OOO or PDA? Can AI and digital assistants support holidaying workers?

Software Developers, App DevelopersAppdrawn Team | Published 3rd August 2023
We look back at the world’s first Personal Digital Assistant (PDA) and question whether similar innovations can help today.

It’s the month of holidaying employees and out of office (OOO) emails. But in an AI age, should we really rely on automated responses and friendly colleagues to support with absentees’ workloads? We look back at the world’s first Personal Digital Assistant (PDA) and question whether similar innovations can help today.

It’s August. It’s summer. It’s holiday time. Whether you’re enjoying an early afternoon finish or clocking off work to jet off abroad, there’s one thing almost all of us will do: set an OOO email response.

The art of out of office

The tone of an OOO is always interesting: some businesses mandate standardised wording, while others are more informal. You may also get the odd response reminding you just how much fun someone is having whilst not sitting at their desk typing out that very response. In an OOO a few years back, for example, former chief executive of Grant Thornton wrote: "I'm off with my family right now, back on 23 July. I'll be reading, diving and playing with my boys while they still want to play with me!”

Most OOOs, however, will simply provide contact details for the colleague or colleagues tasked with taking on the absentee’s workload. ‘Taking on the absentee’s workload’ will mean different things to different businesses – and is often interpreted very differently depending on which colleague you entrust with the task!

Even the most diligent of team members will struggle to take on another’s responsibilities in full – and in many cases, they shouldn’t be expected to. Heading off on holiday, then, doesn’t always mean you’ll be able to entirely log off from work and out of your various apps and devices. Checking work emails before checking the weather forecast for the day, or jumping on a Zoom call before jumping in the pool, are all too common.

Logging out and jetting off?

Few of us want to work whilst we’re on holiday, but no one wants to return to work to find an overflowing inbox or a mountain of tasks. However, relying on a colleague to step into your shoes whilst you’re away – and relying on others to actually take note of an OOO – can be problematic. Could a solution be found in AI and PDAs? After all, we already have Siri and Alexa to answer queries and ChatGPT to draft university essays, recipes, songs (and so much more). Surely we’re not far off an AI OOO assistant to pick up our work while we holiday?

Turn back the clock 30 years and there were high hopes that we could be at the start of implementing such a solution. Before the birth of Siri in 2010 and Alexa in 2014, the world welcomed the arrival of first-born PDA, Newton.

Newton: the first handheld with an ARM

Apple’s Newton MessagePad was released in 1993 and was the first handheld device to feature an ARM microchip. Its specs were impressive and the features equally so: users could save memos and to-do lists, store details of contacts and manage calendars. Newton’s pièce de résistance, though, was Calligrapher, which translated handwriting into text.

It’s (supposed) greatest strength was also its biggest downfall. Calligrapher could only decipher words that were in its dictionary and it took weeks to ‘learn’ to recognise a user’s handwriting. This limited the effectiveness of Newton and was a cause of much criticism. Despite later variations of the device, production of the MessagePad ceased in 1997.

Despite its short lifespan, Newton should be long remembered as one of the first personal digital assistants, freeing office workers from their desks and enabling the kind of working on-the-go that characterises the daily lives of many of us today. This approach is helpful when we want to send work emails during a commute or log into shared workspaces whilst on work trips, but less so when there’s an expectation that we really can work anywhere – including on holiday.

Outsourcing to colleagues or companies?

Since Newton, PDAs integrated with AI have been developed to make our daily and working lives easier. However, tech companies are yet to develop and market an app that can instantly learn the tasks of and replace the role of any worker – or their helpful colleague – when they're OOO. Instead, many businesses are relying on outsourcing tasks to (human) virtual assistants. These assistants take on various roles and tasks and connect with businesses via a growing number of apps, such as Freelancer and Upwork.

This might seem like an attractive solution to the problem of holidaying team members, but there are drawbacks. Quality of work is not guaranteed and workplace culture and team morale could suffer. Interestingly, these are two issues concerning many who have had to rely on a colleague to take on their work while they’ve been on holiday!

Planning your holiday = planning your absence

What’s the solution? Planning and preparation. Just as you’d research holiday destinations, find decent travel insurance and get a good price for your flights to ensure a smooth holiday, you can also put approaches in place to create a smooth out of office. This includes drawing on some fantastic apps that support with time management, delegating work to colleagues and scheduling tasks and reminders for when you’re away from your desk. We’ve rounded up a few of our favourites:

  • Slack: easy-to-use instant messaging/video calling/file sharing (and more) for one-to-one or group chats. Meta’s Workplace (first launched as Facebook at Work) never took off – think of Slack as a more streamlined (and more successful) alternative for creating a digital work community.
  • Trello or Asana: both of these are great for task management and allow users to assign, track and manage tasks. Both have a simple visual interface and ‘drag and drop’ navigation.
  • Remember the Milk: accessible to-do lists and reminders with the added benefit of allowing users to write their own code using MilkScript.
  • Monday: can assist with a whole range of personal time and HR management tasks and promises users will be able to make ‘informed data-driven decisions’ as a result. It’s popular but it can be pricey, so this app works best when you have buy-in from the rest of your team and you know it’ll be put to good use.
  • Clockify: a time-tracking tool for individuals and teams, providing insights and reports. It’s free for an unlimited number of users, which is handy if you’re unsure of the idea of implementing time-tracking tools, and want to try-before-you-buy (many companies opt for more established premium services).
  • Timetastic: an app for booking and managing annual leave requests. This can also help avoid holiday clashes and help teams and managers plan for other colleagues’ time off.

Last but not least, we’d recommend Insight Timer. This is not marketed as a time management tool and has nothing to do with scheduling office tasks. However, meditation apps like this one can help users integrate periods of relaxation and rest into their days – which are pretty important for colleagues in the office during August and for workers trying to switch off on holiday!

Appdrawn Team | Updated 3rd August 2023

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