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: Jason Hanley has been developing commercial software since high school, and is the founder of PMRobot.com.

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

Planning

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.

Tools

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.

Wireframing

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.

Execution

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:

https://news.ycombinator.com/item?id=4910022

http://pm.stackexchange.com/questions/195/minimum-project-management-practices-for-one-man-software-projects

http://stackoverflow.com/questions/1523418/single-person-application-development

http://kiragiannis.com/business/10-tips-to-guarantee-success-on-solo-projects/

- John Mardlin

Perils Of Multitasking infographic

As a follow-up to my productivity post entitled "Multitasking is toxic", Peter Kim emailed me a great infographic with some stats about how bad multitasking really is for you.

Have a look:

The original can be found here.

Top 3 Worst Ways to Manage a Team

Five years ago, I wrote a short post about the worst possible ways to manage people. These are still popular techniques that managers often fall back to.

So what are these common management traps you should avoid?

#3 - The Ostrich Mentality

People fighting? Project running eight weeks behind schedule? New technical challenges are making success look unfeasible?

No problem! Carry on, business as usual. No need for change. Let's just keep doing things the way we've always done them.

This is what I call the Ostrich Mentality. Just stick your head in the sand and hope everything turns out alright.

What do to instead?

Admit problems frankly, have a discussion, and take action to change things.

Not tomorrow, but today!

#2 - The Ditch Digging Theory

This is when a manager believes that every task in a complex business process is equivalent to simple manual labor.

When a project is running behind schedule, they simply add more people.

This concept works fine -- if you are indeed digging a ditch. If you're doing anything more complicated, it fails miserably.

Adding more people to a project that is already late can actually make it take longer! I discussed the details in my post about keeping your teams small.

What to do instead?

Realize that business and information technology projects are complex beasts, involving specialized knowledge, and lots of communication.

If a project is running late, resist the urge to add more people to speed it up.

Instead, focus on trimming the scope to the bare essentials, and getting a solid deliverable out there. Then, create a follow-up project for the remaining lower priority pieces.

#1 - The Warm Body Theory

This one bothers me personally the most, probably because it is so prevalent and so toxic.

When managers have "warm bodies" (ie. people sitting in an office or meeting room) in their field of view, they equate this to productivity.

Nothing could be further from the truth.

If your employees are physically present at the office 10-12 hours a day, how many of those hours do you think they are mentally present, and actively contributing to the project?

Pulling five people into a two-hour meeting to "discuss the schedule" might burn $1,000-$2,000 of budget, and accomplish next to nothing.

What to do instead?

Make the schedule (the real schedule) and task commitments public and accountable.

Track everything in a live, accurate system that the manager, workers, and clients can access and update in real time.

Embrace flexible working hours and telecommuting. Let people balance their work and life commitments.

Once you've clearly defined what needs to be done, and who is responsible for doing it, you won't need to chase people down every five minutes for a status update!

Summary

To briefly summarize, here are the top 3 management "techniques" to avoid, and how:

• The Ostrich Mentality: Keep your head above the sand and take action!
• The Ditch Digging Theory: Don't add more people to a late project!
• The Warm Body Theory: Track accountability, and let people take responsibility!

---

About the author: Jason M. Hanley has owned a software consulting company for 9 years, and is the founder of PMRobot.

You are not 90% done

Have you ever had a programmer tell you that they're 90% done?

It happens all the time. Don't believe them.

I'm a programmer. I should know.

You see, there's a funny thing with software. It's very fluid, and can end up being very complicated.

For simple tasks, it's fairly easy to estimate the effort required, based on previous experience.

An example often used in project management literature is "digging a ditch".

If an average man can dig a 10 meter long ditch in 1 hour, then some excellently simple math can tell you that:

• That same man can dig a 20 meter ditch in 2 hours
• 30 men can dig a 300 meter ditch in 1 hour
• 500 men can dig 50 100 meter ditches in 1 hour

Unfortunately there are a lot of people that still try to apply this same logic to software development.

It simply doesn't work. Here's why. Let me tell you a little story.

Mark the Manager gives Peter the Programmer a specification for a new, complex feature in an existing, complicated piece of software.

Mark asks for an estimate, to which Peter replies, "Well, there are a lot of unknowns, but based on the spec, I think 2-3 weeks. Worst case scenario? 4 weeks."

