Slack + Skype: The fine line between convenience and coercion

Bring-your-own technology doesn't work so well in collaboration or when forced on users

Slack + Skype: The fine line between convenience and coercion

Within hours of Microsoft announcing a beta integration of its Skype conferencing service with the Slack collaboration platform two weeks ago, I got impassioned requests from some users to enable that integration in the Slack service used by my parent company's editors and writers.

The integration lets you initiate a Skype conference from within a Slack conversation for the conversation participants, when the textual discussion needs to move to voice, with all the communications cues that provides.

That sounds great, and I'm sure it is. But this integration also exposed, at least in our corporate environment, several risks and dangers. It made us think long and hard about when "bring your own" (Skype account, in this case) crosses the line into "force employees to use their own resources to do their job."

As longtime readers know, I'm a big fan of the BYO approach to IT, but only for optional activities or the employee's convenience, like checking email from a personal PC or smartphone when away from the desk.

We ultimately decided not to integrate Skype into Slack. After all, we have in place an old-fashioned telephone conferencing dial-in system that doesn't require special equipment, that everyone already knows how to use, and for which sharing the dial-in link within Slack is actually faster than initiating a Skype conference from within Slack.

Other companies might come to different conclusions, but all companies should go through an analysis similar to ours.

BYO is different when it comes to collaboration

When you bring your own technology to do your job, it is -- or should be -- a matter of personal choice, not a job requirement. But collaboration systems require a network of users to function, so if one person brings in his or her own collaboration tool, the rest of the team's members have to decide whether to adopt the same tool or to not participate. You can quickly get separate groups within your teams based on those personal platform preferences -- undermining your collaboration.

We decided that was unacceptable. We didn't want to exclude the people who didn't have and didn't want to set up a personal Skype account to use for business. (The integration with Slack is only for the personal edition, not the corporate Skype for Business version that our company provides, though hardly anyone uses it because it's so bad. Had that business Skype integration been available, most of these queries would be avoided, leaving us only the "does this do the job well?" question.)

When we adopted Slack, we provided a corporate login for everyone and mandated that Slack be used by everyone -- to ensure the collaboration was open to all. And we ensured it was available on all our corporate-issued devices. Although we let people use it on personal devices as well, that's their choice, not our mandate.

Our analysis was that adopting the Skype integration into Slack crossed several redlines, moving out of BYO territory into an uncomfortable world where we imposed on employees' personal technology. When you get into that territory, you open up many unpleasant cans of BYO worms around data ownership, security, wages (for hourly folks), and reimbursements.

"Forced BYO" shouldn't impose costs on employees

An infamous court ruling a few years ago in California says when a company requires employees to use their own technology -- what I called "forced BYO" -- it must bear at least part of that cost. That's a fair principle, one that the courts have not overturned and one we follow.

Though Skype is free, it requires that users set up a Microsoft account (they can't use their corporate Office 365 credentials, unfortunately), which is a nonmonetary cost and thus a burden imposed on them.

Plus, Skype requires the use of a headset on a computer or the use of data on a smartphone. So do we issue everyone a headset for their computers, or at least those for the (majority) of our people who work in open workspaces? Do we subsidize everyone's personal data plan to pay for the Skype VoIP data usage? What about employees without a compatible smartphone? We don't buy phones for staff, so that'd impose a hardware cost on them.

This is where for us, the technical integration of Skype into our work environment got messy: in the supporting technology. Workplaces that gave up the traditional PBX and have already switched to computer-based telephony would have been ready for Skype, but we're not one of those workplaces. And the extra management, operations, and budget don't seem worth it for us.

Compliance matters, even for a BYO-friendly workplace

The publishing business is free of a lot of the regulations and legal fears that terrorize so many companies into straitjacket policies around work tools. BYO has long been acceptable at our company, as long as basic principles are honored like keeping personal and work data separate (and on their respective repositories), allowing basic policy management of personal devices connected to corporate systems, and ensuring appropriate security levels.

In other words, compliance still matters in a BYO-friendly world.

In the case of Skype integration into Slack, both our CIO and I were unhappy about the limitation of using personal Skype accounts. Not only is it inappropriate to expect employees to use or set up a personal Skype account for business needs, it's a potential risk to conduct corporate communications routinely over a consumer service that we have no insight to, much less management of.

We could insist that employees not use a personal Skype account but instead set up a new one solely for corporate use. But of course we couldn't enforce such rule, nor even monitor compliance. Imposing rules you can't actually enforce is a bad idea, as it opens up all your rules for question and even avoidance.

Given the issues with Skype for Business (no doubt why it's not being integrated with Slack), Microsoft and/or Slack should have worked out a way to create corporate-manageable personal Skype accounts for Slack's business users. As it stands now, even if the other issues we encountered were resolved, this use of unmanageable personal Skype accounts would have been the no-go rationale.

It doesn't have to be this way. Vendors over the last half decade have made great stride in supporting responsible BYO. iOS and now Android have strong controls and third-party tools for work/personal segregation that don't hinder employees' legitimate usage. Most cloud storage services offer business and personal versions that can coexist with each other and with other providers. Communications apps are increasingly using passwords and fingerprint readers to secure business content.

Sure, some IT folks still pine for the days of total control (which they never had, but they won't admit that). But the fact is that BYO is a manageable risk, with real payoff in flexibility and productivity -- as long as that risk is, in fact, managed.

I'm glad Slack doesn't cater to the unreasonable control demands of some IT folks. But I wish Slack did a better job of satisfying legitimate IT needs. And I wish it would stop some clearly bad behavior: For example, when an employee tries to integrate a service like Skype themselves into a corporate Slack account (let me tell you, employees try!), the Slack system's response says to contact an admin or to set up a new Slack account outside of the company admin's control -- not cool.

Like many Silicon Valley tech providers, Slack doesn't always understand real business, so its designers don't think through the legitimate concerns a business might have. Never mind that a tool like Slack is aimed at businesses, not merely high-school sports teams, brewing clubs, and codeathon participants.

But as I said at the beginning, the issues we worked through about the Slack-Skype integration are questions that go beyond any vendor or service. BYO is a great thing, but only when done right. It's unfortunately very easy to do it wrong.