After 6 months at Moonshot-Internet, I figured it was time to share my thoughts on my new job and the life of a CTO in a small start-up. And as it turns out a CTO, like a cat, has many lives¹. So many lives, in fact, that the original story grew too big for one post – so stay tuned for follow-ups.

All in a day’s work

Moonshot-Internet is a small company, and its IT department is smaller still. Until last month, it was just our front-end developer and I. (Since then, the arrival of a contractor has bumped up the team size by a mighty 50%.) IT-related topics, on the other hand, are many and varied, and they all have a tendency to land in my lap – that is, after all, what I’m paid for. This means that on any given day I’ll wear some or all of the following hats:

• Enterprise architect
• Full-stack developer
• QA tester
• Web designer
• Project manager
• Security officer
• Sysadmin
• Headhunter
• Procurement expert
• Administrative assistant
• Help desk
• IT poster boy

Most of these tasks are, of course, part of the job description.

Designing and building our IT platform? Yep, that sounds like CTO work. Hiring and managing the team? Check. Making sure everything runs and is secure… We’re getting into COO territory but still, perfectly normal.

Some tasks, such as procurement and administrative duties, are necessary to keep the “real” work moving. They’re like finishing your vegetables before dessert: the bland and slightly demoralizing prerequisite to the fun parts.

And, of course, perpetual help desk duty is the unfortunate side-effect of being the most computer-literate person in the office. Troubleshooting WiFi connection issues, getting the scanner to talk to the shared drive, figuring out why a laptop is behaving strangely (long story short: 2 USB mice plugged in)… All in a day’s work.

Don’t get me wrong: I love the variety of the job, and being able to have a hands-on approach to so many topics. Being considered an IT guru by my coworkers is nice too (guys, if you’re reading this: sysadmin appreciation day is July 28th). But juggling between so many roles also raises a few challenges.

Brain overload

One issue is the sheer number of things to keep in mind. With all the different facets of the job I just described, there comes an equally long list of tasks to schedule, good ideas to implement, features to keep for later, bad ideas to learn from, and generally things to remember.

I don’t have a great short-term memory so I often forget things. Even worse, I’ll sometimes forget I’ve forgotten an idea: even the nagging feeling in the back of my mind that I’m supposed to remember something disappears. And when there are so many topics to juggle, it’s very easy to drop one.

Of course the solution, which has been known to humankind for 5000 years, is to write things down before you forget them. I now use a mind map to keep track of everything.

You’ll notice that it’s pretty large, and this version is only about 75% complete – I’m not lying about all the things to remember. The second point to note is that although the map is very broad, it’s not very deep. I mostly use this mind map to keep track of high-level topics; the details belong in specific, proper documents (which I will definitely write one day, promise). Finally, although it may not be apparent from the picture above, it is also very structured: topics and subtopics are readily apparent and icons help me track ideas, tasks, incomplete nodes and so on. A mind map is also easy to navigate and update, so there’s no extra effort involved in keeping it organized. All in all, switching to the mind map format has been a tremendous improvement over my previous habit of taking notes on loose leaves of paper or post-it notes and strewing them all over my desk, or even worse trusting my memory. (I still do this, of course, but every now and then I go through all these notes and put them where they belong: either in the mind map or in the trash.)

However, knowing what to do is only half the battle: then comes the job of actually doing it, and this means prioritization and schedule management. Speaking of which, I’ve already spent far too long on this post (and you’ve spent long enough reading it ;) so this will wait for a future article. Stay posted!

“Many hats” image credit : stolen from ave45.com

• Management