How To Start A Project: Setting Up Your System

Much has been written on managing projects. From Six Sigma to Agile Methodologies, there are many robust and specific perspectives on how to define goals and work with others to achieve them. Each is helpful, but I’ve found that solid, and simple introductory versions are hard to find. It’s hard to know where to start.

Here I share the system I’ve used over the past 10 years working in research and on change management initiatives at IBM and WeWork. This article is a how-to guide on setting up project foundations using a framework that is creative, insightful, and most important of all, useful.

What do you mean by “project”?

A project can be anything and everything. Usually, a project is composed of many related tasks, and when it’s done, you have something meaningful you didn’t have before. Installing shelving in your kitchen is a project. Hammering in a nail is not. Installing shelving is a project because once it’s done, you can enjoy it, put books on it, and feel like your life is better because of it (depending on your kitchen setup). A project has a purpose, a difference it’s making.

A project is a set of actions that collectively improve an aspect of a specific audience’s experience.

Don’t do a project unless you can put your finger on the difference it’s making and who the difference is for. That’s not a project. That’s busy work. Don’t waste your time on things that don’t make a difference for anyone.

Find the story behind why the project matters and you’ll have your purpose. That’s the thing that will keep you and anyone you’re working with motivated, focused, and clear on who is doing what and why it’s important.

STEP 1: DEFINE YOUR GOAL

What do you want to achieve?

I wrote another article on creating a vision statement and goals that I recommend reading as you think about what you want to achieve. Be smart about framing your goals. It’s the shelf that everything else hangs from, your north star, your reason, your story. Don’t take it lightly, but do be adventurous with it. This is the thing you’ll stand behind that makes you proud. Once you have this, you’re ready to start thinking about the timeline.

STEP 2: CREATE THE TIMELINE

Following the goal, the most important part of starting a project is to map out when work needs to happen and what factors affect that work. The timeline becomes a communication tool.

Get 5 sheets of paper

Get 4 sheets of 8.5” x 11” regular printer paper and one 24” x 36” post-it or similarly sized piece of paper. I think best with a giant sheet of paper, which is how I’ll explain the next few steps. I love how it feels to draw lines and cross things out. I like creating something messy as I think, which I then turn into something simple, clear, and capable of making people’s work easier. Allow yourself similar creativity and flexibility.

Now, list out your constraints

Constraints are your luxury. Seriously. Artists like Twyla Tharp describe the value of constraints. The more you have, the better you’ll be and the more you’ll grow and learn. Here, they help you get it done. Start by listing out all the external factors that constrain you/ necessitate getting the job done (i.e., we rented an event space on November 15th or we only have $200 to spend) on one of the 8.5” x 11” sheets of paper. Whatever it is, write it out. Err on the side of more being more here. No one needs to see this and none of this has to go into your plan. Not yet anyway.

Spend 15–30 minutes analyzing what you’ve written. You’ll likely notice 3 categories emerging:

• Milestones, the markers of progress/ key deadlines.
• Requirements, things your audience needs (requirements answer the question: what needs to be true or what needs to exist at the end of the project?).
• Dependencies, factors that affect your work, be them organizational, financial, etc.

Now, let’s take them one at a time as you build out your timeline.

Lay out your milestones/ deadlines

Start by creating a grid on the large sheet of paper. Along the top is time shown in one-week increments, starting with today on the far left and extending out to the right no more than 3 months. In the image, you can see I’ve mapped out only 2 months. If your project has a longer timeline than that, I encourage you to focus on what would need to be done in 2–3 months and articulate that as your first goal. Go back a step and edit if you need to. I say 2-3 months because it’s hard to plan meaningfully further away than that. Too much changes.

Now, start to lay out the constraints from your list that fit into that milestones/ deadlines category and fit them into the top row of your timeline grid. Leave the bottom blank for now and set aside your list of constraints. Now, that you’ve copied over relevant constraints, start to add other deadlines that you might not have noted while writing constraints. If your project involves a big event make sure you write that on your large sheet of paper. If you have to meet with a few groups of people one week, put that on there. Now start to think about what needs to happen to lead up to each of those deadlines. This is not yet the moment to make a comprehensive to-do list, this is the moment to list out things like, “oh, we need 6 weeks to get a permit for XYZ, to put on the event.” In this example, you would put “get the permit” 6 weeks before the event. You are adding to-do items that have time-dependencies.

As you’re doing this, you might start to feel stressed about not knowing how long something will take, but you know it needs to happen. Or you might feel anxious about not knowing all that needs to take place, that’s ok. Again, write what you know. Take your best guess and remember that things usually take more time than you think. My rule of thumb is to take my best guess and add an extra 30%. So if I estimate something will take 3 weeks, I make it a 4-week timeframe.

Now take a step back and notice patterns. Is everything happening at once? Do you have lots of things happening the next 2–3 weeks but very little that needs to happen after that? Do you have many milestones related to one particular aspect of the project? That’s ok. Document those reflections on a fresh 8.5” x 11” sheet of paper. This is your summary of what you know and a sneak peek of getting closer to identifying what you don’t know.

Now take a breather. Usually laying this all out is exhausting because you start to see all the work ahead of you and you start to see the depth of what you don’t know. It’s part of the process if you’re doing it right. Eat some marshmallows. Go for a walk. Visit a friend. Come back to the rest later.

Next, we’ll start to fill in the gaps and give it some more structure.

