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.

The most important part of writing isn't the writing

I question everything I write.

Until I don’t.

That doesn’t mean I believe my drafts evolve into perfection.

Truth is I haven’t come close to writing the perfect piece, ever.

But what I’ve managed to learn over a few decades of writing is this:

The most important part of writing

is questioning and thinking about

what you just wrote.

This is the writer’s contemplative work that demands unmerciful scrutiny:

• Is this really what you mean?

• Will it resonate with the audience?

• Did you use a helpful example or accurate analogy?

• Did you allow jargon to slip in?

• Can you say this differently but better, quicker, more human and conversational?

• Is it reflective of the brand or individual you’re writing for?

• Would you want to read this?

• Does it educate or challenge what you think?

• Does it make you want to take action?

Here’s an accepted truth:

Anyone can write and putting words on paper or a screen is easy.

But not everyone is a writer – and that’s okay and also acceptable. Not everyone is an engineer either. Which is why it’s helpful for non-writers to understand how writers do what they do.  

Writing (the process) doesn’t look like

writing (the act) at all.

Writing is rooted in everything that is simmering before the first words are hammered out, after the first draft –  and second, third or seventh – or however many are required until you land on a draft worthy of being final.

Writing includes thinking, mulling, stewing, questioning, arguing with yourself, walking away and letting first words calcify, returning to test if they are strong or brittle, tearing elements down and rebuilding.

It looks more like sculpting than writing. That’s because it is art.

Writing also involves letting someone with zero subject matter expertise read your draft to find out if they can follow it, to see if it makes sense even if they don’t know the technical details. Because simplicity outperforms the bravado of expert posturing. Which is to say…

Good writing is hard.

It is never automatic, and never a given.

Writing something good, once, is in no way a guarantee that your next thing will be any good. It requires doing the hard work from scratch, all over again with no shortcuts, in hopes that it too might become good.

The myth of great ideas.

Great ideas (epiphanies!) rarely “just happen” in a first draft or any draft. It’s like the fleeing fireworks display in the sky – it’s looks pretty, briefly, followed by hazy residue once the twinkle fades as you await what comes next. Instead, great ideas are the tortoises in these races to the finish line, always plodding a bit slower than we’d like but worth it in the end.

In fact, epiphanies aren’t unexpected, out-of-the-blue thoughts or ideas at all. They emerge when you prune and edit everything that’s been taking up space – in your brain and on the page. In this sense, the epiphany becomes sudden, recognizable clarity as bloated language and jargon get removed.

The great idea emerges after carefully working and examining the entire landscape and finding it has been hiding in plain sight all along.

Good writing is never over.

However, at some point it needs to be ready or complete. Complete means as far as you can take it, as well as you possibly can, with what you know right now. Because a few weeks or months from now you’ll look at what you wrote and find yet another way, possibly a better way to say it (note: when this was first written, generative AI wasn’t near the concern, a crutch, an aide — however you choose to look at it — that it is today).

For people who don’t do a lot of writing, this takes entirely too long.

For writers, there’s always a desire for more time to allow the best ideas and language to emerge and mature. And that’s because writers know what’s at stake, writers know what the right words can unlock.

We’re seeing a lot of written content that feels disposable, unhelpful, noisy [add your descriptor here]. Many want to call it slop.

It feels like fast food: quick, convenient, seemingly necessary, but also lacking. And just like fast food, disposable content feels even less fulfilling after its consumed.

It doesn’t have to be this way.

Even the shortest post can have a powerful impact.

The deception is in how easy it appears (but you know the truth).

Cut yourself some slack.

The process and the action are part of the iterative and final product.

Think it through (ask more Qs and then think some more).

And then write some really good sh*t.

** For the record, I wrote and edited this piece across multiple sittings, challenging myself and what I believe about the process. Nothing comes easy.

*** The photo image is the cover of Steven Pressfield’s book of the same title and is a must read for writers.

Why every leader should be writing

photo credit: Israel Andrade

If you are the boss, the CEO, the president, the business owner, the executive director, the person the buck stops with, then you might want to heed this advice: you should be writing.

Arguably it could be the most important facet of your leadership. Here’s a bulleted list of why:

• Your people want to hear from you – not just at the quarterly meeting or when things are getting tense. They want insights based on your years of experience, miles on the odometer, your wins and losses, your relatable stories of what they are challenged with right now.

• Your people want to know what’s working and what’s not, what the plan is and what direction the company is headed. Don’t assume they know this or will remember it. Remind them regularly.

• If your company’s mission, vision, and values aren’t well known, or if they don’t sound like you, or reflect how you lead or where your organization is going, it’s your responsibility to consciously connect the dots or redraw the lines so people get it. This is foundational to your writing and messaging. 

• It is a way to crystalize your thinking before you start communicating. Bullet points have their purpose, at the right times and venues, but they are not a substitute for writing with intention or communicating specifics.  