Mark would like it done faster, but agrees to the estimated timeline and gives the green light.

Peter starts working steadily, 40 hours a week, with no vacation, personal, or sick time.

Here are his progress reports:

• Week 1: 35% complete -- Perfectly on schedule
• Week 2: 65% complete -- A bit behind, but still on track
• Week 3: 85% complete -- Uh oh, but at least we'll have it next week
• Week 4: 90% complete -- Ok, now we're late
• Week 5: 95% complete -- Customers are getting anxious
• Week 6: 97% complete -- Customers are irate
• Week 7: 99% complete -- Customers are leaving
• Week 8: 100% complete -- We are bankrupt

Disaster! What went so terribly wrong?

Perhaps the following visualization will help:

This is such a common curve in software development, it should have a name. If it doesn't already, I propose calling it the "Programmer Optimism Curve" or POC.

So what do we do to prevent this from happening? There is clearly no silver bullet solution.

I've written about my 5-step software development estimation method. That can certainly help.

The "story point" methodology from Agile can also work well when you have a long project with the same team members.

Jeff Atwood has some good suggestions about listing todo items too.

Of course, "knowing is half the battle," so now that you're aware of the problem, you can start taking active steps to keep it from sinking your ship.

- Jason Hanley

Forget Flagging Emails - Follow Up Then

I've recently been introduced to a great tool that's helped me in managing projects and fits perfectly into my personal workflow of how I deal with emails and keep on top of things where I need to make sure some action gets taken.

In the past, I flagged emails. First in Outlook and then a few years later using "Stars" in Gmail. It works pretty well. After I sent an email, if I wanted to make sure that the person that I sent the email to actually did something with it, I would go into my sent items folder and Star the email. Once a week or so, I would cycle through my Starred items and see if there were any messages I needed to follow up on…

Enter Followupthen.com. Before I go on. I don't know the people who developed this product and I have no affiliation with them other than being a big fan of their service!

Basically, you can send an email to 1week@followupthen.com, 3hours@followupthen.com, nextmonth@followupthen.com or any other description of time you can think of. After that set amount of time, you'll get a reply/forward from Followupthen (with the same subject line so that message threading works correctly) which basically brings that conversation right back into your inbox.

There's a few reasons I like this. But before that, I'll illustrate the two different ways that I use this service.

If I'm sending an email and I want to basically remind myself to follow up a week later (if I don't hear back from the recipient) it's as easy as BCCing 1week@followupthen.com. No extra action is required. I don't need to look up the email after sending it and mark it. The recipient has no idea about it and I can feel confident that if I don't hear back in a week, that email conversation will magically pop back into my inbox for me to follow up on.

The other way I've used the service is when I receive an email that I don't necessarily want to write back to immediately. Whether it's a good practice or not, I'm a big fan of a clean inbox. So when I get those emails, if I want to remind myself to reply 2 days later, I simply forward it to 2days@followupthen.com and then archive it. Again, it fits right into my workflow, which is what makes the service so useful.

The one downside or questionable part of this is that I am sending some of my emails to this service. I'm careful that nothing with even the mildest amount of confidentiality goes out this way. That being said, considering that Google and Apple basically own most of my information anyway, it's probably not too big of a deal.

Finally, aside from actually using the service, it's also been a good learning for me in terms of creating meaningful business solutions. The service is simple. It does one thing. And it does that thing well. The most important part for me is that it fits into my workflow and as a result, it was really quick to adapt to.

We are taking this lesson into account as we continue to improve PMRobot and looking closely at the workflow of project managers and software developers to ensure that PMRobot slips right into the way most people are working already! Have feedback about how we can improve PMRobot from a workflow point of view? Drop me a line at ramy@pmrobot.com.

Hard deadlines motivate people

The vast majority of people seem utterly incapable of doing anything until the very last minute.

Procrastination appears to be human nature, and tends to defy the best project management practices.

Whether learned or inherited, it's a very real phenomenon that project managers need to deal with on a daily basis.

Some managers try to jumpstart things by setting a "fake" deadline, a week or two before the "real" deadline, so that people actually start working on things and discovering unknown dependencies and challenges before it's too late.

This tends to work -- about once.

Then everyone clues into the trickery and ignores the next "fake" deadline completely.

Nonetheless, I've found that if you want something done, you need to set a deadline, and make people very aware of it.

