How can you create a realistic timeline for an enterprise software project?

On my experience, I've found that having a mix of both optimistic and pessimistic viewpoints within a proposal team, and sharing these perspectives with those who will execute the project, consistently results in the development of a more realistic timeline for an enterprise software project. Furthermore, initiating actionable milestones at the project's inception proves vital for validating estimations in comparison to project ambitions and for monitoring the team's velocity, ultimately contributing to successful project management.

Programme managers need training to identify and eliminate group think in the estimation phase. If people 's opinions are ignored or they feel pressured to agree in this phase a number of problems will emerge later - lack of ownership, passive resistance and a blame culture will damage what was sold as a collective aim.

Remember that any change you bring involves a learning curve across everyone involved. Bake the learning into your estimates and schedules to ensure your team is not on a date driven death march. Carefully assess the nature of changes you plan to bring in and harmonize differing views among the team to instill a sense of strong ownership at the ground level.

Deviations are a constant in a the agile world of project execution. While it is key to detect deviations and communicate them regularly, it is also important to explore ways to minimize the deviations and present options and tradeoffs while communicating. This ensures you earn and maintain stakeholder trust, as well as gives your audience a clear picture and potential ways they can extend meaningful help. Remember sometimes presenting a menu of options to offset the date impact of deviations from plan is a mini project in itself. So don’t hesitate to set reasonable DFADs (Date For A Date) while communicating to buy the time you need to present a thoughtful response.

Many development projects get defocussed by frustrated stakeholders. Senior managers and senior client representatives will inevitably introduce mission creep due to their perception of lack of progress and changing market conditions. This stress in them will enter the development mindset and damage the project culture. Creating and maintaining a "warts and all" communication framework, not shying away from communicating a realistic progress assessment and accepting the threat of having a project stopped or even killed is always an option.

Communication planning is more important than ever before with remote and hybrid work. Regular standups are easy to maintain but many project sponsors and secondary stakeholders might require multiple communication channels to be agreed upon and executed. For example, a work culture could dictate Email + Slack + Project status update. Thankfully automation can replicate across all channels and reduce manual copy and paste.

Retrospectives at the end of a project are a chance for the team to gather and discuss holistic feedback, however that’s too little too late, especially for medium to large projects. The team should retrospect at each delivery point to take stock and apply lessons learned to quickly course correct deviations. A common checkpoint is during sprint demoes. More frequent retros make them more efficient as well.

Having done both enterprise implementation and custom development, I'd suggest using a custom development best practice -- the Agile Discovery phase. Enterprise products have never been more Discovery-friendly. Since enterprise projects tend to slip, often because requirements don't mesh with standard functionality, an Agile approach would start with a 30-60 day out-of-the-box implementation and gap analysis by key stakeholders. From there one can make the hard decisions -- do we need this modification/configuration -- and then estimate phasing and time to delivery for solution iterations 1, 2, etc. And don't forget to pad all of the estimates with at least 10%, since something always comes up.

Create a collaborative environment for the team with the right process, tools and enablers. This includes enabling team members to feel empowered and contribute as a valued stakeholder. While a top down approach may be needed for a program to be successful (including meeting timelines) we need to ensure that traditional team building best practices are not missed out in the “agile” world and necessary investments of management time and bandwidth happens and a mechanism is put in place that not only assess and evaluate teams output but also look at aspects like improvements, risks, individual satisfaction, ability to apply innovation and continuous improvements- allowing for a bottom up view as an additional assurance

Keep it simple. Have a business plan and a product plan to market. Involve the stakeholders and end users in market research or scoping to ensure alignment on needs identification, authenticity of product and solution focus. Be loyal to the reason and flexible to market sensitivity. Maintain a strong quality assurance approach, value end user experience and information design. Professional expertise astride end user needs and experience afe essential

Develop a simple, efficient and collaborative retrospective model. This will help with proper project maintenance, success, and learning about resource efficiency. One or two solid post-project looks at budget - actual (quite easier if using a task capture tool for automated time entry) can save oodles of future project planning frustration.