The web-based project management software landscape can be described as a scattering of silos, oversimplified online tools that focus on one component of project management — time tracking, task management, invoicing. While holing up inside one of these apps may work well for some small businesses, many are finding them inadequate for their needs. Or their small business is evolving beyond the capabilities of the project management software, which feigns indifference to their growing needs.

There are some small businesses who have enough in-house time and expertise to string a few of these siloed apps into one complete tool, but still with moderate shortcomings. Most small businesses, however, don’t have this luxury. They are ready to move on, but not so far that they have to struggle with some bloated enterprise-level do-it-all software package. They need something in the middle. They need software that hasn’t really existed up until recently; middle-weight project management software that compiles the best features of the siloed apps into one online tool. The result is a more comprehensive project management application that can handle their business workflow from beginning-to-end, from starting new client projects to sending over the final invoice.

Considerations to take into account before spreading your business across multiple hosted silo applications

• Multiple monthly payments
• The group of silo apps used may or may not communicate with one another
• Multiple logins. One login per app, and per person using the app.
• Remembering which app does what. It might seem trivial to you, but will employees remember which app to use to track their time, and which app to use for sending invoices, and which app to use to update the last task they completed?
• Beware of the hype. The online hordes have a tendency to uphold each siloed app as the best and simplest project management tool ever. Listen to others, your Sancho Panza, who see the imaginary giants for what they really are.

Considerations to take into account before adapting your business to a more comprehensive hosted application

Project management is an elusive term that can mean multiple things to different people. Keep the following in mind before committing to an online productivity tool.

• Because they are more comprehensive, the workflow within an app is already loosely, sometimes rigidly, defined. Evaluate every feature to make sure it is a good fit for your small business.
• Evaluate the future of the app. Do they have a roadmap? How do they specifically address the shortcomings of siloed apps?
• Make sure your team is on board. Just because you love it doesn’t mean everyone else will. Get everyone on board and you’ll be far more productive.

Whichever route you take, be sure to consider the long term goals of your company and the portability of your data. Otherwise, you may end up committed to project management software that is not a good fit for your small business. Transitioning out of one app to another is a lot more difficult than starting out with the right one in the first place. Fortunately, there are more apps available online then there have ever been. Never has a small business had more options for finding the best project management software for needs.

Sam Barnes has posted a great article differentiating corporate project management needs from those of a smaller web design or development agency, while also revealing how much the two perspectives have in common. If you are struggling with managing web projects, read this article. Meanwhile, consider these wise words when dismissing the importance of planning out your next web project:

The truth is many small agencies and freelancers do not yet possess the skills to confidently plan a web project in its entirety. While I can only implore both to start learning, I do however feel this reason is often used as an excuse to dismiss web project planning as a “waste of time” (I really have heard this said with my own, rather large, ears. I swear I almost fainted).

» Read the rest of the article: Pragmatic web project planning.

Part 3 in a 5 part series

Create design boundaries

While there is no limit to creativity, there does have to be a limit to the number of design iterations you produce for a client. From both the client side and the production side, this is one of the most common areas for projects to run over budget—and we all know why. Design is highly subjective, and often a very personal preference; it is often difficult to intuit what a client will like.

The same applies for site architecture and the HTML/CSS/javascript layer of a web site. Even if not quite as subjective as graphic design, your team still has to design and develop these layers for the web site to capture the interactive intentions of the designers. This process can also take multiple iterations depending on the client’s opinion, and the variety of browser compatibilities required, so make sure you build in safeguards against infinite tweaks during development.

There are a few things you can do to limit guesswork and keep the client constrained within your agreed upon time and budget:

• Set a number on how many design rounds you will go through. A good starting point is to provide two or three unique comps with three to view revisions for the selected comp. While you may not always be able to stick to this, letting your client know there is a limit to the back and forth, or attaching a price tag to design round X through Y will require them to think more concretely about their design expectations.
• Explain to your clients that the web site will look different depending on each users browser and settings. Unlike print design, type-related issues such as word wrap, leading, orphans, widows, typefaces, etc, all have their limitations. Explaining these nuances to a client will spare you from conversations that start with “Our CEO is seeing the text differently and we need that fixed… can force the wrap after the words ‘yada yada yada’ to get rid of that widow?”
• Require constructive feedback. Clients often have a hard time speaking in design terms—“they just know what they like and don’t like.” But asking them to give specifics will not only make your job easier in providing the next round of designs, it will also help them identify what they are really looking for. If specifics are too much to ask, a great starting exercise is to ask them for examples of sites they like and don’t like. This will usually give you enough information to get inside their heads and extract their ideas into web site designs.
• Listen to your client, not your personal preferences. While your company was most likely chosen for its design and development experience, ultimately your job is to provide the best possible design for your client. Ideally, your style will be noted in the design, in the same way a record producer lends his sound to an album. The end result is a truly collaborative and satisfactory effort from both you and the client, work that you are proud to include in your portfolio.

