But, yeah – Microsoft Outlook is hard

I recently told my wife that I thought Microsoft Outlook was hard to use, or complicated, or something like that.

We went on to talk about some other things but a few minutes later she asked me what I meant. I realized I had done what I often do and made a statement of opinion-fact that sure could use some explanation. Of course, everybody does that all the time – pretty much everything you hear in a day is someone’s opinion about something (though most of it is presented either as fact or, worse, as policy). We don’t really acknowledge that “fact” very often. 🙂

I tried to figure out what I meant by saying Outlook is “hard.”

I’ve used Outlook for so many years that I can’t really remember what it was like to originally learn it. I do remember when I first started using Outlook 2010 at the office, I found the user interface overly complicated – I’m still getting used to Microsoft’s new ribbon strategy in its Office product line and I find that every time I look for a menu option that is not yet part of my muscle memory, I have to search around longer than necessary just to get my bearings on the UI layout.

That is part of what makes it “hard” – it doesn’t have a very friendly user interface, at least not in certain views (for example, composing an email gives a much more limited and simpler view – not all views of a software product are equal).

There’s another aspect of the “hard software” problem that was actually more on my mind, though, when I made that glib statement to my wife.

I’ve been thinking a lot lately about this new breed of software (mostly web apps) where there’s an intense focus on making the default options excellent, so that you don’t have to change them often. This helps a lot of things because it means you don’t have to go searching around in the user interface very often.

Closely related to this is the idea of software behaving, by default, in the ways that are most useful. I touched on this in a previous post where I grumped about Outlook’s inability to let you set multiple reminders for the same Calendar event.

As it turns out, that little grump post is the most popular post I’ve ever written on this blog, and the post itself doesn’t even provide anything useful – it just lodges my complaint against Outlook for lacking a feature which Gmail has and makes dirt-simple. I’ve felt bad over the years imagining all the people who do a Google search and land on that useless page thinking that they might be about to find a solution for this missing feature. Oh well.

In Outlook, solving the “hard software” problem is hard, of course – the product has been around for so long and is by now such a complex monster of a product that trying to pick the best defaults for everyone is simply impossible, and would ruin the software for as many people as it helped. Instead, it’s now in that realm of mature software that is cursed to forever live under the burden of its own success. Gmail will get there someday, too. Even Twitter will.

But I can still complain about it. Because today there are options. In fact, there have always been options to the old-farty software that had long-ago grown too complex to be accessible to newbies. In the past, this might have taken the form of a little command line utility or a macro that was written to solve a very specific and limited problem. There has always been a need and a market for small custom software to solve isolated problems. Software such as Outlook fills a different need – it tries to be the One Answer for everything related to personal productivity.

And you can spend your whole techno-life only using those One Answer solutions, if you want, and you don’t mind spending a lot of time reading manuals and watching webcasts. And of course if you’ve been using that software for eons then the learning curve on new versions is usually small. The software can live on because it’s got a dedicated community of users who, for better or for worse, are willing to put up with the warts because it’s easier than moving to a new piece of software, or because it would be too hard to work collaboratively with others if they weren’t using the same system.

The tech world will always be this way.

But the Techno-verse is also big. And as Google once pointed out, when the pie gets bigger then each slice of the pie also gets bigger, and there’s enough pie per slice to go around to satisfy more and more people. It doesn’t matter if some slices of the pie are ones you don’t want – you can spend your whole life eating from another slice.

And that’s what I was trying to get through to my wife. I’m an innovator, as far as software is concerned. I’m always looking for a new and more helpful way to look at a problem that software is solving.

There’s a reason I use Outlook at the office – it’s because it is required by policy and nobody would talk to me if I didn’t. And I do enjoy using it because I’ve gotten pretty damned good at using it over the years. I have a lot of respect for its power.

But there’s also a reason I would never consider using it on a personal level or as a freelance technologist who isn’t tied to any particular office environment. It’s because it’s not the best tool for communicating and organizing communication.

I’m not talking just about email, I’m talking about all the various aspects of personal data management and collaborative communication that we need to use in our work.

Some of that management and collaboration happens via email (the World’s second favorite database, right after Excel :-)).

But if you are open to it then most of that management and collaboration can happen instead via all the various new-fangled collaboration tools (e.g., Basecamp, Remember the Milk, Google Drive, Evernote) that work better in their little niche areas than Outlook tries to work across the whole monstrosity of our personal data.


Tools should support great and flexible work

I once wrote about some of the feaures I want to see in some of the traditional business software.

For example, a few things I would add to Microsoft Outlook, which is an excellent tool in so many ways but which has some tough hurdles to overcome if you truly think of your work as a fluid, flexible utilization of tools that should conform to your own work style.

One example was that I’d like to see Outlook’s Calendar give me the option of adding multiple reminders, similar to what Google Calendar allows. This is a great feature to have because it means that when an actionable item comes in, I can turn it into a date-based Calendar item, and do the mental processing a single time about when I need to think about it again by setting myself all the various reminders I need all at once. Sure, you can also do this by parsing the actionable item into multiple Appointments, Tasks, or other sorts of digital work items, but why not just give the original Calendar a little more flexibility to set multiple reminders?

Another example of a feature I’d love to see in Outlook is tagging. Yes, Outlook has categories. But if you’ve ever used a tool that has true tagging (and implements it with minimal friction), then you know that Outlook’s categories are simply something very different. I will write about my great love for tagging in all tools more in-depth elsewhere, but suffice it to say for now that the only way to get close to great tagging in Outlook is to use an add-on called Taglocity. But unfortunately, the company that once made Taglocity appears to no longer exist, and the tool appears to have died.

Gmail has tagging, and I have to say that Google’s tools (most notably the now-defunct Google Notebook) were what introduced me to the concept of tagging in the first place. In Gmail, tags are called “Labels” but they aren’t quite as quick and easy to use as the implementation that Taglocity installed into Outlook.

Old tools die hard

In general, the problem with most of the typical tools that we all use at work – the business and office software – is that it’s been around for so long that even when it gets great new features, there are still so many burdens and ties to the software’s long history that the great new feature has:

  • More friction than it needs to have
  • Less functionality than it should have

And as a result, many of us (and the companies we work for) continue to spend a lot of money to both buy and provide technical support for software tools that only partly meets our needs.

Are we really still wasting human resources?

A big percentage of the human resources that could be going into growing and causing your company to thrive is instead spent on simply learning and managing how to bridge the gap between what your people need / want to do, and what the tools you give them allow them to do.

It’s a hard cycle to break, but it’s something I’ll be continuing to explore in-depth as we all move toward finding our path to the new workplace where we can work most effectively without unnecessary limits.