List out requirements in the form of micro-goals

Now that you’ve got an initial sense of what’s happening when, go back to your list of constraints and focus on the requirements. What do the people you’re serving need? What are specific things that will solve their problems? These questions are best answered in narrative form. Using your initial list, use another sheet of paper where you write out things like “the client needs a communications strategy” and then “the client needs an assessment of how their communications are doing today”. Within each one of those things that a client needs, is a series of smaller things. List those out. You’re basically taking your initial list of constraints and building them out into a series of micro-goals that meet the requirements of your target audience. Your requirements are things that need to exist and micro-goals are the things you’ll do to address those needs. While you created a timeline already, write these micro-goals out without thinking about time just yet. And if you want to be an overachiever and think about time, just hold off for now, you’re overloading your brain. One thing at a time. This is where you’re making the to-do list specifically for the audience your project serves. Keeping in mind the shelving in my kitchen example, the audience benefitting from your project could be you.

Now that you’ve written out the micro-goals and the tasks that need to be accomplished to achieve all of them, take a step back and notice patterns. Notices micro-goals that are related. Notice how the micro-goals address or over-address the audience's requirements. Notice where the requirements haven’t been fully addressed by the micro-goals. Edit your micro-goals and tasks within the micro-goals to better address the requirements.

Now go back to the timeline you started while working with milestones. List out the requirements and micro-goals along the left side of the timeline in the space beneath the milestones. Each requirement should be a row of its own. Add the task-like things you wrote before while working on milestones to the row where it belongs in line with the requirement. At this point, don’t get so concerned about the terminology of the work (i.e., micro-goals vs. tasks). I’m using the language to help you approach planning from a few different angles to get as holistic a plan as possible. As long as you’re getting that part right, you’re doing great. That said, if you have tasks that don’t belong in a requirement, ask yourself if they really need to happen or not. Again, don’t do busy work. Busy work has a way of creeping in and looking at a lot like important project work.

At this point, you are probably starting to feel like things are clicking, you’re starting to see the project plan come together.

It’s a beautiful thing. Eat some more marshmallows and celebrate.

List out dependencies

As you look at the whole, ask yourself three questions:

• Who else needs to be involved besides me?
• What needs to be true in order for us to take action?
• Who owns some system that is affected by this work?

It might be really simple, like “I need time the week of Oct 27th so I should make sure I don’t have a lot of meetings then,” or it might be more involved “I need to figure out who will lead the design, and get budget for them to join the team.” Dependencies are where you identify things you need from other people, and you start to understand and hold yourself and others accountable to the limits of time, space, and ownership.

Write out your dependencies on the third piece of paper.

Bring it all together

Now that you’ve considered all these things, edit your milestones and requirements, and add dependencies to your timeline. Dependencies will likely come in the form of to-do items on your timeline (i.e., ask Dave how to get a permit). Try your best you can to align them with the correct requirement and milestones that they affect.

STEP 3: CREATE YOUR PROJECT CHARTER + PROJECT PLAN

Create your project charter

A project charter is the wrapper for the project plan. While you’ll use the project plan the most frequently, you’ll want the project charter to define some other key components of the project, like who’s involved. The project charter is where you also distill and build out the other work you’ve done. I recommend using a google sheet and having your project charter in one tab and your project plan in the other.

Using your handwritten timeline as a guide, start to answer the following questions in your digital project charter template.

• What’s the project goal? What problem is it solving?
• Who has a vested interest in the success of this project?
• What indicators can you identify that will tell you if the project is successful or not?
• Who is on the core team? What roles do they play?
• Who is consulted by the team/ is on the extended team?

If answering these questions feels overwhelming and perhaps even impossible, that’s ok. Start with what you do know. On most projects, the answers to these questions change. Arguably, the answers should change, that is, if you are indeed learning and listening as you go.

Create your project plan

With your project charter created in one tab, start to turn your handwritten timeline in a digital format in the second tab. Pick something malleable. Pick something that can change because you’ll need it to. Pick something you like to look at, that other people will like to look at. There are also tools like Monday.com that work for this kind of planning. What’s important is showing what is happening and when. Many project management systems are more oriented towards task management rather than planning, so keep that in mind as you reference other options.

Get feedback: Part 1

Until this point, you’ve been working on your own. You’ve created much of the container the team needs. But as I mentioned before, you don’t have all the information, so now is a good moment to get it. Schedule two meetings with key people.

In the first meeting, bring up what you’ve created on a screen and talk them through it, starting with the framework of the goal, the constraints, and the broken down into milestones, requirements, and dependencies. You want them to correct things. You want them to move and add things, or even redefine the goal. You are wiser and more successful for it.

It’s important for whatever you show to be polished enough that people see that you’ve created a container for them to rock around it, but still rough enough they understand they can change it. Take copious notes and push on the questions they raise. Encourage them to give full answers, and draw them out.

Note: Depending on where you are in the organization, you might have the first meeting just with the core team and the second meeting with a broader audience and you run it more formally.

Validate: Part 2

Now go back to what you have created, and update it based on the feedback you got. Polish it up, make it look nice, and revisit other templates or Google examples to see how you can make it better. Once you’re ready, reshare the materials and have your second meeting. In that second meeting, review what you integrated, show them what you changed, calling out how it reflects their input.

You’re set up, you’re good to go, and with any luck, you’re feeling very proud. You should be, getting to this place requires a lot of work.

You have successfully initiated a project and created foundations that will keep you and everyone else focused for the next 2–3 months. Yay. Now give yourself another treat.