Harry Bailey

Harry Bailey works directly with agency leaders to improve how delivery works — helping them understand what's driving overruns, rework, and delivery friction, prioritise what to tackle first, and build the habits and ownership that make improvements stick. With more than twenty years in project delivery, agency leadership, and operational change, he brings hands-on support to the people and practices at the heart of how growing agencies deliver.

Embedding AI: High value and low value client interactions

photo of girl laying left hand on white digital robot

I keep noticing how much effort agencies put into every client interaction.
Everything is treated as high stakes, high touch, and deeply personal.

It comes from a good place. No team wants to feel like they are giving clients a thin or automated experience.

But over time I’ve started to question whether all of that effort is actually valuable.

Some interactions genuinely benefit from care and judgement. Others mainly need to be accurate and delivered when promised.

When those two types of interaction get treated the same way, it usually causes problems. Senior people get buried in admin, and the moments that really need judgement get squeezed.

I see this most clearly in delivery work.

Continue reading →

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.

Continue reading →

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.

Continue reading →

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.

Continue reading →