How To Manage Projects with More Than One Person

My last post on side projects turned out to be very popular, so I thought I’d continue the series with this follow up post.

We have all had our fair share of projects to deal with in every aspect of our working lives. In many projects, we are not working alone (nor should we be). The addition of a partner can be an excellent force due to enhanced motivation and sharing of work load, but it can also bring communication, accountability and planning difficulties which at worst can destroy a project.

After plenty of trial and error, I have begun following a system that keeps things simple and moving forward all the time. This approach will work for professional “on the job” projects as well as side projects of any sort. I use it to manage all of my small and large projects at work and at home, and this system easily scales to support more team members (within reason).

What I am about to describe is not a project management methodology (there are plenty of good ones), but rather an effective, step by step “how to” system of actions, dependables, and available tools. Best of all, this system works just as well when working with people remotely.

When beginning a new project with someone, here are some of the key questions commonly wondered about:

- What are we trying to achieve?
- What is the scope of work?
- How can we easily prioritize the work as we go?
- How do I know what the other person is working on?
- How will we stay accountable?
- How do we make all this easy to track? I am busy enough as it is.

Let’s begin.

Phase 1: Starting and defining the project

Every project should begin with a brief, 1-2 page “scope” document agreed upon by all parties. As it may change over time, I recommend using Google Docs.

In a new Google Document, give the project a name, title the document “<project name> Scope Document”, list the partners and when it was last edited and by whom (this is useful to be able to see in the document).

Next, add and number the major headings to the document that describe what the project is about, what the goals are, and the high level plan to succeed. Here are my typical headings:

1. Project Overview (2 sentences on what this is all about.)
2. Problem (What is the problem? Why does this project need to exist?)
3. Solution Description (How will this project solve the problem? Describe it in a few sentences.)
4. Goals and Time Frame (What are the specific goals? By when must they be achieved?)
5. Resources Required (What may be needed in terms of people, tools, time and money.)
6. Roles (What is the responsibility and role of each partner? Note that projects can differ greatly in terms of effort required and nature of role of the different partners.)

The body of each description should be kept as brief and succinct as possible. Use of bullet points and tables is recommended. Remember, this is not a pitch to impress anybody- it is a functional explanatory document for and your partner(s) to refer back to.

The next step is to better define the short-term milestones and resources required. I recommend using a new Google Spreadsheet for this.

In the first tab (name it “Milestones”), write out the major objectives that the project needs to accomplish over the next few weeks or months. Then group them according to expected completion. Depending on the size of the project, this can be split into weeks or months. For small projects I recommend doing this for the next 4 weeks ahead, and for larger ones 3 months ahead.

Next, create a new tab called “Resources”. For projects that require capital, create a basic monthly budget and add both a “Forecast” and “Actual” column to each month. (The actual column will only be updated when money actually changes hands). If no money is required, look back to the scope document and assess whether any other resources (e.g. help of a friend) will be needed and by when.

Once you’re all set up, on the same page as your partner and know what to go after, you are ready for Phase 2.

Phase 2: Managing work and making progress

This is the part when using a good tool makes all the difference. After trying plenty of project management tools over the years, I have to recommend one that beats the lot hands down: Trello. Trello has a killer combination of simplicity, visual understanding and functionality that other tools simply don’t match. And there is no learning curve either.

Register a new board for your project on and invite your partner. This is essentially a virtual whiteboard (a kanban board to be precise) where you can add lists (columns) and tasks (cells) that can be easily moved around. Names and number of lists vary from project to project depending on complexity, but here are the lists that I usually create right in the beginning, from left to right on the board:

General Backlog (all upcoming tasks not to be addressed immediately)
To-do: Sheraan (tasks I need to complete immediately/short term)
To-do: <Partner> (same as above for your partner)
Doing (tasks that are being worked on right now)
Done (completed tasks, awaiting team review)

Each task added to a list on the board should be succinctly described and always start with a verb, e.g. Research A, Prepare B, Start C, Write D, Contact E, Register F, Test G, etc. Try to avoid using the word “do” is it is often too vague and does not inspire specific action. Each task can have comments or files added to it if necessary. Once all of the tasks are on the board, take some time to prioritize them- highest at the top of the list and lowest at the bottom.

The Trello board is a work space that will constantly change and be updated. When you are working on a task, move it to the Doing list, then to Done when complete. As new ideas or issues pop up in the project, add new tasks to the board and reprioritize them all.

Note that I am specifically not mentioning email as a way to get things done. We are all snowed under with enough email as it is, and trying to use email to manage tasks in a side project is a sure fire way to cause confusion and lack of follow up.

Trello gives the team a fantastic way to immediately know what order to do things in, as well as full visibility on what each other are working on. As ground zero for management of the project, this workspace will be used and viewed on an ongoing basis.

Phase 3: Maintaining momentum and accountability

This is the most important Phase of managing a project successfully. The first step is to engender a sense of personal accountability by checking your project status often (I recommend at least once in 3 days). This involves a quick viewing of the Trello board to see what has changed and what hasn’t. If tasks are not moving across the board, your project is stalling and rapidly losing momentum. All parties need to be realistic about the need to achieve a certain rate of progress in order to succeed.

In order to foster strong communication and joint accountability, schedule a weekly one hour meeting with your partner that you can both stick to. Try not to move this meeting around as it can undermine commitment to the project. During this meeting, start by going over the tasks on the Done list in the Trello board and if satisfied, archive them so that they are removed from the board. Next, evaluate the priorities for the week ahead and adjust the board as necessary. This type of review session will make it very clear if the work is getting done.

At the last meeting in a month, perform an additional review of the monthly milestones Google spreadsheet to see how you have fared. Learn and adjust these as necessary. Then update the Trello board once more.

It is crucial that you physically review every work item completed during the week together as a team, and mark off completed items. It is woefully inadequate to simply discuss things without reviewing the written to-do items and milestones, as talk is often a cheap excuse for lack of effort and progress. This trap is especially easy to fall into when both parties have slacked off on their responsibilities. Remember, a light discussion about work not done may make both feel better, but it will kill a project. If you fall off the wagon so to speak, it’s much better to stare at that truth in the mirror, admit it, and get back on with it as soon as possible.

Make these meetings sacred. If one party can’t make it, reschedule it during a time that works for all. If one party misses a meeting twice in a row or doesn’t seem that interested, they need to restructure their role or be cut from the team.

If you keep repeating the process described in Phase 2 and Phase 3 over and over, it is guaranteed to produce real, ongoing results!

To recap, here is a summary of my project management process:

1. Write project scope document with specific overall goals. (Tool: Google Doc).
2. Define short term milestones; weekly or monthly depending on scope. (Tool: Google Spreadsheet).
3. Prepare project budget/resources needed, forecast and actual. (Tool: Google Spreadsheet).
4. Set up Trello board and add upcoming tasks. (Tool: Trello).
5. Use Trello board on an ongoing basis as work is done.
6. Attend weekly meetings to review and update Trello board, as well as project milestones and budget once a month. (Tool: Skype, phone, coffee shop, apartment).

Final thought

The greatest risk to any project usually is not a poor outcome, but instead a lack of any outcome at all due to abandonment. Most people don’t finish the projects (especially side projects) that they start. Before committing to a project with a partner be sure that both parties are motivated, dependable, and taking things seriously.

While it is no replacement for committed hard work, I do hope that the system I have described makes the process of executing your next project simpler, faster and more rewarding.