Why the org chart is almost always the wrong starting point
Organisational design is the piece of work scaling founders most often get backwards. They wait until the business is already painful, then they draw boxes and lines, then they wonder why nothing flows any more smoothly than it did before. The boxes are the wrong starting point. The real question – the one that unlocks everything else – isn’t what should our structure look like? It’s how does the value actually get created here?
I spend a significant part of my fractional COO work on organisational design projects for clients. I’ve done enough of them that I sometimes wake up at 4am with my mind racing through permutations of structures and roles, which is a sign either that I care too much or that the work really does matter to the businesses involved. Both are true. This article pulls together what I’ve learned about where founders get organisational design wrong, the question they should be asking instead, and what workflow-first design actually looks like in a scaling business in 2026.
The mistakes founders keep making
Across the org design work I do, a small set of mistakes keeps showing up. They don’t look like mistakes at the time – they look like common sense. That’s why they’re so persistent.
Building structures around people you don’t want to lose. A senior hire is brilliant, so you build a function around them. A year later they’re running an empire they never really wanted and the structure makes no sense to anyone else. Structure should serve the work, not the personnel.
Creating departments based on assumptions rooted in early careers. Founders who grew up in big agencies recreate account management, creative, production. Founders who grew up in tech build engineering, product, design. The imprinting is real and almost always premature, because the shape of your scaling business isn’t the shape of the business your own career prepared you to expect.
Elaborate hierarchies to flatter egos. Middle-management layers exist not because the work demands them but because a promotion is how you reward a high performer without losing them. Over time, the org chart becomes a reward scheme dressed up as a structure, and nothing flows through it cleanly.
Rigid designs built on the assumption that tomorrow looks like yesterday. Traditional structures are rooted in the belief that you can predict and control what’s coming. But markets shift, customer needs evolve, technology disrupts. The unexpected happens every day, and rigid structures break under that pressure while more flexible ones bend.
Unclear roles that create hidden cost. Two people think they own the same decision, or nobody does. The cost shows up as duplicated work, missed handovers, slow decisions, and people quietly burning out from role ambiguity nobody ever names.
The question founders should be asking
Most people start organisational design with the wrong question. The question they ask is what should our structure look like?, and they answer it by drawing boxes and lines. The question they should be asking is how does the value actually get created here?
Here’s a thought experiment. Imagine a customer placing an order in your business. What actually needs to happen for that order to turn into something useful to them? Information flows from a sales lead to someone who qualifies it, then to someone who delivers it, then to someone who supports it. Decisions get made at various points. Problems get solved along the way. Materials or artefacts move through logistics or systems. That’s your value stream – the actual path that work takes to become value for a customer.
Everything else in your organisation is overhead that exists to support that value stream. If you design structure around the value stream first, you get an organisation where work flows. If you design structure around functions first, you get an organisation where work gets stuck at every functional boundary. It’s that simple, and it’s also that rare.
Workflow-first org design: what it actually means
A while ago I was deep in a Miro board sketching out high-level org structures for a client and I had one of those moments when something clicks a couple of hours later than it should have. The options I’d drawn on screen looked sensible. They also completely missed the point of what actually created value in my client’s business. So I closed the tab, made a black coffee, and started again – this time from the workflow, not the functions.
Here’s why that switch matters more now than it did five years ago. In the old world, you designed your org chart around functions because humans were the primary resource, and humans needed to be organised into stable teams with clear reporting lines and career paths. Today, the primary resource is usually a mix – humans, AI agents, and automations working in harmony depending on the task at hand. That changes everything about how you should think about structure.
When parts of the workflow become substitutable – some with AI, some with humans, some with automation – the workflow itself becomes the durable piece of the organisation. The functions become less important. So the obvious move is to organise the business along the lines of the workflow, not along the lines of the functions.
