How we fixed our task management in these 3 steps

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Task management can be a burden. Without proper structure, and accurate tools designed to assist you with monitoring the progress and summarizing the results, it can turn into a never-ending cycle of incorrect estimations, inconsequentially logged hours, and chaotic, incomplete reports. 

Trust us - we’ve been there.

Our team has come a long way from a small group of people planning and estimating tasks in what felt like a good way to do it, to the Product Department of today, following the highest standards, and utilizing tools that help us reach our goals in the most efficient way. 

In this article, we will guide you through our processes, and share our best practices to help you master task management, and make it work for your team’s benefit.

Step 1: Half of the success is a good plan

And what constitutes a good plan? It should effectively guide you toward achieving a specific goal, while being realistic, cooperative, adaptable and transparent. For us, there was a challenge hidden in each of the three aspects:

• Realistic expectations: Plans we’ve created tended to be too ambitious, and not grounded in reality, resulting in inaccurate estimations, and unreached goals.

• Cooperation: Planning meetings were conducted with the whole team present, and yet somehow turned out to be strangely passive and one-sided, executed mostly by the one person leading them.

• Adaptability: Although we work in the spirit of Agile, in practice we found ourselves stumbling whenever a plan required quick changes, since our methods lacked the required flexibility.

• Transparency:  We didn’t have established ways of effectively communicating the plan changes to everyone in a transparent, timely manner, which often hindered us from applying continuous modifications.

The above issues resulted in plans that seemed good at the first glance, only to keep uncovering more and more issues along the way, getting further and further away from the plan’s main mission: to guide us effectively toward achieving a specific goal.

Seeing how these issues persisted from Sprint to Sprint, we figured there must be something wrong with our planning process. And so, we’ve decided to take a closer look at where we are, and where we want to get when it comes to planning. After investigating this matter for a while, we’ve created a list of Sprint planning statements we wanted to make true:

• The whole team actively participates in the Sprint planning: Enough with passive watching how others are making plans for the whole team! We want everyone to be able to easily join the planning effort and make direct changes to the plan.

• Team members' capacity is transparent and up-to-date: To make effective plans we need to have a clear understanding of available resources, and be able to manage them easily.

• Issues can be effortlessly moved around the schedule and reassigned: If we want to be Agile our tools also need to be Agile. Enabling quick, transparent changes to the plan is crucial for this to work.

• All changes made to a plan are readily visible to the whole team and stakeholders in real-time: For the plan to fulfill its role, everyone in the team must have trust in it and be sure it's always up-to-date. 

To achieve these goals we tried out a number of different methods - we attempted to plan using Jira boards and backlog. We also tested external planning tools, but the results were not satisfying. We needed a solution that would be integral to the rest of our work and wouldn’t require us to hop around different platforms. It also needed to be simple enough not to take too much time to learn and manage.

These conclusions inspired us to design an app that would match our needs and make Sprint planning a comfortable, valuable experience for not only our team, but also everyone else who struggles with similar challenges. During the designing process we focused on collaborativeness and flexibility, creating an app that makes planning into an intuitive team experience. We’ve decided on a simple, transparent table view, with all necessary features and information at hand. That’s how our app for Jira, Team Planner - Resource Planning and Capacity Planning, came to be. 

How we elevated team collaboration and engagement

One of our main objectives was to let everyone plan together, and we achieved this by implementing a simultaneous edition feature. Multiple users can edit the plan at the same time by putting their workload on a time line, checking what capacity is still available for the team, or simply reorganizing work if necessary. All the changes are visible to others straight away. It helped to activate the whole team and make everyone participate in the planning process.

How we improved the adaptability of our plans

Issues can be easily moved around the table with an intuitive drag and drop feature, allowing users to assign tasks and modify their planned time frames. To quickly find the right issues during planning, we’ve added a list next to the plan. It can be filtered by project, sprint, issue type, assignee and status, or searched by text input.

How we perfected our plan transparency

Plans being accessible by all permitted users at any given time highly improved transparency in our teams. With any changes clearly visible on the plan we can be always sure that no new information gets lost in the noise of countless different platforms. All decisions land directly on the plan. 

We also made sure to support capacity planning to achieve better results when it comes to estimations and ad-hoc plan modifications. Users have their capacity summarized directly on the plan (available working days, number of assigned issues, total estimated time/Story Points currently assigned), allowing everyone to quickly verify user workload and make more informed decisions when assigning tasks. It is also possible to mark non-working days and days off to make sure they are taken into account during planning. 

How we learned to forge realistic expectations 

The new planning tool allowed us to significantly improve our planning process, and create plans that are more integrated with our daily work. It also helped us in adjusting our estimations to make them more grounded in reality.

Here are some of the positive changes we’ve noticed since we’ve implemented Team Planner into our routine:

• We create plans that are more in tune with all team members and their capacity. It translates into better work results, since we’re more likely to avoid overloading the plans with tasks. 

• Our plans are more accurate, allowing us to make more informed decisions. We’ve grown to trust our plans more, and use them as guidance while constructing high-scale goals.

