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The difference between ‘I love you’ and ‘I’m in love with you’ is only a few words but they can mean very different things. Just a couple of words, a very different situation or conversation. Words have clout, they can make you smile, cry, panic, agree, disagree, sign up, unsubscribe, follow or buy and those are just a few of the ways they affect us.

Words also have the ability to influence how you sound. Will your tone be informal, sympathetic, corporate, simple or complicated. Will you call people customers, users, clients, partners? Do you deal with patients, sufferers, victims or those in need? Do you want people to register, join or sign up? Each has its own tone and connotations.

But only when I started using a 1920's Underwood typewriter to send letters did I start to focus on each individual word I wrote and with that came the reaffirmation that every word counts.

As I typed, I was so distracted by the hypnotic click click click of the vintage keys, soon followed by the delightful high pitched ping of the bell as the carriage reached the end of the line, that I hadn't quite noticed the number of mistakes in what I had written.

We're so used to being able to hit the delete key and wipe our mistakes from existence without anyone knowing. We can remove that word here or swap those words over there. Heck, we can make the whole thing disappear and come back with the click of a button.

On a typewriter the mistakes aren't so temporary. Correction tape helps but then it doesn't look perfect, the way we like things to be so the facade of our abilities doesn't seem cracked.

I had written 600 words of an article on my typewriter earlier this year and then it happened. The clicking held me in its hypnotic audible joy and I pressed the wrong key.

I tore the paper out of the typewriter and started again. 300 words later I made a different mistake. I went back a space and typed over the wrong letter with the right one but now I had an illegible character that stood out like a sore thumb.

Tear; load, align, start again. It was the fifth attempt that got me from the first to the last word of the article without a mistake. On the third the carriage shifted so one word was higher than the others. On the fourth the H key stuck and when I put it back in place I knocked the ink ribbon and the perfectly formed words were blemished with a smudge. Thankfully the click click ping as the words unfolded kept me calm and optimistic.

I'm fairly efficient at using a typewriter now. The clicks are quicker, like a piano player climbing through the ranks of different grades and ability. The mistakes are less frequent too but the feeling of frustration when you notice one never wanes or becomes less frustrating.

It takes every ounce of my concentration when I use my typewriter. I have to focus on every letter and therefore every word as I press one letter at a time with complete care. That process has made me a better writer. I now know where I can be more succinct with my writing and how I can be more stringent with my self editing process. I've realised that whether writing for the web, a brochure, a tweet, a call to action or a thank you note, every word counts and we need to take care in choosing them wisely.

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One year ago

“You’re all doomed.”

When my wife introduced me to the world of opera a few years ago, I assumed it’d be a peek into high culture, not a lesson in keeping technology projects on track. But as we sat through Les Troyens — The Trojans — I watched a familiar story unfold.

Cassandra is a familiar presence in Greek mythology. She can see the future, but spurning Apollo’s amorous advances earns her a curse: no matter how accurate her prophecies are, no one ever listens to her. Les Troyens finds her in the city of Troy in the final days of its brutal war with Greece. When the Greek soldiers surrounding the city mysteriously disappear, leaving a gigantic wooden horse behind, all of Troy celebrates.

Obviously, the end of a decade-long siege means that it’s time to break out the champagne! Cassandra warns them that it’s a deadly trap, announcing that they’ll all be killed... but of course, no one listens. They’re too busy feasting and admiring their new monument. Their Trojan Horse.

Spoiler warning, folks: the horse is full of Greek soldiers.

Stop me if you’ve heard this before

If you’ve ever been the skeptical person in the room during a new project’s first, joyous planning session, you probably know how Cassandra felt. You’re seeing bad omens, and your spidey-senses are tingling — but everyone else is smiling and saying, “Let’s crush this!”

The horse is full of crazy deadlines, and no one will listen.

Getting stuck in the role of the naysayer is never fun, especially in the very early stages of a project. Often, the warning signs you’re picking up are vague, and easy to dismiss.  At those moments, it’s easy to lean back and turn the concerns into Cover-Your-Ass disclaimers. “Perhaps,” I sometimes think, “tacking an ‘assumptions’ section onto the project plan will shield me from the consequences of a disaster I fear is inevitable...”

As tempting as that can be, I try to remember Cassandra’s fate. She was right when she warned Troy that it was doomed, but she lived there, too. When disaster struck, she perished along with the rest of the city. If we really care about the projects we work on and the people we work with, there’s no joy in saying “I told you so.” The entire team suffers, and we’re right there with them.

Dodging Cassandra’s curse

In a mature team under ideal circumstances, gut checks can be enough to get a decision-maker’s attention, but there are always times when something more concrete is necessary. How can we overcome Cassandra’s curse, and turn our vague portents of doom into clear, unambiguous advice? There’s no magic bullet, but a handful of basic techniques can improve our chances.

  1. Catalog the uncertainty. Is there a hard deadline, but a fuzzy and ill-defined list of required features? Is unfamiliar or immature technology required to make it happen? Does the team lack an unambiguous set of success criteria? Make a list, and map out those scary shadows. Sometimes, there are answers and they’ll assuage your fears. When there aren’t, though, it can help decision-makers realize they need to head back to the drawing board.

  2. Compare the work to similar tasks and projects. If the early estimates for a large project feel too optimistic, it can be difficult to explain why. Whenever possible, find examples of similar projects or tasks from the past. Show how long they took, and if the estimates for those projects shared the same early optimism, point it out. As unpleasant as it is to keep time sheets and logs, they can be critical ammunition in the fight for sanity.

  3. Identify deep dependencies, in technology and teams. Are you building a mobile app that relies on a third-party library... which relies on a fourth-party service... which relies on a fifth-party startup? Does one department control the infrastructure your project will need to launch, while a second is responsible for content and a third handles the development? The more external dependencies a project has, and the deeper those chains go, the more risk there is. There’s no way to avoid reliance on outside teams or tech, but mapping them out makes the risks clear.

  4. Identify fuzzy authority roles. Few things are as depressing as ironing out a project’s requirements, building it to spec, and preparing for launch  only to discover that your client wasn’t really in charge. The last-minute emergence of a VP with different aesthetic tastes, or ongoing conflict between two or three equal stakeholders, can sabotage an otherwise well-run project. If you hear talk of “running the plan past a few other people” before it can be approved, or it’s unclear who’s in charge of key decisions, don’t be shy. Get a list of people with veto power and ensure there’s a single buck-stops-here person for key decisions, or wave a red flag. 

  5. Time-box and prototype. Especially when new or unfamiliar technology is involved, accurately judging risks and sketching out timelines can be impossible. Carving out a small chunk of time for a prototype is critical. If the exercise reveals unanticipated challenges or problems, you have concrete evidence to offer rather than vague concerns.

Towards a happy ending

The goal of these techniques is twofold. First, the work that goes into them can reveal solutions to the problems and clear answers to the troubling questions. Obviously, that’s the best outcome: successfully routing around danger rather than grumbling about it. If that isn’t possible, though, carefully articulating the concerns can make the pitfalls clear and unambiguous.

It’s an approach that goes beyond avoiding blame and puts important information in the hands of people who need it. It doesn’t always work, and we can’t always avoid the dangers, but it’s far better than the cynical alternative. 

Now, if you’ll excuse me, I have to look into the next trip to the opera. This time? I think we’ll try a comedy...

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