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.

Open image files in Shottr by drag-n-dropping them

I recently moved from Monosnap to Shottr for screenshots on my Mac. Shottr has a whole lot going for it, and it was the right move, but the biggest frustration was how to open images in Shottr quickly.

In Monosnap I almost always dragged the existing image from a browser, or Finder onto the menubar icon. Monosnap would show a little drop zone, you dropped your image file and Monosnap would review it in a new window. Shottr doesn’t yet allow dropping onto the menubar icon.

Also, shottr has a lot of shortcut key options, but none of them are ‘Load from Clipboard’. This is only available via the options list. So my clumbsy workflow was… right click and copy an image, click Shottr menubar icon, move down to ‘More’ then move down and click ‘Load from Clipboard’.

I decided there had to be a better way which allowed drag-and-drop, and after a little whle trying things out I found it.

Using the Shortcuts app in MacOS you can create a dock icon which receives the dropped image, copys it to the clipboard then triggers Shottr to open from clipboard.

It uses a combination of standard items, like copy to clipboard, open app, and trigger local app url scheme destinations.

Once you have the Shortcut built (or installed), click ‘File => Add to dock’ in the menu bar. If you make any changes to the app you might need to remove the existing app from the dock before using ‘Add to dock’ again.

You should now be able to drag any valid image to the new shortcut dock icon and after a second or two it will open in Shottr.

If you want to try this out for yourself, you can access a copy here:
https://www.icloud.com/shortcuts/60cb594b644d483097fd8e6d10321ddc

If you want to set it up from scratch, here are screengrabs of the Details and Privacy tabs. You might have to run inside Shortcuts with the play icon to give permissions before it functions correctly.

You can let me know if:

  • ‘Allow running when locked’ can be unchecked
  • ‘Receive what’s on screen’ can be unchecked
  • You truly need to trigger open Shottr before triggering the open clipboard url

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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.

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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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