The first 90 days I’d do differently

What cracked open in a whiteboard session that never should’ve happened

Several years ago, it was two weeks into my role as the first marketing hire.

I found myself in a small conference room with the head of sales. We had zero customers. No public launch. A product that was close, but not fully ready. Engineers moved quietly on the other side of a glass wall, finishing the last features before we could open the doors wide to the world.

Inside the room it was sterile. White walls, no warmth, and no plants because the office was brand new. I was at the whiteboard, marker in hand, mapping out the customer lifecycle stages in HubSpot as if an entire engine of leads was rushing toward us and the only bottleneck was my brilliance.

He sat at the table, one hand propping up his head, eyes blank.

I kept writing. Contact. MQL. SQL. Opportunity. Customer. Each stage felt like evidence that I knew the playbooks, that I had mastered the craft of bringing order to chaos. I imagined he would see my diagram and feel relieved that someone finally understood how to build this engine.

Then he asked a single question.

Why are we doing this now?

My heart fell to my feet. The marker froze in my hand. I went from feeling like the best marketer in the world to the worst one. The first flash of emotion was anger. How could he not see how brilliant this was. How could he not see that I was building something important?

The second flash was truth. At the time, we didn’t have customers. We barely had leads. We didn’t even have a website that reflected what we did. Nothing I was writing on that whiteboard mattered yet. I had walked in determined to impress him with my playbook, and instead I was performing a framework for a business that did not exist yet.

In that room, a belief died. The belief that being a great first marketer meant knowing the playbooks.

What I eventually learned is that proximity to the buyer matters more than any framework you walk in with. Understanding the founder’s vision matters more than the order of operations.

And that in the first 90 days, your job isn’t to build an engine. It’s to create the problem that the engine will eventually solve.

If I could relive that moment, here is what I would do differently.

I would put the marker down.

And I would walk out of that conference room.

Why “negative capability” is the source of your spark

I’m reading “Mastery” by Robert Greene (highly recommend) and he writes that “we are by nature fearful and insecure creatures.” We don’t like what’s unfamiliar or unresolved. So when we step into new territory, a new role, a blank whiteboard, we reach for opinions and ideas that make us feel certain. Not because they’re right, but because they make us feel safe. “Many of these opinions do not come from our own deep reflection,” he says. They’re borrowed. And once we hold them, letting go feels like a wound to the ego.

Greene points to what John Keats called negative capability - “the ability to endure and even embrace mysteries and uncertainties.” He argues that it’s a source of creative power.

“The need for certainty is the greatest disease the mind faces. To put Negative Capability into practice, you must develop the habit of suspending the need to judge everything that crosses your path.”

Staying longer in that suspended state feels uncomfortable. Greene writes:

“As it remains in this state…ideas will come that are more dimensional and real than if we had jumped to conclusions and formed judgments early on.”

That’s where the spark comes from.

Don’t get me wrong - I’d still ship something useful on day 1. But I wouldn’t try to put everything into neat and tidy marketing-strategy lifecycle-stage boxes just yet.

Here’s how I would do it:

The first thing I’d do: immersion (proximity, not playbooks)

In the version of this story I wish I’d lived, I walk straight to the head of sales’ desk (or Zoom room, or whatever). And, I flip the entire dynamic. I’m the one asking questions, not supplying answers. They’re the one at the whiteboard.

I tell them I’m here to understand their world and help remove friction. Then I ask about the conversations that went well and the ones that went sideways, the deals that should have closed but didn’t, the objections that show up again and again, and the patterns they’ve seen that never make it into a report.

I listen without interrupting. I don’t try to add my own insights or show that I’ve solved something similar before. I make space for their expertise. I ask for one tactical thing that, if I fixed it quickly, would show I’m here to make their job easier. And then I ship it. Not perfectly. Not after three brainstorms. Immediately.

A small win to make clear that I am here to help, not to theorize.

Then I go back to my desk and turn into a detective. A borderline stalker of the ICP.

I spend hours in Reddit threads and community forums, collecting the raw, unfiltered language our ICP uses when no one is watching. I look for emotional signals. Frustration. Delight. Confusion. Hesitation. Anything that reveals what actually matters to them.

If we have recorded calls, I listen to them on a walk or during my commute. I start to notice patterns in tone, not just content. The moments when someone’s energy drops. The moment they lean in. I write down the exact words people use to describe their problems. After a while, a picture starts to form.

Not a persona, but a human. Proximity, not playbooks.

