The rate of technology change is increasing at an ever-accelerating rate. Staying current with latest versions of practice management and financial systems software is a necessity if for no other reason than to ensure you have the latest security patches from the software vendor.

As a certified project manager with nearly 20 years of experience, I’ve participated in my fair share of software upgrades. Why do some software upgrade projects go smoothly while others falter and stall? Many factors contribute to an on time, in scope, and within budget upgrade process. Essential to this process is applying a proven methodology that comprises five key elements: vision, strategy, execution, go live, and closure. I’ll explain each.


The first step for an effective software upgrade is the vision phase, during which a launch meeting and new features overview sessions occur. For the purposes of this article, I’m assuming that you’ll work with either the software vendor’s services team or an appointed services partner to assist your internal team with the upgrade process.

Launch Meeting

Once you’ve identified who you’ll work with, the project formally begins and a launch meeting is typically organised by your software services partner. The launch meeting provides the opportunity for initial contact between your internal IT team, your project sponsors, the services partner’s project members, and any other key members of the project team. The main objectives of the launch meeting are to:

  • Ensure the services contract is correct in terms of software and services required
  • Confirm any optional services
  • Define and record project success factors and reasons / drivers for upgrading
  • Provide an overview of a typical upgrade and the steps required
  • Set expectations across the project and clarify budget, scope, and timeline along with required resources from both sides
  • Review the project approach and methodology
  • Supply and review key project and technical documentation
  • Plan initial tasks following the launch meeting

New Features Overview

Another part of the vision stage is to organise and deliver brief overview sessions that explain new features of software being implemented. These sessions can be delivered remotely and provide an opportunity for you to understand how the software has changed. These sessions allow you to determine if any process changes are required and help to identify future training requirements.


The strategy phase allows you to define and agree upon the technical, training, testing, and project management aspects of the project. For each of these elements, you would define all of the related requirements so you can then refine the project plan for each.

Technical Strategy Review Meeting

Part of the technical strategy is to organise and deliver a technical strategy meeting. After reviewing all technical documentation and prior to building servers and loading any pre-requisite software, a technical review allows any outstanding questions to be answered. For example, you might need to clarify the type and capacity of servers and OS software along with compatibility issues in respect of virtual servers and also responsibilities and approach to the technical tasks. You can then complete a pre-install checklist, which is a mandatory pre-requisite and allows a technical consultant to access the systems and implement the software for testing, training, and purposes of familiarisation.

Training strategy

Delivering training correctly and efficiently is paramount to ensuring a fast return on investment. Consideration must be given to the scope of training, who requires training, and when and how this is to be delivered. As such, a strategy for training is important to capture all of these requirements.

Testing strategy

One of the most important elements of any software project is testing. A robust and repeatable testing methodology is vital to improve the quality of the final deliverables and reduce the risk of issues occurring at go-live and beyond. Unit, system, integration, and user acceptance testing are amongst the key elements to successful testing cycles. A significant proportion, if not the largest proportion of effort within a project needs to be allocated to testing. A testing strategy to include a robust methodology as well as success criteria, associated to quality gates along the project timeline, are crucial to a successful project.

Project strategy

Successful project management and delivery relies on a strategy that provides adequate controls across all elements of a project. From a clear set of reasons to initiate a project, to a final set of measurable delivery and success criteria, these will all play a part in defining a robust project strategy. A project strategy must provision for delivery against scope, budget, and timescale to ensure that defined quality measures are met. Controls to ensure this would include specific and best-practice methodologies, approach, and documentation to ensure successful delivery.


Once all members of the project team agree on all aspects of the strategy, the execution stage begins. A project gate or milestone for this purpose is necessary prior to the execution stage and this provides a best practice project control. All of the core project tasks are performed within the execution stage according to the agreed plan and runs from the initial software load across testing and training and finally to the go-live itself.

Go Live

The most important stage of any project and the reason for all of the prior preparation is the go live itself. The live implementation represents a culmination of all the project effort and planning to date.

To facilitate a live upgrade, a minute-by-minute plan for just the go-live period is produced in collaboration between the law firm and the services partner. Timings and responsibilities are set out in the plan and once agreed upon, it is distributed to the project team and specifically those with relevant go-live tasks. Contingency and roll-back planning is also important in case of any unforeseen critical issues.

Communication is also an important factor for a successful go live. For example, you could set up a team email including all involved parties to provide updates following each critical step. You could also conduct ad-hoc meetings via remote sessions if required.


The closure stage should follow after at least one month-end cycle has been performed and subsequent to the live upgrade. This measure allows any teething issues to be resolved between the project team or software vendor’s support team depending on the nature of the problem. This also enables and encourages a smooth transition to support.

Project Close Meeting

A project close meeting covers any outstanding issues, lessons learned, and helps to ensure any success factors captured at the outset of the project were met. It also allows for a formal sign off of the project, if possible.

One of the most important and sometimes overlooked aspects of a close meeting is the lessons learned process. To facilitate constant improvement for forthcoming projects for both parties, understanding what worked well and what could be improved is vital for any future engagements. These should be recorded and a formal log for all projects updated so that the benefit of such an exercise is fully utilised.


These are just some of the key elements and best practices involved to help ensure a successful upgrade. In summary, a recipe for a successful upgrade is to:

  • Ensure success criteria is defined at the outset
  • Follow a well-defined and tested project methodology
  • Ensure all strategy and plans are reviewed and agreed prior to executing any major tasks Preparation and planning is essential
  • Test, test, and test again with as many different individuals and variables as possible. Follow formal test scripts but also ensure ad-hoc and scenarios specific to your firm are tested Testing can be up to 50% of the total project effort or timeline, the more testing the better
  • Have a comprehensive plan for go-live and build in contingency in case of critical issues
  • Learn from any successes and failures and ensure they are remembered for subsequent projects

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