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.

Who owns delivery improvement?

As a consultant you can’t simply arrive, grab a cup of tea and start making a team deliver work better.

And it’s not just about understanding the context either.

There are too many moving parts for that, and the people leading delivery are usually the ones with the least capacity to absorb change — and the most connections to everything else that needs to move.

Thanks to my experience I’m relatively quick to understand the challenges of a delivery team in agency delivery. I’ve done it many times, I have a solid set of questions and measures that I run through. I’ve learned that each situation is unique, but the patterns repeat more than people expect.

I can create a solid status report with input from all the key people within a week or two. When I read it back to stakeholders everybody nods and agrees and gets excited for the opportunities. In their eagerness to get started, they ask what comes next.

And then, almost immediately everything slows, because change is hard, and an agency prioritising that change over billability is harder.

The understanding and the planning are easier to work through. The action is always where things stall. Meaningful improvement in a delivery team requires the following elements.

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The Move to Pods, Squads or Workstreams

At some point, many agencies start thinking about pods. Not because things are failing, and usually not because leadership is deliberately trying to redesign delivery. More often, it happens after a period of growth where the work is good, the team is capable, and clients are happy, but delivery begins to feel heavier than it used to.

Projects start overlapping more often, and leaders find themselves pulled into multiple streams of work at the same time. Planning takes longer than expected, even when the work itself is familiar. Clients begin to sense uncertainty earlier in projects, not because the team lacks capability, but because coordination has become harder.

The agency is growing. The delivery model hasn’t caught up yet.

That is when pods begin to feel like the natural next step. Splitting the team into smaller groups promises clearer ownership, parallel delivery, and less coordination overhead. The idea is simple enough to feel low risk, particularly when the intent is not transformation but relief.

And often, it works.

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What Are We Awarding Anyway?

Lego figures holding a trophy stand in front of gold lighting

There are more agency awards than ever.

More categories. More ceremonies. More tables to buy. More reasons to attend.

And somewhere along the way, it becomes reasonable to ask:

What are we awarding anyway?

Because when you look closely, the volume starts to dilute the meaning. Not always, but often enough that agency leaders are weighing the effort, cost, and value with more scrutiny than before.

This is not really about whether awards are good or bad. It is about whether they still make sense. And when they actually serve the agency, rather than the other way around.

The growing weight of awards

For established agencies, awards tend to appear at a particular stage.

You have strong clients. The work is good. The team is proud of what they are producing.

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I live in the gaps

Not the obvious ones. The quieter spaces where something is missing, but the system still appears to function. Where people are busy, well intentioned, and doing their best, while quietly compensating for something nobody has named.

One of those gaps became very clear in a process I was asked to spend some time with recently.

The business had done what it believed was the responsible thing. Time and care had gone into producing a detailed specification internally. Requirements were thought through. Edge cases captured. Decisions signed off. On paper, it looked solid.

And yet, the same questions kept resurfacing. Clarifications. Reinterpretations. Small misunderstandings that did not feel serious enough to escalate, but persistent enough to slow things down. Nothing dramatic. Just enough friction to make the work heavier than it needed to be.

It would have been easy to pin that on execution. Or communication. Or individuals not reading closely enough. That is usually where these conversations drift.

But sitting with it for a while, something else felt off.

The specification was doing its job inside the business. It created confidence. It reduced perceived risk. It allowed decisions to move forward. Once it crossed the boundary to the delivery team, though, it became something different. A document to interpret. To infer from. To work around.

No one had failed. The gap sat between contexts.

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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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