Table of Contents for “Boiling the IT Frog”
Pulling Back the Curtain
- Who Should Read This Book
- This is not a technical book.
- How to Get the Most Value from this Book
Chapter 1: Poof, There It Is!
Magic in IT isn’t a Good Thing
- Secret 1: Technology that crosses the line into magic leads to unreasonable trust, illogical thinking, and inappropriate wizardry.
- Secret 2: New technology always disappoints before it succeeds.
Chapter 2: In IT We Trust?
Without Trust, IT is Useless
- Secret 3: Information Technology is all about infrastructure, projects, maintenance, strategy, and trust.
- Secret 4: If your company doesn’t have a mutually trusting relationship with its IT organization, then IT won’t be successful.
Chapter 3: The Stuff Inside Your Walls
IT Infrastructure
- Secret 5: IT infrastructure is just like the stuff inside the walls of your house.
- Secret 6: There is no “right” amount of money to spend on IT infrastructure.
- Secret 7: Almost any software and hardware will work in the short term, but you’ll see the difference in the long term.
- Secret 8: The fewer Information Technology products you have, the better off you’ll be, as long as you’ve chosen good products.
Chapter 4: Keeping the Pipes Clean
Optimizing your IT Infrastructure
- Secret 9: Keeping software users up-to-date on current versions is much more difficult than you’d think.
- Secret 10: If you’re going to use off-the-shelf software, then use the business processes that come with it. Otherwise you’re just paving the cow paths.
- Secret 11: The biggest revolution in Information Technology in years is in the area of middleware, integration broker technology, and web services.
Chapter 5: Think of a Number Between 1 and 1,000
Picking the Right Projects
- Secret 12: A key to successful IT projects is selecting the right projects to do. A bad project selection process will lead you to the wrong projects.
- Secret 13: Using Return on Investment (ROI) for project selection is a ticket to failure unless some stringent rules for calculating ROI are put in place.
- Secret 14: Adding strategic alignment to the project selection process ensures that IT projects move the company in the right direction.
Chapter 6: You Want It When?
Making Projects Successful
- Secret 15: Good project management is asking the right questions.
- Secret 16: All projects have risk. Good projects deal with it, and bad projects just hope for the best.
- Secret 17: Most projects fail for the same reasons.
Chapter 7: It’s Not Just Like Tuning Up the Car
Maintenance — Keeping up with Business Change
- Secret 18: Software “maintenance” follows different rules from hardware maintenance, and should be planned and budgeted differently.
Chapter 8: Are We There Yet?
Creating an IT Strategy
- Secret 19: An IT organization without an IT strategy is like a sailing ship without a destination; it’s anybody’s guess where you’re going or when you’ll get there. But pick a destination, and you’ll begin to see progress.
- Secret 20: The IT organization should actively participate in setting business strategy in order to leverage their technology expertise for maximum business benefit.
Chapter 9: Can Nine Women Have a Baby in a Month?
QCSS — Pick Three
- Secret 21: When you define the requirements for a project, you can’t specify quality, cost, schedule and scope; only three of the four can be required, and the other variable is dependent on the process being used for the project.
- Secret 22: Adding more resources to an IT project (especially one that’s running late) can make it take longer.
Chapter 10: How’d We Get into this Mess?
Why isn’t Information Technology Simple?
- Secret 23: Information Technology seems more complex than it has to be.
Chapter 11: Simple, Simpler, Simplest
How to Simplify Information Technology
- Secret 24: The easiest way to simplify technology is to not use it at all.
- Secret 25: Lack of focus leads to unnecessary complexity. Follow the 80-20 Rule to focus on the important things, and your IT will be simpler.
- Secret 26: Systems are unwieldy and complex because we let them get that way. To make systems simpler, keep project scope under control.
- Secret 27: Systems that are built in layers are much easier to manage and change.
Chapter 12: Your System was Bad Today
Building a Partnership
- Secret 28: The Information Technology organization is your partner in creating and managing systems and data, with shared responsibilities.
- Secret 29: Emotionally, it’s more difficult to deal with a system problem that you inherit in a new job.
Chapter 13: Parlez vous Anglais?
Dealing with IT People
- Secret 30: IT people are very focused on the how, not on the what. The most common mistakes they’ll make are errors caused by doing the wrong things, not by doing things wrong.
- Secret 31: The best way to communicate with an IT organization is to talk to members of the organization as if they’re from a foreign country and don’t speak English very well.
- Secret 32: Motivate an IT organization the same way you’d motivate any other organization, by measuring its contribution to business success.
Chapter 14: Sprechen sie Business?
Dealing with Business People
- Secret 33: Although business people want long-term success, they easily get caught up in the apparent urgency of shorter-term goals. The most common mistakes they’ll make are errors caused by a focus on inappropriate shorter-term goals.
- Secret 34: Like IT people, some business people are also somewhat focused on the how, but often inappropriately so. Overly-specific definition of system requirements by the business is a leading cause of excessive IT spending and low IT morale.
- Secret 35: Good IT analysis work can ensure that the real problem is being solved – not just a symptom. But a business focus on symptoms will prevent work on the real problems.
- Secret 36: Telling someone in the IT organization about a problem doesn’t mean that the IT organization is committed to fix it; but business people tend to see things that way.
- Secret 37: The best way for IT to communicate with a business user is by using the language of the business – not the language of IT.
Chapter 15: Have Your “Guy” Do It
Should IT be Outsourced? Offshored?
- Secret 38: Parts of IT can be outsourced or offshored, but it’s a business decision, with risks and rewards.
Chapter 16: Who’s the Designated Driver?
How to Improve Your IT Organization
- Secret 39: When you look past the technology itself, IT is all about change: changing the business in ways that make it more efficient and effective.
- Secret 40: To increase the effectiveness of an IT organization, align direction, leadership and resources.
- Secret 41: Achieve your IT objectives faster by focusing on what’s truly important. Focus includes preventing work on things that aren’t relevant or productive.
- Secret 42: To increase the efficiency of an IT organization, optimize people, processes, and tools.
- Secret 43: To achieve IT objectives which are important but not critical, take advantage of your company’s “wind direction.”
Chapter 17: Putting It All Together
- Secret 44: We wouldn’t be where we are if we’d planned it; but now that we’re here, we don’t have to stay.
Endnotes
Acknowledgements
Index
About the Author

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