This is my biggest weakness as a leader
And how I work to overcome it
In this morning’s blog I’ll cover:
My biggest weakness as a Leader
Using the Stockdale paradox to explain
How to balance optimism with harsh truths
Bonus notes: How stoicism helped
My biggest weakness as a Leader
I grew up in a house where ‘be reyt’ was a phrase thrown around every day (For those not from Yorkshire, it basically means ‘everything will be alright’)
Since I can remember I’ve been the most optimistic, positive person in almost every single room. An old boss of mine said to me once ‘I just want to check you’re doing your job right, becuause you haven’t complained or moaned once that I’m a little worried somethings going wrong’.
It’s a trait I feel super lucky to have, and it’s something I use philosophy and Stoicism to work on every day to keep up… HOWEVER…
Things in the world are genuinely sometimes shit. And using the philosophy ‘Be Reyt’ to a member of your team when they come to you with worries and concerns is completely unfair and unhelpful.
Not only that, it was never actually good for me individually as a human to never allow myself to feel rubbish.
A mentor I had last year really helped me to see how I was often being toxically positive with my team. So I went down a rabbithole of learning and understanding, alongside equipping myself with the tools to make sure I could continue to live in my bubble of optimism, but without being toxically positive to those around me who needed me the most.
Here’s what I found… A great explanation to start us off is The Stockdale Paradox.
The Stockdale Paradox
Admiral James Stockdale was the highest ranking US military officer, he spent 1965-1973 (18 YEARS) in a military prison. A prison with zero human rights, no release dates and absolutely no hope for prisoners to even make it out alive.
But Stockdale was one of the very few prisoners that actually made it out.
When asked “Who didn’t make it out”
Stockdale said “That’s easy, the optimists”
He went on to say… The optimists were the ones who said “we're going to be out by Christmas.” Christmas came and went.
Then they'd say “we're going to be out by Easter” But Easter would come and it would go.
The optimists would pin their dates on Thanksgiving, then Christmas again, and eventually… They lost all hope and died of a broken heart.
Stockdale concluded:
“You must never confuse faith that you will prevail in the end with the most brutal facts of your reality, whatever they might be”
And that's precisely what Stockdale did to survive unbroken.
How to balance optimism with harsh truths
Your job as a leader is to balance aggressive optimism for the world, your mission and your team, all with the facts of your organisation’s reality.
In my mission to understanding my greatest weakness and arming myself with the right tools to deal with it, there are 2 coping mechanisms I decided on:
Allow emotions to be felt and heard
If you or a member of your team is worried, nervous or upset, it does not mean they are weak. It means they care.
Often Leaders will train their team day to day with the aim of them ‘not feeling nervous’, or aim to fill them with positivity by telling them to ‘look on the brightside’ ‘at least nobody got hurt’ or ‘not worth getting upset about’.
None of this is helpful.
We need to first recognise these emotions as valid, teach your team that all emotions (even anger, jealousy and fear) are all human, are valid and should be felt and explored.
The definition of courage is to feel fearful of something, but not letting that get in the way of actually doing it. Courage isn’t to deny yourself of feeling the fear in the first place
The next time a member of your team comes to you upset, all you need to do is listen and make them feel heard. They need to feel these emotions and they need to know they are what makes them a caring, living breathing human.
Recognise the difficulties in others' work
Ever heard any of these from your boss?
“I’ve got a quick question” “I’ve got something I need you to do, it shouldn’t take too long”
Don’t be that boss
When presenting a new project or task, ask THEM how much space and time they need for it. Recognise the bits that are new and potentially tricky, but that you know they’re the best person to help figure it out.
By doing this, you’re not pushing overly optimistic ideas onto people, but instead allowing them to give you a realistic timeline of how long something will take. And at the same time you’ll be giving them the accountability over the deadline and owning the work.
I’d love to hear in the comments… What is your biggest weakness as a leader, and how are you working to overcome it?
Peace,
H.
Bonus notes: How Stoicism helped in accepting emotion
The last 5 years of my life has been re-shaped almost entirely studying and practicing Stoic philosophy, and when writing this article just now, I realised it turned way too Stoic to not include a bonus section here on Stoicism and the recognition of emotion.
While Stoicism is often seen and referred to as repressing emotion, this was never actually part of original Stoic doctrine. And I quickly learnt that neither emotionlessness or constant positivity are a hallmark of successful Stoic practice.
“In general, resilient people have intensely negative reactions to trauma,” writes Emily Esfahani Smith. “They experience despair and stress, and acknowledge the horror of what’s happening. But even in the darkest of places, they see glimmers of light, and this ultimately sustains them.”
That’s all we’re looking for. We accept the trickiest and darkest of emotions are valid and necessary. But always with sense of optimism about the world and how all humans are capable of incredible things.