LinkedIn Story Challenge 2023

30 days. 30 stories

Every day in April I’ll pop up a story prompt for you.

Use that prompt to write a LinkedIn post and share it with #linkedinstorychallenge

I’ll be following the prompts too.

Who is this for?

You’ll benefit from this challenge if you’re an ambassador for your business. Maybe you’re the business owner, or part of the senior executive team. You might be in sales or business development. Or you’re a consultant or a coach, a subject matter expert whose smarts contributes to the reputation and revenue of your organisation. In short, you’re the sort of person who’ll benefit from building your personal brand.

This is also for you if:

  • You’ve been trying to pluck up the courage to post.

  • You promised yourself this is the year you get jiggy on LinkedIn.

  • You’ve been posting for a while but it’s not really doing the do.

You’re a bit bored and you’d like to try something new.

Why the hell would you bother with a LinkedIn challenge?

I think a better question my friend, is why the hell would you not?

The benefits of posting on LinkedIn are many and juicy.

  • Make your ideal clients aware of you and what your business does.

  • Encourage people to feel they know and trust you.

  • Attract more business enquiries.

  • Increase your conversion rate on proposals.

  • Attract opportunity, community, and top talent.

When you get good at LinkedIn, instead having to pluck up your courage to make cold calls, people come to you to ask for help. You check they can afford your rates, diagnose their problem, propose a solution, send a summary of your recommendations, and most people say, great when do we start? I haven’t made a sales call since I started my business. Everything has come in through LinkedIn and word of mouth.

But it’s not just about new business. Opportunity comes in other forms. Speaking engagements, collaborations, invites to speak on podcasts or write for industry publications. All those things raise your profile and build your business. Maybe best of all, they attract a group of likeminded folks who dig your vibe, share your interests, and cheer you on.

This story challenge will build you a new habit, grow your LinkedIn community, and help people see how excellent you truly are. Heck, you might even win some new business too.

But why stories?

Storytelling has an effect on our body that simple information doesn’t. Brain scans of people listening to stories show our brain responds to descriptions of movements, textures, and smells as if we were experiencing that sensation for ourselves.

Stories that evoke empathy release oxytocin which makes us feel more trusting and connected with other people. Neuroscientist Uri Hasson found as we listen to a story our brainwaves synchronise with the storyteller. Stories bring people closer.

Stories are more memorable because they make our brains release powerful hormones that evoke emotions. Our brain stores memories far more effectively when they’re associated with emotions. A great story makes us feel, so it makes it easier for our brains to store and retrieve memories. The more emotive a story is, the longer we remember it.

With so much power to evoke a physical and emotional response, stories make your content far more engaging and impactful. So why wouldn’t you tell stories on LinkedIn?

So, what is a story? How do I do this?

So, a story is very simple. You only need three elements.

1.     There’s at least one character.

2.     There’s a place. A story has to happen somewhere.

3.     There’s change. You take your main character on a journey from Point A at the beginning of the story to Point B at the end.

Master storyteller Matthew Dicks says every story is really about five seconds in your life when something fundamental changes. He calls those the moments where you feel your heart move.

  • I was once this, but now I’m this.

  • I once felt that, now I feel this.

  • I once thought that, now I think this.

But ultimately, don’t get too hung up on whether you’re telling a story. This is about getting you writing and sharing on LinkedIn. No one is going to be tapping you on the shoulder and saying, “Erm, where’s your main protagonist and your dramatic conflict bro?”

The story prompts

  • April 1. What’s the biggest professional cock-up you’ve ever made?

  • April 2. Take us along with you on your perfect day.

  • April 3. Tell us about your very first job.

  • April 4. What would 15-year-old you say to you today?

  • April 5. What would you go back and say to 15-year-old you?

  • April 6. How did you come to do what you do for work today?

  • April 7. What’s the strangest thing you’ve ever done for money?

  • April 8. What does a delicious moment mean to you?

  • April 9. What do you want to learn next?

  • April 10. Tell us a secret no one on LinkedIn knows.

  • April 11. Tell us about your favourite project this year.

  • April 12. Tell us one good thing that happened to you yesterday.

  • April 13. What was your favourite game when you were a kid?

  • April 14. What’s your superpower?

  • April 15. Tell us about the most inspiring person you’ve ever met.

  • April 16. Tell us a nightmare interview story.

  • April 17. What surprising skill do you have?

  • April 18. Teach us how to do the thing you do in a single post.

  • April 19. What would you like engraved on your gravestone?

  • April 20. If you could go back to the first day of your business / job what would you tell past you?

  • April 21. Take us to your favourite place in the whole world.

  • April 22. What’s your fantasy start-up?

