If I knew then what I know now…

“What do you wish you had known on Day One?”, she asked. 

It was an almost throwaway question 45mins or so into a call with someone I’d recently got chatting to on a Slack community. She’d reached out to the group asking for input on a leadership opportunity she was considering, and since there was a lot that resonated with me in her situation, I offered to talk with her about my experiences.

I thought about it for a moment or two. The Day One I had been discussing specifically, and indeed every Day One I’ve had in a leadership role, either acquired through being hired or being elevated.

Each Day One had been different. I arrived at the role with a different and increasingly accomplished set of skills. I arrived at each role in a different climate: organisationally, economically and politically. The personalities and egos at play were different. The expectations were different. 

But as I considered what each role became after Day One, I realised there was a common thread running through them all:

Even with the tightest job spec, and clear measures of success, once you peel back the layers of any role, things change. Things shift. 

If I had a time machine, I would go back and remind myself of that. Nothing is as simple as it seems at the start. If it were, then the middle wouldn’t feel so frustrating, and the finish would be clearer and more fulfilling. 

I would remind the slightly-younger me to pay close attention to the people as much as the processes. And I don’t mean even just the people who reported directly to me, or my own leadership chain. I would advise that it’s important to figure out who the egos are in the organisation. Who can make or break your chances of success? Who do you need to work harder to build bridges to, before they burn those bridges for you because of some misunderstanding or minor conflict? I would be more watchful of how they play the politics game, and who their allies were and what they were most interested in succeeding at.

Beyond that, I would tell my earlier incarnation to figure out what the major power centres of the organisation were. Are they sales-focussed, or retention-focussed, or feature-focussed, or customer satisfaction-focussed, or marketing-focussed or even economy-focussed? Whatever the major centres of interest are, and these probably mostly align with the biggest egos in small organisations, then you need to ensure you frame your successes in ways that align with those power centres.

I’d really make sure that previous-me knew, without doubt, that when you’re stepping into a role in an existing organisation, particularly where a lot of the structure (or expectations of the structure) are fixed in some people’s minds, it’s a LOT like buying a run-down old house. You move your furniture in, throw a rug down and discover a leak. So you shift a couple of things around and pull up some floorboards. Then, and only then, do you start exposing the real issues. Botch jobs. Old standards. Rotten beams. Maybe even a corpse or two (mice, obviously).

But, I’d also say that with any fixer-upper comes a lot of joy. The satisfaction of making things better. Uncovering the gems. Fixing the problems. Leaving your mark on the place and maybe even making a real home of it.  

I would encourage and forewarn in equal measure. Yester-me, listen up. You are at the start of an as-yet-unmapped journey. You think you know how this all fits together. You think you know how to fix it all now. You don’t. You will, though. It’s a journey and a maze all in one. If you pay attention along the way, you will learn a lot.

And, in fact, I did.