Curiosity, not construction. The groundwork for everything else.

The second thing I’d do: capture the manifesto

At some point in the first or second week, I’d walk to the founder’s desk and ask when they have 30 minutes for something important. I wouldn’t bring a deck. I wouldn’t bring a proposal. I’d tell them I want to write the origin story of the company in the form of a manifesto that never has to be published. Maybe eventually it could be more, but for now, it’s just for us.

That always lowers the temperature. People speak more clearly when the pressure to perform is removed. I’d sit across from them with a list of questions and a quiet mind. No interruptions. No filling in their sentences. No trying to translate their thoughts into positioning before they finish speaking.

I’d ask until I understood the problem they fell in love with.

The moment they realized the world was broken, the change they wanted to see, and the legacy behavior they wanted to replace.

This is where the emotional spine of the company comes from. Not the website. Not the sales deck. Not the features. The manifesto becomes the internal compass that quietly guides the team’s decisions long before the outside world sees it.

The third thing I’d do: write the messaging

There’s always a morning when the fog clears.

A moment when the immersion insights and the founder’s vision sit in your hands at the same time, and you finally feel like you’re no longer guessing. That’s when I’d start the messaging doc.

I imagine it early in the day, coffee steaming beside me, the office still quiet. I’d surround myself with inputs. Quotes from prospects, threads from Reddit, fragments of the manifesto, notes from sales calls. All the raw material that shows me how buyers speak and how the founder thinks. It’s like being a translator between two worlds.

AI would help me form the first draft, but I would push it with hard questions. Would this resonate with someone who has no context? Is this true to the founder’s voice? Does it sound like the buyer? Is it specific enough to matter? Is it simple enough to remember?

What comes out isn’t just messaging. It’s the first real articulation of what we believe, who we serve, and why any of this deserves to exist. It’s the foundation for the website, the sales deck, the onboarding experience, and even the product roadmap.

The backbone for the growth engine: building the levers & tactics as I go

This is where I start executing. Throughout the entire ninety days, I would keep a running document open. My levers and tactics list.

A single place to store every growth idea that emerges from conversations, research, and late-night thinking.

The best ideas show up when I’m not looking for them.

After a call with sales, I’d jot down the stray growth idea that showed up in the last thirty seconds. After a user interview, I’d note that crazy partnership idea I had. If a content idea hit me during a walk or right before bed, it would go in the list before it faded. Some ideas would be small. Some would be weird. Some would feel useless in the moment. But they all belong there.

But instead of running on ideas, I’d tie each one to a growth lever, which could look something like:

Grow awareness.

Create demand.

Improve conversion.

Accelerate sales cycles.

Increase ACV.

Expand existing customers.

Reduce churn.

Open a new market.

This is how you avoid becoming the marketer who is always busy but never driving the business forward. Ideas are abundant. Leverage is rare. And, prioritization is hard.

This way you can prioritize the ideas that are moving the right levers at the right time, and solving the problems in the right order (for example, creating demand creates the “problem” of having to improve conversion). I have wasted a lot of time solving problems that don’t exist yet.

This list would evolve all ninety days, and keep evolving forever. And it would help me execute with intention (and become the backbone of the next ninety, and the next, and the next).

What these ninety days really are: creating the right problems

I keep coming back to a quote by Jensen Huang that puts all of this into plain language:

“Of all of the things that I value most about my abilities, intelligence is not top of that list. My ability to endure pain and suffering, my ability to work on something for a very, very long period of time, my ability to handle setbacks and see the opportunity just around the corner, I consider to be my superpowers.”

That’s “negative capability” in practice. Not brilliance or speed, but the willingness to stay with something when it’s unclear, uncomfortable, and unresolved, trusting that clarity comes to those who don’t rush past the hard parts.

The first 90 days are not a playbook, or a checklist, or a perfectly ordered sequence of tasks.

They’re a series of lived moments that create the right problems in the right order.

Problems that emerge naturally from being close to the buyer and close to the founder’s vision (for example, understanding the vision and buyer so deeply creates the problem of how to bring that vision to that buyer).

Problems that generate momentum for the company instead of structure for its own sake (for example, creating demand then creates the problem of optimizing for conversions).

If I could redo those first ninety days, I wouldn’t start with the whiteboard.

I wouldn’t start with lifecycle stages or funnels or automation. I would start with immersion. With curiosity. With listening not just with my head, but with my whole being.

And when you can stay there long enough to understand the buyer and the vision deeply enough, the strategy writes itself.