Harry Bailey

Harry Bailey helps agency leaders fix the planning, ownership, and delivery issues behind overruns, rework, and delivery friction. With more than twenty years of experience in project delivery, agency leadership, and operational change, he supports growing agencies to make delivery clearer, less reactive, and easier to manage.

Why Project Management Guides Make Delivery Worse

Subtly misaligned tiles

When delivery starts to feel harder than it should, most agency leaders do the same thing. They look for clarity.

Not a reset. Not a wholesale change. Just something sensible to read that might explain why plans keep slipping, why outcomes still surprise people, and why teams feel busy without things becoming more predictable.

So they search for a guide. Often something like “mastering agency project management in 2026”.

What they find looks reassuring. Long, confident, recently updated. Full of methods, tools, templates, and best practice. It reads like a comprehensive answer to a complicated problem.

It feels current. It feels responsible. It feels like the right thing to be reading and taking action on.

Months pass. Planning is still slow. Risks are noticed early but only discussed once they start affecting delivery. Outcomes still surprise people who believed they had done the right preparation.

That pattern is worth paying attention to.

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Setting Up Partial Digital Inheritance with 1Password

1Password is brilliant for keeping your online life secure, but it does not yet have a simple way to pass on selected information after you die. There is no built in legacy contact feature, and organisers cannot access your private vaults. This leaves a gap for anyone who wants to share only some things with family in the future without giving away their whole account.

After testing different options, I found a straightforward approach that works well. It gives your family the information you want them to have, keeps your private vaults private, and avoids complicated workarounds.

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Should you manage work in progress in agency teams?

a neon sign that says actually doing the things

How many complex things can a human do at the same time?

It’s not a trick question. The answer likely came to you immediately. Correct, it’s one.

Doing more than one complex thing at the same time leads to terrible outcomes. Take driving and using a mobile phone as the extreme example.

In product teams — who often focus on a single goal for many weeks at a time — there are strict limits on work in progress. A person can be assigned to only one thing. Teams work on one thing per team member, minus one thing to ensure redundancy.

In agencies these rules are often less clearly defined, and sometimes don’t exist. People are commonly multi-assigned. They could be spending time across two or more projects, while also covering support agreement work.

It’s not uncommon for me to see people assigned to ten or more tickets. Yes 1-0, ten.

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Thoughts on the sales process

How often is there a mismatch between your agency sales and delivery process?

How often do we deliver something fundamentally different from what we thought was agreed with a client?

It’s rare for the sales process to include much time from the delivery team. It inflates the cost of sales, and unsuccessful pitches feel significantly more risky. So is it worth it?

Is it worth it?

For me, absolutely. Agency sales teams aren’t always able to consider the risk that’s baked into the projects they sell without experienced members of delivery. There has to be a better approach that isn’t many times more expensive.

I see this reduction of project risk, and the multiplying effect on team and client engagement as an investment in the future. An acknowledgment that project failure and client churn is significantly more expensive than bringing forward discussions about project delivery. Even if some projects never happen.

What would early delivery involvement look like?

Start with the ‘why’. Why now, why this, what will success look like and how will we measure it?

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