What a decade of writing for one CEO taught me

For nearly a decade, I wrote perspectives and opinions for a CEO – what the business world calls thought leadership. This is what it looked like:

Each month, the CEO of a privately held services company gathered a hand-picked team of trusted professionals to discuss and debate issues – what’s trending, what’s around the corner, what’s being overlooked, what’s is being misrepresented, and what matters to her company’s audience.

One of us would be charged with drafting the perspective, and occasionally two of us would take a crack at the same topic to examine two different approaches.

We didn’t always agree but we never failed to uncover a truthful perspective, something to say with conviction that we hadn’t heard articulated. The process forced us to think more deeply about what was happening in and around our work, and what clients might find valuable as they wrestled with their own work.

Then we revised, edited, and edited some more before putting it into the world.

Always to an email list first, then to the social feeds.

What came next was the remarkable part.

“How do you know this works?”

It’s the question everyone asks. The response the CEO gave wasn’t what anyone on her team expected. It was atypical of the work-and-response rhythms of client work.     

In that decade of writing, not once did anyone bring analytics to our meetings. Not. Once. And nobody asked for them. The extent of our group’s awareness of “effectiveness” was in the earliest days, confirming emails were sent, noticing an unopened rate to consider a second send, and then making adjustments to dead emails or unsubscribes, which we rare.

Instead, our time together was intentional, focused on mapping and pressure-testing the next set of ideas. That was the important thing – thinking through issues and perspectives that would benefit clients.

In time, it was as though the written content became a secondary byproduct of our robust dialogue, strengthening our perspectives and resolve on key issues.  

Yet the questions from the outside persisted – how do you know this works? – the CEO’s answer was unexpected and refreshing. She said plainly – I don’t know.

And by I don’t know, she meant that she didn’t know what the analytics were, even though she could access them.

That data, if she chose to trust the numbers, easily could’ve killed our work early on.

So why did she persist for a decade?

It became personal

Here’s the thing — she experienced something more valuable than numbers and percentages could reveal.

Before we developed a cadence or monthly expectation among her audience, her peers in the c-suite we responding – first to the to the listserv email, and then to her personal inbox, providing affirming comments, their own thoughts, and occasional pushback, which she welcomed and responded to thoughtfully. At meetings, events, and galas, leaders would tell her they read her latest perspective.

She would share the written comments, unedited, with her hand-picked team. These were supposedly busy executives who didn’t have time to read monthly thought leadership, let alone respond to it.   

It was the only metric that mattered, her tangible proof this was valuable to others, revealing itself in an email, a comment on a client call, a random encounter out in public. It became about personal engagement: her thoughts, their reactions, and ongoing dialogue.

She would openly admit there was no conclusive proof that any of it translated to a specific piece of new work. But she knew it put her top of mind among her audience, creating recall when they bumped into similar issues she’d already wrestled with and shared.  

We didn’t check a thought leadership box with expectation of what would happen the following week or month. We were coming together to challenge ourselves, putting a stake in the ground on what we thought, and sharing our own wrestling match with others where she had the final say on what she believed and attached to her name.

This was true thought leadership — the kind that was never intended to become another cog inside a sales funnel.

Instead, we created authority through the candid and consistent work of thinking through hard issues so that when people needed perspective or expertise, they knew where to turn. She was adamant that we would not turn this exercise into a blatant sales pitch.

What I carry forward

I was an outsider this CEO trusted. I wish I could pinpoint the initial why of that trust, but I worked hard to maintain it, mainly by questioning, pushing, and presenting other perspectives. Sometimes my arguments could shift her lens. Often it galvanized her original thinking and views, spurring language for us in how to defend it.

In retrospect, that decade-long assignment was one of my favorites. And it led to opportunities to work with her and her team in other ways. That’s what trust does.

It also sharpened my thinking and counsel to clients on what I see as effective thought leadership. I believe it has four essential components.

1. Understand the commitment. I’ve worked on several multi-year campaigns with clients. I’ve also had just as many stall after a few months because they expected thought leadership to do their sales work for them. Knowing what you’re committing to – creating authority, not sales conversion – determines if you have the stamina for the work and its intent. Commit to showing up and see what emerges. 

2. Make it a collaborate effort. Working in a small collaborative of trusted thinkers helps to pressure-test every angle and find your unique position. Even when you think you have great ideas, allowing others you trust to poke at it to see how it holds up before writing is essential. Find the people you trust with your ideas and ask them to challenge it and to show you other points of view over your own bias. This is perhaps the most valuable part of thought leadership.  

3. Have courage. You must convey a distinctive point of view. Regurgitating what others have said is neither leadership, nor is it your unique thinking. Having courage to address hard things and experiences, with resolve and empathy, is what makes you memorable. 

