Microsoft just announced a chat-based enterprise collaboration tool. It’s called Microsoft Teams, and the implications are deeper than one might imagine, at first blush. Whether those implications realize themselves or not depends (of course) on how enthusiastically the market embraces this SaaS.

One’s first assumption might be that Microsoft Teams is a “Slack killer”, and this might certainly be the case, if Microsoft were to have a fantastic track record of imaginative and impactful marketing. It does not. It’s unlikely that Microsoft Teams will have much initial impact on Slack user numbers, given the fierce loyalty of Slack users to the brand. The same applies (to lesser extents) to Basecamp, Smartsheet, Asana, Podio, Trello, Samepage, Quip, Projectplace, Yalla, and, and, and…

Each of these collaboration platforms provides an experience with which its users are – for the most part – quite comfortable. You don’t often see an Evernote user of longstanding jump over to OneNote, or vice versa.

So what’s the big deal with Microsoft Teams? There are two big deals, in fact.

First, if the solution is well-thought and intuitive, and if it integrates with Office 365 in as fluid and seamless a fashion as intended, it will secure those enterprise users of the Office Suite, and prevent their adoption of the other aforementioned “standalone” collaboration toolsets. Microsoft will be strengthening its enterprise software ecosystem, not by preventing escape, but by making the notion of staying more attractive. More of a golden cage, than a walled garden.

The second implication, however, is more dramatic: Microsoft was almost going to acquire Slack earlier this year – a move I did not quite understand, given both the $8 Billion price tag and Microsoft’s existing holdings of SharePoint, Yammer, and Skype, to mention just a few. Opting to withdraw from the purchase has made a silent statement that will, I believe, reverberate through the already flawed VC world. For the past years, convention and hubris have driven the notion that companies will purchase and absorb promising or threatening products and solutions, as a matter of course and self-preservation. On balance, this has not proven as cost-effective or innovative as many have pretended. Whether intentionally or not, Microsoft, by opting to pursue internal development and release of their own Swiss Army collaboration tool, has communicated that their IP, combined with internal dev talent, are sufficiently robust to offer solutions that do not require Slack.

Admittedly, this remains a risk. Slack users tend to comprise small businesses that “graduate” toward Google suites of product offerings, rather than the traditionally heftier Microsoft suites. However, the Microsoft brand (somewhat inadvertently, I feel) has been ceding its Goliath mantle to Apple and Google, of late, and many small businesses with which I work are less intimidated by the brand than they once were.

If Microsoft manages to position their Teams offering properly, this could be the moment when all the vaporware startups out there realize they are standing in the street naked, and need to actually develop something unique and truly valuable (read: unrealizable by others without great investment), or risk being eclipsed by developers who have finally wised up to the fact that a snappy presentation does not a mighty valuation make, even if it’s in PowerPoint.

I love productivity and efficiency. I preach it, I evangelize on its behalf. I campaign for its adoption across every enterprise and initiative that seeks my advice and counsel. There is a line between Utility and Assistance, however, which cannot yet be crossed – no matter how many startups try valiantly to ignore the prevailing reality. Utility is a largely passive operation, which must be activated and managed by the user to fulfill its potential. It’s a useful tool such as OneNote or Wunderlist. Assistance is an active function that manifests itself independently, and must anticipate and manage multifarious unqualified scenarios to be truly effective.

The list of Virtual Assistant startups grows daily. It’s the present fad. For every variation that promises to reinvent the VA space yet flames out (Zirtual), another two replace it with air-dancing artificial plums (e.g.: Genee, The new holy grail of tech startups is AI virtual assistant apps. For the next 6 months or so, all the early adopters will fall over each other, just to be able to claim they had “Amy”, “Genee”, “Cortana”, “Siri 2.0”, et al, before everyone else. What you won’t hear much about is the fact that all these AI solutions fall far short of useful. Virtual assistants have existed for years, and work with varying degrees of success. Productivity apps have been around for a long time as well, exhibiting capricious achievement in their own right (yet but few pretentions to actually *replace* staff). Zirtual did not fail to provide the services they promised to clients. The company failed because, like so many startups today, it was encouraged to grow too fast, in an unsustainable quest for lightning ROI. The likely result was an inability to meet financial covenants, founders and investors working at cross-purposes, and lack of transparency between stakeholders seeking markedly different objectives. Whoever takes over the operations, such as they are after this negative brand impact, will assuredly restructure for more realistic growth metrics, if any future is to be realized for the employees and their clients.

I have no doubt that after various highly overvalued iterations churn through talented developers, employees, and investors, the chasm between AI VA concept and reality will begin to narrow, such that solutions that provide useful value finally establish themselves on semi-solid footing, and scale sustainably. Until then, you will have to contend with one offering that has access to your calendar, but not the other party’s calendar; another unable to process plain language text or speech; and probably none that take “drive time”, “weather”, or “distance” in to consideration when booking meetings back-to-back, not to mention the probability of client A being notoriously late, or client B correspondingly early, by habit. In short, none will be able to do what a proficient human assistant can do.


Sometime in the future, our human administrators may well be replaced by competent digital, or even robotic, facsimiles. However, the truest measure of a great assistant is their ability to adapt to and accommodate the unexpected scenarios, and no algorithm can proactively absorb this aspect of the job, yet. Artificial Intelligence learns and improves with use, but most companies and executives who require assistants cannot afford to patiently wade through failure, in an iterative quest for efficiency and reliability. If the day comes that Artificial Intelligence Apps crowdsource their refinements, machine learning will accelerate exponentially, and I’m frankly not sure how comfortable I’d be with an employee who mathematically assures me they know what’s best for me, simply because they know more than me.