Every now and then I do an overhaul of the devices and software I use for organization and communication (computer, smart phone, even moleskin, etc.).  I recently went through the very high-stress task of transferring all my contacts and calendars to sync on the Google cloud and upgraded from Outlook to Thunderbird with the Zindus add-on for my address book. Despite backing everything up before making the transfer, there was still a near-paralyzing level of anxiety when it came time to delete all my contacts and appointments from the phone and start syncing with the cloud.  ”What if in that very second my computer crashes, hard-drive burns up, and Google dies loosing all 1,000+ names?”  Well don’t worry, the sync was seamless and my digital valuables are now safely on the cloud and my life is tad bit (actually significantly) neater.  I did the same for my aunt who, despite her technophobia, was somehow coordinating AOL, Hotmail, Gmail, Random-iPhone-contacts and Outlook.  She is equally happy now and the frequency of her panicked phone calls has slowed; “right click, now breathe, click properties, now breathe again…”

Suffice to say that while Google (Sync)/iPhone/Thunderbird may not be the most streamlined setup, it works a whole lot better than the physical USB tethering I was doing to Outlook every week. More importantly, though, I watched yet another Microsoft icon bite the dust on my taskbar. Outlook has now been demoted to the Windows Recycling Bin graveyard to reunite with its comrades Microsoft Internet Explorer (swapped for Firefox and recently Chrome) and Windows Media Player (swapped for iTunes and VLC Media Player).  The others likely soon to fall include Word (Google Docs is already making a bid), PowerPoint (Prezi or something like CognitiveMedia), and Excel (Google SpreadSheets, though may be a while). It all begs the question, what happened.

A wealth of opinions already exist on the web analyzing how the former pioneer continues to “miss the boat” these days, so rather than try to formulate a worthwhile thesis on the matter, there are some fundamental takeaways to highlight that are of value to any entrepreneur trying to build a business, or keep one fresh:

1. Avoid complacency at all cost; sharks that stop swimming die (supposedly). This rule is as relevant to businesses with products in the market as it is to start-ups bringing new ones to market. Even at the seed stage, it is easy to get comfortable with your business model, your product development timeline, your target customers, your brand and marketing materials, etc. However all of the above change and grow daily as new channels for distribution are made available by other upcoming start-ups and new trends modify what people are interested in purchasing and consuming. Leverage these assets to your benefit and stay relevant. The heart of your business, that crazy idea that got you this far along in the first place, will guide the overarching direction of your business but it is essential to not get lazy and one-dimensional with how you implement in a dynamic environment.

2. As you innovate, don’t wait too long to release you latest version (of the whatever you’re working on), even if all the bells and whistles are not perfectly tied on.  So long as the basic functionality that addresses the customer’s real problem is there, they will use it, even if it’s not perfect.  Moving the idea from your head into tangible form is an unending process of improvement.  We always seem to wake up from great dreams just before they finish, yet the reality is that there really is no finish and the dreams would going on in perpetuity.  What you are creating has the same elusive ”end” that is never quite what you want or expect it to be, so don’t waste time looking for answers in a perfect ending (and delay your product launch) when there is so much to learn and gain by making a more basic version available to your customers now. There is time to refine and improve your product/service (and feedback from your users will help tremendously), but if you never make it available in the first place, then no one will be using it and they’ll probably look for something to fill the void that you originally identified. Here is great editorial that studies this process.

3.  Finally, know the market and customer you’re focusing on intimately. Founders especially, meet with your customers one-on-one and see how they use the product/sevice.  Don’t hire or get someone to do this dirty work for you, because unless you hear for yourself what is and isn’t useful to the customer, you will never believe the criticism and ultimately waste a lot of time stubbornly pushing through work that is unnecessary.  Don’t expect to know exactly what customers want, and respond tactfully to the things they find annoying, non-intuitive, cumbersome, etc. Professional cyclists spend hundreds of hours working with their support team to make the bike “disappear beneath” the rider and enable him to focus on what is more important.  So think about getting to know your customer (the rider) so well, that the product/service seamlessly integrates with their needs.

On that note, maybe there is hope yet for future innovation at Microsoft as they hit the nail (and their customer) right on the head with their latest ad campaign,