Parachute Leadership
And what I now know about trust.
👋🏼 Hey, I’m Anna; a founder and startup consultant in an ongoing relationship with writing. Welcome to my weekly newsletter where I share insights and ideas across career, business, personal development, creativity, productivity...and everything in between. If you’re not a subscriber, here’s what you may have missed this month:
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I was once told by a CEO that I was walking too slowly to the photocopier and should pick up the pace so I could be more efficient. It was a display of leadership at its finest (…not) and has stuck with me for over 10 years.
More recently, I experienced leadership of a different kind within my consulting client Packsmith; a venture-backed Silicon-Valley tech-startup building an Uber-like marketplace to connect ecommerce brands needing to send orders, with people at home ready to pack them.
I was engaged to launch its Australian business; a herculean task. I secured the first customers, set up the first operations, found the first people and built the first processes, all while ferociously feeding learnings back to the team in Melbourne and Sydney, LA and San Francisco, Valencia and Kyiv.
With such a high stakes project many founders would have peered over my shoulder every chance they got. But not these ones. These ones handed me the baton, passed me a Gatorade, then cheered from the sidelines as I sprinted off alone.
They assumed I’d do my best. They empowered me to ask questions. They piloted me into the sky, strapped on a parachute and nudged me headfirst out the window knowing that I’d pull the emergency cord if things went awry.
They trusted me to deliver…and deliver I did.
Nobody likes a micromanager.
I’m a little ashamed to admit that as a budding new leader early on in my career, trusting people in this way didn’t come easily. Maybe it was because of that pace-policing CEO but I wasn’t sure I could rely on anyone, so I micromanaged despite knowing better and trying my hardest not to. I spelled out the simplest tasks step by tedious step, then perched like a hawk to make sure things got done. I cringe (oh how I cringe!) thinking back.
The thing is, my micro-managey behaviour had absolutely nothing to do with the team and precisely everything to do with me. It stemmed from the belief that if someone made a mistake on my watch I wasn’t capable enough to deal with the fallout.
When someone alerted me to the detrimental impacts of my somewhat-controlling very-stifling behaviour I started following my fear to its final conclusion, playing out the worst case scenarios if someone in my team made a mistake. Perhaps a budget blew up or a deadline blew out, but I quickly realised the world wasn’t going to implode. If someone failed, we’d learn, we’d bust out the Pine-O-Clean, mop up the mess and move on.
These days, I know that by trusting others to deliver they have the chance to step into their own. And I know that by trusting myself to deal with any screw-ups I also have an opportunity to do great work.
In teams we trust.
In my humble opinion the only way to build a high performing team is to put trust at its centre. Trust builds openness. Openness builds psychological safety. Psychological safety creates healthy environments. Healthy environments cultivate flourishing people. And flourishing people build great stuff.
On the flip side, when someone is breathing down your neck the only thing you build is a harbouring resentment and desire to lace their morning latté with salt.
So take the leap and trust others.
Even more importantly, take the leap and trust yourself. Trust your ability to fix things on the fly if they go wrong. Trust in your strength to navigate brutal situations.
And if shit hits the fan, trust yourself to pull the parachute’s emergency cord on the way down.
🙏🏽 Share this with someone who needs to back off
Just kidding. I wouldn’t suggest you act passive-aggressively and forward this to a colleague who micromanages. But…perhaps print it off and gently leave it on their desk?
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Anna. What an incredible essay.
This line deeply resonated “It stemmed from the belief that if someone made a mistake on my watch I wasn’t capable enough to deal with the fallout.”
And your comments on trust and environmental safety. Brilliant. I read on happiness in Denmark, one of the top factors were found to be the high levels of trust between citizens.
Some of the greatest lessons I’ve learned in my career have come to me via micro-managers. It took me a long time to trust myself as a leader because I was somewhat damaged by the awful examples I’d had modelled for me.
As a leader today, I love being able to empower my team to go away and get the job done. And I love the freedom it gives me to get my job done.