  • April 23. What’s the best / worst conversation you’ve ever overheard?

  • April 24. What’s the hardest thing about what you do?

  • April 25. Introduce us to someone you love.

  • April 26. What thrills you most about what you do?

  • April 27. What are your favourite smells in the world?

  • April 28. Intro us to your dream mentor.

  • April 29. Tell us what you’re here on this planet to do.

  • April 30. Re-intro yourself to us all.

Let’s take a closer look at those prompts…

This ain’t all going to be business time

Some of the story prompts will be business related. But lots won’t.

So, you may find this a bit exposing if you’ve never shared anything on LinkedIn that wasn’t business socks to the max. This is especially for you. We’re going to break out the person behind your business and share some of the things that make you, you.

And we’re going to do that because personal stories build trust and credibility.

And also, because it’s fun.

April 1. What’s the biggest professional cock-up you’ve ever made?

Let’s jump straight in there and bring out the skeletons.

Please don’t treat this like that horrendous interview question, “What’s your biggest weakness?” FML team. Has anyone in the history of job interviews ever answered that question truthfully?

Share a real cock-up here. There’s nothing to be ashamed about getting things wrong. In fact, the opposite. The smartest people I know would say that if you’re not getting things wrong regularly, it’s a sign you’re not pushing yourself enough.

Sharing your fails on LinkedIn makes you seem more human, real, and relatable. It’s also a chance to unpack what you learned from your most almighty snafu.

April 2. Take us along with you on your perfect day.

Just a bit of beautiful escapism to help people know you better.

April 3. Tell us about your very first job.

Sometimes our first jobs have no connection to what we do today. Other times you can draw a direct line between that first immersion in paid employment and your current career.

And whether your profession is an evolution of that first gig or a dramatic reaction against it, either way those first forays into the workforce are always a damn fine yarn.

April 4. What would 15-year-old you say to you today?

We’re so many people stacked up in one consciousness. Yet how often do we make space for those people to talk?

15’s such a tricky age. We feel so much so hard. Our brains are charging on all cylinders. We think we know so much, but so often have little autonomy,

What would that person think if they met you now? What would they want you to know?

April 5. What would you go back and say to 15-year-old you?

Yesterday we went back and sat with 15-year-old you and let them have their say.

Today it’s time for you to gift your hard-earned wisdom to that kid. What do you wish you’d known then that you know now?

April 6. How did you come to do what you do for work today?

Some of us know what we want to do from an early age. Yet, for many of us the road we take to meaningful work is long and circuitous. And many of us may not have found a purpose we relish yet.

Wherever you are on your journey; it’s always fascinating to see the path people take.

April 7. What’s the strangest thing you’ve ever done for money?

I always adore the section in author’s bios where they recap their eclectic careers.

We edit our CVs and LinkedIn bios to be neat coherent narratives. But what about that summer spent cleaning hamster cages at the roller disco? Bring the random back.

April 8. What does a delicious moment mean to you?

Author Florence Given talks about living deliciously.

Every week she asks her community to share what delicious living they’ve done that week, and they deliver delightfully, from moon lit walks to eating fancy olives in the bath.

The thing I love about this is how idiosyncratic and manageable delicious is. While a perfect day is a big deal (maybe too big, given the stress that accumulates around days like weddings, Christmas, and family holidays) a delicious moment is a spot of sun just for you.

April 9. What do you want to learn next?

Sometimes I get bored of myself. There’s 48 years of stories and experience packed into my brain, but some days the inside of my head still feels stale. The best way to get the zing back is to learn something new. Even the smallest learning adds a new lens to old knowledge.

What do you want to learn next?

What wash of colour would you like to lay over the tapestry of your life, and why?

April 10. Tell us a secret no one on LinkedIn knows.

Humans love secrets. Nuff said.

April 11. Tell us about your favourite project this year.

I’m sure there’s someone out there ambling through life at a lovely, measured pace, relishing the pace of their days, stopping to smell the roses.

It’s just I haven’t met them yet.

If you’re living the frenzied hustle where every moment of your day is accounted for as you rush from task to task, welcome to the club. There’s a good chance you’re not taking the time to stop and reflect on your wins. So, let’s do that.

What’s your favourite project been so far in 2023? Who was it for. Why did you like it? What did you learn? How are you going to get more of that action in your life moving forward?

April 12. Tell us one good thing that happened to you yesterday.

Some folks think gratitude practice is wafty hippie shite.

And those folks couldn’t be more wrong.

We’ve our negativity bias to thank for our charming tendency as a species to let the good things slide and the bad things stick. And if we pursue that negativity bias to its roots, it’s an outdated survival instinct from when we were a vulnerable young species in a world full of teeth and claws. We needed to be acutely attuned to small signs of danger because they were the difference between life and death.

