GarthBox

Your AI agent deserves a weird hat and a performance review.

The great mistake of the “comment CLAUDE and I’ll send you my magic prompt bundle” carnival is not that the prompts are bad.

Some are useful. Some are laminated oatmeal.

The mistake is believing the agent is the asset.

It isn’t.

The relationship is the asset.

An AI agent without context is not an employee. It is a raccoon with a keyboard. It may produce something shiny. It may also drag a half eaten burrito into your workflow and call it strategic sourcing.

You would never hire someone, sit them at a desk, say “make me smarter,” and then wander off to eat a bagel. (Right? Right?!)

You would onboard them. You would tell them what matters. You would explain the customer, the category, the emotional weather of the business, the weird taboo nobody says in meetings, the board level pressure, the internal politics, the thing the CFO actually cares about but calls “visibility” because adults are apparently forbidden from saying “I do not want to look surprised in public.”

AI needs the same treatment because useful intelligence grows out of context.

The better the setup, the better the output. Kinda silly to be typing that because that’s the way it has always been and continues to be.

Give the agent your company’s point of view. Give it the audience. Give it the constraints. Give it examples of great work and examples of work that smells like conference room carpet. Then check in. Ask what it misunderstood. Ask what assumption it is making. (Seriously, do this. Mine recently read about launching a coffee shop [true] and optimized my side for local coffee…despite me removing that from my bar model two years ago…) Ask what it would do if it had to make the work 30 percent more interesting.

That last part matters most.

Uniqueness is the missing ingredient.

Too many people are building AI agents that think like them, write like them, prioritize like them, and then they act surprised when the output sounds like their own brain wearing LinkedIn cologne.

You can build an agent with a background unlike your own. A skeptical CFO. A procurement leader who has seen too many auto renewals sneak through the pantry window. A brand strategist who only cares about what people repeat at dinner. A grumpy operator with a clipboard, sore feet, and zero patience for software that creates “alignment” by adding twelve more tabs.

That is where the juice lives.

A procurement team, for example, does not just need an AI agent that finds contract dates. That is table stakes with a haircut. The remarkable agent asks why three departments bought similar tools, why nobody negotiated before renewal, why intake feels like punishment, and how to turn spend visibility into the one thing every finance leader secretly wants: fewer surprises.

That agent does not merely retrieve information.

It changes the angle of the room. Kinda makes you gasp a bit, doesn’t it. Or better yet, it makes you feel something.

The research world has a polite name for this. Context engineering. Prompt design. Cognitive diversity.

Fine. Call it whatever you want.

The point is ancient and practical: minds work better when they are fed better inputs, challenged by different perspectives, and corrected before they wander into the swamp wearing tap shoes.

Stay Positive & Inspire Them To Inspire You

Every product has a Sicily inside it.

Not the brochure Sicily. Not the airport Sicily. Not the polite little hotel lobby with the laminated map and the chair that looks like it has been waiting since 1973 for someone’s uncle to sit in it.

I mean the real Sicily.

The version where someone is three bites into pasta alla Norma, two sips into limoncello, and suddenly the tiny accountant inside their skull takes off his visor, throws the calorie ledger into the Ionian Sea, and says, “To hell with it. We live here now.”

That is the moment.

Every product or service has one. The moment when the user stops evaluating and starts believing. The moment they stop asking, “Is this worth it?” and start asking, “How much more of this can I get?”

For a trip, it might be the meal where restraint melts into olive oil.

For a gym, it might be the first time someone sees a muscle they thought had been discontinued.

For a procurement platform, it might be the second a finance leader sees the contract renewal, the duplicate spend, the supplier risk, and the savings opportunity all sitting together like suspects under a hot lamp.

Not data as decoration.

Data as a loaded fork.

Data as, “Oh. Now I know what to do.”

Behavioral science has been whispering this for years in its lab coat and sensible shoes. People do not remember every moment equally. We remember peaks. We remember endings. We remember the strange little emotional fireworks that tell us, “This mattered.” That means the job is not to make every inch of the experience equally delightful. That is how you end up sprinkling parsley on a vending machine burrito.

In product marketing, this is where the story gets useful. Not cute. Useful.

The value moment is not always the feature with the most engineering hours behind it. It is not always the thing sales likes to demo first. It is the moment when the customer feels smarter, safer, faster, more in control, more alive in their own job.

When someone is already deep into the limoncello, do not hand them a coupon for next Tuesday.

Hand them the bottle.

