I was recently asked to tally up a list of the “top 5” issues that cause the most delays in getting a new IT system deployed.  So, I thought I would share them with you guys. Here you go.

Installation Parameters

When *not* a Windows Installer package (.msi, .msp, etc.), it involves command-line interface (CLI) parameters, but occassionally, it involves MSI packages as well.  Getting the right syntax.  Does it require a response/answer file or can it be done just from the CLI? Is it documented?  If not, factor in a few hours (or days) to chase down blog posts, forum discussion threads and YouTube videos done in some foreign language by someone trying to hold a shaky cell phone camera with one hand.  Is that parameter all UPPER case, or does it care?  Is that a 1 or a i?  Hmmm, who knows.

Silent Installation

This dovetails from the Installation Parameters wonderfulness.  Basically, does the product even support a “silent” (aka “unattended” / no user-input required) installation process?  Does it support a silent uninstall as well?  How about adding updates?  Does it force (or expect) a reboot somewhere in the process?  Was the vendor smoking a bong with their room full of cats, watching Family Guy, while programming this cure for world hunger?  Is there any documentation on the vendor web site?  Does the vendor have a web site? Is it really a “vendor”, or just some homeless guy with a stolen laptop, using free wifi at the nearest McDonalds, and posing via a boilerplate Wix web site that looks like a real business?


Some application installers handle them for you, most do not.  For those that don’t: it involves time-consuming reading and visiting web pages to download the missing components.  Some of those require registering your name, email, blood type, sexual preference and white blood cell count, in order to access their precious binaries.  Are those documented steps for Windows 2012 R2?  Or 2003?  Is that a role/feature or a separate download?  Registration required?  Ha ha ha….. drink up!

Hotfixes and Updates

How many hotfixes and updates are needed BEFORE starting the installation?  How many after?  How many during?  I dunno. Let’s ask Mr. Owl.  (TV ad reference, for old farts like me).  Oops? – building this package for someone else?  Does the update sit behind a vendor user login?  Do you need the contract number and user account to log in and download the files?  Can you download them or do you have to submit a request and wait for a reply?  Does the vendor (I know, I almost let that get by me), have a phone?  Do they check email more than once a week?  Does their cat review requests and pass them on to their dog to approve?  Can you merge the updates into the package or do they have to run in serial before or after the main install?


Ah, yes.  The sweet smell of a delicate UAC fist to the face.  Boom!  Not today, pal!  You no have rights?  You no play with our software.  Sorry.  Can you execute the package as a proxy/service account and still allow other users to launch it afterwards?  Or does it require installing under the user context?  Does the product require hardware interfaces?  Does it perform runtime interface polling? (that’s for those pesky 1990’s contraptions that customers just can’t stop loving).  What about the antivirus app they use?  Firewalls?  Registry?  Services?  Aside from technical stuff, what about the organization’s “change control” process?  Do you have submit a request and wait for approval?



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