Anant Jain

Managing risk in software projects


Navigating the complexities of project leadership in engineering can be daunting, especially for those new to this role. Throughout my career, I've discovered that one of the most effective strategies for ensuring success is to proactively minimize risks across three critical dimensions: User ExperienceExecution, and Integration & Testing. By addressing these areas early and thoroughly, we can significantly enhance our team's ability to deliver high-quality products on time and within budget.

1. User Experience Risk

Without a clear understanding of what problem you're trying to solve for the user, and how your proposed solution solves it for them, we risk shipping stuff that misses the mark. Here are some ideas on how to mitigate this class of risk:

  • Design Validation: Collaborate closely with your designers to ensure that every aspect of the UX is well-defined. Make sure to think through edge cases or engineering limitations early in the design phase.

  • Customer Validation: Engage with real users through usability testing. You want to catch potential usability issues early and adjust your approach before significant development time is invested.

  • Engineering Verification: Ensure that the engineering team understands and agrees with the proposed scope. Make sure that everyone on the project understands how you're breaking the work down into milestones and what's in scope for each deliverable. A mismatch in expectations here can lead to a lot frustration down the line, both for engineers as well as our product/design partners.

2. Execution Risk

Smooth execution is the backbone of any successful project. Execution risk often arises from fuzzy API contracts unresolved dependencies:

  • API Contracts: Ensure that all necessary API contracts within and across teams are in place early in the project lifecycle. For eg., two teams collaborating on a project may agree on an internal gRPC contract between their services, or frontend/backend engineers within a team may kick off work based on a GraphQL API serving mocks. When collaborating with external teams/vendors, closely track whether the API actually fulfills its contract, and is well documented and supported.

  • Dependency Trees: Chart out a dependency tree for complex projects that have interdependencies with other in-flight projects or migrations, and track all these dependencies diligently. A common execution risk I've seen time and again is being "surprised" that a certain project or migration hasn't fully landed, and the project team presumed its completion as a prerequisite.

3. Integration & Testing Risk

The final step to a successful project rollout is ensuring that integration and testing plans are robust and well thought out:

  • Integration Plan: If sub-teams within a project have been working independently based on an API contract, make sure that you start integrating as soon as possible. A common failure mode I've seen is assuming that each sub-team has the exact same understanding of the API contract, and have not made any assumptions or interpreted the contract differently --- in practice, I've seen "minor" gaps here lead to large project delays (and yes, a ton of frustration!)

  • End-to-End Testing Plan: Develop comprehensive testing strategies that cover all aspects of the product. Create detailed test plans that mirror real-world usage scenarios, and make sure to test in multiple environments and with varying loads. Finally, pay attention to how your feature could have entanglement with other features/migrations that are in flight, and make sure to test thoroughly.

  • Rollout Plan: Streamline the rollout process as much as possible. By this point, you already know all the dependencies of your rollout (eg., "a certain company-wide data migration is required to be completed for any account that your feature can be enabled on"). Record the exact process for rolling out (and rolling back!), as well as any automated monitoring and metrics dashboards that the team should be keeping an eye on. Launch checklists are particularly helpful for coordinating rollouts.

By proactively addressing risks across these three dimensions, engineering leaders can significantly reduce the likelihood of project failures. These tactics not only help in delivering a product that meets user expectations but also ensure a smoother development process and a manageable rollout. As you grow in your leadership role, continually refining your approach to risk management will be key to your (and your team's) success.