Category: Blog

Four generations of my family sold baby strollers. I’m the fourth.

I didn’t grow up dreaming about it. I don’t obsess over fabrics, wheels, or suspension systems. But I understood exactly what parents needed — and why. And that understanding shaped everything about how I think about the work I do now.

The Thing Nobody Tells You About Doing Good Work

The best people in any field aren’t necessarily the ones who love the work itself.

They’re the ones who deeply respect the people they serve.

A great surgeon doesn’t love cutting. They love giving people their life back. A great teacher doesn’t love grading papers. They love watching someone understand something for the first time.

The work is the vehicle. The person it serves is the point.

What I Actually Care About

I don’t love operations in the abstract. I love what happens when operations work.

I love watching a founder stop putting out fires every day. I love seeing a team that used to miss every deadline start shipping on time, consistently. I love the moment a business owner looks at their week and realises they finally have space to think.

Operations creates that space. And that’s worth caring about deeply.

Why Most Small Businesses Don’t Have It

Most small businesses can’t afford a full-time COO. A senior operations leader runs £150K–£250K a year. That’s outside the budget of any business doing under $5M.

So the founder fills the gap. They handle strategy, sales, client delivery, hiring, admin, and operations simultaneously — and none of it gets the attention it deserves.

The result? Great ideas that stall. Talented teams that underperform. Businesses that should be scaling but feel permanently stuck.

It’s not a talent problem. It’s a structure problem.

Why I Do This Work

The same mindset I carried from strollers carries into operations consulting.

Parents deserve products that make a hard job easier, not harder. Entrepreneurs deserve the same — systems that support their vision rather than fight against it. Too many great founders are running on duct tape and willpower when they should have a proper operating system underneath them.

That’s the gap I work in. Not because I have a passion for spreadsheets, but because entrepreneurs are the ones building things that matter. They deserve the infrastructure to actually succeed.

What This Means for Your Business

If your business is running on you personally — your memory, your relationships, your ability to hold it all together — that’s not a business. It’s a dependency.

You need structure. Not because it’s exciting, but because it’s what gets you out from under the chaos and back to doing the work you actually built this for.

The first step is understanding where the gaps are. The OS Readiness Score does exactly that — a free assessment that gives you a clear picture of your operating system in under five minutes.

I’ll be blunt: your business is not special. And that’s not an insult.

It means AI will affect your workflows, your team, and your competitive landscape — whether you adopt it or not. The question isn’t whether it applies to you. The question is whether you’re going to lead the change or get dragged by it.

Most small business owners are either ignoring AI or playing with it casually. Neither is enough.

The Mistake Most Founders Are Making

The common reaction goes one of two ways: total dismissal (“my business is too relational / creative / technical for AI”) or surface-level adoption (“I use ChatGPT to write emails”).

Both miss the point.

AI isn’t just a writing assistant. It’s a workflow layer that can handle research, analysis, first drafts, customer communication, data processing, documentation — entire categories of work that currently take your team time every week.

If you haven’t mapped your workflows against what AI can actually do, you don’t know what you’re leaving on the table.

Where to Actually Start

Don’t start with tools. Start with your workflows.

Pick a process that runs every week — onboarding a new client, generating a report, answering customer questions, creating proposals. Map it out step by step. Then ask: which of these steps requires genuine human judgement? Which ones are just time?

The ones that are “just time” are your AI candidates.

Once you’ve identified them, then you look for tools. Doing it the other way around — starting with “what does this tool do?” — leads to buying shiny things that don’t fit your actual operations.

Getting Your Team on Board

Here’s what I see in practice: the owner is sold on AI, but the team is either sceptical or using it without any framework — introducing inconsistency and errors nobody’s catching.

Neither works. Getting your team properly on board means:

Explaining the why, not just the what. What’s the actual business case? Why does this matter for how they work?

Starting with one workflow, not ten. Pick a win. Build confidence. Then expand.

Setting guardrails. What should AI handle autonomously? What needs human review? Write it down.

This isn’t a technology project. It’s a change management project with a technology layer. Treat it that way.

The Competitive Reality

The businesses that build AI into their operations over the next 12 months will have a structural advantage over those that don’t.

Not because AI is magic — but because it compresses time. A team of 10 with proper AI workflows can do what used to require 15 people. That’s a margin advantage, a speed advantage, and a capacity advantage, all at once.

You don’t need to become an AI company. You need to run your existing company with AI handling the repeatable work.

