI Ben is not a therapist, does not make diagnoses and does not replace psychological or medical support. Nor is it a substitute for human relationships, professional challenge or an experienced executive coach who can observe, sense and explore what happens during a conversation.

AI Ben can help someone organise their thoughts, formulate a question more clearly, prepare for a difficult conversation or look more honestly at what is really happening. It can open a conversation that may later need to be continued with a partner, colleague, doctor, therapist or coach.

AI can help a leader begin the conversation. It does not automatically know when that conversation needs a human being.

The Person Remains Present in Every Leadership Decision

The most important observation from this initial period of use is not that leaders discussed private matters with AI.

It is that the personal and professional sides of leadership proved almost impossible to separate.

Leaders do not leave their doubts, relationships, fears, values or need for meaning at the entrance to the boardroom. That personal reality influences how they listen, communicate, trust, decide and lead.

The first 63 users of AI Ben do not prove that this applies to all leaders. The group is too small and not representative. The conversations themselves were not examined either.

But the way AI Ben was used does reveal a pattern I recognise from years of entrepreneurship and executive coaching: what appears on the surface to be a business problem is often also a personal question.

That is why better leadership does not always begin with a better strategy.

Sometimes it begins with a question that the person behind the leader finally feels able to ask out loud.

Methodological note: This article is based on an exploratory analysis of anonymised topic categories from 63 early users of AI Ben over a period of two and a half months. No conversation transcripts or detailed conversation content were read or analysed. The users were a self-selected combination of personal contacts and spontaneous visitors. These observations are not representative of leaders in general and do not demonstrate the effectiveness of AI coaching.