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Last week I wrote about building a virtual board of advisors — books, podcasts, people who've done what you're trying to do and documented it. This week, I want to take that one step further, because there's a difference between consuming someone else's thinking and actually having a conversation.
AI tools like ChatGPT or Claude are something I've started using as a sounding board when I'm stuck on something and there's no obvious person to call. I want to be careful about how I describe this, because I'm not about to tell you that a chatbot can replace the mentors from my career. It absolutely can't.
But, when you're sitting with a specific problem — a difficult conversation you need to have, a decision you're going around in circles on, a situation at work where you can't quite work out what the right move is — you can describe it in detail and get a response tailored to exactly that. Not general advice about leadership, but a reaction to your particular situation, with the variables you've described. You can push back on it. Ask it to look at the problem differently. Explore the same question from three different angles without anyone losing patience with you. What may take you time to find on your bookshelf could be instantly available.
It strikes me as a more modern thinking process; a good coach will hep you create space and time to think things through. They will help you generate options, and evaluate next steps. I’m not arguing that AI can replace a good coach or mentor, but if you have a time sensitive decision to make, a good coach might not be available to help. But if a tool can help you generate options, while the judgment call is still yours?
That's real value. Not a shortcut, but a way of externalising your thinking when you need a second perspective and there isn't one available.
It falls short in ways that matter though. It doesn't know you. Every time you open a conversation, you start from scratch — it has no memory of your history, your patterns, the way you tend to react under pressure, or what you've already tried, unless you invest time and effort in creating that, and I believe firmly that time would be better spent building a relationship with a person.
A mentor who's watched you for years brings something that no tool gets close to. They've seen how you behave when things go wrong. They know your blind spots. They have a stake in how things go for you. And they can pick up the phone and recommend you to someone, or flag an opportunity because your name came to mind. None of that is available with an AI tool.
There's also a subtler limitation. Because AI is trained to be helpful and balanced, it can sit on the fence in ways that a good mentor wouldn't. A mentor who knows you well will sometimes just tell you you're wrong, or that you're overthinking it, or that the answer is obvious and you already know what it is. You have relationship capital. AI tends to present options. If something is time sensitive, you may be able to get that answer quickly if you have a strong relationship with someone who will answer your call.
Which is how I want to finish this series. Because all of this — the books, the podcasts, the AI tools — is a way of filling a gap. And the gap it's filling is the absence of a real mentor.
If you've been reading these pieces and thinking that sounds like something you'd like but don't currently have — go and find one. Think about someone you respect, who's been where you're trying to get to, and ask them directly. Most people, when asked with a bit of thought and honesty, say yes. People love to give an opinion, and most people will help if asked. The worst outcome is that they say they don't have the time right now.
And if that genuinely isn't possible at the moment, think about your peers instead. Three or four people at a similar stage, across different areas of experience, who agree to meet regularly and actually be honest with each other. Done properly, a peer group is more valuable than most people realise, and considerably easier to put together than you might think.
The tools are useful. But they're a substitute, not the real thing. Go and find the real thing.
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Ben Stark
Founder, Leadership101