4. Play the long game. Authority and trust aren’t handed out freely. They are earned over time when reliability and relatability converge in the reader’s mind. That said, the practice of gathering for deep thinking and idea sparring forges discipline and defines a path forward, becoming as important as any written product. Give it six months to a year, minimum, and listen closely. Watch your trusted team grow in confidence.

That 10-year assignment didn’t feel like a decade of work. It felt like fun that went way too fast. And when the work is fun and valuable to others, you’re on to something.

Letting go of old narratives

What if “letting go” actually affords you the momentum to move ahead?

Playing it safe often means clutching to things with a too-tight grip.

This includes your outdated stories.

But if you loosen your grip and let go, your hands – and mind – are free to consider new possibilities.

What narrative are you clinging to that is no longer working?

Some stories have a limited lifespan.

They will run their course – even as others try to convince you to stay still and unchanged.

But you’re growing and evolving.

You’re ready for what’s next.

And that reassessment is essential for the growth you desire.

The story you tell is the one impression that lives on with those you’re trying to reach.

Tell the story you want them to embrace.

If you need help defining that narrative, reach out and we’ll craft it together.

The creative act of owning the box you're building

THEM: We need something.... "out-of-the-box and more creative."

BOLD VERSION OF YOU: No, I don't think that is the real need.

This isn't confrontational or a posture of unwillingness.
It's being helpful.
It's choosing to speak truth.
It's being the problem-solver you were called to be.

It's why they hired outside eyes and brains and proven talent to give them an honest, unvarnished perspective they lack.

Because you work in nonfiction, working hard to tell real and not made-up stories to real people (and target audiences) over algorithms, which is the opposite of a fictional marketing fantasyland.

Because you read in an old brief somewhere or the owners told you why they started this business in the first place, which, based on the "creative" they now want to be more creative, doesn't look or sound at all like why they created this business in the first place.

Because people don't like being marketed and sold to, let alone sliding down a brand's sales funnel.

Because people who make purchasing decisions often have a built-in BS detector that clients struggle detect in their own work.

Because people simply want good service from people they can trust, people that remind them of them, even if they don't look or think like them.

Because "creative" is wildly subjective.

Because the "creative" shouldn't be about their likes, but their customers' wants, needs, desires and solutions to pain points.

Because you're not trying to win trophies, you're trying to help them grow their business.

Because creativity for creativity's sake can mask a good straightforward story with unnecessary distractions.

Because the best creativity doesn't steal the show, it puts the spotlight on the show itself.

Maybe what's needed isn't something more creative or out of the box.

Maybe what's missing is getting back to that reason the business was started in the first place: to do things differently, to break away from the crowd instead of following it, mimicking it, competing with it.

Maybe reminding them, giving them permission, and pushing them toward having the audacity to do their thing, their way, and in a way that speaks to the heart of others who also find that way compelling -- is the most compelling and creative thing you can do.

Maybe it's about unapologetically owning the very box they've built.

Or there's this, which is possibly the worst-case scenario where everyone wilts just a little bit more and as they maintain the status quo:

NON-BOLD VERSION OF YOU: Sure, we'll take a stab at making it more creative.

It's time to be more bold.

Bold is honest, direct and often simple (that doesn't mean it's easy).

And businesses need boldness now more than ever.

Short attention spans, content deficits, and disconnects

You have 1.3 seconds.

One. point. three.

That’s the length of Gen Z’s attention span according to a new global study.

The good news is you’ll get a few seconds more with older generations.

To clarify, this is about active attention spans regarding advertising.

But advertising is a form of messaging. A sliver of storytelling.

And it either grabs one’s attention or it doesn’t. It’s memorable or it’s not.

This is an age-old challenge for advertisers and marketers: How to grab that fast-fleeting attention for a few seconds. And then a few more. The stakes have been raised and there is pressure-cooked dilemma of attention deficit driven by social media scrolling.

But don’t worry. Your marketing team will creatively crack the code.

You’ve got bigger fish to fry. Like answering this question:

What will we say once we have their attention?

More than two decades of asking company leaders what they do, why they do it, why people should choose their product/service – and then asking their people the same question – and it’s pretty clear most orgs don’t have clear-cut answers.

Vague ones? Yes.

Succinct and consistent? Rarely.

1.3 seconds of cool may be just that — cool.

What it cannot do is convey your complex message, even when distilled to something simple.

However, creativity can point to your story that connects emotionally to an audience.

Of course you know your story, right?

The one your team knows inside and out?

That conveys your unique value and what you bring to the market?

That underscores why people – employees and customers alike – are all in on what you do?

Yes? Vaguely?

This takes more than 1.3 seconds.

So breathe.

And let your creative team be creative when it comes to grabbing attention.

Don’t let an audience attention deficit lead your business into a content deficit.

You still need to nail your story. Know your why. Clarify what makes you worth their time.

Remember that old-school metric about how an audience needs to see/hear your message nine times for before truly acknowledging it for the first time?

The same is true in a generation of scrollers.