The Simple Version

Map your workflows. Find the time sinks. Pick one to automate or assist with AI. Measure. Repeat.

Not a revolution — an improvement loop. The business owners who do this consistently over the next two years will be in a fundamentally different position from those who waited to see what happened.

Want to see where your current operating system — AI readiness included — has gaps? The OS Readiness Score gives you a clear picture in under five minutes.

I spend a lot of time in Notion and Asana. Automations, integrations, AI workflows — the whole thing.

And the whole time, I was completely ignoring the most basic layer of my business infrastructure: where files actually live, how users are managed, and whether anyone can find anything.

Sound familiar?

The Part of Operations Nobody Talks About

Most small business operations content is about project management and team workflows. Fair enough — those are the visible problems.

But underneath all of that sits the infrastructure layer: your storage, user accounts, email system, and access controls. Most founders just wing it. Google Drive with no structure. Files named final_v3_ACTUAL_final.pdf. Folders nobody touches for six months.

It’s not glamorous. But it’s costing you time every single day.

What I Actually Found in Google Workspace

I finally gave it a proper look. Not just Gmail and Drive — the full setup. User management, group management, org-wide settings, the lot.

The thing that caught me off guard? Labels in Google Drive.

You can tag any file with a label, and labels have custom fields. So instead of digging through folder hierarchies, you can search and filter by those fields. Think: all marketing assets from Q1, tagged by campaign, by format, by status — filterable in seconds.

For a small business without a dedicated IT person, that’s powerful. You’re not building an enterprise document management system, but you’re also not drowning in disorganised folders.

Why This Matters More Than It Should

Here’s the compounding problem with bad file organisation: it gets worse over time, never better.

The team member who can’t find the brand guidelines wastes 10 minutes today. Six months from now, they’ve wasted 40 hours. Files get duplicated. Processes get repeated. Decisions get made on outdated documents.

Fixing it once — getting your storage and labelling set up properly — pays back every month going forward. This isn’t technology for its own sake. It’s ops hygiene.

Where to Start

If you’re on Google Workspace (or considering it), start with three things:

1. Audit your Drive structure. What does it actually look like? Shared drives or just personal drives with links flying around in Slack?

2. Set up labels for your most-used file categories. Marketing, Finance, Clients, Operations. Add fields that matter to each.

3. Review user access. Who has access to what? Is your last contractor’s Google account still active?

None of this requires a technical background. It’s 2–3 hours of work that pays off for years.

The Bigger Point

I was probably five years late to this. I’d been optimising the visible layers of my operations — the workflows, the integrations, the dashboards — while the foundation was a mess.

Most small businesses do the same. They invest in the front-end of their operations and neglect the back-end. Then they wonder why things keep slipping through the cracks.

If you want to know exactly where your operating system has gaps — not just the file storage, but the whole picture — take the OS Readiness Score. Five minutes. Clear answer.

Last year taught me something I didn’t want to accept: I’m the bottleneck.

I started working with small businesses as a fractional COO in June. Within six months, the demand was clear — and so was the problem. I can’t give every client 110% and serve four or five of them simultaneously. Not the way I work. Not with the depth these businesses deserve.

So I changed the model. And the lesson is one every founder eventually hits.

What Actually Happened in 2025

On the product side: our e-commerce push into the US didn’t work. The market got difficult, the numbers didn’t stack up, and we made the hard call to pivot. Sometimes the right move is knowing when to stop.

On the service side: the opposite happened. Small businesses need operational structure, and they know it. Six months in, the pipeline validated what I’d suspected — there’s real demand for this work.

The gap? Capacity. And capacity is a systems problem.

The Trap of Being Too Good at Your Job

If you pour everything into every client, you create two problems.

First, you can’t grow. Your ceiling is the number of hours in your week. Second, you build client dependency instead of client capability — and that’s bad for everyone.

The fractional COO model works because you bring high-level thinking at a fraction of the cost. But if your “fraction” is still 80% of your attention, the math doesn’t work.

The only real fix is to stop being the product. Systematise what you know. Turn your expertise into something that can operate without you in the room.

How I’m Changing the Approach

In 2026, the model shifts. Courses, cohorts, a private membership — the goal is to take the depth I bring to individual clients and make it accessible to more businesses.

Not a watered-down version. The same frameworks, the same rigour — delivered in a format that scales.

The insight that pushed me here: AI has commoditised information. You can ask any AI tool anything about business operations and get a decent answer. What you can’t get from AI is the judgement that comes from actually doing this work across dozens of businesses.

