Have you ever asked yourself, “are we doing software project management well?” or tried to evaluate your team’s health but didn’t know what data to assess? I have. These and other experiences got me thinking more about the most successful projects I’ve been part of as an IC or PM.

In this post, I want to share the 5 questions I came up with that align with the methodologies and supporting processes I’ve fallen in love with on successful projects with healthy teams. The answers you and your team give are strong indicators of success and will elevate opportunities to improve your project management processes so that you will:

1. Understand the utilization of your teams
2. Derive contextual projections for the proposed scope of work
3. Manage client expectations
4. Ensure client acceptance
5. Ensure proper team allocation

Not sure where to begin? Read on to learn 5 key questions that will help your team evaluate their project management processes and identify areas for improvement.

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Google “Software Project Management” and you may find this entry on Wikipedia with the following definition from Applied Software Project Management:

Software project management is an art and science of planning and leading software projects.[1] It is a sub-discipline of project management in which software projects are planned, implemented, monitored, and controlled.

The bulk of the Wikipedia entry for software project management is about the Software Development Process. Instituting this well-defined process is what Project Managers on software development projects are doing most of the time.

The Software Development Process is all your favorite management-y things: risk management, requirements management, change management, software configuration management, release management, and of course, people management, including conflict resolution.

Honestly, I don’t want to talk about those things, at least not directly, because there’s more than enough (too much?) material out there on these topics. I want to talk about the useful indicators of proper software project management. The questions you should be asking your teams, and the supporting data you should be tracking.

Let’s answer this question: How can you stand before your leaders and your teams and show how work is being completed, when work will be complete, and whether or not it is the correct work?

I believe there are five questions every healthy software project team can answer with data and consistent processes to prove each answer. If you aren’t able to answer these questions, talk with your teams, and discuss what processes you can institute.

Heads-up: A significant portion of my experience is derived from client services. The terminology I use is “team/client”. However, I think these concepts apply whether your language is more “team/business”, or even “we/they”. Either way, real user feedback is an assumed part of the software project management process described below.

Question #1: How is the team able to use their time?

The wording of this question is important: how is the team able to use their time? The question assumes the team wants to use their time well and asks whether they can achieve their goals.

A good software project manager should clearly show how the team has been able to use their time. This is only possible if there is a consistent and effective process in place with a healthy degree of trust between the team and the project manager.

Some clarifying questions may be:

• What amount of time is being spent in meetings?
• What amount of time is being spent contributing to deliverables?
• What amount of time is being lost to unplanned activities?
• What work is currently in progress?

If you can answer this question and the clarifying questions with real data, you understand the utilization of your teams.

Question #2: How well does the team understand the proposed scope of work and how it enables the client’s business goals?

Healthy and high performing teams pursue understanding the scope of their work well enough to optimize their time, processes, and the fidelity of deliverables to achieve the larger project goals.

If only the Product Owner, Strategist, Business Leader, Architect, or Team Lead are the keepers of understanding for the work being performed, you don’t have a healthy team. You have a fragile upward-oriented system of leadership.

Some clarifying questions may be:

• Does the team have clear definitions of “done” as expressed in a series of deliverables documented in a project management tool?
• Does the team review the full definitions of done together?
• Does the team break the definitions down into reasonable, consistent sizes, that reflect the functional work that needs to occur?
• Does the team provide estimates for the individual components of work?
• What is the current projection for the current definition of work to be “done”?
• Does the team present their estimates with a level of confidence?
• Does the team express concerns about the progress, velocity, fidelity, or correctness of the work being proposed?

If you can answer this question and the clarifying questions with real data, you can give contextual projections for the proposed scope of work.

Question #3: How well does the client understand the proposed scope of work?

Key stakeholders must have an accurate understanding of the proposed scope of work. This helps set expectations, and provide clear avenues for feedback.

If key stakeholders are not regularly involved in the assessment of proposed work, the team is at risk of producing the wrong deliverables and incurring costly rework. It is worth noting here that “client” can refer to many different stakeholder groups, including end-users whose feedback is a critical component of producing the correct software.

Some clarifying questions may be:

• Does the client regularly review the definitions of “done” as expressed in a series of deliverables?
• Are the team’s estimates regularly conveyed to the client?
• Does the client understand the level of confidence the team has in the estimates that are provided?
• Does the client give feedback on what is shared, and has that changed the project plan in any way?
• Does the client give feedback on the fidelity or correctness of the proposed scope of work?

If you can answer this question and the clarifying questions with real data, you are managing client expectations, which is critical to project success.

Question #4: Does the client regularly review and accept work that is being completed?

The second side of client management is ensuring the work being produced is correct through regular review and acceptance. This line of communication is critical to creating a strong partnership with your client. As I noted before, “client” can refer to many different stakeholder groups, including end-users whose acceptance of work is a critical component of producing the correct software.

If you’re waiting until demo day to show progress because you want your Don Draper moment, you’re taking unnecessary risks and keeping your client further from work, weakening your partnership.

Some clarifying questions may be:

• Does the client participate in review sessions?
• Does the client provide feedback to chunks of work delivered on a regular basis?
• Does the client express concerns about the progress, velocity, fidelity, or correctness of the work being submitted?
• Does the client see progress during a working cycle, or only after work has been completed?

If you can answer this question and the clarifying questions with real data, you are ensuring client acceptance, which is critical to project success.

Question #5: Is the project adequately staffed, and on track to deliver work on time and on budget?

Budgets and allocation aren’t just for LOB owners, teams need to understand the constraints they’re working within well enough to recognize tradeoffs in service of the best outcomes. This understanding creates a culture of trust and openness when challenges arise with Question #2 and #3.

A healthy team will have clear answers to this question with supporting data to make their case if they’re answering questions #2 and #3 with data supported by a process. If you aren’t able to answer this question, go back to the earlier questions, and ensure that teams are well informed about expectations.

Some clarifying questions may be:

• Are there gaps between the project plan, the definition of work, etc. and the team members who will own the functional work that has been identified?
• Does the team regularly communicate the project plan and any changes to the client?
• Does the team regularly communicate team member allocation and any changes to the client?
• Does the team give feedback or express concerns about their ability to deliver on the scope of work as they understand it?

If you can answer this question and the clarifying questions with real data, you are ensuring proper allocation, which is critical to project success.

Conclusion

The way you and your teams answer these 5 questions is a strong indicator of their project’s health and the likelihood of achieving an outcome that meets or exceeds your stakeholders’ goals while boosting (rather than draining) your team’s morale.

But as you may have already noticed, these questions only elevate the strength or weakness of supporting project management processes. As a team, coming together regularly to evaluate and improve the supporting processes is the only way to ensure these indicators will remain positive.

If you and your team feel incapable of providing clear answers to these questions with supporting data, start discussing improvement opportunities today!

Thanks for reading, I hope this content has been helpful to you. If you have any feedback or would like to share some of your own indicators, please reach out on social media, or directly at hello@joel.software.