Friday, May 31, 2013

Top 5 Software Project Management Mistakes

Software projects are hard. Running out of time and budget is the norm, rather than the exception.

How can you prevent your project from ending in disaster?

Here are the top 5 mistakes you should avoid:

1. Following the Waterfall model

The Waterfall development model has long been considered fundamentally flawed for software development. It works for engineering projects in the physical world, but software development is very different from building a house.

Using the Waterfall model assumes that you know absolutely everything about the final system, before you even start.

Software is a living, ever-changing organism that grows and responds to changing needs and specifications.

A much better model is iterative development. This breaks the lifecycle of software down into many "mini-waterfall" phases that help you respond effectively to ongoing changes.

2. Insufficient upfront planning

In contrast, following an iterative process can sometimes lead to lack of sufficient upfront planning. It is tempting to start writing code on day one, before the problem is fully understood.

Instead, earlier iterative phases should focus on creating high-level documents explaining the "big picture" and major problems the software aims to solve. Depending on the complexity of the software, it doesn't need to be a full functional specification. It should simply have enough information to make sure everyone on the team understands what the software is supposed to do.

Next, it helps to rough out layout and interface details using mockups or wireframes.

Finally, before full implementation, it pays to build a "working prototype" that contains most of the user interface, but perhaps not all of the backend. This allows users to try things out and make suggestions when the cost of change is low.

3. Overly optimistic estimates

Programmers are notoriously optimistic when it comes to estimating how long programming tasks will take.

I blame this primarily on the "Programmer Optimism Curve" (POC) that I describe in the popular "You are not 90% done" article. This results from the actual scope being larger (often 4-8X) than originally expected.

I recommend being prudent and following these 5 steps to estimate software development time.

4. Adding too many people

Ever since the dawn of software development, managers have assumed that building software is just like building things in the physical world.

Nothing could be further from the truth.

In 1975, a brilliant computer scientist named Fred Brooks wrote a book called "The Mythical Man Month".

One of his many observations was that for a complex process like software development, you should keep your team as small as possible to reduce the total number of communication channels.

In fact, "Brook's Law" states that "adding manpower to a late software project makes it later," followed by the cheeky "Nine women can't make a baby in one month."

This holds true now just as much as it did when he wrote about it in the mid-70s.

5. Incorrect use of todo lists

Projects to-do lists often end up as a brain dump of specifications, questions to be answered, unapproved features, and miscellaneous chores that need to be done.

As I summarized in my personal blog, the best practices to make a to-do list work are:
  • Using verbs
  • Being specific
  • Grouping by context
  • Focusing on next
For a detailed account of why most todo lists don't work, and how to manage them better, be sure to read David Allen's "Getting Things Done" (GTD).

Summary and recommendations

In conclusion, to avoid making these common mistakes:
  1. Use an Iterative development model, not Waterfall
  2. Do enough upfront planning
  3. Make realistic time estimates
  4. Keep your team small
  5. Use the GTD methodology for todo lists
Following these guidelines will give your project the best chance of success.

About the author: has been developing commercial software since high school, and is the founder of

Friday, May 24, 2013

The Agile Boulder

I recently guest posted on Jim Ewel's great blog,, about creating roadmaps for agile marketing,
a technique I advocate for to help reconcile the potential for fragmented agile marketing campaigns.

Afterwards, Jim and I were discussing the difficulties of transitioning to Agile and Agile marketing. He made the good point, that there seem to be two different approaches to the organizational change necessary to implement agile practices. You can either go all in, or you can try to ease your way in.

Going all in means, taking the time to get full buy in from the executives and hiring a coach to guide the transition.

The other option is to easy your way in. Don't even use the words "agile" or "sprint" and certainly don't post up a manifesto! Rather, introduce one practice at a time and slowly reveal a better way of doing things.

My previous transitional effort was very much an attempt to ease the organization slowly into Agile. That experience led me to believe that it can't work. My conversation with Jim has me seeing it differently.

Organizational change is like moving a boulder

Introducing agile practices will only work if the processes aren't counter to the current culture. If the culture is in place, you're at the top of the hill. Simply apply a gentle amount of pressure; the boulder will gain speed on its own. Without the culture, you're in the wrong valley.  Outside help will be needed to help you get to the top of the hill and down the other side.

