The Secret of Better Project Management: Timeboxes, Rhythm, and Incremental Value



It’s been a few years since I met with Loren Kohnfelder.

Every now and then Loren and I play catch up.

Loren is former Microsoft. If you don’t know Loren, he’s famous for designing the CLR security model and Internet Explorer security zones several years ago. He created a model for more fine-grained control over security decisions and he’s a constant advocate for simplifying security.

The last time we met we had some pretty interesting discussions.  You might think two guys that do security stuff would talk about security.

We didn’t.

We ended up talking about project management, blogging, social software, and where I thought next generation guidance is headed. I’ll share the project management piece.


I told Loren I changed my approach to projects. I use time boxes. Simply put, I set key dates and work backwards.

I chunk up the work to deliver incremental value within the time boxes.

This is a sharp contrast from the past where I’d design the end in mind and then do calculated guesstimates on when I’d be done, how much it would cost and the effort it would take.

If you are somebody that wants to change the world, or if you care a lot about quality, this can be a tough shift to make.

It was for me.

Because when you are thinking about big impact and, and you want things to be good, it’s more natural to think that “it’s done when it’s done.”

That’s how scope creep happens.  That’s how missed deadlines happen.  That’s how things never ship.

The key here is to chunk things down so that you can focus on quality, you can improve things through iteration, and you can accrue towards the bigger vision, but it will be rooted in reality, and it will be informed through feedback along the way.


This is all about getting the trains leaving the station.  If you miss the train, catch the next one, but establish a rhythm for shipping.

I use rhythm for the time boxes.

I use a set of questions to drive the rhythm … When do stakeholders need to see results?

What would keep the team motivated with tangible results?

When do customers need to see something?

I realize that when some windows close, they are closed forever.

The reality is, as a project stretches over time, risk goes up. People move, priorities change, you name it.

When you deal with venture capitalists, a bird in hand today, gets you funding for two more in the bush.

Incremental Value

Loren asked me how do I know the chunks add up to a bigger value.

I told him I start with the end in mind and I use a combination of scenarios and axiomatic design.

Simply put, I create a matrix of scenarios and features, and I check dependencies across features among the scenarios.

User stories, system stories, etc. are a simple way to chop bigger deliverables down into more discrete and actionable chunks of value.

I ask the following questions:

  • What’s my minimum set of scenarios my customers want to have something useful?
  • Can I incrementally add a scenario?
  • Can I take away scenarios at later points and get back time or money without breaking my design?

Sounds simple, but you’d be surprised how revealing that last test is.

With a coupled design, if you cut the wrong scenario you have a cascading impact on your design that costs you time and money.

Timeboxes, Rhythm, and Incremental Value

We both agreed time boxed projects have a lot of benefits, where some are not obvious.

Results breed motivation.

By using a time box and rhythms, you change the game from estimating and promising very imprecise variables to a game of how much value can you deliver in a timebox.

Unfortunately sometimes contracts or cultures work against this, but I find if I walk folks through it, and share the success stories, they buy in.

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  1. JD,

    Sorry if I have missed it – but is there more detailed information on this somewhere? Is it a system you developed? It sounds like something the would really work for me with my startup!

    BTW< I am amazed that you have success doing this in a big company like MSFT….you must be really good at being persuasive and effective 🙂

    I am also loving the book you recommended – Thank you for arguing…It is giving me so much insight into the relationships in my domestic life – I love it- so thank you 🙂

  2. Hey Maya

    Great questions …

    The best place to start would be The Zen of Results:

    Note that the PDF is short because it was a test of what I could do in 15 minutes or less, but it will get you going. I use it for myself and I’ve used it on teams of 2, up to teams of 10. I’m even using it for the project for my current book – the Microsoft playbook for Application Architecture ( )

    I drive a lot of project and I’ve run a lot of teams so the approach is from the school of hard knocks. For years, my manager valued time. He goaled me to chunk down my work and ship it incrementally. Meanwhile, our teams were early adopters of agile and scrum. Because I often had a distributed team, I needed to create a highly effective 40 hour work week and keep everybody focused on results. The challenge was, I was goaled on time, keeping people happy, and producing outstanding results. The growth years, were painful years.

    One of my toughest years was managing more than 27 vendors and managing a multi-million dollar budget for more than 20 projects. Something clicked that year — sort of like the secret of results. I shipped a key product, finished two books, filed 8 patents … etc. So much pain, created so much learning. After that, it was like having the secret formula for powerful days, powerful weeks, powerful months — but most importantly, work life balance. I learned more that year than another other year in my life.

    It’s an effective system. Vendors on my team that run their own teams use the approach. Here’s a story from one of the members on my team:

    I do need to cover the approach in more depth, and I will, but I think this at least gets you started.

    I’m very glad to hear that Thank You for Arguing is living up to expectations!

    BTW – one quick book that will change your life is The Dip. You can read it in a half hour but trust me, it will help you with your startup.

  3. “Results breed motivation.” Now, there’s a three-word quote that could well serve as my mantra.

    I guess I’m kind of doing the time-box thing (without having labeled it as such,) by setting a date for my Big Debut Show, which still is not firmed up, therefore making me a little antsy about the whole thing. And the clock is a-ticking. I know I’ve let windows of opportunity close for me, as I should’ve been on this sooner. I think mid-May would be perfect timing. You see, I’m still getting my musical chops together.

    Bla, bla, bla.