• You will  have a record of your messaging and what was shared; a written reminder of what has – and hasn’t – been said.

• You will be sharing stories (making you more relatable) instead of regurgitating talking points (making you come across as unauthentic). 

• You provide important perspective to data, trends, successes, and where things fell short.

• It gets what is in your head onto paper or screen where you can refine your thinking. Because your first draft isn’t your final draft.

• You begin articulating what you believe about business, leadership and success based on real-life trial and error, not someone else’s that is captured in a book.

• By communicating, first in writing, and then finding additional ways to bring those stories to life, you are consciously setting and reinforcing the culture. 

• Because every business challenge is first a communication challenge, and open communication cures many ills.

• Because bad news never ages well, and the grapevine distorts reality.   

• You will cast a shadow of what good leadership looks like by sharing deeper insights, plans and priorities.

• You will be building the archive; leaving a legacy and a blueprint. And you will be more attuned to the passing of time and the inevitable passing of the baton when the time comes (and it always comes).

WHAT THIS FORM OF WRITING IS… AND ISN’T.

This isn’t thought leadership or convincing existing customers and prospects that you have the pulse or unique perspectives on business. That is an entirely different endeavor, and something you might consider as well.

This is internal communication, the most urgent of business communication.

It is a function that might not exist or is relegated to a communications team without your regular input.

This is culture building by the chief culture officer – you.

This is the priority you might never have considered your priority.

This should be happening already. If not, you can start now.

If you don’t know how to start, let’s talk, and then start writing.

If you are already writing, make sure you have a person you trust to challenge, question, push you and, perhaps most importantly, call your bluff when necessary.

Bounce ideas off them. Determine what sticks and what doesn’t. Decide what’s worth committing to type and then sharing with others in various formats.

Because writing isn’t as easy as it sounds, and can come across in ways you never intended without a good edit.  

Even if you don’t see yourself as the writing kind, there are ways to get your ideas to paper/screen. But you must convey them out. Look at them. Chew on them. Own them.

Your people will thank you. The next generation of the business will thank you.

And you will have zero regrets articulating what mattered most during your time leading the people who helped propel the business forward. It is what success looks like when your team believes in, and acts upon, what you’ve chosen to share.

Thoughtful leadership requires more of this overlooked habit

“I don't have time to read – I’m too busy.”

For years I’d hear that kind of a remark from a leader and assume I had no idea the kind of pressure they were under. Being none the wiser, I would give them a pass. After all, it is hard to make time for something that isn’t a priority.

Today I know better.

I get that some people don’t enjoy reading and that it feels like more work on top of the work they already must do. But keep reading (or stick with me through this post). It doesn’t have to be drudgery, and I believe it can become a priority if we focus less on the act of reading and instead look to outcomes reading presents.

Recently, James Clear shared this thought on the value of reading and it struck a chord:

"Reading is like a software update for your brain. 

Whenever you learn a new concept or idea, the "software" improves. You download new features and fix old bugs."

That should push us to think about how many “old bugs” we have that need fixing, as well as how many new ideas that could be of real benefit if we’re open and curious enough. 

Now imagine the leader of your organization working on Windows 98, using a decade-old Blackberry, and sending email from an AOL account. They’ve signaled that these tools are necessary if not important, but refused relevant updates for their tools, processes and practices to advance the business. 

Processing new information, and then applying that which is useful or helpful, is in part the art of remaining relevant — and we need our leaders to be relevant leaders who know where to guide us and our organizations. 

Looking back, I can pinpoint which leaders and mentors of mine were avid readers and curious thinkers, in part because we talked about books and new ideas. It shaped my thinking and encouraged me to dig in and dig deeper.

Conversely, I am also reminded of those whose leadership style was less about curiosity, innovation and new ideas. Instead they held fiercely to rigid views and a “this is how we (meaning you) do it” mentality.  

Still think you don't have time to read?

In the last three years I've nearly tripled the amount of books (ideas) I consume. Like you, I’m still the same busy human — running a business, raising a family, and being pulled and distracted in multiple directions. My consumption of deeper content (vs. social scanning and intermittent browsing) has grown by listening to books — in the car, while exercising or walking the dog. This is not a new idea, but I was slow to adopt it. But I’m choosing to steal back some of that lost time, reclaim bits and pieces of it, while also leaving enough margin to think and also unclutter the mind.

Last year, I completed 71 books. It wasn't a chore. Only a third of the titles were overtly about business. I track them not to “keep score” but simply to remind me of what I’ve read and what I might want to revisit. A log also reminds me if I’m active in my reading and if I’m getting derailed.

I'm continuing to gain perspective on things and people that I was previously ignorant about (software update). And no doubt I'm thinking differently and more broadly than I did just a handful of years ago. My curiosity quotient continues to rise.