Our environment has evolved beyond all recognition. But our brains take longer to come along for the ride. So, we’re still fixating on the little irritations just in case a sabre tooth tiger’s hiding behind that sarky email from Steve in IT.

Fortunately, we have tools to counter our own innate tendency towards despond. We can rewire our brain to become better at noticing the small wins and the everyday sublime. A regular reflection practise helps counter our negativity bias. People don’t bang on about daily gratitude out of toxic positivity, but because a gratitude practice helps redress the balance our negativity bias creates.

A simple way to start a gratitude practice is to begin a habit of noting one good thing that happened to you yesterday, because no matter how tough a day it was, we can almost always find one good thing.

April 13. What was your favourite game when you were a kid?

Are we the purest expression of ourselves before life comes along and teaches us fear and self-doubt? Do we spend our adult lives trying to find our way back to that un-self-conscious existence we had as a young kid?

Revisiting things we loved as a child can remind us of who we really are. What would happen if we played that way again? What could an adult form of that game look like? Could you even incorporate that game into your daily work?

April 14. What’s your superpower?

Since I moved to New Zealand 20 years ago, I’ve heard people talk about tall poppy syndrome. How our tendency to chop confident people down to size has an effect on our culture. That people struggle to own their excellence out loud in case they’re mocked.

Well frankly sod that.

You don’t have to rush around telling the world how you’re all that and a bag of chips. In fact, a hallmark of most confident people is that they don’t feel the need to big themselves up, because they know they’re enough. That calm confidence speaks louder than words.

But confidence starts with being able to state your superpower. What’s the most valuable thing you bring to the table? Who does that help? Why does it matter to you, and how does flexing your genius muscle feed your soul?

April 15. Tell us about the most inspiring person you’ve ever met.

  • How did your paths cross?

  • Where did you meet them? Take us there.

  • What was the weather like that day?

  • What were they wearing? What were you wearing?

  • What did they say to you? And what did you say to them?

  • Why does that encounter stick in your mind?

  • What made this person so inspiring for you?

  • How did they change the way you think, feel, or see the world?

I’m asking for the detail because that’s where the story lives. A story isn’t a summary of a situation. A story takes you to a moment in time, introduces you to real people, and shows you a moment when something changes. Make it real for us all.

April 16. Tell us a nightmare interview story.

We’ve all got at least one horrendous interview story stashed up our sleeve.

And this doesn’t have to be a job interview.

You can be speaking to someone you want to help you with a task. Maybe you were interviewed for an article, and it all went wrong. Perhaps you were at the doctor? Interviews come in many forms and it’s remarkable how often that meeting of people can go very wrong.

April 17. What surprising skill do you have?

Don’t worry if the skill is a bit dusty from misuse. You don’t have to be an expert.

I’m hunting those esoteric nuggets of ability you learned when your life took a left turn into a picturesque cul de sac. You don’t live there anymore, but if the zombie apocalypse came along tomorrow, you’ve got some mad skillz that’d come in handy.

April 18. Teach us how to do the thing you do in a single post.

Yes I am an arsehole. This is a very hard question.

I once heard this framed up as imagine you’re riding on a bus.

Your destination is half an hour away. You’ve only got the duration of your bus ride to teach the person beside you to do what you do. What do you say?

April 19. What would you like engraved on your gravestone?

Many of us don’t think or talk about our death often enough in white New Zealand culture. We like to pretend it isn’t really a thing, even although none of us get out of here alive.

Even when we know someone we love is dying, we can push that knowledge away with all our might. I interviewed a palliative care specialist who said she sees families fighting to keep someone alive even although it’s a futile exercise that affects the quality of their remaining life.

And that’s a sad thing, because by denying death, we don’t open space for important conversations. Conversations at the end of life are a gift. That’s when people pass on important memories, share how they want to be remembered, forgive and ask forgiveness, express love, and tell us who they are.

Bit of a heavy preamble to a LinkedIn story post, innit?

You can interpret this as your eulogy or funeral notice if you prefer. Once, when I asked this question someone was very concerned about the word count they had on their gravestone because engraving is expensive. So, for the purposes of this exercise imagine your gravestone is vast, and your budget stretches to 3,000 characters.

April 20. If you could go back to the first day of your business / job what would you tell past you?

I often ask people this when I interview them for LinkedIn ghost writing and they never find it an easy question to answer. I don’t know if this is because this is genuinely a hard question or because most of us don’t have a regular reflection practice.

Regular reflection is so valuable because it helps us to transfer our wins and learnings from day-to-day life to our long-term memory. I try for a daily, weekly, and annual reflection cadence (with varying degrees of success).

