The Art of Managing Complex Projects – Lessons Learned

November 12, 2021 |  By Alexis Sabor and Danielle Rossoni

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Calling all Project Managers! This post is for the Project Managers out there who may need some guiding principles for managing remote, iterative projects. By iterative projects, we mean projects that are subject to ongoing change and require collaboration and input to adapt over time. These tend to be more agile and less linear projects. How do you plan when the landscape is constantly shifting? Below are some of the best practices we apply at Transform Health for tackling large, complex projects that may only be clear in hindsight. Every project tells a different story and each project has its own unique set of challenges, but these tried and true tips in your back pocket can be incredibly useful over the project lifespan.


Use a shared project management tool that fits the needs of your team

Tracking tasks, deliverables, deadlines, and assignments for collaborative, agile projects is integral to project management. Think of the project management tool as a means to an end. It is not going to solve your problems for you, but it can corral the masses, get everyone organized and on the same page, and produce some spiffy reports when used proactively. These systems can be especially useful if the project deliverables are everchanging or if your project team has multiples phases occurring at the same time.

Agile development chart
Source: BaJau

In a traditional project environment (sometimes described as waterfall project), tasks, deliverables, deadlines, and assignments are often flushed out and sequenced before the project even begins. The project manager is responsible for ensuring this plan translates to reality and thinks ahead to anticipate problems, pitfalls, and deadline independencies. In an iterative, agile environment, this is not always possible in real-time. For example, you may have project milestones laid out for the next six months, but you can’t plan for any time beyond that until more information is made available by the project sponsor. This is the point at which you may create a “strawman” as they say, something to react to rather than wait until things become clear. In our work with health systems change, often there is no clarity until the end, so in these types of environs, you need to be willing to put your best laid thinking out there for people to react to, adapt, and change. The most challenging aspects of these types of projects is staying organized in the present while collaborating with your team on future phases – and the onus of this often falls to the Project Manager.

It seems obvious and straight-forward, but everyone needs to buy in to usage of any tool before committing to a tool. In our work, we find the use of a cloud-based project management information system (PMIS) is essential to our project management infrastructure. A good PMIS integrates with your existing systems, so you are not duplicating efforts (i.e., double-backing, or double-billing time). But finding the right tool can take some trial and error. For one of our projects, we originally selected a PMIS without input from staff, instead we focused on what the project manager was looking for. This became a challenge for us when the system we set-up did not meet the needs of the project team at large and we ended up moving away from our original tool. To help determine the right tool for our team, the project manager polled all staff on the most important features they would like in a PMIS, such as board views, Gantt chart exports and progress reports, and collaboratively we determined which system best fit our needs. Through this effort, we were able to build out a platform that functioned as our source of truth and was as flexible and nimble as we needed to be. More information on the PMIS systems out there can be found here. We are personally big fans of Teamwork Projects for the HIPAA privacy compliance features, but Smartsheets or Microsoft Projects are a close second. (To learn more about HIPAA see here).

If purchasing a PMIS is not possible, have no fear! There is a plethora of free resources out there to support you in project tracking. Some cloud-based tools have free versions – such as, Trello, and Asana. These free versions will have the baseline features needed to track, anticipate, and report out on work. If cloud-based is not your jam, Microsoft Excel have many templates to choose from – including Gannt Charts, Project Timelines, and Project Budgets. Pro Tip: working on a strawman for an emerging deliverable? We often use Excel internally to begin planning out anticipated scoping that may not be ready for prime time. That way we are still prepared to jump into new phases when we receive clarity.


Break up larger milestones into smaller, manageable goals

In big projects spanning multiple years with stakeholders from different sectors, it is simpler to work towards smaller goals, as in the whole is the sum of its parts, and you also get the added reward of completing something – which doesn’t always happen if you have one goal you are working towards. Think about your deliverables and what milestones must be reached to complete that deliverable. If one of your deliverables is enrolling 100 eligible adults in Medicaid, one of your first milestones could be hiring outreach workers. Now you can break down this milestone into tasks that can be owned and completed by members of your team. One person could oversee creating the job post while another is assigned to review applications. Make sure that all the tasks build up to the milestones. Another way to approach this process is to start with project workstreams and parse out what tasks comprise each workstream. You can bring in subject matter experts (SMEs) when the work is technical to understand how to break the work down. For example, your team is on a new product line, and you are not familiar with all the processes involved. Calling on a subject matter expert in that area will help you identify milestones, deliverables, and/or tasks for the successful completion of the new product.

