Kevin Kieller
Kevin Kieller is a partner with enableUC, a company that helps measure, monitor and improve UC and collaboration usage and...
Read Full Bio >>

Kevin Kieller | July 13, 2017 |


Success with Skype: Confronting the Monster in the Mirror

Success with Skype: Confronting the Monster in the Mirror Here are five common ways an IT leader ends up becoming a primary source of monstrous Skype for Business issues.

Here are five common ways an IT leader ends up becoming a primary source of monstrous Skype for Business issues.

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.


October 24, 2018

With disparate workplaces and ever-expanding volumes of information to manage, the challenges for collaborating effectively are only intensifying. Many critical applications are not integrated, and

October 10, 2018

Businesses are growing across international borders quicker than ever, but scaling operations to follow suit can be a harder, longer process.

This webinar focuses on scaling your next-generat

September 26, 2018

Join Kevin Kieller, Microsoft UC&C expert, along with Ribbon Communications and Polycom, for an update on Microsoft Ignite, and a focus on critical things you need to know about your voice deployme

March 12, 2018
An effective E-911 implementation doesn't just happen; it takes a solid strategy. Tune in for tips from IT expert Irwin Lazar, of Nemertes Research.
March 9, 2018
IT consultant Steve Leaden lays out the whys and how-tos of getting the green light for your convergence strategy.
March 7, 2018
In advance of his speech tech tutorial at EC18, communications analyst Jon Arnold explores what voice means in a post-PBX world.
February 28, 2018
Voice engagement isn't about a simple phone call any longer, but rather a conversational experience that crosses from one channel to the next, as Daniel Hong, a VP and research director with Forrester....
February 16, 2018
What trends and technologies should you be up on for your contact center? Sheila McGee-Smith, Contact Center & Customer Experience track chair for Enterprise Connect 2018, gives us the lowdown.
February 9, 2018
Melanie Turek, VP of connected work research at Frost & Sullivan, walks us through key components -- and sticking points -- of customer-oriented digital transformation projects.
February 2, 2018
UC consultant Marty Parker has crunched lots of numbers evaluating UC options; tune in for what he's learned and tips for your own analysis.
January 26, 2018
Don't miss out on the fun! Organizer Alan Quayle shares details of his pre-Enterprise Connect hackathon, TADHack-mini '18, showcasing programmable communications.
December 20, 2017
Kevin Kieller, partner with enableUC, provides advice on how to move forward with your Skype for Business and Teams deployments.
December 20, 2017
Zeus Kerravala, principal analyst with ZK Research, shares his perspective on artificial intelligence and the future of team collaboration.
December 20, 2017
Delanda Coleman, Microsoft senior marketing manager, explains the Teams vision and shares use case examples.
November 30, 2017
With a ruling on the FCC's proposed order to dismantle the Open Internet Order expected this month, communications technology attorney Martha Buyer walks us through what's at stake.
October 23, 2017
Wondering which Office 365 collaboration tool to use when? Get quick pointers from CBT Nuggets instructor Simona Millham.
September 22, 2017
In this podcast, we explore the future of work with Robert Brown, AVP of the Cognizant Center for the Future of Work, who helps us answer the question, "What do we do when machines do everything?"
September 8, 2017
Greg Collins, a technology analyst and strategist with Exact Ventures, delivers a status report on 5G implementation plans and tells enterprises why they shouldn't wait to move ahead on potential use ....
August 25, 2017
Find out what business considerations are driving the SIP trunking market today, and learn a bit about how satisfied enterprises are with their providers. We talk with John Malone, president of The Ea....
August 16, 2017
World Vision U.S. is finding lots of goodness in RingCentral's cloud communications service, but as Randy Boyd, infrastructure architect at the global humanitarian nonprofit, tells us, he and his team....
August 11, 2017
Alicia Gee, director of unified communications at Sutter Physician Services, oversees the technical team supporting a 1,000-agent contact center running on Genesys PureConnect. She catches us up on th....
August 4, 2017
Andrew Prokop, communications evangelist with Arrow Systems Integration, has lately been working on integrating enterprise communications into Internet of Things ecosystems. He shares examples and off....
July 27, 2017
Industry watcher Elka Popova, a Frost & Sullivan program director, shares her perspective on this acquisition, discussing Mitel's market positioning, why the move makes sense, and more.
July 14, 2017
Lantre Barr, founder and CEO of Blacc Spot Media, urges any enterprise that's been on the fence about integrating real-time communications into business workflows to jump off and get started. Tune and....
June 28, 2017
Communications expert Tsahi Levent-Levi, author of the popular blog, keeps a running tally and comprehensive overview of communications platform-as-a-service offerings in his "Choosing a W....
June 9, 2017
If you think telecom expense management applies to nothing more than business phone lines, think again. Hyoun Park, founder and principal investigator with technology advisory Amalgam Insights, tells ....
June 2, 2017
Enterprises strategizing on mobility today, including for internal collaboration, don't have the luxury of learning as they go. Tony Rizzo, enterprise mobility specialist with Blue Hill Research, expl....
May 24, 2017
Mark Winther, head of IDC's global telecom consulting practice, gives us his take on how CPaaS providers evolve beyond the basic building blocks and address maturing enterprise needs.
May 18, 2017
Diane Myers, senior research director at IHS Markit, walks us through her 2017 UC-as-a-service report... and shares what might be to come in 2018.
April 28, 2017
Change isn't easy, but it is necessary. Tune in for advice and perspective from Zeus Kerravala, co-author of a "Digital Transformation for Dummies" special edition.
April 20, 2017
Robin Gareiss, president of Nemertes Research, shares insight gleaned from the firm's 12th annual UCC Total Cost of Operations study.
March 23, 2017
Tim Banting, of Current Analysis, gives us a peek into what the next three years will bring in advance of his Enterprise Connect session exploring the question: Will there be a new model for enterpris....
March 15, 2017
Andrew Prokop, communications evangelist with Arrow Systems Integration, discusses the evolving role of the all-important session border controller.
March 9, 2017
Organizer Alan Quayle gives us the lowdown on programmable communications and all you need to know about participating in this pre-Enterprise Connect hackathon.
March 3, 2017
From protecting against new vulnerabilities to keeping security assessments up to date, security consultant Mark Collier shares tips on how best to protect your UC systems.
February 24, 2017
UC analyst Blair Pleasant sorts through the myriad cloud architectural models underlying UCaaS and CCaaS offerings, and explains why knowing the differences matter.
February 17, 2017
From the most basics of basics to the hidden gotchas, UC consultant Melissa Swartz helps demystify the complex world of SIP trunking.
February 7, 2017
UC&C consultant Kevin Kieller, a partner at enableUC, shares pointers for making the right architectural choices for your Skype for Business deployment.
February 1, 2017
Elka Popova, a Frost & Sullivan program director, shares a status report on the UCaaS market today and offers her perspective on what large enterprises need before committing to UC in the cloud.
January 26, 2017
Andrew Davis, co-founder of Wainhouse Research and chair of the Video track at Enterprise Connect 2017, sorts through the myriad cloud video service options and shares how to tell if your choice is en....
January 23, 2017
Sheila McGee-Smith, Contact Center/Customer Experience track chair for Enterprise Connect 2017, tells us what we need to know about the role cloud software is playing in contact centers today.