• We now communicate and cooperate more effectively, since it’s easy to check the current status of work, notice any delays that need to be investigated, and make required changes depending on the situation.

With the right mindset and the perfect tool, our plans have become dynamic, living references that adapt to changing circumstances, consistently guiding us in the right direction.

Step 2: Time tracking and analyzing the results

Having made sure everyone can do their tasks effectively and use our new collaborative, transparent plans as a reliable guidance, we could finally comfortably track their logged hours, and generate time reports to monitor different aspects of our work or simply keep an eye on our projects’ budgets and have input for invoicing. For this purpose, we’re using another app of ours - Worklogs - Time Tracking and Time Reports. 

It utilizes native Jira time tracking, allowing seamless integration with our workflow, while at the same time providing comprehensive reporting features that enable monitoring a variety of different data combinations throughout different time periods.

In this particular case, we wanted to compare what the Original Estimate of particular tasks in a particular Sprint was vs how much time was actually logged. To do that, we’ve selected a project and a Sprint, and then set the following:

Categorize by: None (issues)

Group by: Assignee

Secondary Grouping: Original estimate

Using this report allowed us to verify whether our estimations made during the new planning process were accurate, and get a closer look at the hours logged to each issue along with their assignees.

The above example is just one of many possible time reports that can be generated with Worklogs. The amount of hours spent on a particular project directly impacts the project’s budget. Therefore, time tracking has its significant role in high-level decision making. Worklogs provide us with flexibility since we can create reports from different levels such as project, user or issue, and adjust their structure to the current needs. It also supports efficiency, allowing to create time report templates and sharing them with other Jira users. 

Data gathered in Worklogs also shapes our inner processes. We use it to analyze individual users’ time logs, compare different aspects of multiple projects, check hours logged to particular sprints, and more. By applying custom fields, we can easily track time for any aspect of our work we need.

Step 3: Staying in sync with tasks

Once we’ve established an effective planning process and integrated it with our time tracking, it all went nice and easy from there… Or so we hoped. Although the accuracy of our plans greatly improved, we soon realized that there is another issue, previously hidden beneath our problems with planning.

People kept on forgetting to log their time! And it’s impossible to track and analyze something that is simply not there.

To tackle this problem, we first tried persuasion and different types of reminders. It was somewhat effective, but took way too much time and effort to serve as a long-term solution. We’ve decided to investigate the roots of the problem, and it turned out that people are getting lost in all the different boards and projects in Jira, and are too focused on their tasks to spend the time counting hours and searching for issues to log their time into.

After pondering this problem, we came up with a solution. We’ve designed an app for Jira with a purpose of assisting users in logging their time - Time Assistant - Time Tracking and Workload Dashboard.

It was crucial for us to make an app that would be intuitive, easy to use, and serve the simple purpose of making time logging less burdensome. It does a few different things, all supporting this main premise:

• Gathers in one place historical data on actions related to the user or performed by the user. It applies even if the user is not assigned to the issue.

• Allows you to add issues to favorites to have them always close at hand.

• Allows you to quickly log time, and displays the sum of your logged time (daily, weekly, monthly).

• Supports automatic time tracking with timers accessible both from Time Assistant dashboard and from the issue level.

The addition of this app to our daily work made time tracking much more approachable for many of our team members. Here are a few things we achieved with Time Assistant:

• More users are logging their time regularly, since it now takes less effort to find the right issues. It is further supported by the active timers that allow the users to track the time automatically as they work, without the need to count and log every hour manually.

• For those who still prefer dealing with time tracking only once in a while, it is now much easier to retrace their steps, and see what issues they’ve been working on for the past week or month. With that information they can more accurately log their time even if they don’t do it on a daily basis.

• Being able to easily check the current status of their logged hours, everyone is more in tune with their time. Time summary serves as a helpful point of reference for those who tend to get lost in time while focusing on their work.

Streamlining the process of time logging helped both regular users who now find time tracking less overwhelming, and their supervisors who no longer have to waste their time on constant reminders. 

Turning burden into a secret weapon 

Transforming task management wasn’t easy, but it was worth every step. We started by rethinking how we plan, replacing chaotic and unrealistic processes with collaborative, adaptable workflows. Team Planner became our cornerstone, turning planning into a team effort with real-time updates and transparent capacity tracking.  

Next, we tackled the issue of time logging. With Time Assistant, we eliminated the stress of chasing lost hours, introducing features that make logging time almost effortless. Finally, Worklogs empowered us to dig deep into the data, comparing estimates with reality and uncovering insights that guide us toward better decisions.  

If you’re facing similar struggles, here’s our advice:  

1. Start with clarity - Make sure your plans are realistic and visible to everyone.  

2. Choose tools that work for you - Find or create solutions that align with your team’s needs.  

3. Keep it simple - The best tools are the ones that make life easier, not harder.  

With the right mindset and tools working together, you can turn task management from a burden into your team’s secret weapon.