Cherwell IT Service Management Blog
Resources, Best Practices, and Solutions for ITSM Pros

Speed Dating for IT Service Desk Software

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man looking over a long letter.

I recently attended the SDI’s Service Desk Software Showcase event in London, where attendees had the opportunity to identify the IT service desk software that best fits their organisation and needs. These are great events, and I am sure they provide service desk analysts, team leaders and managers with a glimpse of service desk tools available that may match their requirements. It’s a little like speed-dating with eight vendors providing a 30-minute presentation. At break times, attendees can chat with vendors and see the products in more detail.

These events supplement the larger selection process that can take months and months and involve numerous demos and Q&A documentation.

Following 15 years of consecutively working in the IT service management industry in either sales, sales management or account management roles, I estimate I have read and directly replied to (or via a partner) more than 150 Requirements Lists, RFPs, PQQs and ITTs.

We work in a mature industry, which not surprisingly, now requires more due- diligent when investing in replacement help desk systems. I have seen 350 question documents for 20-to-30 concurrent license requirements. My record so far is 579 individual questions.

So, if you were asked today to select a new service desk solution, what would your initial reaction be?

  • “OMG! Where Do I Start?!”
  • “No problem, I have done this multiple times before.”
  • “Hmm; who can I ask to help me with this?”

In my experience, the top reasons organisations change their current service desk system are:

  • Growth issues
  • Trouble issues
  • Up-grade issues
  • Improvement of processes

Growth, as you can imagine, is often much easier to justify since growth usually brings investment budget with it.

Trouble is much tougher, however if the current solution is holding back the company or poorly supporting staff and customers, it is a powerful justification to change solutions.

Upgrades can be costly if they involve starting over again and if your organisation does not have the skill set, or more likely the internal resources, or the tool is not able to upgrade easily. This may mean a review of the market since the cost of a new toolset may be similar to the cost of upgrading the one you currently have.  

Improvement of process; whilst IT service management is a mature market, there are a number of organisations with older products in place that lack the latest best practice processes.

My view on how you should approach ITSM tool selection:

  1. Vendor Selection
  • Only enter into vendor selection if your decision timescale is within 12 months. Create documentation, carry out surveys from staff, collect requirements, and gather information on the marketplace and its vendors.
  • Why? Because, typically, the solutions you see now will be upgraded by the time you need to select and implement, new vendors may enter the marketplace that are better suited to your needs, and some current vendors may either be acquired or move out of the ITSM marketplace.
  • Use all key areas of validation available to you, including industry analysts firms, professional membership organisations, industry specific websites, etc.
    • This will enable you to get a feel for which vendors are regarded as ‘top’ amongst the 300 plus vendors/products in the marketplace.
    • Remember: to be covered/included in some analyst reviews, vendors must meet certain criteria set by the analyst firm. So, at the same time you’re looking for a new product, you may also find yourself carrying out company and financial checks.
    • Attend events and get an understanding of the product and the vendor’s staff. At an event, you will only get a quick overview of the product. You will never receive a full demo because the products are too function-rich to show during a brief period of time.
    • Any list of possible vendors should never really exceed seven. There should only be about three on your short list.

2. Creating the document

  • Remember: a 300+ question document can tell you far less about a vendor than a 75 question document.
  • Most IT service management tools offer PinkVERIFY ITIL® processes, and therefore, most vendors can all answer “yes” to almost every process question asked of them.
  • Write a document that includes the following:
    • Summary of your business and the key reasons for the review and change from the current solution. Why are you going through this process?
    • The good things you have now with your existing tool.
    • The pain points you quickly need to overcome (e.g. ease of reporting, ease of configuration, web portal etc., upgrades, customer support and technical support).
    • What “quick wins” would have an immediate effect on both the quality of the IT department, its managers and support personnel, and your customers’ satisfaction?
    • A section on the areas of requirement/functionality that you need to deliver over and above everything else and the timescales for these to be delivered.
    • Detailed information if the new tool is required to support multiple service desks and service desks based in multiple time zones.
    • Information about your SLAs OLAs and UCs.

Ask questions about how easy the product is for YOU to administer, add to, and change. Remember, these solutions often last anywhere from six to 10 years. The two things you definitely require are flexibility and scalability.

Ask questions about the vendor’s resources, both direct and via certified partners, and from where and how the support is delivered. What would happen if you suddenly found out your supplier did not have enough resources? Where would you look for additional resources?

If you are asking for pricing, get an idea of both first year and ongoing costs for support, subscription, training and consultancy.

Ask about the areas that could delay the go live date and what the vendor would you do to negate this.

Lastly, ask about the expected time the vendor will need your organisation’s resources and who and when these resources will typically be required.


  • Visit reference sites and ensure you ask as many questions about the company as you do about the product and how it acts from a support and account management/customer experience perspective.
  • Try to get a feel for what a long term relationship with the vendor will be like. Visit both new customers (see first-hand what your experience will be like) and longer term customers (hear what the journey has been like: upgrades, support etc.).
  • Due to upgrades being a top pain issue, try to find out: do upgrades require vendor customisation consultancy cost? How often are new versions released?
  • In your view, does the vendor have a financial vendor culture or does it have a customer centric culture?

That’s 1,000 words to summarise 15-plus years-experience.  If I saw you in London, you’ll know that what truly matters to me, is that you find the tool that’s right for your organisation. Yes, I work in sales, but I’m also a consumer and a buyer. I also have firm views on what makes a good or bad demonstration/presentation meeting, but I will leave that for another day. Stay tuned.