Here’s a real example. A B2B SaaS client of mine has a standard customer workflow: find potential customer, qualify lead, demo the product, negotiate and close the deal, onboard, provide support, expand the account, try not to lose them. In the old world you’d have separate teams for each function – SDRs, AEs, customer success, support – and handovers at every boundary. What we did instead was organise them as a matrix around the workflow itself. Each “stream” owns the entire customer journey for a particular vertical, from outreach to account growth. The functional knowledge still exists, but it’s in service of the stream, not in charge of it.
The effect is that they’ve reduced friction in how work gets done, and – more importantly – they can now substitute AI agents and automations in and out of any point in the workflow without disrupting the organisation, because the organisation is designed around the workflow rather than around the people who used to do each step.
The traits of good scale-up organisational design
Across the scaling businesses I work with, the organisational designs that hold up under real-world conditions tend to share a few characteristics.
Fewer managers, more people in roles that enable flow. When structure is designed around the value stream, you realise you don’t need as many managers as a functional structure would suggest. What you need is enablers – people whose job is to unblock flow rather than to supervise headcount.
Less hierarchy, more networks. The best scale-up structures I’ve designed look more like a connected network than a traditional pyramid. Information moves faster, decisions get made closer to the work, and the founder isn’t sitting at the top of a funnel through which everything has to pass.
Multiple pathways, not single points of failure. A good design gives work more than one way to get through the organisation. A single gatekeeper in a critical path is a bug, not a feature, and will become the reason your business stops scaling at exactly the moment you most need it to move.
Decisions made close to the action. Empowered people making decisions where the work is, rather than escalating everything up the chain. This is almost always a function of the operating system around the structure – without clear goals, guardrails and accountability mechanisms, people won’t make decisions even if the structure says they can.
Role clarity without rigidity. Every role has a clear primary accountability – the one thing that belongs to this person and nobody else. Around that, there’s flexibility to collaborate, cover and flex. Unclear roles are one of the hidden costs scaling businesses rarely measure but always pay.
The leadership team is part of the design, not separate from it
Here’s a question I get asked constantly: what’s the right structure for my leadership team? It’s one of the most common questions from founders who are scaling, and it’s usually answered badly – by picking a template that worked in somebody else’s business and trying to map it onto your own.
The honest answer is that the right leadership team structure is the one that follows from the value stream and the operating system beneath it. A scale-up with a single primary workflow needs a different leadership team than one with three distinct revenue lines. A business that’s heavily dependent on a complex delivery engine needs a different shape from one that’s dependent on a big sales engine. Start with how value is actually created, and the leadership team falls out of that analysis. Start with job titles, and you’ll get the wrong shape every time.
“Simon has carefully negotiated the often challenging restructure of the business for changing times. I can’t think of anyone better suited for such a task; taking the time to understand the situation but being decisive and fair in delivery and hugely empathetic to the team.”
Georgia Branch, COO, We Create Popular
A practical starting point for founders
If you’re reading this and thinking you might need to redesign your organisation, here’s what I’d do first – before you touch an org chart.
Map your primary workflow end-to-end. From the first customer touchpoint to the last piece of post-sale value delivery. Don’t sanitise it. Draw it as it actually works today, including the re-work, the bottlenecks and the re-escalations. This is your value stream.
Identify where work currently gets stuck or slow. Every bottleneck is a design signal. If it consistently takes three days to move from qualification to proposal, something about the way the work flows is badly organised. Note every stick point.
Separate “who owns the work” from “who owns the decision”. In most scale-ups, those two things are muddled. A clear design names both, and they’re not always the same person.
Then – and only then – draw a structure that supports the workflow. The structure is the last thing you design, not the first. If you start with boxes, you’ll paper over the problems with more boxes.
Next step. Organisational design is not a one-off project. It’s a discipline you build into how you run the business. The businesses I work with that do this well tend to revisit their workflow-first design every six to twelve months, because the thing that worked at £5m will stop working at £10m. The good news is that once you’ve done it once, with the right questions, you’ll never draw another org chart the same way again.
