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How to manage project timelines

Projects often get out of hand. They run over time or over budget. Many end up not getting completed at all. This has happened to everyone - myself included. Each project that I jumped into and started work without running through my system to fully understand the project ended up poorly. Poor initial planning, not knowing why the project is underway and what needs to happen in depth were some of the causes of projects running over time or budget. Other times loose project expectations proved problematic when defining what done was.


The majority of project issues stem from one thing: communication. Communication is important in all aspects of business, and even more so when you have multiple stakeholders collaborating together. It might seem un needed, but I believe everyone involved in the project needs to know at a minimum: why you are doing the project, what needs to happen, what the goals are and what the next step is to make it happen.


Below I outline six ways to help manage project timelines. Three of these methods are proactive, meaning things you do before the project is fully underway. If your project is already underway, you can implement the last three methods to benefit your project at any stage. Lets dive in.

Run a project planning session

This should be the first step of any project. I have learned this method from GTD by David Allen. Use the steps below to help run a planning session if you are unsure where to start.

1. Identify purpose of project and principles.

  • Why are you doing this project?
  • What guidelines are in place to help you along the way?

2. dentify vision / outcomes.

  • What is the end goal of the project?
  • What changes will be made?
  • How will this impact your organization?
  • How will this impact the client?

3. Brainstorm.

At this phase, use the no bad ideas brainstorm. Encourage your team to speak anything that comes to mind. There are no bad ideas. You need to get everything out there. Eventually patterns will start to emerge. Thats when you move onto step four.

4. Organize.

Now that you know why you are doing the project, what needs to happen and have a wall of ideas to make this happen - organize the ideas from the brainstorm phase. Identify which ones are best, which ones are not the way forward.

5. Next Step

Identify the next step that needs to happen with this project.
Often this first step is skipped - leaving it up to contractors or team members to figure out. It is important to do this step within your organization to get started with your best foot forward.

What this does

Identifies why you are taking on the project, the goals, and the steps that need to happen.

Run a discovery session

This is about the deep dive. If you ran your project planning session, you now have a good overview of why you are doing the project, what the end goals are, and what you are going to do. The next step is to run through a full discovery session. This can be done with your team internally or with an outside contractor. Best results often come working with an outside contractor. Why? You cant see the label from within the jar. Often times we become so set in our industry that our focus becomes narrowed. A fresh perspective is important to ask questions you assumed you know the answers to. Here are the general steps of running a discovery session.

1. Understand the problem.

2. Generate new ideas.

3. Converge on solutions.

4. Create roadmap.


What this does

Dive in and explore the problem at hand in more depth. If this looks familiar to project planning, thats good. A discovery session takes the project planning session to the next level.

Create a project brief.

I started writing project briefs for all my client work a few months back. At first I thought it was kind of silly. Often times it‘s just me doing the work, or I work with a small team. Communication is easy. Why write this out? Turns out - when you put something in black and white, a bunch of questions come up you did not think to ask. Assumptions that you had made get challenged. What I thought, may not be what you thought. Here is what goes into a project brief.

  • Summarize the goal of the project
  • Identify target audience / users
  • Plan parameters / considerations
  • Identify checklists
  • Identify milestones
  • Identify delivery specs
  • Identify task assignments
  • Share project brief - everyone is on board. Super important. Share with your clients, your team, whomever is involved.


What this does

Breaks the project down into chunks. Sets clear deliverables and timelines. Manages expectations. Provides clarity on process. Everyone knows what needs to happen from start to finish.

Have regular updates

Have weekly updates. Most projects end up off the rails due to poor communication. Check in to update a client or coworkers, built trust, identify issues and resolve them as soon as they arise. Here is the format I use for weekly check ins.

  • Work done this week
  • Work planned for next week
  • Any challenges I am facing
  • Any questions / big decisions we need to make

Lock completed milestones

After a milestone is complete, lock it. This means you prevent change from happening further down the project having you to redo the work. If you need to go back to a previous milestone - Communicate change implications. Budgets will be changed, along with timelines. This is especially important in creative projects where phase two, three and beyond depend on finalizing phase one. This waterfall methodology has gotten a lot of bad press lately, but it is a great method for getting work done that requires sequential completion of events.

Cut features / minimize objective

If things are not going according to plan, make sacrifices. To quote Jason Fried -“Its better to make a kick ass half, than a half assed whole.” When your project is dangerously running close to over budget or time take some steps to pair it down. Cut out non primary features. Lower the objective if you have a deadline that needs to be met. What can you accomplish and still hit the project objectives? Its better to have a solid project completed on time or on budget then to run months over and deliver on something that the team or client is just completely frustrated with.

Overview: Plan / Communicate / Set expectations / Understand

As a recap, here are three things you can do prior to a project start to manage timelines

  • Run a project planning session.
  • Run a discovery session
  • Write out a project brief


In addition, here are three things you can do during a project o help manage timelines

  • Have regular updates
  • Lock complete milestones
  • Cut features and minimize the objective.


Have you had a project that ran spectacularly? What about the way you approached the project made it such a success? I want to know! Please send me your project success stories to: edward@dock90.io - I look forward to reading all of them!

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Edward