53 In-Depth Legacy Systems Questions for Enterprise CXOs

What is involved in Legacy systems?

Find out what the related areas are that Legacy systems connects with, associates with, correlates with or affects, and which require thought, deliberation, analysis, review and discussion.

Many organizations utilize multiple diverse Legacy systems that are clumsily interfaced to each other. Many of these systems utilize batch processing and operate on different transaction cycles.  A batch system that is designed to operate on a weekly transaction cycle is not much help in the face of a four day reporting requirement. In fact, it is not unusual for the Legacy systems of an organization to be in sync with each other only at the monthly period end. This situation can exist where information systems are wholly in-house. What happens when portions of the business process are outsourced?

This checklist helps you to find out, lead and drive what actions must be taken in order to successfully integrate legacy data from earlier systems.

How far is your company on its Legacy systems journey?

Take this short survey to gauge your organization’s progress toward Legacy systems leadership. Learn your strongest and weakest areas, and what you can do now to create a strategy that delivers results.

To address the criteria in this checklist for your organization, extensive selected resources are provided for sources of further research and information.

Start the Checklist

Below you will find a quick checklist designed to help you think about which Legacy systems related domains to cover and 53 essential critical questions to check off in that domain.

The following domains are covered:

Legacy systems, Application retirement, Backward compatibility, Data migration, Forward engineering, Legacy-free PC, Legacy code, Legacy encoding, Software maintenance, Software rot, Vendor lock-in:

Legacy systems Critical Criteria:

Do a round table on Legacy systems and know what your objective is:

  1. Is a credible migration plan (for data, applications, and Legacy systems phase-out) from the existing to the proposed environment presented?
  2. What are the existing methods, techniques and tool support to enable migration of legacy software towards cloud-based environment?
  3. Is the system capable, or can it be made capable, of being interoperable and integrated with other systems?
  4. Who will be responsible for extraction of the legacy data and will work with the vendor on transformation?
  5. Is there an expectation that the migrated solution will be run in parallel with the legacy solution?
  6. Can we understand the timeframe given replacing the current Legacy systems with the new systems?
  7. Do different parts of the organization use different processes for the same function?
  8. What are the main practical motivations behind legacy migrations towards the cloud?
  9. Should there be a complete replacement of legacy mainframes and applications?
  10. How much dependence affects the productivity of each activity?
  11. How do we integrate the Legacy systems with the new system?
  12. Do procedures exist that formalize the activity execution?
  13. Are all Stakeholders supporting this vision?
  14. What is the production time of the output?
  15. Scope – How much now and how much later?

Application retirement Critical Criteria:

Investigate Application retirement and do something to it:

  1. How do senior leader actions reflect a commitment to the organizations Legacy systems values?
  2. What tools and technologies are needed for a custom Legacy systems project?
  3. How do we maintain Legacy systems Integrity?

Backward compatibility Critical Criteria:

Closely inspect backward compatibility and get going:

  1. In a project to restructure Legacy systems outcomes, which stakeholders would you involve?
  2. Risk factors: what are the characteristics of Legacy systems that make it risky?
  3. Regulated Backward Compatibility and Version Numbering?
  4. Is it Addressing existing Legacy Software?

Data migration Critical Criteria:

Deliberate over Data migration and get answers:

  1. The process of conducting a data migration involves access to both the legacy source and the target source. The target source must be configured according to requirements.  If you’re using a contractor and provided that the contractor is under strict confidentiality, do you permit the contractor to house copies of your source data during the implementation?
  2. Data migration does our organization have a resource (dba, etc) who understands your current database structure and who can extract data into a pre-defined file and format?
  3. With the traditional approach to data migration, delays due to specification changes are an expected (and accepted) part of most projects. Does this sound familiar?
  4. Are there any external users accounts existing and will these user accounts need to be migrated?
  5. Who is responsible for ensuring appropriate resources (time, people and money) are allocated to Legacy systems?
  6. How will you measure your Legacy systems effectiveness?
  7. Are there data migration issues?
  8. How to deal with Legacy systems Changes?

Forward engineering Critical Criteria:

Adapt Forward engineering and look at it backwards:

  1. Do the Legacy systems decisions we make today help people and the planet tomorrow?
  2. Have the types of risks that may impact Legacy systems been identified and analyzed?
  3. What is the purpose of Legacy systems in relation to the mission?

Legacy-free PC Critical Criteria:

Investigate Legacy-free PC and don’t overlook the obvious:

  1. What are your results for key measures or indicators of the accomplishment of your Legacy systems strategy and action plans, including building and strengthening core competencies?
  2. What prevents me from making the changes I know will make me a more effective Legacy systems leader?
  3. How do we go about Securing Legacy systems?

Legacy code Critical Criteria:

Think about Legacy code and look at it backwards:

  1. How do you determine the key elements that affect Legacy systems workforce satisfaction?
  2. How are these elements determined for different workforce groups and segments?
  3. Who will provide the final approval of Legacy systems deliverables?
  4. Does documentation exist?

Legacy encoding Critical Criteria:

Pay attention to Legacy encoding and know what your objective is:

  1. Think about the kind of project structure that would be appropriate for your Legacy systems project. Should it be formal and complex, or can it be less formal and relatively simple?
  2. Do we all define Legacy systems in the same way?

Software maintenance Critical Criteria:

Wrangle Software maintenance and find answers:

  1. If the path forward waits until a new generation of devices essentially replaces an old generation of devices which could be somewhere between 5 and 15 years, what does the path forward look like for the legacy devices and their software maintenance?
  2. Does Legacy systems analysis show the relationships among important Legacy systems factors?
  3. How likely is the current legacy systems plan to come in on schedule or on budget?

Software rot Critical Criteria:

Analyze Software rot and ask:

  1. In the case of a Legacy systems project, the criteria for the audit derive from implementation objectives. An audit of a Legacy systems project involves assessing whether the recommendations outlined for implementation have been met. In other words, can we track that any Legacy systems project is implemented as planned, and is it working?
  2. How can you measure Legacy systems in a systematic way?

Vendor lock-in Critical Criteria:

Dissect Vendor lock-in and pay attention to the small things:

  1. What should an organization consider before migrating its applications and operating system to the public cloud to prevent vendor lock-in?
  2. Do you see areas in your domain or across domains where vendor lock-in is a potential risk?
  3. What is an example of cloud vendor lock-in?
  4. Who needs to know about Legacy systems?


This quick readiness checklist is a selected resource to help you move forward.

Learn more about how to achieve comprehensive insights with the Legacy systems Self Assessment from my new book:

About the Author:

Gerard is the CEO at The Art of Service. He has been providing information technology insights, talks, tools and products to organizations in a wide range of industries for over 25 years. Gerard is a widely recognized and respected information expert. Gerard founded The Art of Service consulting business in 2000. Gerard has authored numerous published books to date.

By: Gerard Blokdijk, CEO, The Art of Service |


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