Where are you now?

If your culture already shares elements with the agile mindset, you can probably go with "easy does it". What does this culture look like?

- Shared accountability for delivering high quality products on time
- A collaborative approach between different disciplines
- A relatively flat structure
- Willingness to be wrong
- Adaptability

If most of these cultural elements are already in place, the processes will fit more easily.  Daily stand up meetings, visual task management and retrospectives won't go against the grain.  This allows you to make some small changes, demonstrate some easy wins and gain trust, before loudly declaring "WE'RE DOING AGILE NOW"!

If the culture you see around you doesn't so much look like that, you're not just looking at process changes, you're looking at cultural changes and culture comes from the top. In this case, you're better to focus on executing effectively under the status quo, building trust and slowly selling management on a better way of doing things. In this instance, you can benefit from the large volume of literature. The fact that "Agile" is becoming a buzz word can actually be your friend.

In this case, hiring an outside consultant is probably what's required to signal to the team the intention to change how people interact. Outside energy (the right outside energy) can also inject some enthusiasm around the possibility of a better way of doing things.

photo credit: cobalt123 via cc


Wednesday, May 15, 2013

5 ways to lose your job by "going agile"

 Yes, this is written from personal experience. With previous employer, I went to bat for the benefits of Agile project management. Though leaving was not a direct result of that effort, the relationship capital that I spent had a huge impact on my ability to add value. Eventually, I was clearly unhappy, they were clearly unhappy and we fairly amicably went our separate ways.

That said, the remainder of this post won't be written it in the first person. Doing so would  introduce too much of my own biases. Also, some of these points are slightly exaggerated from the actual occurrence so don't assume I'm as dumb as all that. 

I hope is that these hard-won lessons can be helpful to you in creating the change you want to see in your organization.  Regardless of  who you are or where you work, either as a project manager or team member;  in a large enterprise or a small consulting shop, in digital marketing or software development, I bet there's at least one pitfall I can help you avoid.

1. Complain about the current system

If you’re laboring under something like waterfall, or  a basic lack of project management processes, you can probably see that the grass is greener on the Agile side. If you're really antsy about it, you’ve probably read tons of great material at or maybe, and you know that things could be better.

Awesome, you are almost undeniably correct. But so what?

Bitching and moaning about the status quo is not a good way to create organizational change. Instead it’s a great way to create a rift within your team. Some of these people were involved in creating the current processes, conscious or not. Beating up on the these process doesn't make you look smarter than everyone else, it makes you look like you think you're smarter than everyone else.

Negativity begets pessimism. If you focus on what’s not working about your current project management processes, the natural tendency is to look for the downsides of any alternatives as well. Instead, paint a picture of the possibilities that you see for your team going agile.

2. Be stealthy

So, you’re using positivity to draw a compelling vision to get people on your side. Unless you’re an exceptional salesperson, you’re almost certain to get some push back. It can be frustrating. You might be tempted to just put up a taskboard in your office one day, in the hope that the value of making work visible will be immediately appreciated.

That can even work to some extent, it is really cool to actually see all the work in progress and in the backlog. But simply putting up a task board does not an agile team make. Assuming that everyone will follow your lead into agile is actually a very un-agile way of operating.

You’ve drunk the kool-aid and you know things can be better. Unfortunately, the truth is that things won’t get better if you don’t have proper buy in from the rest of your team. Take the time to have the conversations required to secure this buy-in, both above and below you. 

3. Get hung up on the software

When you’re at your most enthusiastic about the potential of transitioning to agile, it’s easy to get caught up in the fun of checking out all the different software tools out there. It is important, but it can be a distraction from the real issues.

A focus on software can easily devolve into a debate between the current “waterfall-y tool” and whichever shiny new “agile tool” you’ve got your eyes on. That’s not where you want the focus of your discussion. It should be about the processes used and cultural practices needed around those processes.

4. Drop balls

There’s nothing like an angry client or executive to put a damper on your efforts to create change. Never mind that things probably weren’t going all that smoothly in the first place; rational or not status quo bias makes it very likely that the blame will be laid at least partially on the transition to agile.