If the user is salivating over a piece of insight, make it shareable. Give them the chart they can send to the CFO. Give them the savings opportunity summary that makes procurement look like the heroic adult in the room. Give them the board-ready snapshot. Give them the internal “look what we found” artifact that travels through Slack, Teams, inboxes, budget meetings, and executive eyebrows.

This is remarkability at its finest.

Remarkable does not mean “better than average.”

Remarkable means worthy of being remarked upon; a feeling that must be shared about with words.

A few questions to force yourself to answer:

• Where does the user lean forward?
• Where do they stop clicking and start caring?
• Where does the product stop being software and start becoming leverage?

Find that moment. Polish it until it winks. Package it until it travels. Name it so the customer can repeat it in a meeting without sounding like they swallowed a feature matrix.

Stay Positive & That Is Where You Build The Story

The future is never late because the future never arrives.

It just keeps changing costumes in the alley behind your roadmap.

One quarter it shows up wearing an AI badge and a suspiciously expensive blazer. The next quarter it arrives as a customer behavior shift, a budget freeze, a competitor launch, a regulatory sneeze, or a sales team saying, “Yeah, but the market is asking for something else now.”

This is the part that makes CPOs and CMOs either age like oak barrels or curdle like gas station yogurt. (That made me wince just typing…)

The trick is not to predict the future perfectly. That is fortune cookie theater. The trick is to build an organization that can move while the future moves.

Nature figured this out before the first quarterly business review was ever born. Rivers do not argue with rocks. Roots do not submit a business case before finding water. Bees do not spend six months debating whether flowers remain strategically relevant. They respond. They adapt. They keep the system alive.

Companies should try that sometime.

A few useful ways to work with a moving future:

First, treat your strategy like a compass, not a cage.
A good strategy tells you where north is. A bad one handcuffs you to a PowerPoint from six months ago and calls it discipline. Keep the direction sacred. Keep the path negotiable.

Second, listen for weak signals before they become screaming goats.
Customer questions. Sales objections. Support tickets. Churn reasons. Weird product usage. These are not random crumbs on the carpet. They are the early language of the market. Pick them up before someone else bakes a category out of them.

Third, build small bets into the operating system.
Not every idea deserves a task force, a kickoff call, and twelve people named Brad giving feedback. Some ideas need a landing page, a prototype, a customer conversation, or a quiet test with twenty users. Motion loves evidence. Evidence loves small bets. (My watch-out-for here is to at least get an executive to sign off. Soft-skinned colleagues will feel vulnerable not being engaged in this and that’ll hurt your trust bridges across the org.)

Fourth, stop worshiping certainty.
Certainty feels professional. It wears loafers. It says things like “we need alignment” while the market is outside stealing your bicycle. Progress usually starts with informed uncertainty. The brave teams admit what they do not know, then go learn faster than everyone else.

The future will keep moving. That is its whole personality. It is not malicious. It is just caffeinated. Just like me. Just like you?

The leaders who win are not the ones who guess every turn correctly. They are the ones who build teams with flexible knees, curious eyes, and enough nerve to adjust the plan without treating the old plan like a dead relative.

Stay Positive & Companies Die Standing Still (So Do We)

Procurement pain does not usually kick the door down wearing brass knuckles and a name tag.

It seeps.

It hides in the renewal nobody noticed (turnover never helps you here…). The software tool nobody uses but everyone pays for. The contract that rolled over like a lazy dog in a sunbeam. The vendor negotiation that never happened because the deadline was buried under nine tabs, three calendars, and one person named Brad who “thought Legal had it.”

This is the strange little circus of procurement pain: everybody owns a feather, nobody sees the ostrich.

That is where great product marketing earns its lunch money.

The job is not to say, “Our platform saves time and money.” That sentence has the emotional voltage of a beige stapler. True, perhaps. Useful, maybe. Memorable, absolutely not. (This was one of my favorite takeaways from Pendomonium 2026)

The real work is to make the invisible visible.

A CFO does not wake up in the morning craving another dashboard. A procurement leader does not lie in bed whispering sweet nothings to contract metadata. What they want is control. They want the fog machine turned off. They want to walk into the board meeting with the calm authority of someone who knows where the money is leaking and where the value is hiding.

That is emotional value.

Visibility is not just a feature. It is relief.

Spend intelligence is not just reporting. It is confidence.

Procurement orchestration is not just workflow automation. It is the difference between feeling like the organization’s financial crossing guard and feeling like the person holding the map, the flashlight, and the keys to the building.

And here is the punchline with teeth: in a crowded market, the best product does not always win. (The product guy in me winces just typing that…) The clearest story often does. (But the story guy in me is ecstatic typing that…)

If every company is shouting about savings, dashboards, integrations, and AI powered procurement wizardry, the category becomes a blender full of buzzwords.

