Being part of a small business or startup is great for a number of reasons (read: cool people you actually like, fun projects, and endless beer on tap), and a big one is flexibility. Flexible hours, flexible work environment, flexible projects… flexible everything, really. And while all this flexibility is great, it can create a bit of a headache, especially when we get to the thorny issue of which (software) tools to use on a daily basis.

Big Company Cruisin’

Let’s be honest. Sometimes not having to make decisions is nice. Big companies do this right from your very first day: “here’s your desk, here’s your stapler, this is your shredder, and here’s your copy of the Office Suite. HR is down the hall to the left, and the bathroom is across the room. All set?” There really is something comforting about having everything in place, the supporting structure, to help you do your job.

Now, there are obvious downsides to all this like endless layers of red tape to get the latest copy of CS5 , and a general unwillingness to try new things. So how do smaller companies stack up?

Jack be nimble…

On the other end of the spectrum we have small businesses like EchoUser: no systems in place, no pre-set list of software to use, no nice HR lady (or man) down the hall. “Don’t like Firefox? Use Chrome. Want to run a Linux machine? Go right ahead.” Being part of a small team is all about being able to make choices for yourself, to customize your support structure exactly the way you want it. If Goldilocks had to choose, she’d probably want to work for a small company.

Jack be…picky?

But all this freedom comes with a price. I don’t know how many tools we’ve tried out and shelved over the past few years. From basic things like browsers (we’re mostly on Firefox or Chrome now) and CRM systems (no Salesforce for us, we use the lightweight HighRise), to more complicated tools around project management (Gantter and Asana) and time tracking (Toggl), we’ve got quite the array of tools at our disposal. But we didn’t get here without lots of time to figure out the best solution, and sometimes I really wish the choice had been made for us. Consensus, even in a small team, can be hard! Here are a few things we learned along the way:

1. Take the time to test things out

First things first: choosing the right tool will take time, so be sure you plan appropriately. Want your salespeople to be up-and-running on a new CRM tool by next week, with 3 to test out? Fat chance. In our experience a 2-4 week window is about the time you need to sort the wheat from the chaff, and even longer for tools that you don’t use very often. Which leads me to lesson #2:

2. Try out the tools in the real world

This means that you should test the tools out in a range of conditions (depending on the application). So, if you want to want to use a project management tool to juggle multiple projects, don’t test it out when your pipeline is on the leaner side or you won’t get a feel for how it works under pressure. Testing out a time tracker with a mobile app? Make sure your people are on the road during the testing period, or the mobile app won’t get touched. In the end, the only way to make a smart decision is to have real world, relevant information.

3. Include everyone in the process

This is a tough one. To paraphrase Spiderman, “with more people comes more responsibility – and more opinions.” This is good and bad, because the bigger the group the more elusive you’ll find consensus, but in my mind, if you leave people out it’s just A. mean and B. ignoring reality. Teams don’t work in a vacuum, so testing a tool this way doesn’t make sense either. Even if your HR person will never use the CRM tool, they might still have valid thoughts – and these should be included.

4. If you like free/cheap, get used to having a big toolbox

Startups like to save money. It’s just who we are, and inevitable when the line between being in the black and in the red is so fine. The good news? There are plenty of free tools out there. The bad? Almost none of them talk to each other, so you’d better get used to the idea of using quite a few tools to get the job done. Some are getting better (37signals has basic integration with other products, while Zoho’s suite is pretty well tied together), though others are most definitely “standalone”.

5. Engage with the people behind the tools

Free/cheap tools for startups are often offered by startups too, and as everybody knows, startups are all about getting feedback and engaging with customers. So don’t be shy, reach out to the folks behind whatever tool you’re looking to use, they’ll no doubt be thrilled to get your thoughts – and might even give you a sneak peak at up-and-coming functionality.

We love the teams at Asana and Toggl for just this reason, so don’t be shy – reach out! Questions, comments, feedback on what I’ve mentioned here? Feel free to comment below or drop me a line at felix (dot) desroches (at) echouser (dot) com. I look forward to hearing from you!