If you’re championing the transition, then you’re placing some of your own credibility on the line. Be aware of this, and be willing to put in the extra time and effort to protect your credibility by staying on top of information and deliverables.

5. Do it in a culture of fear

Take a look at your organization, and your own motivations for wanting to go agile. Maybe the agile manifesto speaks deeply to the kind of environment you’d like to work in. That may not be the case for the people around you. There’s a certain kind of safety in having a silo between you, and the developer two desks over.

Creating an agile culture requires that people step up and take responsibility for the quality of each deliverable (or story) at each stage of the process. Face it, your coworkers might not be cut out for agile.

If this describes your situation, it’s not worth the emotional energy required to fundamentally change the culture. Or more eloquently put:
Should you find yourself in a chronically leaking boat, energy devoted to changing vessels is likely to be more productive than energy devoted to patching leaks.

-Warren Buffett
Be open to the idea that Agile will never be a fit for your organization... then polish up your resume.

Doing it right

Having gone in depth about what not to do, here's a very quick list of how it should be done.
  • Be humble
  • Talk to people one on one about your vision, and what you see in it for them
  • Get outside help
  • Get training
  • Be honest about the pros and cons
  • Be patient, now might not be the time for your organization
Also, make sure to do your research, so you know what you're talking about. Here are some good starting points:

Agile Software

Agile Marketing

What do you think? Have you had similar experience or difficulty transitioning an organization to Agile practices? Any insights to share about how it should be done? Let us know in the comments.


Wednesday, May 1, 2013

A Guide to Effectively Managing Your Solo Software Project

This article will help you create some very basic systems for managing your solo software project. It won’t help you decide what projects are good ideas, or successfully market your software, but following its advice will make you more likely to get to a finished product, instead of giving up in despair.

Who will find this helpful?

  • a hobbyist or pro using their spare time to build something they want
  • an entrepreneur building a minimum viable product for a business idea
  • a freelancer building a web or mobile app for a client
  • anyone who wants to learn by doing

I’m sure many people are already on board with the need for some systems to help guide the creation of their software, but I can literally hear some of your bloodshot underslept eye-balls rolling in their sockets and saying “processes and project management systems are for the office, this is just overhead that gets in the way of getting stuff done".

I beg to differ.

Why you need a system

Even a simple project has multiple moving parts. It may be that you’re capable of keeping track of them all, but that requires effort and costs you brain power, your most precious resource for software development. The reason for this is known as the Zeigarnik Effect:

The Zeigarnik Effect is the tendency to experience intrusive thoughts about an objective that was once pursued and left incomplete (Baumeister & Bushman, 2008, pg. 122). The automatic system signals the conscious mind, which may be focused on new goals, that a previous activity was left incomplete. It seems to be human nature to finish what we start and, if it is not finished, we experience dissonance.

The take home is, unfinished tasks will trouble your worried mind.  Storing your tasks somewhere trusted and finishing them as fast (or faster) than you start them, will free your mind for coding.  A simple system will serve this purpose, while introducing minimal extra effort.

1. Getting Started

It may seem obvious to you what your project is; but until you’ve written it down, and explained it to a few people, you can’t be sure that it’s well defined. Figuring out why you’re doing this project and what your goals are doesn’t take long, and will pay dividends down the road.

Create a one-page project charter to outline the scope, objectives and people involved with your project.  Your charter should answer the following questions:

What are your goals?

Get high level, ask yourself WHY you’re doing this, and what success looks like. If it’s a freelance project, establish this with your client.  If it’s a side project, by straight up about it. Are you developing a minimum viable product to test a business idea or is it just something you think would be cool to see or make your life easier.

Who are the stakeholders?

Whose input is important to guide your project to success? Maybe it’s just you, maybe it’s potential customers or a client.  How will you communicate with these people? How much influence will they have?

What will the product enable you to do?

This is akin to an epic user story for your product. Don’t talk about how the product will do what you want,  focus on what you want.

A basic user story format is:  "As a <role>, I want <goal/desire> so that <benefit>". This keeps the focus on solving the problem and avoiding tunnel vision around specific features for solving the problem.  For example the epic user story for your product might be “As a bowler, I want to know how what I eat for breakfast correlates with my bowling score, so that I can always eat the right pre-bowling breakfast”

How much time are you willing to spend on this?