That’s what’s worth paying for. Experience + execution + AI leverage.

The Lesson That Applies to You

Whether you’re a service business or a product company, this question will eventually catch up with you:

What in your business only works because you are there?

If the answer is “most of it” — that’s not a sustainable business. It’s a well-paying job.

Building a real business means making yourself less essential over time. Not by stepping back, but by building systems and people that carry forward what you know.

That starts with mapping what you actually do — all of it. Then asking: what can be documented, delegated, or automated?

What 2026 Looks Like

2025 confirmed the market. There are tens of thousands of small businesses running on duct tape and founder willpower that need proper operating systems. They just need them in a format they can actually access.

2026 is about building that machine. The membership launches. The courses go live. The frameworks get packaged properly.

If the same lesson is staring at you — you’re running everything and nothing scales without you — start with the OS Readiness Score. It’ll show you exactly where your operating system is holding you back.

Everyone remembers Michael Jordan. The dunks, the rings, the flu game. But the Bulls didn’t win six championships because they had the best player. They won because they had the best system.

Phil Jackson’s triangle offense was the architecture behind the dynasty. It wasn’t built for one star — it was built for five players moving as one, reading the game in real time, and executing with clarity.

Your business needs the same thing.

What Is the Triangle Offense — And Why Does It Matter?

The triangle offense was designed by assistant coach Tex Winter. Three players always form a triangle on one side of the court, creating passing lanes, movement, and decisions based on what the defence gives you.

It wasn’t a rigid script. It was a structured framework that created freedom.

The players weren’t guessing. They knew where to be, where to move next, and how to respond to changing conditions — all because the system had already accounted for it. Your operations should work the same way.

The Business Translation

Let’s map the Bulls to your org chart:

Phil Jackson — the CEO. Visionary. Sets culture and direction. Doesn’t run plays — creates the environment where the system thrives.

Tex Winter — the COO or systems strategist. The architect. Designed the structure everyone else could execute within.

Jordan and Pippen — your leadership team. Brilliant executors who trust the system and push it forward.

The roster — your wider team. They don’t need to reinvent the wheel every day. They need clarity, a defined role, and trust that the structure holds.

(Dennis Rodman? Head of Controlled Chaos. Every company has one.)

Systems Without Culture Still Lose

Here’s where most businesses go wrong: they try to build the system instead of building the culture.

The Bulls didn’t win just because of the triangle. Jackson layered mindfulness, collective purpose, and real leadership on top of it. The system was the engine. Culture was the fuel.

Great documentation doesn’t replace great leadership. Asana doesn’t fix a team that doesn’t trust each other. A well-designed org chart means nothing without people who believe in the mission.

Systems give shape to your business. People give it direction.

What This Means for You

If your business feels chaotic, the instinct is to hire more people or push harder. That’s the wrong move.

Build the system first. Map your workflows. Define roles. Create accountability structures. Document the playbook so anyone can pick it up and run.

Then — and only then — does adding people actually work. Because now they’re stepping into a structured environment, not a moving mess.

The Bulls didn’t draft Michael Jordan and say “figure it out.” They built a system worthy of his talent. Do the same for your team.

Build Systems That Serve People

The real lesson from Chicago isn’t about tactics. It’s about what happens when a proven system meets strong leadership and a team aligned behind one goal.

Systems give shape to your business. But they need fuel: vision, leadership, culture, and alignment. A business is a living organism — systems give it structure, but people give it direction and purpose.

So if you want sustained success, don’t just build systems. Build systems that serve people. Build people who align with the vision. Create a culture that moves as one.

That’s how dynasties are built — in basketball, and in business.

Want to see where your operating system has gaps? Take the OS Readiness Score — a free 5-minute assessment that shows you exactly where to focus first.

AI is everywhere.

Every SaaS tool has an AI button. Every LinkedIn post promises it will 10x your output. Every consultant is selling an AI transformation package.

And most of it is noise.

Here’s what nobody’s saying: adopting AI doesn’t automatically make you more effective. Used the wrong way, it makes you slower, sloppier, and more reliant on a tool than you were before.

I’ve watched business owners automate the wrong things, generate polished garbage, and build teams that stopped thinking for themselves — all in the name of AI adoption.

So before you add another tool to your stack, here’s how not to use AI. Avoiding these five mistakes is worth more than any prompt library or AI course you’ll find online.