Except today it’s going to take a lot more than nine times.

But once you grab their attention, it’s game on.

To keep their attention you need to make a meaningful connection.

And in case you need reminded, that is why your company exists in the first place.

Four missteps organizations make with storytelling

If you asked a variety of people in different roles across your organization – what’s our company story? –what kind of reaction would you get? Would your colleagues accurately tell the company story? Chances are you might hear them say something like: “that’s not part of my role” or “marketing is in charge of that” or “I don’t really know.”

It begs this important question about storytelling – whose job is it anyway?

The marketing department? C-suite? Management-level employees? Those working the front lines with stakeholders? Sales teams? People behind the scenes? Those with the longest history within the organization?

The short answer is – yes. Yes to all of them. Storytelling is everyone’s responsibility.

However, it’s not surprising to see most organizations delegate the role of storytelling to the marketing department.

This is misguided thinking and where many organizations miss the point of that all-too-trendy term – storytelling. Here are four missteps that organizations commonly make with storytelling.

1.     Confusing story management with storytelling

Someone or some assigned team needs to take the lead in unearthing and positioning the organization’s most important stories. It should be their task to write them down for the sake of sharing in-house with employees and externally/online for stakeholders and customers in a clear and consistent way. The marketing function is a logical choice for establishing these pieces and developing the repository where the organization’s history, key messages and must-share stories can be found.

But let’s be clear – this is simply the act of story management.

What we’re talking about is storytelling – the verbal articulation of something deemed important – and that should be everyone’s business.

2.     Failing to connect the story with actual storytellers

Most of us don’t like the idea of being marketed to or sold something, at least not until we are ready to engage on our own terms. That fact alone makes every other function outside of the marketing department, and the vast majority of employees in an organization, critical storytellers. When people within an organization are empowered to tell stories about the business and their business – what we do, why we do it (purpose), who we seek to serve, why it matters, how we’re different, and why you should care – it is no longer marketing or sales. It is the sharing of ideas and of a larger ideal. It is storytelling.  And this becomes immensely valuable in cultivating a desirable work culture, attracting and retaining new hires, and stirring the curiosity among people who become clients, customers and advocates.

3.     Overlooking the importance of empathy and delivery

Consider this excerpt regarding the nuance of story from the English novelist E.M. Forster:

“If I say to you the king died, and then the queen died, that is a sequence of events.

But if I said the king died, and then the queen died of grief, that’s a story. That’s human. That calls for empathy on the part of the teller of the story and on the part of the reader or listener of the story.”

Read this again:  “Empathy on the part of the teller of the story...”

That is significant.

If we rely on marketing for our stories but don’t have an intimate knowledge of those stories ourselves and how to tell them – with empathy – our attempt at telling stories becomes little more than a list of facts, talking points, or a sequence of events. Worse yet, if we rely solely on marketing to be the mouthpiece of our stories we miss untold opportunities to engage people on the importance of our purpose and our work.   

And there’s this:  “...and on the part of the reader or listener.”

This is an important reminder that our audiences will engage and process our stories differently.

Every time I deliver a messaging document to a client for the first time, I ask them if they will humor me as I read it aloud. They are perfectly capable of reading it on their own, but I know that people interpret what they hear differently from what they read. Inflection is added in the right places for needed effect, and my voice becomes the audible highlighter of words and ideas that they otherwise might skim over.

We need the marketing team’s help to craft stories and position them for a compelling read in all formats – from the tweet that piques interest, to the website copy, to tangible printed material that compels a stakeholder to slow down and sit with our words.

But we also need the c-suite to lead by example – to know and convey stories with the passion we should expect from leaders, so that managers and employees (as listeners) can make a personal connection and become storytellers themselves by following their lead.

Marketing has its place.

Content is valuable and can be readily accessible.

But there is no replacing the sound and impact of a point well-made coming from a leader. 

4.     Ignoring the history of a story and failing to pull from it

David McCullough, the Pulitzer Prize-winning American author and well-known historian, said this about the importance of history and story in a 2004 commencement speech at Ohio University titled The Bulwark of Freedom:

“We have to know who we are if we are to know where we are headed. This is essential. We have to value what our forbears did for us or we are not going to care about it very seriously, and it can slip away.”

While McCullough refers to the story of one’s country and the importance of knowing history as it informs the future of a nation, the same can be said for nearly any organization or institution. Past and present stories provide the factual and credible narrative needed to set us apart from others. It is what we must lean into, it is our compass as we seek to chart new and exciting futures. 

Is your organization recording the stories that matter by writing them down, reciting them and sharing them regularly?

Do you and the people in your organization know its rich history, its defined purpose and how it intends to make a difference?

This isn’t arbitrary work. Your organization’s reason for being is rooted in story.

If you don’t know the story, you can’t tell it.

And if it’s not seen as something to take seriously, then there’s truly a lot at risk of slipping away.