Further, a diverse selection of reading material can open us up to becoming more empathetic and aware of those around us. But it requires us to humbly approach new ideas, different perspectives, and unique voices with an “I don’t know what I don’t know” attitude. Although this HBR article isn’t a recent one, it’s still relevant. And it’s comforting to know we’re in good company as we embrace this critical leadership habit.

We owe this kind of upgraded thinking and curiosity to our clients and colleagues, family and friends. We also owe it to ourselves. And it’s as easy as opening a book or pushing play on an audio version.  

So to all busy leaders and those who aspire to lead others: read to learn, read for enjoyment, but also read to lead. There’s no doubt that you, and those around you, will see the benefits of being not just well read, but more engaged and curious in contrast to that time when you didn’t have time to read.  

READING OLD NOTES: gaining insight through reflection

I keep a stack of moleskine notebooks and serviceable knock-offs on a bookshelf in my writing studio. They are filled with meeting notes, doodles, writing prompts, sketches, and lists of peculiar word pairings that I imagine using in future pieces. There’s also some wise advice I’ve picked up and scribbled into the margins during this work-and-life journey.

I admit that once these notebooks are filled, I rarely pick them up or thumb through them again.

That is until recently.

I had been feeling anxious about a writing assignment and a personal project. I was struggling to start, to finish, to find the right words. They weren’t coming. More than writer’s block, it was a questioning of my abilities to perform my core work.

So I began thumbing through old words. Past projects. Thing that at one time seemed daunting. Things that felt important to commit to paper.

I wasn’t looking for anything particular. I was simply revisiting and reflecting on past experiences and old ideas.

And it made me stop and think: why is it that we scan old photo albums (or file folders) with a sense of wonder and excitement? Why does Facebook send us anniversary milestones of friendships? Why do we painstakingly curate playlists in Spotify from the 80s or 90s when there’s so much new music across any genre for us to enjoy? Why do we show up and honor, in our own special way, those whom we’ve lost?

Because we need to be reminded.

Reminded of what’s important and what matters;

what we’re striving for and what keeps us in the game;

what gives us life and purpose, hope and joy.

Looking for the right words and answers continues to be an imperfect and ongoing search. If not now, then assuredly later. And you, I’m assuming, will have your own specific search that demands resolving – from the mundane to the monumental challenges.  

As I thumbed through some old notes, I found some words of advice and inspiration, and a few that served as a kick in the pants to keep going, to pick ourselves up, to get better, and to never stop.

In some cases it was as if I was reading these points for the first time. For others, I had a different perspective thanks to the experiences I’ve has since I first scrawled the words.

Maybe these words – forgotten and tucked away in a notebook on a shelf, from writers, creators and, more importantly, doers – are exactly what I need to reflect on when the load feels heavy. And maybe you, too. Maybe these words needed some light thrown back on them to push us forward. Perhaps new eyes on these once-written, spoken and acted-upon words can breathe new life into whatever it is we need to do but haven’t.

I hope they are helpful, encouraging, or a kick in the pants. If they are, then write them down. Put them in a notebook. Add to them. And consider revisiting them from time to time.

Traveler, there is no road;

you make your own path as you walk.

As you walk, you make your own road,

and when you look back you see the path

you will never travel again.

– Antonio Machado // poet

“How we spend our days is, of course, how we spend our lives.”

– Annie Dillard // writer

“When we are merely competent, the value of our work is diminished until it can eventually be outsourced to the lowest bidder – making us a dispensable commodity.” (Don’t be merely competent. Be unmistakable.)

– Srinivas Rao // business author, podcaster

CRITICIZING IS EASIER THAN CREATING.

(shut up and get to work.)

“The trouble with comparing yourself to others is that there are too many others. Using all others as your control group, all your worst fears and your fondest hopes are at once true. You are good; you are bad; you are abnormal; you are just like everyone else.”

– Sarah Manguso // poet

“Emotion before evidence. Otherwise data will kill a good story on contact.”

– Todd Henry // writer, creativity consultant

“Keep being curious. Keep being a student.

As soon as you stop doing that, as soon as you stop playing,

you stop creating great things.”

 – Matthew Luhn // writer, Pixar Animation Studios

At the end of my suffering, there was a door.

– Louise Glück // poet

“If you listen to everyone, you will lose yourself.

You were hired for your expertise. Deliver that.”

– Ruth Carter // costume designer for Black Panther

But what if I’m not a real writer/artist/entrepreneur/etc.? Just sit down and do it.

What if my idea isn’t any good? Just try. Do it anyway.

What if nobody sees it? It’s not about who sees it, it’s about why you did it.

What if I’m stuck? When you’re at an edge, push through it.

What if this was a gigantic waste of time? Trust that it won’t be.

 – Allison Fallon // writer, coach, adapted from perspectives on writing

DARE. MIGHTY. THINGS.

Then do the work to achieve those things.