Mistake 1: Using AI to Avoid Thinking

This is the most common — and most damaging — way businesses misuse AI.

Strategy. Judgment. Critical reasoning. These are what separate good operators from average ones. They’re also what people are most tempted to hand off to a prompt.

When you ask AI to figure out your positioning, decide your hiring criteria, or tell you what your priorities should be — you’re not using AI as a tool. You’re using it as a replacement for the thinking that’s literally your job.

The result is predictable. You get output that sounds reasonable but has none of the context, nuance, or grounding that comes from someone who actually knows your business. You act on it anyway because it looks confident. Six months later you’re wondering why the strategy isn’t working.

AI is a thinking partner, not a replacement. Use it to pressure-test ideas, find angles you missed, challenge your own assumptions. Keep the judgment in your seat.

Mistake 2: Using AI to Polish Bad Ideas

This one is subtler — and more dangerous.

AI is exceptional at making weak thinking sound impressive. Give it a half-baked idea and it will hand back a confident, well-structured, grammatically clean version of that same half-baked idea. Supporting points included. Sounds authoritative.

That’s the problem.

When poor strategy wears polished language, people believe it. They approve it. They spend money on it. And when it fails, the failure is bigger and more expensive than it would have been if the flaws had been obvious from day one.

Clarity beats fluency. Substance beats style. A bad strategy in confident language is still a bad strategy — just harder to question.

Before you hand anything to AI to clean up or expand, ask yourself: is the core idea actually sound? If you’re not sure, don’t polish it yet. Work on the thinking first. Let AI help you write once you know what you’re saying.

Mistake 3: Using AI Where Accountability Matters Most

Some decisions should never be handed off to AI — and the most important ones involve people.

Hiring decisions. Performance reviews. Letting someone go. Difficult conversations with clients or partners. These require human judgment, emotional intelligence, and — critically — someone who owns the outcome.

AI can help you prepare. It can help you structure a difficult message, think through how to frame a tough conversation, draft an initial job description. That’s useful.

But when you let AI make the call — or when AI-generated language creates distance between you and a moment that requires your full presence — you’re not being efficient. You’re dodging accountability.

There’s also a practical problem. AI doesn’t know your history with this person, your company culture, or the full context of the situation. A technically correct response that misses the human dynamics can do real damage — the kind that takes months to repair.

Use AI to prepare. Stay in the room for anything that actually matters.

Mistake 4: Using AI Without Context

Generic prompts produce generic output. This is the most fixable problem in how most businesses use AI — and almost no one is fixing it.

The quality of what you get out is directly proportional to the quality of what you put in. Walk in with a vague, context-free request and you’ll walk out with a vague, context-free answer. It might look polished. It won’t be useful.

Context means: who specifically is the audience? What outcome are you driving? What constraints are you working within? What has already been tried? What does a good output actually look like?

The businesses getting the most out of AI aren’t using better tools. They’re giving better inputs. They’ve built internal prompts loaded with company context, tone guidelines, customer profiles, decision criteria. They brief AI the same way a good manager briefs a team member: specific, complete, clear about what success looks like.

If your AI outputs feel generic, look at your inputs first.

Mistake 5: Confusing Speed for Progress

AI makes you faster. That’s not the same as making you better.

Faster in the wrong direction is still wrong. If your strategy is off, AI will help you execute it more efficiently — which means you go further down the wrong path before you catch the problem. Speed amplifies mistakes just as reliably as it amplifies wins.

You see this in content constantly. Teams use AI to crank out more blog posts, more social posts, more email sequences — faster than ever. But if the underlying content strategy is weak, they’re just producing more forgettable content at scale.

Operations is no different. Automating a broken process doesn’t fix it. It just breaks it more consistently, at higher volume.

Before you use AI to accelerate anything, stop and ask: is this actually the right direction? Are we solving the right problem? Is this process working the way we think it is?

Execution speed only matters when direction is correct. AI doesn’t check your direction. That’s still on you.

What Intentional AI Use Actually Looks Like

AI is one of the most powerful tools available to operators right now. That’s exactly why it’s worth being deliberate about how you use it.

The businesses that win with AI won’t be the ones using it most. They’ll be the ones using it with the most judgment — pairing capability with accountability, strategic clarity, and people who still think.

Discernment isn’t the opposite of AI adoption. It’s what makes AI adoption actually work.

The question isn’t whether to use AI. It’s whether you’re using it on purpose — or just because everyone else is.