Loud. Expensive. Difficult to clean. Grows mold fast.

The leader steps out of the blender and says: “You are not buying a procurement tool. You are building modern spend intelligence.”

That is the category frame.

Now the conversation changes.

It is no longer, “Which tool has the better feature checklist?”

It becomes, “Which company understands the future we need to operate in?”

That is positioning at the adult table.

That is the work: Collect the scattered pain, translate the spreadsheet into a human feeling, and name the category before the market names it for you.

My favorite moments in marketing: Once you define the problem better than anyone else, you do not just enter the conversation… You become it.

Stay Positive & Will You Be The Talk Of The Table?

Here is a strange little lantern to hold up to your work:

If you gave it away for free, would you still be excited to hand it to someone?

Not forever. Not as a business model. Calm down, capitalism, put the foam finger away.

But for one honest second, strip away the invoice, the title, the campaign goal, the quarterly goblin math. Imagine giving the thing to someone because you believe it should exist. Because it might help. Because it might make a person blink twice and say, “Well, hell, I needed that.”

If the answer is yes, there’s a good chance you’re building something with a heartbeat.

If the answer is no, that doesn’t mean quit. It means look closer. Sometimes the work is meaningful, but the method is murdering it. Sometimes the project is right, but the audience is wrong. Sometimes you’re not bored by the mission, you’re just buried under fourteen approvals and a spreadsheet wearing a little executioner’s hood.

A few other tests help.

Would you tell a friend about it without needing to sound important?

Would you put your name on it if nobody else’s name was attached?

Would you still care about the outcome if you didn’t get credit?

Would you defend the work in a room full of skeptics without turning into a PowerPoint raccoon?

Would you be proud to explain it to your kid, your neighbor, your bartender, your future self?

Would you feel a little electricity if someone improved it, shared it, stole the idea and made it bigger?

That last one is the spicy pickle. Meaningful work isn’t always precious. Sometimes it wants to travel. Sometimes the best ideas are less like trophies and more like seeds with suspicious little backpacks.

Stay Positive & Remarkable Work Has A Pulse Before It Has A Price

When the room feels crooked, check your own pockets for the bent ruler.

It is easy to blame the meeting, the inbox, the traffic, the mood of the whole bewildered circus. And sure, sometimes the circus really is on fire and the clowns are unionizing in the parking lot.

But start inside.

Your tension leaks. Your hurry hums. Your resentment puts on boots and tracks mud across the room before you say a word.

The outside world is not always your fault. That would be too heavy a backpack for one bony little soul.

But your energy is often the first match.

Before you demand better from the room, become better in the room.

Take a breath. Loosen the jaw. Choose the next generous move.

The world may not change instantly…. but the weather might.

Stay Positive & What’s The Forecast Again?

“One step forward, two steps back” is one of those phrases we treat like wisdom because it has been wearing a cardigan in the attic of language for a hundred years.

But I don’t buy it.

Not always.

Sometimes what looks like two steps back is actually two steps up.

You move forward. You hit resistance. The project gets weird. The meeting gets foggy. The plan sprouts six elbows and starts tap dancing on the conference table. The old story says you’re losing ground.

Maybe.

Or maybe you’ve climbed high enough to see the shape of the thing.

That’s the strange gift of perspective. From the ground, a detour looks like failure. From the balcony, it looks like strategy. From the basement, a pause feels like a problem. From the roof, a pause feels like a moment to redefine the map.

Leadership lives in that difference.

The average panic merchant sees a setback and starts shaking the vending machine of certainty.

“We were making progress. Now we’re behind. Now we have to recover. Now somebody must be blamed, preferably someone not in this room. And definitely not me.”

But foresight leadership asks a better question: “What can we see from here that we couldn’t see before?”

That question changes the room.

A missed deadline might reveal that the goal was poorly defined.

A difficult conversation might reveal that two teams were using the same words to mean entirely different species of snake.

A failed launch might reveal the customer truth everyone politely stepped around because it smelled like emotional labor.

That is not always backward movement.

That is elevation.

Two steps back says, “We lost something.”

Two steps up says, “We gained a view.”

And the funny little cosmic banana peel of it all is that both people may be right. The person who says you moved backward is not necessarily wrong. There may be rework. There may be delay. There may be a spreadsheet somewhere wheezing like an asthmatic accordion. But the leader’s job is not to win the vocabulary argument.

The leader’s job is to choose the frame that helps the team move forward better.

Stay Positive & Perspective Is Not Decoration; It Is Equipment … If We Choose It To Be