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.

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 →

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?

Continue reading →

Thoughts on stand-ups

Stand-ups are used by most creative and digital agencies. Teams have daily meetings where they align around their progress, challenges and discuss what’s coming next.

At least 15 minutes a day is spent on those calls. The whole team attends. Listening is the primary activity for attendees. It shouldn’t be controversial to state that the time should be used wisely.

But what does wisely mean? Well for me it means that it’s a good use of time for all who attend. From the most experienced to the least experienced team member. No matter what the role. Everyone should walk away believing they benefited from the call.

The focus of these stand-ups however is all too often a turn taking exercise where an individual’s status is shared. They read out information that is stored in accessible digital tools that the team can access.

What if stand-ups were about planning instead of reporting?

Continue reading →