The professionalisation of conversation

Sonnie Bailey

13 March 2020

I’m going to wear my “futurist” hat  and make a prediction:

In the future, there will be a boom industry of people who are paid to have one-off conversations.

In a sense, these people will be professional conversationalists.

People with means will pay other people to have one-off conversations with them. The purpose of these conversations will be narrow in nature, and are likely to relate to specific topics, such as money, careers, relationships, physical health, and sex.

These conversations will not involve the provision of advice. They won’t be part of ongoing engagements. The major benefit people will receive from these conversations are different perspectives and insights.

These perspectives and insights will come from being able to think out loud with a dispassionate person who is good at asking relevant questions.

These conversations won’t be about receiving answers. They’ll be about helping people find answers for themselves.

This is different from chatting with friends

I mentioned this hypothesis to a friend recently. His response: isn’t this a reason for having good friends?

Yes. It’s like having an in-depth conversation with a friend. But it’s a little different.

Friends aren’t dispassionate. There’s an incentive to be overly positive and supportive when it comes to friends. Friends also have their own idiosyncratic conflicts of interest, including a need to rationalise their own decisions and views.

Friends also don’t have expertise in all areas and might not know the best questions to ask. If you’re asking them about a situation that is relatively unique and/or specialised, the conversation you may be looking to have might be the only conversation of that nature they will ever have.

Friends also probably share many of the biases and blind spots that you have. That’s probably one of the reasons you’re friends.

Another reality is that a lot of people don’t have friends with whom they can have these decisions. When you live the full catastrophe of a rich life, you get busy, and you drift apart from friends. To get to the level of intimacy that’s necessary to have hard conversations takes time. It’s hard to find the time to invest in friendships, even if this is important and worthwhile.

Depending on what I want to discuss, for example, certain people in my orbit are better to talk with than others. My wife is awesome and great for chatting about a lot of things. But she’ll acknowledge that she’s not interested in everything, and can’t contribute valuably to everything. (And vice versa!!!)

I have friends for certain topics and kinds of conversations. But even with my tendency to “collect” friends over the years, and the fact I try hard to maintain these relationships, it’s sometimes hard to think of who best to chat to. Sometimes I might want to chat with multiple people.

No, this isn’t life coaching

As I’ve thought through these ideas with others, several people have equated what I’m talking about as something like having a life coach.

I get the comparison. As I was formulating this set of ideas, I initially focused on accountability.

The first example I used was personal training. I would LOVE to have a personal trainer who isn’t a personal trainer in the normal sense of the term, but who simply spoke with me for an hour every week or so, and provided accountability for the other 167 hours of the week. I’ve trialled a number of personal trainers and explained that this is what I really want, but none of them has seemed to “get it”.

On reflection, however, I think that example was the wrong one. My prediction isn’t really about regular conversations and helping instil accountability.

My prediction is about one-off conversations, that are more about eliciting insight in relation to specific topics or areas of life.

(This is a practical impediment to my prediction: it’s not aligned with business models that are based on ongoing, recurring revenue streams. It’s more about one-off engagements. This is something I’m conscious of in relation to my own business: unlike other advice businesses, which have value in the form of recurring revenue, my business only has personal value to me in that it creates work for me. I’m not building an “asset” in the way that other advice practices are. That’s my cross to bear, and the price of building a business that’s truly aligned with how I want to operate.)

This type of service is (more) immune from automation

One reason I have high confidence in this prediction is that it should be relatively immune from automation.

Let’s face it: a lot of rote tasks are going to be automated as time goes on. This is relatively inevitable. Technologists will continue trying to turn labour into capital, and they will continue to be successful.

Personally, I’m not afraid of robo-advice in relation to the type of financial planning services I provide. The main reason: computers ain’t conversationalists. I think some other financial advisers who conceive their role in a different way may be at greater risk.

This extends more broadly. Computers and technology are GREAT at certain things. But dealing with people… not so much.

You can Google to your hearts’ content about a topic or something you’re dealing with. But talking to someone who can ask you the right questions is likely to get you better answers (from within!, not Google). I don’t think this will be automated easily.

As other types of work becomes obsolete, these types of skills which computers can’t do will become more valuable.

Maybe I’m rationalising; maybe I’m betting on the future

My final comment is that I’m a little biased in making this prediction, because it relates to a new service which I recently introduced (initially as a trial) via Fairhaven Wealth — an “INSIGHT” service, for $500 including GST (currently).

Perhaps this article is a complex rationalisation in support of this service.

But really, I’d like to think that I’m explaining why the introduction of this service is a bet on what I think the future holds.

(Where does the line between “rationalising” and “starting from first principles” sit? It’s hard to tell.)

Personally, it’s the type of service *I* would want.

I would love to have someone who was smart and dispassionate and socially skilled who could be a devil’s advocate for some of the decisions I make. This relates to financial matters, but there are other domains where I’d love to chat with someone who has expertise and can ask terrific questions in a tactful, clear, and compelling way.

My view is that for many people, most of the time, they aren’t looking for answers. They’re not even looking for advice. They just want help to find the answers themselves, and want to gain comfort and confidence about what they think and feel and do.

I predict that people will be paid generously for being able to facilitate conversations like this on niche topics.

At the moment, I call it the professionalism of conversation. I’m interested in what this phenomenon ends up being called!


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