Success with Skype: Confronting the Monster in the Mirror

During my "Making the Right Choices with Skype for Business" session at Enterprise Connect 2017, I talked about monsters: Godzilla, vampires, werewolves, Alien, the blob.

I find Godzilla especially interesting and relevant. Per Shōgo Tomiyama, who has produced more than 15 Godzilla movies since 1989, Godzilla is neither good nor bad. He will fight alongside humans against a common enemy, but will turn against human allies on a whim. Sometimes Skype for Business feels a lot like Godzilla, abruptly turning against you.

However, more often the most insidious monster is the "monster in the mirror." It is not Skype for Business turning against you à la Godzilla, but rather a case of you working against yourself... a Dr. Jekyll and Mr. (Mrs.) Hyde story.

You may be the lead cheerleader for Skype for Business in your organization. You may have done an exceptional job following best practices regarding architecture and design. Yet, many organizations stumble, trip, or plunge headfirst off a cliff when it comes to effective implementation and ongoing operations. In far too many cases, when IT leaders wake up and look in the mirror, they come face to face with the primary source of their Skype for Business issues.

In my experience, well-intentioned "Dr. Jekyll" leaders transform into problem-inducing "Mr. (or Mrs.) Hyde" characters in five common ways. They:

1. Rush to get a UC project done before establishing clear success criteria

Of late, businesses have been prioritizing speed and agility as the most important project attributes. "Fail fast" is a common mantra associated with startups. Notwithstanding this, knowing where you are going is important before you start running. Failing fast with Skype for Business often dooms your organization to simply failing -- finito!

To be successful in a UC project or your IT career, you need clear, defined, and documented objectives before starting a project.

2. Agree to unrealistic dates (or other parameters)

You can pay me now or pay me later. Sometimes paying late is smart, especially in today's climate of low interest rates. Sometimes pretending to commit to unrealistic completion dates imposed by a "top down" autocratic boss is smart... fire me now or fire me later.

However, discussing unrealistic timelines, resourcing, or budgeting early in a project increases the chance of success for most teams. As difficult as these conversations may be, you'll find far more mitigation options available early in a project lifecycle. Sometimes having an engaged external party convey problematic messages can foster positive discussion without negative career implications.

3. Fail to practice strong project management

All UC projects are complicated. As such, practicing strong project management greatly increases your chance of success. Specifically, this means:

• Building a project plan with clear tasks (everyone understands the output/deliverable), estimates based on effort (versus elapsed time), and responsibilities assigned to a single person (just because someone is responsible to ensure a task is completed does not mean she/he is the only person working on the task! Putting no name or group as "responsible" generally ensures no one completes the task)
• Meeting weekly to discuss status, clearly tracking and documenting progress and obstacles
• Adjusting target completion dates when required, and documenting the reason for changes
• Encouraging and soliciting team input. The objective is to know about any obstacles or potential risks as early as possible in the project

4. Believe technical enthusiasm can make up for experience

Project leaders should promote, reward, and cultivate enthusiasm. Yet enthusiasm alone is not going to deliver a successful Skype for Business implementation. You need experience, at least some people on the team who have done this before.

It's great that Exchange engineers want to become UC experts. I applaud traditional Cisco, Avaya, or Nortel telephony experts who want to apply their expertise to Skype for Business. But this is not enough.

5. Focus on architecture, engineering, and implementation, but don't establish ongoing operations and management processes

Success with Skype for Business is about operating a solution that provides reliable, quality communication and collaboration services that meet the needs of your end users while delivering high levels of satisfaction.

Unless you totally screw up, the duration of the operations phase of your project will, and should, greatly exceed the architecture, engineering, and implementation phases. And yet, most organizations focus on the initial project phases. Architecture has technical sex appeal. Operational process, while a much greater predictor of long-term success, is seen as superfluous and optional -- something we may get around to documenting after we get the "important" implementation done.

If you do not have a clear, documented, resourced operational process by the time you migrate the first user to your Skype for Business environment, then you have transformed into Mr. Hyde.

The sun will come out tomorrow (optimism via Annie the Musical). And when it does, take a good hard look in the mirror and ask yourself these questions:

1. Does my Skype for Business project have clear, documented, measurable objectives?
2. How confident am I, and the key team members, that we will deliver by the target completion date? (Thinking in percentages works well: 100%, 80%, 50%, less than 50%?)
3. Do we have an accurate project plan? Are we holding weekly status reports with documented meeting minutes? Are we updating the original project plan as things progress?
4. Have some of the team members previously implemented Skype for Business (or Lync)?
5. Have you documented the daily, weekly, and monthly operational processes, and do you have the staff to execute on them?

Skype for Business is not perfect. Maybe the product is the problem. Or, maybe the problem is the well-intentioned face staring back at you in the mirror.

I spend my time helping organizations and IT teams succeed implementing communication and collaboration systems, most often Skype for Business, and I am committed to helping you succeed. If you have specific questions please comment below, send me a tweet @kkieller, or message me on LinkedIn.