In PMRobot, we've added a bunch of cues to remind people about deadlines.

The "Due in X days" text turns red at the 3-day mark. Ticket subjects turn bold and red at the same time. Reminder emails are sent out.

In project management, there's no easy way to fight the tide of procrastination, but I've found that it works best to:

1. Set a realistic due date. Make sure people know what it is.
2. Enforce the due date. Ensure that people know the consequences of missing it.
3. Communicate about the due date. Ask people regularly about their progress.
4. Don't push back the due date. Deliver on time, create a new milestone, and reschedule the missed work items.

How about you? What tools do you use for motivating people to keep on track?

Is email draining your productivity?

Mark Suster recently posted an article about "Why Email May Be Draining Your Company's Productivity."

Although I agree with some points, like batching email:

He suggest you never check first thing in the morning. He also suggests you only check periodically and leave your email off at other times so as not to be disturbed.

...I don't agree with this:

“I would far rather give out my mobile phone number than my email address.”

The good thing with email is that you can shut it off. I like to reserve my cell phone for urgent, time-sensitive communication.

Email, meanwhile, can be batched and processed when convenient.

And not all of it needs to be responded to. You don't really need to reply with "Thanks Bob" when Bob sends you the attachment you asked for.

So is email draining your productivity?

Probably, but there are some straightforward ways to be more effective. I wrote about "How to get people to respond to your email" a while back and suggested:

• Make emails as short and concise as possible.
• Write a concise, relevant subject line!
• Separate your short sentences into paragraphs with a space between them.
• If you are making multiple points, or asking multiple questions, put them in a numbered list.
• Edit your emails multiple times, and cut out unnecessary words and sentences.

Then on the other side, batch process your emails, as Mark (and Tim Ferris) suggest.

Hopefully those tips will help you tame the lion that is email :)

5 steps to estimate software development time

Here's an oldie but a goodie from my personal blog summarized for you here:

Estimating software development time is really, really hard. Here's my method:

1. Come up with your best, realistic estimate using your favorite technique.
2. Ok, you have your absolutely realistic number now, right?
3. It's not realistic. There are aspects you haven't thought of. Double the number. This is your best case scenario estimate, if there are no snags or major changes along the way.
4. Now double it again. This is your most likely estimate. This is how long the project will probably take.
5. Now double it a final time. This is your worst case scenario. This is how long is might take if you run into several major issues.

So to sum up:

• E = Your original time estimate
• 2(E) = Best case scenario time in reality
• 4(E) = Most likely time in reality
• 8(E) = Worst case scenario time in reality

- Jason Hanley

Multitasking is toxic

Everybody multitasks. But should we?

People consistently overestimate their multitasking ability.

There is huge power and efficiency to be gained by batching similar tasks, or "single-tasking" as I like to call it.

Email, social networking, and especially chat programs are notorious for breaking focus and concentration.

I discovered what a difference this makes when I was running my company from New Zealand and all my clients and employees were in North America.

There was a more than a 12-hour time difference, so I was essentially forced to track and batch all my tasks using an early version of PMRobot.

When I got up in the morning, the day had already ended in North America, and I was able to get work done with zero interruptions.

This resulted in a huge productivity boost!

As I'm writing this blog post, I have a number of tabs open for related material, but I've closed Gmail, Twitter, Facebook, and anything that could interrupt my flow.

I do the same thing when I'm programming. Before I open Eclipse to write code, I close everything else that's not related.

What time is it where you are right now? What major goals have you accomplished today? How many interruptions have you had?

Trust me, give single-tasking a try! I guarantee you'll be more productive.

You have to spend time to make time

"We're too busy to try something new."

Trust me, I completely understand.

Syllogistic Software used to have project information scattered across 5 different systems.

I would spend 8 hours a day emailing, and copying stuff back and forth.

There had to be a better way!

We invested hundreds of hours testing and tweaking a system to track and automate the repetitive stuff.

Soon, it took only 2 hours a day to manage the same number of projects!

Now you can benefit from this same system.

Think carefully about how much time you'll spend today doing manual project management tasks that could be automated.

Each month you delay, you could be wasting 100+ hours of billable time!

So spend some time today, and make time for tomorrow...

---

Ready to invest the time, but not sure how to get started? Post your questions here, visit PMRobot.com, or email me directly at jhanley@pmrobot.com.