How to Break Up a Project into Milestones

In response to my previous article How to Project Manage Part-time People, a commenter named Tristan Bailey asked me, “How do you break up the project or decide on milestones to keep everyone with a similar goal but small time?” That’s a great question and something that goes hand-in-hand with project managing a small part-time team. At Uncover, we’re five people, but only one out of the five of us is full-time, so picking good milestones and project managing is really important for us if we’re going to successfully push product updates.

One of the many hats I wear is the equivalent of Head of Product. That means different things to different companies, but generally it’s the job of the Head of Product to figure out what you need to build to be successful, while developing the roadmap and milestones. You make use of the feedback from your team and from your customers, together with your intuition, to determine what the best course of action is.

Communicating with customers, conducting usability tests, doing research, and so on are potentially a full-time job, but as this bundle of activities amounts to only one of my many roles, I need to prioritize what are must do’s ahead of everything else.
Determining a must do is actually a lot simpler than it sounds. Does your product absolutely positively need this feature, design, copy, etc., for you to not only ship it but for it to be successful? If it’s not going to add to the success of what you ship then it’s not a must do. When we’re talking about success, we’re generally talking about increasing our customer base and – more importantly – revenue.

Revenue is very important to us because, as a small company with few resources, the more money we make the more resources we can apply to grow our business. More resources generally means more hours and more hours means more money if we’re smart about how we put those hours to use. Nice to have’s don’t increase revenue and therefore should be tabled.

After I’ve gathered together the must do’s for the next update to Uncover, I get together with my team to discuss them. We don’t worry about the future beyond the next update, as we don’t have the time do so, so every question I ask them is simple: Is this something that we need to have or do to be successful in our next update? Everything that we agree on as a yes gets added to the project management spreadsheet and everything that gets a no is stored away in a Github Issue as tbd.

After we have our must do’s in our project management spreadsheet, our next milestone is set. Things will get added and removed during the production phase, but that’s unavoidable. Planning is now mostly complete, and then begins the development, design and project management phase. Proper planning and avoiding milestone bloat will really help you ship faster updates that have bigger impact.

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Spencer Fry

I’m a 29 year old entrepreneur. A Business Guy turned Programmer. Co-founder & CEO of TypeFrag ('03 - '07), Carbonmade ('07 - '11) and currently Uncover ('12+). Uncover is everything you need to start and run an employee recognition program for your company. My hobbies are squash, soccer, cooking, music, and art. You should follow me on Twitter.

Comments

5 comments on “How to Break Up a Project into Milestones

  1. “More resources generally means more hours and more hours means more money if we’re smart about how we put those hours to use.”

    I certainly agree! One step at a time with your great team to work for, I think you can hit your level of success.

    Anyways! Best of luck to your Team Uncover.

    • Thanks for reading!

      One step at a time is all you need to be successful. Too many entrepreneurs give up quickly after not seeing something through. It’s a real shame.

  2. I liked your article Fry. I have been a programmer more than 7 years and now wanna start my own products. I have my small team consists of 5 people and my plans get ruined when I get a new project from client.

    We are service providers and wanted to a product based company. Any advice for us ??

    Regards
    Adnan

    • Thanks for reading. I’m glad you like it.

      If you’re having a hard time finding the time to do the project, my advice would be to scale back your milestones to simple ~1-2 week sprints. If you try to do anything larger than that then it’s going to continue to drag on. It’s important for people with time constraints to set milestones that are simple enough that you can see the finish line before you even start. That way psychologically it’ll be easier to find the time to complete.

  3. Thanks for reading. I’m glad you like it.

    If you’re having a hard time finding the time to do the project, my advice would be to scale back your milestones to simple ~1-2 week sprints. If you try to do anything larger than that then it’s going to continue to drag on. It’s important for people with time constraints to set milestones that are simple enough that you can see the finish line before you even start. That way psychologically it’ll be easier to find the time to complete.