    Just Do It, Jannie

    The results of researching a good venue and setting a date should breed motivation, right?

  4. @ Jannie

    Setting a date is a very good move. I’ve noticed that the people in my life that are the best at getting results set a date and work backwards from it. I’ve noticed this especially with the marathon runners that I know. As much as they hate committing to the races, it ends up being their best motivation.

    I’ve always hated setting dates because I always wanted to wait until I was ready or it was good enough to share … and that’s exactly how not to ever be ready or ever finish. I’ve learned that lesson the hard way, and now I’m quick to set dates and chunk things up. Here’s how I apply it to my life — each new year I decide on a handful of experiences I want under my belt, and I decide which months I want them. I then workaround those. For example, in October I plan to be in Key West. Sure, it might change, but at least I have a nice warm vision in my head of swimming with the dolphins later this year 😉

  5. Time boxes sound like a very interesting idea! I did not realize that you are so good in what you do at work! I just got to know you better through this post. I was intrigued enough to check out your about-me page. You must be excellent in time management since you can find time to blog, on top of working, managing staff, writing books and mentoring others! I’ve got much to learn from you!

  6. @ Evelyn

    Thank you Evelyn for your kinds words.

    I have a lot of battle scars from many adventures. When I joined Microsoft, I went from a frog in a pond to a minnow in a big ocean. At the time when I joined Microsoft, there was a big emphasis on key success factors:
    – Results
    – Customer Feedback
    – Teamwork
    – Long-Term Approach
    – Passion for Products / Technology
    – Individual Excellence

    The sum is more than the parts. Individual Excellence was my favorite category of skill building.

    I had great mentors and models along the way, and I was constantly surrounded by people way better than me at all sorts of things. It’s how I realized I didn’t have to be the best at everything. Instead, I needed to make the most of what I’ve got and leverage the network around me. Again, the sum is more than the parts.

    I’ve learned a lot of things, and I’ll share what I’ve learned.

  7. Hey JD,

    I really like the synopsis and lessons learnt you write about books.
    Some of them I purchased after reading your insightful comments.
    It turns out that these books are proving very valuable.

    I am currently reading a book “Brain Rules: 12 Principles for
    Surviving and Thriving at Work …”.

    It is really amazing one.

    Thanks for your help and really appreciate your writing.

    Nilesh Joglekar

  8. Hi JD

    Sounds interesting. Looking forward to hearing more.

    You share so much of your experience – thank you


  9. @ Nilesh

    Thank you. I find books to be one of the best sources of profound knowledge.

    I’ve heard of Brain Rules, but I haven’t read it yet. I’m glad that to hear it’s amazing. I’ll add it to my hit list.

    @ Dror

    Sure. The simplest way to think of it is daily, weekly, and monthly results. Each day, think of 3 things you’ll accomplish. I just ask myself, what are 3 things I have to get done before I go home. Each week, identify 3 things that if you got done by Friday, you would feel like you had a great week. Each month, have a rough idea of 3 major accomplishments.

    Within each of these timeboxes, you’re biting off something you can chew. You’re basically using time to help figure out scope. This reduces a lot of risk. The opposite is to make up a laundry list of things you’ll accomplish and imagine that someday in the future you will be done. This is scope based. It’s very natural to default to scope based, dream up great things, and then get lost or frustrated along the way, simply because it’s incredibly difficult to estimate time.

    What I do is combine both. I dream big, so I have a vision of something to drive towards, but then I use time to chunk things down. If I ever get lost, each day is a fresh start … what are 3 things I must accomplish today? Each week, if I fell off the wagon, I can ask again … what are 3 key things for the week? Each month is a great way to see the forest from the trees … am I moving towards or away from the bigger picture.

    Because it’s an approach, and not a tool, it’s easy for me to quickly adjust based on how much or how little structure I want, as well as how much energy or motivation I have. The beauty is, being able to accomplish 3 outcomes each day, 3 outcomes each week, and 3 outcomes for the month, it actually builds momentum. It’s constellation of successes that support each other.

    @ Juliet

    Thank you. I hope to make this a continuously valuable resource for you.

    @ Bunny

    Thank you.

  10. Cool system JD.

    I think the reason it’s effective is that the brain is actually pretty terrible at judging how much we can get done in a set amount of time. The end result is that tasks will almost always take as long to finish as the time you’ve set for them. Consequently, tasks with no defined end point are very very easy to drag out.

    Also the amount of quality attention you can devote to something and give it your best is limited. So I think your time boxes idea works very well to get around this other limit of the big wet gray sponge on our shoulders.


  11. Thanks JD!

    Look forward to more on this in future posts!

    For me deadlines dates are always a motivator and usually met!

  12. @ Patrick

    You’re right. That’s the key. Estimation is tough. Even if it’s work you’ve done before.

    Drucker teaches us that people aren’t very good at knowing where their time goes. His key point is that most people think there time goes where it should go. It’s just like when people actually log what they actually eat for a week. There’s usually a big gap between what they think they eat and what they actually eat.

    The beauty of this approach is it’s boundary based versus dictatorial in how to run your day. It’s just enough routine and flexibility that it’s adaptable for just about any scenario.

    @ Diane

    Sounds good. I’ll have plenty more coming your way. Helping people get results is my specialty.

  13. I’d like to play the game of how much value I can deliver in a timebox. I love the concept of identifying key outcomes for the week every Monday and reflecting on what went well and what can be improved every Friday.

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