Put your paddle in the air

I went surfing in Maui today and caught a few really nice rides. I also had an experience that has given me clarity over how I approach things, and how I want to be treated as a CEO.

As a big wave was looming, the guy I was out with said ‘just push your board behind you and dive under this one’. So I did. The strength of the wave snapped the leg-rope cord, and I felt the board release from me. I came up to the surface behind the wave and the guy asked me ‘can you swim?’ as he went to retrieve my board, and I replied ‘yip’, and as I saw him paddle off after it, and also saw the set of waves coming towards me, yelled ‘but I don’t want to be left alone’. I still had my paddle with me, and held on to it as I dove under the next few waves, surfacing for a decent amount of breath between each. And then I realised - I can see waves on either side of me, I’m feeling some rushes of adrenaline and a little anxiety from being in this situation, and I can’t see anyone. And I thought - I do not feel like I am probably going to drown, but I feel like this is the start of a situation that could eventuate in that. So I put my paddle up vertically in the air and waved it. When the guy paddled over to me I said explicitly ‘I feel really anxious right now’, and we proceeded to get on his board together and head towards shore, where on the way a couple of other surfers paddled out with my board to hand it over and said nice reassuring things as they did.

None of this was that dramatic, I’m guessing no one else will really think about it again.

But as I was recounting the experience to a friend this evening, I realised that the way I acted is the exact same way as I act in business, and it’s the way I expect my team to act with me.

I call it ‘managing up’. As a CEO, I have to make a lot of decisions every day, some of them tiny, some of them carrying a lot of weight. The most valuable thing my team can do for me, is to surface issues/concerns/opportunities as soon as possible.

When I held my paddle in the air I thought - I’m not about to die, but ‘I would like help’. And then I found it fascinating that in the back of my mind I felt a bit guilty, like I shouldn’t be asking for help unless it was absolutely critical - and then I quickly realised, but that’s now how I like to be treated. Asking for help isn’t what you should do when you’re desperate, it’s literally when you would like help. I dearly appreciate it when someone surfaces an inkling of a concern in time for me to deal with it.

If you think of a graph of a company’s performance, showing a proposed line leading to success and a line leading to failure (of whatever measure you find most valuable), you don’t want someone to raise the flag 1mm before failure. The attribute you would most value, is someone’s ability to call it when you are 1mm below the line of success, at the very beginning of the divergence.

A few months ago I had a board meeting. At the start of it I said to my board - "I’m worried about money and I need your help". We proceeded to write down all the opportunities on the table, the likelihood and the other paths we could chase in different scenarios, and we got on the same page regarding what we would do if different looming opportunities went away etc. As it turns out, all of the things on the table closed, and the result was a solid and positive outcome. But that’s not the point. The moment I felt discomfort, and an inability to be ‘sure’ we would nail what we set out to do, I raised it. I didn’t wait ’til my last breath to raise my paddle. I did it as soon as I realised the outcome was no longer certain. I didn’t for a moment worry about being embarrassed that I needed help.

The result is that those with their hands on the levers are immediately able to act and respond, and to help create settings that will lead to success.

It took me a long time to really understand what ‘managing up’ meant. I remember in a previous role, my employer would talk to me about it, and I would try, but it was a long time before I ‘really’ understood the essence. It’s hard because of the layers of doubt and fear we have around being judged for failures. By our thoughts of ‘even though this isn’t going well, it’s so minor I can probably turn it around on my own and no one will know’, without realising that asking for help, even just surfacing our thoughts that things aren’t going as well as they could, is what makes all the difference between succeeding and failing.

I felt a bit embarrassed to wave my paddle in the air today, but I’m damn glad I did.