Let’s say–benefit of the doubt and all–that the tools and systems you put in place when you launched your startup were the best choices you could have made at the time. That day, though, was probably a while ago. For many founders, that means years or even a decade or two ago.

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Startups don’t stay startups forever. New organizations become not-so-new ones. But just because time passes doesn’t mean these ventures scale. And the more time that does pass, the less the technology is likely to stay up to par. Just because something wasn’t broken at one point doesn’t mean it won’t need to be fixed later. And the longer you wait to fix it, the harder time you’ll have trying to grow and move forward. Here’s how to know whether your scaling troubles have to do with technologies that aren’t keeping up. Technology changes. But we all know that. So much of your organization changes, too, and those changes have real impact on whether your systems are still working for you. Take a look at your org chart. Notice anything different today, compared to whenever you adopted that CRM system? Take a look at your org chart. Notice anything different today, compared to whenever you adopted that CRM system or website or project management tool? Chances are the main difference is that there are now more people using those tools than there were originally. Whatever system you’re relying on can probably accommodate some extra users or licenses. The impact of adding more people to the company, though, isn’t that you need more people using the same tools. It’s that you now need people using the same tools for things that they just aren’t built for. As companies expand, the business areas and specialties covered by staff also expand. And as employees take on more and different work, the tools and systems they rely on to do that work have to change to meet those needs. But they very often don’t. Regardless of what kind of technology you’re using, there’s nothing that’s great at everything.

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Add to this mismatch the fact that new staff also bring with them different skills and proficiencies. So you may try to hire folks who have experience with certain systems, but it’s probably better for your company to hire people with the best overall job skills, regardless of whether they’ve worked with X invoicing system or Y database. Successful professionals always find a way, which can be a double-edged sword: If your company-wide tools don’t work for them, they’ll eventually use something else, creating data silos, process breakdowns, and worse. How To Know If Your Tech Is Keeping Pace Staff come and go, but the work stays the same, right? Not in 2017. As customers cycle in and out, market needs evolve, and organizations’ roles in their sectors and communities change, their products and services have to either expand or adapt. That isn’t a bad thing. But it means you need a smart tech-evaluation process to make sure your tools are keeping pace. These five questions can get you started: 1. What other systems do we use? It isn’t likely that you’ll adopt a tool for all of or even some of your staff that’s intended to stand alone entirely. What other tools are you using simultaneously? Think about how it all works together–and where it currently doesn’t. What are the integration options? What options will you have for integrating tools in the future? 2. What are employees’ top technical needs? Beware of the shiny-object syndrome–don’t get sidetracked by a great pitch from a seasoned sales rep highlighting bells and whistles. Stay focused on the technical tools your employees actually tell you they need. If a given system does more than what’s needed at a given time, that can be a bonus; if it does other things that seem great without meeting your team’s core needs, you’ll end up buying something they’ll have to find their own workarounds for. Unless you plan to have every question and support request go to someone on staff (good luck to them!), you’ve got to ask about support from the get-go. 3. What’s the technical skill level of the people who’ll use it? Adoption is key. If the system is too cumbersome or technical for everyone on your team to use–even if it can do all the things you’re looking for–they won’t. Always ask for a sandbox, and have your employees (not just the tech staff, but folks all across the company) test it and give feedback. 4. What level of support is available? Unless you plan to have every question and support request go to someone on staff (good luck to them!), you’ve got to ask about support from the get-go. This includes far more than the paid customer-service phone support, by the way; consider things like active contributors or a community of users.

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5. What does my community think? Is there an aspect of this system that customers and people outside your organization will interact with? If so, you need to involve those users in the evaluation, too. Whether you already have a community user group established for ongoing engagement or not, invite them to play around and weigh in on any tech tool you’re considering. From small projects to a massive system overhaul, it’s all about keeping your humans and the tools they use in close alignment. That isn’t easy, but when the gap between them widens, your whole organization’s growth slows down. Sometimes scaling troubles aren’t about anything wrong with your business model–they come from smaller, peskier issues that you’re writing off as livable annoyances. Because chances are they won’t be for long.