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How to Choose Project Management Software for a Small Business

Warren Mayer
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Your small business thrives when work gets completed on time or (even better) ahead of schedule. In fact, you’re one of those successful SMB owners who consistently wows new customers by under-promising and over-delivering. However, as you grow and seek to move profitability to the next level, you’ve begun researching the best SMB project management software to meet your specific needs.

That’s a smart move.

All too often, as a small business begins to take off on its way to becoming a medium-sized business, communication snafus and ambiguity as to employee roles and responsibilities take a toll on efficiency. “I’m sorry, I thought you were taking care of that” becomes a frequent refrain. Customers begin to take notice. The need to automate various processes makes itself apparent. Your whole business begins to groan under the weight of “Not Enough Time.”

No need to panic. Nowadays, there’s no shortage of options to answer an SMB owner’s need for project management software. The trick will prevent you from becoming overwhelmed by choices. Here are some simple ways to help you thin the herd.

Five Things To Do

1. Conduct a thorough, mission-focused needs assessment.

While you obviously can’t predict the future, you do need to plan for it.

One common temptation is to jot down a few immediate needs and start searching online for freebie software. While this approach often can meet an immediate need, it’s probably not a successful strategy for the long haul. It will pay significant dividends further up the road to jot down primary concerns, yes, but couple that with a bit of daydreaming.

As your small business grows, what would you like to be able to accomplish quickly and painlessly? As you target various pain points and procedural problems, these specific issues should inform your ultimate choice of platform. Separate your identified needs into at least two piles: “Must Have” and “Nice to Have.”

2. Test-drive some inexpensive (or free) solutions.

In all likelihood, the research phase is where you will spend most of your time.

Budget plenty of time for you, your employees, and (if applicable) select customers to interact with the new technology and provide you with ideas and feedback. Compare the systems you are considering against existing procedures.

Guard against “test-drive fatigue” by scheduling select times for this across at least a few weeks. You will want to take copious notes or delegate this to someone more skilled with note-taking than yourself. If you attempt to cram all your research and evaluation into the space of a few days, you may be more prone to picking something just to stop your head from spinning.

3. Compare associated costs against paid staff time.

Are you looking into SMB project management software because someone you respect suggested it? Or do you really need it to meet current needs? It’s easy enough to be wowed by recent advances in project management software to the point that you lose sight of what you actually need in your specific context.

The best way to ensure you aren’t entering into the project management software fray ahead of time is to put numbers to the issue. Will future efficiencies meet or surpass the cost of the staff time you lose to miscommunications and project delays? Reading a few case studies for larger businesses can help you appropriate principles and extrapolate them to your SMB.

4. With any vendor, let your initial ask be big.

Assume that you’ve landed on the right product and ask for whatever will work best for you. Let your primary goal be allowing your best employees to retain what’s working well and adopt the proposed solution only in areas currently proving problematic.

For example, one of your most productive employees may be using Slack to keep track of their work-related tasks. Will the system you’re considering integrate with Slack? Many do, but not all. While you might be unable to accommodate every individual’s preferences, the more significant point is not to lose existing efficiencies as you roll into a new system.

In a perfect world, the project management software you adopt will enjoy immediate acceptance by 100% of your existing staff. However, if you encounter multiple instances where your best people are being asked to throw away applications they use daily, your system might introduce problems rather than solve them. Proceed cautiously.

5. With any paid solution, talk to current and former clients.

Of course, nothing beats experience. If you can’t get a firsthand referral from a current customer of the platform you’re considering, cast a wider net. You will want to hear frank accounts from existing customers in addition to the client contacts a vendor provides, if at all possible.

Assume any platform has imperfections and bugs. The main issue will be whether problems are addressed effectively and promptly. What provisions are there for getting the support you need?

Five Things To Look For

The good news is that today’s tech marketplace offers a variety of software-driven solutions, many of which can be customized for businesses of any size, from two employees to 2,000 and beyond. Keep the following five things in mind as you seek out what works best in your niche and context.

1. Insist on scalability for short- and long-term growth.

Any project management software package should provide options for future growth. What’s less noticeable at times is the costs associated with scaling up. Before investing staff time in any solution, paid or otherwise, make sure you aren’t inadvertently placing artificial limitations on your future. Are businesses of all sizes on the list of satisfied users?

2. Look for seamless integration with legacy systems.

Be wary of solutions that force you to fit your existing infrastructure into their architecture. After all, the whole point of buying into SMB project management software is so you can continue to work without a hiccup. If the system or software you are considering requires weeks of training and implementation, keep looking.

3. You want something that’s feature-rich but stops short of overwhelming.

Flexibility and customization are highly desirable, but the ease of use equals or trumps them both. Any platform you select must be usable on Day One of implementation. For example, many platforms offer end-user experiences that can be tailored to specific roles and tied to login credentials. Relevant interfaces are displayed; non-essential information remains hidden. This vital feature keeps workers focused exclusively on the tasks that concern them and helps eliminate time lost to needless distractions.

4. Put your people in the driver’s seat.

Any project management software is only as good as its satisfied users. As you implement any platform, pay attention to the various snags encountered. At this point, one of the more common sources of confusion lies in distinguishing between software glitches and human preference. As your people begin to interact with the platform, record every bump in the road without passing judgment in the moment. In short, let your people beat on the new system for a few weeks.

5. Don’t compromise on cloud-based security.

The number and scale of cyberattacks targeting small businesses are astonishing. One of the primary reasons hackers are now going after “smaller fish” is because SMB employees get careless with passwords, safety protocols, and staying current on human engineering tactics. The underlying assumption is that criminals always go after larger, wealthier companies.

That may have been the case, but no longer. Before entering sensitive information into any SMB project management software, ensure you’ve battened everything down 100%. Get your system security and backup pledges in writing when working with paid vendors. If your system goes down, your provider should be on the hook. Make sure you and your people always have a fallback position in place.

Finally, as you consider a project management software platform, keep your company culture and vibe at the forefront. What works great for an auto parts store may or may not work well for an architectural firm. The plethora of choices available today give SMB owners the freedom to pick and choose what works well in their niche. In short, resist the urge to end your search quickly.

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