Be firm, but also know when to get out of the way of a disagreeable client. Not all clients are willing to share your creative vision, and may insist on micromanaging the design process. This happens more often than we’d like, and often the micromanager doesn’t reveal themselves until the project is later in the design phase. If this is the case, choose your battles wisely. Often times it is better to just get through a project, like a puppet gets through a show, and move on to the next project rather than dragging this one out over pride.

How Pelago learned this the hard way

Most designers I have ever met, including myself, graduate from design school with this naïve idea they are going to change the corporate landscape through good design. The reality is most clients won’t understand ‘good’ design, nor will they want to. They just want to ‘like’ how the site looks. After a few years of frustration trying to convince clients of the expertise driving the design, I’ve realized my goal as a designer is to compromise with clients when giving life to their vision. I learned to read between the lines when interacting about design and present to them a blend of their ideas filtered through a designers lens. The results may not be award-worthy, but nor is our audience a jury of our peers; we are designing for our client and their customers.

I am a cyclist at heart. I ride everywhere I can. Work. Meetings. Coffee shop. Farmers market. But there are limits to my pedal-powered circumference, times when I have to jump in the family car and motor to my destination. The multitude of online time tracking, task management, and project management tools are of a similar purpose. There are the silo apps that operate much like a bicycle, connecting the dots between the few online needs a small business might have. And there are a new class of tools evolving, much like cars, designed to transport the small business into the great wide open more intuitively and efficiently than has ever been possible. (Before I continue further, I’d like to apologize in advance for beating the metaphor to a bloody pulp)

A bicycle is not a car

An example of this would be Basecamp. While it is a great task management program for getting small teams on the same page, it is not a project management tool. It will get you down to the corner store for some milk just like a bicycle would, but don’t think you can take the lane on the interstate with it. Basecamp just wasn’t built for this purpose, and they would be the first to admit it. The beauty of an application like Basecamp is that it has taught many small businesses how to use web-based productivity tools, creating a culture of customers unafraid to venture online. They’ve taught a market how to ride a bicycle, and now the market is evolving and asking for the keys to the car.

A car is not a bicycle

The inverse is also true, and Intervals would be an example. Intervals was built to do the extra hauling required by some projects — finance and time tracking, reporting, payments, expenses and invoicing. The goal is to pick up where other silo apps have left off and reach deeper into the market for small businesses who need more than a fleet of two-wheelers. With time tracking and task management at it’s core, Intervals is like a car with a bunch of bicycles loaded on the back of it. Not only will it get you to greater small business destinations, it also gives you the mobility to move about your immediate surroundings.

Every mode of transport has its alternative. The same is true with online project management software. However you choose to ride, the important thing is to be properly fitted with what works for you and your small business.

Part 2 in a 5 part series

Establish internal policies and procedures.

After you and your client sign the contract, be sure to keep it handy. Refer to the contract to manage your internal team, even if it’s a team of one. This will help maintain a professional relationship with your client. In our experience, it’s mostly been the buddy-to-buddy or “bro deal” projects that take a turn for the worse due to a lack of professionalism.

Determine who is responsible for each deliverable, what are the deadlines and milestones your team needs to hit. When you set up the various tasks for your team members, make sure they’re tracking their time against each task, and accurately recording their activities every day. If they spend an hour on design and an hour in a conference call with a client, those should be two separate time-item entries. Falling behind just one day, letting small bits of time slip between the cracks, or incorrectly categorizing time entries can produce fissures in a project.

Make sure everyone understands what their part of the project entails, including the client’s feedback. Then hold each one accountable for their work and deadlines. In the case of subcontractors we have found them most productive when we encourage them to track their time in our web-based task management system because it results in more collaboration and them getting paid sooner.

This will help you down the road when the client asks you where you are in terms of budget, or if she wants to know why a particular aspect of the project took so much time. You’ll have the information you need at your fingertips—often it is the client’s own requests that ring up a lot of time, and unless you track and document that time, you’ll have a hard time justifying your invoices. I can’t say this enough. Accountability is one of the key components to keeping clients happy and getting paid.

Freelancers should follow these guidelines as well. You wouldn’t allow another designer to spend twice the allotted time on a project assuming that someone else will “make up their time” in development, but it’s much easier to convince ourselves that we will somehow manage to “make it up later.” This often results in missed deadlines and twice the work for the same price—never a winning deal.

At Pelago, we keep track of our people. Since we’re a small business, we have weekly meetings at the local diner; where we go over each project, touching base with each member of the team to see how things are going and if there are any issues the rest of the team needs to be aware of. A followup meeting on Wednesday usually gets us over the hump and keeps the ball rolling until the end of the week.

How Pelago learned this the hard way:

Several years ago, one of our developers informed a client their web site was going to be the “Ferrari” of web sites, with all of the latest and greatest features. Once informed of this conversation we pulled the e-brake and reviewed the contract with the client to explain why that wasn’t the case, explaining to him that he’d been misinformed. The damage had already been done, however, and the client could not understand why he wasn’t getting everything promised to him by our developer. Despite a well articulated and agreed upon contract, the client demanded that we stay true to “our” word. Needless to say, the relationship did not end well.