MASTERING ENTERPRISE SOFTWARE SELECTION

INTRODUCTION

In this article, I would like to share with you my recommendation of a very useful resource that has served me well on multiple occasions over the last several years.? The resource is a book titled “Rethinking Enterprise Software Selection - Stop buying square pegs for round holes” (Chris Doig, ?(2017). Wayferry, Inc., https://www.wayferry.com).

THEME AND OBJECTIVES

The theme of the book is that enterprise software selection and implementation is often extremely complex, and the overwhelming majority of such projects fall short in some material way and many outright fails.? Also, given that no one likes to talk about or publish these failures, many organizations do not appreciate the risk and complexity associated with these projects from the start.

The two main objectives of the book then are to assist the reader with all aspects of the software selection process, with an emphasis on large enterprise solutions, and secondly, to help with the identification and mitigation of a variety of risks.

CHAPTER LISTING

Below is a listing of the 13 Chapters that make up the book.?

1.????Tthe software purchasing problem

2.????Why selecting software is so difficult

3.????Software selection risks and mitigation

4.????The benefits of best-fit software

5.????Select Software for Value, Not Price

6.????Software strategy

7.????Project management

8.????Software selection toolbox

9.????Requirements

10.?? Evaluation

11.?? Selection and purchase

12.?? Post purchase

13.?? Selection summary

CHECKLIST VALUE FIRST THREE CHAPTERS

The book was very helpful to me as I led a project to move our organization to a new Unified Communication and Contact Center Platform.?? Furthermore, I’ve found Chapter’s 1, 2 and 3, especially helpful in many other situations even outside of a major Enterprise Software Selection (ESS) project.?

Chapter 1 discusses what ESS success looks like (e.g. on time, under budget, expectations met, etc.) and, more importantly,? the different kinds of failures (e.g. benign failures, partial failures, functional failures, complete failures), ?what the author calls “pains” (e.g. business, technical, personal), as well as the potential costs of a poor purchase (e.g. business disruption, delayed ROI, etc.), that we need to be concerned with.

Chapter 2 then goes on to provide answers to the question of why selecting software is so difficult. What I found highly valuable with this chapter was the comprehensive list it provides of potential reasons broken out by general categories of (1) lack of organizational interest in a rigorous process, (2) problems and pitfalls with relying on a committee to select software, and (3) doing work in the wrong order (e.g. starting projects with vendor demos).? On the one hand, there is nothing that a seasoned IT professional probably does not know about or would be surprised by, but there is value in having it comprehensively laid out with short, to-the-point, insights alongside.

Finally, in Chapter 3, the author provides a comprehensive guide of software selection risks and recommended approaches to mitigate them.? He categorizes these as follows (I’ve included just a few of the examples for each category but there are many, more):

Organizational risks - political interference, Inadequate executive sponsorship, lack of business experience in IT, lack of software selection experience in the business, etc.

Project management Risks - immature evaluation and selection process, overconfidence, underestimating the amount of work, limited project resources, scope creep, etc.

Requirements Risks - poorly written requirements, missed requirements, not rating requirements, etc.

Selection Risks - going with the market leader, following the competition, falling for the latest and greatest, etc.

Vendor Risks – skipping due diligence, trusting vendors, not auditing vendor responses, etc.

Plus, Contract Risks, Implementation Risks, and, finally, Personal Risks (career or reputation damage).

Taken together, Chapters 1-3 provide the basis for an excellent “checklist” to review as part of any new software project, of any real size, or of many IT projects, in general.? ?This works well for me as I am a big “list guy.”?? Ask any of my direct reports what I will say if they tell me “we’ve got a bunch of problems with ‘X’” and they will tell you “he’ll tell me to put them in a list.”? You can’t work “a bunch” but you can work “a list!”

REST OF THE BOOK

The subsequent chapters of the book address the many other aspects of large enterprise software selection and they include real-world case studies to highlight various points.? The content here is presented in concise, straight-to-the-point language, with some useful tables, charts, and bulleted lists.? I appreciate that!

Here are just a few of the topics covered:

·?Considerations, common errors, and insights into calculating TCO, ROI, and best-fit scoring

·?Managing vendors

·?Mapping software selection to overall business and application strategy

·?Managing the software selection project

·?Understanding and managing your software selection maturity level

·?Utilizing various tools, such as gap analysis, fit scores, and requirement weighting

·?Approaches to capturing requirements, as well as when/how to use them

·?Evaluating, Selecting, and Purchasing

There are also three appendixes at the end that address selecting consultants, product demos, and vendor references.

CLOSING THOUGHTS

In summary, consider that airline pilot crews, even those with thousands of hours of flight time, use checklists each time they take-off and land.? They do this because what they do is complex, multi-faceted, and lives are on the line.? The same is true for major enterprise software selection initiatives (well, maybe lives are not on the line, but it certainly can feel that way sometimes!).? I’ve found this book helpful as a source for my IT checklist, and more, and I hope it can assist you as well.

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Author:

Al Castro , Director of Information Services, Los Angeles Angels

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#SoftwareSelection

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