April 21. Take us to your favourite place in the whole world.

Please transport us away from our desks. We could all do with a spot of escapism.

April 22. What’s your fantasy start-up?

You’ve permission to go into the realms of pure fantasy here. Don’t feel you need to have the skills or the resource to create this start-up. Let your imagination rip. This is a no reality zone if you wish it to be so.

April 23. What’s the best / worst conversation you’ve ever overheard?

They say eavesdroppers will hear things they don’t want to hear.

And that can be true.

But I’m a shameless eavesdropper in cafes, bars, and on public transport, because I’ve overheard the most hilarious, touching, and improbable things.

If I’d invented some of those conversations, I’d be accused of being too far-fetched.

April 24. What’s the hardest thing about what you do?

This can be the stuff you hate.

But hard doesn’t always mean bad. Sometimes hard things are things we relish because they’re a challenge we can really get our teeth into. That scared excited feeling.

The philosophy of the stretch zone encourages us to deliberately push ourselves to do hard things to grow our skills and confidence. Not so hard that we bleed if we fail, but hard enough that our muscle tissue tears a little and grows back bigger.

April 25. Introduce us to someone you love.

Tell us about the moment you first met.

Share a beautiful memory.

Or show them moving through their day.

Show us the things you love about them rather than telling us.

April 26. What thrills you most about what you do?

Why do you bother getting up and going to work each morning? Where’s the buzz?

I know for many people a thrilling job is a luxurious dream.

And if that’s you right now, feel free to change this prompt and talk about what thrills you most about your life. Even if it’s a tiny thing.

April 27. What are your favourite smells in the world?

I read the other day that smell is the only sense babies have in the womb. I’m not going to fact check that one, because I love the idea too much to have it disproved.

Smell is so powerful and evocative. I remember walking down the road in Auckland a few years ago and a waft of cologne transported me back in time. Suddenly I was 13 again, flooded with a wave of memories and emotions I thought long gone.

How does happiness smell to you?

April 28. Intro us to your dream mentor.

This can be your mentor, a historical character, or even a fictitious character.

  • Who are they?

  • Why are they your dream mentor?

  • What do you want to learn from them?

April 29. Tell us what you’re here on this planet to do.

Part of me hates this question because it’s so self-aggrandizing. We’re one of 8 billion tailless monkeys. Zoom out to take in the whole span of human history, and we’re just one of 117 billion souls who’ve lived on this little rock in space. And in the context of the history of the planet, humanity is a sparrow’s fart.

So, who the heck are we to talk about purpose? We’re animals, whose most marked characteristic appears to be a remarkable propensity for pissing in our own drinking water.

But if I’m a little kinder I have to admit that we’re also the most heartbreakingly lovely creatures, with our ability to create beauty and our quest for the transcendent. Part of that is our other defining characteristics are our self-awareness, our ability to tell stories, and seek patterns and meaning. We can’t help asking ourselves what this is all for.

And you can tell I’m torn by this question, so if your take is that life is meaningless and purpose is a mirage, then I can’t say as I’d argue. Just tell us why you feel that way.

April 30. Re-intro yourself to us all.

I saved the most conventional question to the end, and there’s a reason for that.

This question is commonplace, and people’s answers to this question are often commonplace as well. How arresting is your elevator pitch really? How often does a facilitator ask people to intro themselves to the room and prompt a round of charming, memorable introductions that get you all fired up about working with such awesome people?

But if this month of LinkedIn stories has showed you anything, I hope it’s this. You are so much more than your education, your day job, your postcode, or the information you habitually share with the world.

So, when you re-intro yourself to us, draw on the stories you’ve shared. Tell us something you don’t usually share. Surprise us. Make us sit up and pay attention. Make yourself stand out from the crowd by telling a story that sticks in our mind.

Re-intro yourself and make it count.

The not rules for this LinkedIn story challenge

You don’t have to sign up anywhere. This isn’t a sneaky ploy to grow my e-mail list, although you might enjoy the Friday Content Crumpet because it’s buttery AF.

You don’t have to post every day … although it’ll make way more difference for you if you do. But if you do play along, please use #linkedinstorychallenge so I can see (and share) your stories.

And I’ll be writing along to the story prompt every day, so you can pop the link to your post in the comments under my post on LinkedIn to make it easier for folks to find your story.

That’s it. Them’s the no rules.

The 30-day LinkedIn story challenge starts Saturday 1 April 2023.

Can’t wait to get to know you better.

Not convinced by this LinkedIn malarkey?

Fair play to you. Check out these two case studies to see what LinkedIn can do for your brand and your bottom line.

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