Particularly if this is a side project, it will almost inevitably take longer than you think. At the outset, we tend to see the work breakdown at very low resolution. Once you’re face to face with a particular task, you see the fine details and nuances much more closely. In one of the most popular quora answers ever, Michael Wolfe deals with the reasons for this very astutely.

When it’s no longer fun and exciting, will you keep plugging away, or will you accept the sunk costs and move on? Decide beforehand how far down the rabbit hole you’re willing to go.

2. Doing it and Managing it


Since you’ve already created a scope now you just have to break it down into manageable tasks, ideally things which aren’t much more than what you can do in a given evening or two worth of project time.  Keeping your tasks small will help you to see your progress and feel great when you check something off.   

Tasks that are further down the road, will inevitably be more ambiguous; no problem, as they come closer to being executed on, you can split them up further.

Write each of these tasks on a sticky note, we’re going to use them to fill up your personal kanban board.


The Kanban Board

Find a visible place in your workspace and put up a whiteboard. Keep your kanban board really simple with three columns: Backlog, Doing and Done.

There are two simple rules for using personal kanban:

  1. Keep your work somewhere easy to see
  2. Limit your work in progress. Typically no more than 5 tasks at a time in the “Doing” column.   

Both of these rules would make Zeigarnik happy; they ease the burden of how much you have to store in your limited grey matter and put it somewhere you can trust you’ll see it.

Even when there is extra space in your “Doing” column, have a bias towards finishing a task over starting a new one.  Only introduce new tasks into “Doing”, if everything else is stalled, and there’s absolutely nothing you can do to move it forward.  

If you’re waiting on a domain transfer, go ahead and start working on wireframing. Don’t create a separate column for stalled or waiting items, even if you’re not working on it right now, it’s occupying precious brain cycles.

Time Tracking

No one likes tracking their time, and most time tracking software makes the process even less fun, but if you keep it simple, it can help to give you very valuable data and improve your sense of how long a task really can take.

Use your personal kanban to track when you moved a task into “Doing”, when you moved it into “Done”, and how many hours you spent on it.  You can do this just by writing it on your stickies like so:

Setting up these tools adds minimal extra time to the initiation of the project, and will pay huge benefits by releasing your mind from having to track all these items and allow you to focus on the execution.


I do believe that wireframing and mapping out the workflow of your product are very much worth your time. We use Moqups, which is really user friendly and takes no time to figure out.

Version Control

Even though it’s just you, using version control will help you to undo your mistakes and create an easily trackable history of your progress.

Git Immersion is a great tutorial for setting up a git system. If you want a cloud based repository, with pretty graphics illustrating your branches and merges, Bitbucket’s free plan should be totally adequate for you.


Here’s the fun part, I hope that creating the charter and setting up your tools only got you more excited about the awesome code you’re going to write.  

This is your project, it’s not my place to tell you which languages, frameworks and other technologies to use, you know what works for you. Unless this is a project intended to help you learn some new technologies and frameworks, you probably just want to get going with the least amount of new learning required.

Scope creep is the great enemy of getting things done. If your imagination, your client or other stakeholders are introducing new and wonderful features to distract you, nip that in the bud.  This is why you created your project charter. Keep it beside your Kanban board, where you can see it and remember what you’d first set out to do. If the project drifts from the charter, make sure there’s good reason for it.

Keep moving, do what you can to make some progress every day to stay motivated.  

3. Releasing 1.0 and/or Closing

Maybe you release your 1.0 and this project blow up into a huge success and becomes your life’s work.  Or perhaps you’ve met the goals of your original charter, but you see potential to go further.

On the other hand, maybe you’re completely done with this piece of software;  it’s served its purpose of satisfying a client, or teaching you what you set out to learn, or is now serving you as a handy little tool.

Either way, upon completing the first version of your project, it’s worth doing some work to close it out.  The scale of this effort really depends on the project.

At a minimum, you should archive your post it notes somewhere safe.  When starting your next project, they’ll be useful for remembering what tasks and time commitments were required last time.

Now sit down, have a beer, and contemplate how awesome your shiny software is.

From D.A.K Photography

References and inspiration: