Harry Bailey

Harry Bailey is a technology and delivery leader who specialises in turning agency project chaos into clarity. With more than twenty years of experience as a developer, agency founder and fractional CTO, he helps digital and creative agencies build stronger engineering and delivery cultures and improve commercial outcomes. He focuses on practical, immediately actionable strategies, not theory, so teams can ship work on time and with less drama.

Why Agencies Can’t Quit Their Really Bad Estimates

If estimating things is so hard, why don’t agencies just stop doing it?

The majority of agency leaders I know don’t like estimates much. Never accurate enough to be trusted, and usually too optimistic. If delivery teams could just be better at creating them, there would be more certainty around timelines.

Delivery teams don’t like estimates either. They take a lot of time to create, and although called ‘estimates’ they often lead to expectations about delivery dates.

So let’s just stop estimating!

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But… can we deliver it?

There is a lot of focus put on the sales process at agencies. Sell more things to more clients. Sign contracts quickly and fill in all the details later. Keep the sales function separate from the challenges of project delivery.

It can be tempting to rush through the early stages of a client relationship. Promising the world to build trust and worrying about how to deliver on those promises later.

Saying no to that project that won’t be able to start for at least 3 months is hard. Surely there’s a way to make it fit earlier?

Agencies solve sales problems early. Niche down. Clear pitch. Know your market.

You know you can sell things
You can certainly schedule them in
You’ll plan what needs doing, and by who
You can track progress to the minute
You can even be prepared to support what you create

The big question is… can you deliver it?

Getting a great outcome for the team, the client and your bottom line.

Updating PHP on an AWS Lightsail WordPress Stack – Version 2

Note 1: Read the guide in full before you do anything. You’ll want to confirm it matches your situation and expectations.

Note 2: You can’t simply update PHP on an AWS lightsail WordPress stack. You have to migrate to a new instance with the latest version of PHP in it. That is what this guide shows you how to do.

Note 3: This guide assumes you have a static IP on your current Lightsail instance. If you don’t, you could possibly assign one in advance, but otherwise this guide isn’t for you.

I last ran through this guide myself on 26th January 2026 on this very site, which is about 750MB. I took it from PHP 8.2 to 8.4. WordPress 6.9 was installed on both source and destination instances during the process. With fast broadband it was down for less than 5 minutes.

I decided to rewrite the previous version of this article. The original has been cloned and copied loads of times, and to be honest it got bloated with updates and comments. I also prefer this new way. It’s fast and avoids issues with SSL certificates.

This guide aims to only take you through the steps I use now when a PHP version update is needed for my AWS Lightsail Bitnami WordPress install.

No fluff. Limited details. Just 7 steps and 3 optional ones.

You follow this guide at your own risk. Back up your site and read the full article through first. The older version of this article is still valid if there isn’t enough information for your needs here.

The main change here is we’re going to use a very simple maintenance plugin which shows a message in the short time required between moving the domain over to the new install and importing the migration file. This does away with the potential complexity of the Lightsail IP address being saved to the database as part of the migration.

Ready?

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Agile Principles & Your Agency: How to Live and Love Them

Text on what. "What works for your agency over Agile Frameworks"

Many agencies aspire to be Agile. Stories fly around social media about the successes of software teams who implemented an Agile Framework and immediately began reaping the rewards.

If you’re wondering how agile actually works in agency environments and why frameworks alone rarely fit, this tends to be where agency teams start looking for tailored agile coaching for agencies.

But Agile was created solely by men working in product (or product-led) and service focused organisations that built software. They didn’t focus on creative agencies when they coined the principles and values, being more service agency centric. They weren’t considering Agile as a way to delivery things other than software.

Agencies are not product-led organisations. They are project-led organisations. They have complexity and unknowns, where product-led organisations often have focus and clarity.

That doesn’t stop agencies valuing agility. And agencies can implement much of what it means to be Agile. But it does realistically stop off-the-shelf implementation of an existing Agile Framework (such as Scrum).

So if existing Frameworks can’t shortcut an agency to agility, how do we begin our journey, and what should we value when looking for better ways of working?

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Overcoming Agency Hurdles: How to Embrace Automation

office full of people. cartoon style. Lots of computers and robots

What is automation?

Automation isn’t a modern phenomenon. People have been automating tasks for centuries. Originally this meant creating a mechanical solution to a manual task, but more recently we’re automating using software and cloud services.

What started with fishing and waterwheels is now focused on writing code to offload the work of a person to a computer.

IBM defines Automation as “the application of technology, programs, robotics, or processes to achieve outcomes with minimal human input”. Nice!

There’s a massive opportunity for agencies to remove the need for ‘human input’, allowing your people to focus on work which returns more value for clients.

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