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Getting the most out of your project management tool

Getting the most out of your project management tool

Getting the most out of your project management tool

There are several project management tools on the market that all aim to help your team gain productivity. Each tool has guiding principles and philosophies for managing projects and structuring your team. These stratagems may only sometimes apply to your team, or your team may evolve and discover new priorities they want to track. In this post, we’ll cover the concepts you should consider when understanding how your team operates and how project management tooling principles can impact your teams. Once you have a tool, we’ll share how you can set it up to align with your team through an example of how we achieved results.

Understanding how your team operates

Does your team run an agile workflow? Are you a waterfall organization? Do you ascribe to Kanban methodologies? Do you take pieces of each of these processes and merge them to allow your teams to organize and operate in a meaningful way? I discuss this topic in more depth in our Engineering Leadership podcast, but these methodologies need to align with the metrics you care about.

As organizational leaders, you need to share what you’re tracking with your teams. These typically include Objectives and Key Results (OKRs) or Key Performance Insights (KPIs) curated for your team’s functional area. Your project management tool could inform some of the metrics you select. For instance, DevOps teams may care about DORA, or customer success teams may need to track the time to resolve customer-facing issues. Development teams may leverage these tools to coordinate the work on efforts to avoid duplication of effort, while others may invest in velocity metrics to inform product teams of capacity. Regardless of what metrics you’re gathering, validating that your tool can provide these metrics is essential.

Tooling Principles

I’ve used various project management software, including Jira, Linear, GitHub Projects, Pivotal Tracker, Asana, and Trello. Each tool is structured slightly differently and has different best practices and approaches. For example, Jira attempts to be the all-in-one tool for organizations giving extreme flexibility in how you set and configure projects. On the other hand, you have tools like Linear that are strongly opinionated and have clear guidance on how to use the tool. When selecting a tool, it’s essential to understand its operating principles and how they relate to your team’s operating habits.

This isn’t to say these tools cannot be adjusted to work for your use cases and needs, but some will be easier to adapt than others for specific situations. It’s important to select tools not only for their user-friendliness but also for their adaptability to your organization’s needs. In some cases, this may lead to your team utilizing multiple tools. Given any budget constraints, this may not be ideal, so as organizational leaders, it is vital to have those discussions with our peers to determine what would benefit our team the most. If a single tool cannot solve all your needs, try to limit each department to a single tool. Given their functional area and KPIs, you can likely manage this situation easily through monthly and quarterly reporting shared with your organization. If your department is using different tools, you will probably need to set up external reporting means to aggregate those sources of truth or find a way to connect these apps. Some of these tools have integrations that allow you to sync them, but I’ve found those setups to be clunky and create more overhead for simple reporting facets you need. Regardless of your decision, you must configure these tools for your organization’s success.

Setting up your tool for success

With our operation practices determined and the tool that makes sense for our team based on principles and experience found, it is time to set up the tool for your team’s success. I will share my setup based on how my team operates to demonstrate what this could look like for you.

As a consultancy, my team tends to operate in a waterfall model, as clients have us coming in for specific projects with defined scopes. However, we demonstrate progress to clients on a weekly or biweekly basis. This means we need a tool to help us plan out several months of work and milestones while allowing us to manage it weekly. Our clients aren’t typically interested in micro-details for these projects but care about the macro level of deliverables against milestones. Given these parameters, our team leverages GitHub Projects for our project management. We like it as the tickets stay close to the code, and we can use GitHub’s built-in functionality to manage most of our needs. This prevents our team from learning multiple tools and allows us to build custom workflows quickly using GitHub Actions as needed.

This is an example of a project we ran. I’ve omitted details for privacy reasons, but we ran weekly iterations on this project. We also tracked priority and sized issues to help us understand what deliverables we could demonstrate each week. This helped our team organize around how much we knew we could complete each iteration and allowed team members to pull in additional work each week, given we prioritized other issues and their size. If they needed another issue on a Friday before the iteration ended, they could pull the next issue assigned to them from the next iteration or backlog, allowing for a continuous flow of work week-over-week. If an iteration was not completed, it gave us the information we needed to understand why the work may not be complete and allowed us to plan better for the next iteration. Screenshot of GitHub Project with 5 iterations and additional metadata for priority and size

This workflow allows our team to focus on the client's needs and operate in a way they have ownership over the work as each team member commits to the work they agree to before it’s brought into an iteration. If we needed milestones, we could also assign those to tasks and track them, leveraging other GitHub built-in features. These are generally the types of things you should look for when setting up a tool for your team.


Project management tools are not just for project managers to dictate work to teams. When aligned with how teams operate and their goals, these tools can help your teams achieve at a higher level. Creating processes that don’t align with your team’s daily function to gather non-priority metrics through tools creates resistance and challenges leading to non-performing teams. Suppose your team is struggling because deliverables are not aligning with business goals and metrics. In that case, this is an excellent opportunity to check your processes and team operations and realign them if you discover they are out of sync.

At This Dot, no single process works for all teams and organizations. We work with our teams and clients to determine what processes align with their objectives and goals. The process described above works great for our team but may not work for your team. However, the principles outlined above can aid you in finding the process that works best for your team. If you need help finding your process, contact us to help your team find their groove.