Can leadership suck & still be great?

I watched a YouTube video years ago and unlike hundreds I’ve watched since then this one stuck with me. I still remember the prickle of the goosebumps that appeared as I got sucked into the story and the feeling of deep connection with the point of the tale.

The video was of Drew Dudley talking about ‘lollipop moments’. Have you seen it? If not, it’s worth taking 5 minutes out of your day to watch it here.

The CliffNotes version is that Drew is handing out lollipops on the first day of university and a girl, who was about to turn around and run home convinced she wasn’t ready, decided to stay and tough university out because of his goofy actions. It was a life-changing moment for her; he can’t even remember it happening.

I think the video resonated so much for me all those years ago because I saw that leadership didn’t have to be this BIG thing. That leadership came from simply inspiring others to challenge themselves, to be bolder and braver and more authentic, to solve problems and to see things from a different perspective.

I re-watched the video this week and I’m glad I did because I realised that I had lost the lesson. I had got caught up in comparing myself to others. I once again got stuck thinking that leadership was a big thing. A thing that other people, smarter and more impressive people, had. That it came with the fancy job titles or the glossy headshot images I envy.

I forgot all about the bloody lollipops!

So I reflected on all the moments that matter for me. The butterfly effect situations that appeared like an insignificant flutter at the time but became life-changing:

🍭 My dear friend who, as we joked about my online dating matches on the backseat of the bus on our way home from work, said I’d end up marrying the guy with the weird name. I almost backed out of the first date, but decided I had to go and see if she was right (she was).

🍭 My old supervisor who handed me a bulging and slightly ratty file to me years ago because she thought I’d like the nerdy reporting tasks. I did, and this kickstarted my D&I journey.

🍭 A manager who left a lolly jar on my desk with a note that told me to just be myself. I was acting in a role at the time and thought I had to adopt the other person’s harder approach to succeed. That gift gave me the confidence to kill it in my own way.

🍭 A colleague who shared with me her infertility journey involving 11 rounds of IVF not knowing that I was undergoing treatment too. After a miscarriage and many unsuccessful IVF attempts I had given up hope and was considering giving up treatment. Her story of strength and persistence gave me the resolve to keep going. This gorgeous being is the result ❤️

Having recently left a role, I am in the fortunate position of having been enlightened about some the lollipop moments I’ve inadvertently been a part of (because all the best stories come out when you leave a job right?!?).

Conversations I had in kitchens and elevators or over Skype that encouraged people to put their hands up for projects, to apply for promotions or to totally change career. The career coaching conversation I had with a junior employee who missed out on a graduate role and decided to transfer to a regional office to get more experience… where she quickly met her husband... and their sweet baby arrived last year.

My reflection over the past week has led me to really assess what leadership means to me, and it really came down to two words that kept running through my mind: impress and inspire. So, just like millions of high school students in every essay ever, I decided to consult the dictionary to define each;

There are loads of people who ‘impress’ me. They work at cool companies, have PhD’s, get published in Forbes or HBR, lead global functions or host podcasts. I look at them in admiration (and with a little envy from time-to-time if I’m being really honest) but I wouldn’t say they ‘inspire’ me. I’m not enrolling in a doctorate, I’ll never work at Google and I highly doubt this witty blog will be picked up by a leading business journal.

There are loads more people who ‘inspire’ me. Some of them have the fancy impressive stuff, but most don’t. They are just people doing great stuff that makes me feel like I can do great stuff too, like;

🍭The connection I spoke to yesterday who started a not-for-profit leadership course because she wants to share her skills and experience with people who wouldn’t ordinarily have access to leadership development.

🍭A woman I chatted with who, rather than job hunting herself after losing her job due to COVID, is focused on lobbying LinkedIn to make changes that would better support job seekers now and in the coming months.

🍭The plethora of women around me who have started their own businesses because they want flexibility and freedom in their lives. Those who have quit jobs, started side hustles or are re-skilling to chase their dream of doing something they love in a way that works for them.

At the beginning of the Lollipop Moment video Drew says that ‘we’ve made leadership into something bigger than us, something beyond us. We’ve made it about changing the world’.

I think that considering leadership in the context of being inspirational (and not in a weird motivational poster way) and not impressive

makes leadership far more accessible.

If your words or actions make someone else believe that something is possible, you are the best kind of leader my friend!

My call to action is simply hijacked from the video:

🍭 Think of the lollipop moments that have impacted your life

🍭 Go and thank the person involved if you haven’t already

A lot of people are having a tough time right now. You never know if your small act of gratitude will be someone else’s lollipop moment.

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