Project waterfall chart
Milestone Approach
Workstreams chart
Workstream Approach

Automate consistent tasks whenever possible a.k.a. “workflows”

Workflows define your process, articulate a mapping of sorts for people to follow, and enable your team to track tasks and project progress. Visual learners require a workflow, but all benefit. Project managers benefit from workflows by understanding what you can and cannot predict. Most times, even agile projects will have some workflows that are repeated on a recurring basis. For workflows that will remain consistent, get into a rhythm, and set a standard the second you can. For example, if you know you will need to submit a report to the State every six months, map out those activities as they are determined. That way, when the time comes to do the work, the planning is already started. This is where those strawmen can help, too! Prepping what you can in advance will reduce the number of decisions that need to be made in a day (which research shows is important for productivity) and will save your energy for tackling less defined activities. You can also consult with subject matter experts or your Project Management Office (PMO) to get a handle on which workflows you can predict.

Recurring tasks can be automated in a PMIS so that you are immediately notified when you need to work on something. For example, if your team is responsible for developing content and facilitating a monthly stakeholder meeting, roles and tasks can be established the minute the workflow begins. You can set tasks that trigger you and your team to identify agenda items, manage meeting rosters, and these tasks will even have specific team members assigned to them. This level of consistency will come in handy when training new staff or facilitating knowledge transfer with departing staff.

Knowledge transfer is especially critical here. On one of our projects, we had a core team member leave without documenting processes for any of their ongoing work. As a result of this, the remaining staff had to take time to piece together what activities these workflows encompassed, which took time and energy away from components of project planning that were still in process. But once those workflows were built out and saved in our PMIS, we no longer had to worry about disruptions caused by departing staff – we had knowledge transfer built in. This will not only save the Project Manager time and energy, but it will also protect the integrity of your work because you will not be beholden to specific people.

Conceptual drawing showing knowledge transference between two individuals .

Adapt, Pivot, Rinse and Repeat

Don’t get too attached to your plans, stay nimble because as input is gathered over time, new information allows you to refine your goals and improve your end-game. Make adjustable plans by building in time to review and reassess tasks. Getting a project approved is a huge win, but any project’s scope can be subject to change. For example, external factors can result in the project getting extended or personnel changes could shift team priorities. Laws and guidelines governing your industry could impact costs or timeline. To mitigate the effects of change on your project, it is important to have a Scope Management Plan and Change Management Plan. Leverage the experience in your organization and any relevant subject matter expertise to forecast changes. To be transparent with your stakeholders, provide timely updates whenever possible. Changes can impact different stakeholders and they could have input that would further affect the project.


Plug into the matrix

There are a few mechanisms to assist in determining the work assignments. Organizing tasks with tools like MOCHA, RACI, and similar matrices allow the project manager to track the roles of members of the team are for each task and milestone. In this project, we leaned heavily on the MOCHA to keep track of workstreams and tasks. “MOCHA” is an acronym standing for Manager, Owner, Consulted, Helper, Approver. This role delineation can help break the project down into smaller parts while spreading the workload across the project team.

With any project, having people that work well together goes a long way to success. We are all experiencing new workplace environs due to the pandemic. With a geographically spread-out workforce different remote challenges arise. (See our blog post about remote work here) Virtually or in person, communication that is succinct, to the point, and as soon as possible is crucial. Your work culture plays an important part of a successful team. Ensure that all members of the team understand their work and learning styles. As project manager, knowing the strengths and stretch points of your team allows you to better delegate tasks and activities. Tools like the DISC assessment or StrengthsFinder give insight on how members of your team work. Communicate often with the team to ensure that they feel supported and have the resources they need.


Art, and Science

Project Management requires self-direction, assertiveness, and trial and error to find a groove that works for all parties involved. These key-takeaways can help you and your team find that groove:

  1. Implement a project management system that all staff are bought into and meets the needs of the project.
  2. Use milestones and workflows to break up the project into smaller, more manageable goals.
  3. Understand what you can and cannot predict. For tasks you can predict, remain consistent, get into a rhythm, and set a standard as soon as you can so your energy can be reserved for unknowns.
  4. Learn how your team communicates and use organizing tools to set roles and expectations for how staff work together.
  5. Stay nimble and remember, project management is best laid plans! Stay attached to your end-game, not the plan to get you there.

Contact Us

If you would like to learn more or work with Transform Health, please contact Heather Bates at