A fictional conversation between two CEOs about getting help

CEO 1: How’s it going? Your CEO life I mean.

CEO 2: Not bad. Tricky, I suppose. Things seem permanently fluid.

CEO 1: Yeah, I hear you. They say that things will only get trickier – kind of makes me nervous about what it’ll be like to lead a business in 5 years’ time.

CEO 2: I feel the same. How do you think we know when the right time is to get some help?

CEO 1: I don’t know. Maybe never. I reckon there are more average coaches than good coaches. Sometimes it’s intuition that tells you, sometimes there’s a clear hole that needs plugging. But that’s pretty seldom.

CEO 2: I’m trying to figure out if I can do this on my own or not. I’m not sure – coaches can be iffy. I’m not convinced they know my business well enough to help.

CEO 1: Many don’t. Finding someone who can help is not as easy as it sounds. I also struggle with admitting that I need help – my tendency is just to muddle my way through it. It generally works out okay.

CEO 2: What do you think you need help with?

CEO 1: I’m not sure. It’s just a nagging feeling that things are getting beyond me a little. I read a book the other day about the future of AI – ‘Scary Smart’ – that put the fear into me. AI is just one example of things I don’t know about that I feel I should. One of many.

CEO 2: It’s a pretty big decision to let someone in. In some ways, it’s easier not to. But I know I should. The last time I worked with a coach it felt like it took ages to actually get anywhere. Even then, it wasn’t convincing.

CEO 1: I’m also not certain where my business is heading, so it’s hard to know the need. Although, maybe that’s the need: helping me chart the next lap.

CEO 2: That makes sense because you’re not seeking expertise as much as you’re seeking a sounding board.

CEO 1: Sometimes the nudge is what matters. I’ve found that before – what I thought I needed had nothing to do with what we eventually worked on. That was a learning for me. I guess I had a blind spot.

CEO 2: Trust is so key though. I’m not sure coaches always appreciate that their advice has consequences. They walk out after a session and we get busy making the changes – and I’m not convinced they spare another thought.

CEO 1: I think that we CEOs give over far more control to the coach than we should. It’s our agenda, not theirs.

CEO 2: What’s the decision tree here? Is it a clear-cut thing?

CEO 1: No, definitely not. Maybe it’s more intuitive than that. Listening to that voice and then exploring it. Not being too set on an outcome.

CEO 2: Reckon that inner voice is reliable?

CEO 1: Mostly, but you’ve got to be pretty realistic about it and make sure you’re not tricking yourself into some false conclusion.

CEO 2: I do that a lot. It’s hard for me to really acknowledge the problems in the business. Sometimes it feels easier to ignore them.

CEO 1: Yup, definitely easier. But then some days I get the love back and feel really motivated to shift things and get my plan back on track. It seems to come and go.

CEO 2: Maybe that’s the lesson here. To not be in it alone and have someone there to witness us. That would be helpful for me. I find that I get away with a lot ‘in the dark’ where I operate on my own solo CEO-mission.

CEO 1: Yeah, maybe that’s it. Just to have someone bear witness. Then to let things go where they need to go in terms of the relationship.

CEO 2: Feels right. But I’m still slightly resistant.

CEO 1: Stay that way. Coaches need to meet our needs and standards. That skepticism is healthy.

CEO 2: Reckon that AI thing might one day replace us?

CEO 1: Hopefully, I’ve been planning my sabbatical in Italy for 15 years…