What No One Tells You About Small Employer HR Tech Implementations: An Interview with Our Payroll & Operations Manager

Here’s the scene: You’re running a small HR department, or maybe it’s just you, wearing every hat from recruiter to payroll to office therapist.You’re underwater. Every day. Drowning in manual processes, late-night compliance checks with Google and your favorite HR resource group, and that one (or maybe 10) Excel sheet you pray never breaks.

So you finally make the call. You’re going to invest what little budget you have into some kind of HR tech. Something, anything, to help automate the chaos and give you room to breathe.

And that’s where things get tricky. At that point, you’re not always thinking strategically. You’re tired. Burned out. Maybe even a little desperate, which is the last place you want to be when needing to make a level-headed decision. Additionally, you might not have a clear plan for how to vet systems or how to manage next steps after you sign the contract.

Because no one really tells you what happens after you sign the contract. The messy middle between “we picked a system!” and “this thing actually works.” The hours you’ll spend cleaning up data, rewriting processes, chasing down login issues, and translating tech-speak into real-life workflows.

We’ve been through a lot of these. And by we, I mean me, my entire team, and our Payroll + Operations Manager, who’s been in the thick of every implementation we’ve supported.

I asked her to sit down with me and share what she really wants small employers to know before jumping into HR tech. No sales pitch. No buzzwords. Just real talk from someone who’s lived it.

Here’s what we talked about:

Marie: Let’s start with the big picture. When a small business is about to implement a new HR system, what’s the #1 thing they need to understand going in?

Penelope: The system won’t run itself, success depends on inputs and follow-through. It’s important to be realistic about this upfront: planning, clear roles, and steady follow-through make all the difference.

Marie: You’ve supported a lot of implementations. What are the most common mistakes you see small employers make early in the process?

Penelope: Rushing setup, not involving the right people, and assuming the tech will solve everything on its own. Taking time to plan carefully and get the right people at the table early will save you headaches down the line.

Marie: Let’s talk timelines. What’s a realistic expectation for how long implementation takes, and what tends to slow things down?

Penelope: 6–12 weeks is typical. Delays usually come from unclear goals, missing data, or poor communication. Sticking to a clear schedule, assigning ownership, and keeping everyone accountable can help stay on track.

Marie: What role does data play in the success or failure of an implementation? What should companies be doing with their data before go-live?

Penelope: Clean data is everything. Audit it early, and don’t wait until go-live to spot issues. A systematic review now prevents bigger problems later: double-check, verify, and make sure you know where every piece of information is coming from.

Marie: How important is internal communication during this process? Who needs to be looped in and when?

Penelope: Critical. Involve decision-makers and end users early, not just at training time or after going live. Clear updates at each stage help people feel informed and prevent surprises. Good communication keeps everyone aligned.

Marie: What’s one piece of advice you always give to small business leaders who are nervous about switching systems?

Penelope: Don’t panic. Prep well, ask questions, and lean on your team. It’s normal to feel uneasy about change. A steady approach, clear milestones, and trust in the plan will get you through it.

Marie: You’ve mentioned before that 'tech doesn’t fix broken processes—it just makes them more visible.' Can you unpack what that means for small employers?

Penelope: If your workflows are messy, tech will just spotlight the mess. Fix the process, then layer on the tool. It’s worth taking the time to map out where things aren’t working now so you’re not just moving problems into a shinier system.

Marie: Finally, if a company gets to the end of implementation and things aren’t working smoothly, what should they do next? Is it too late to course correct?

Penelope: It’s not too late. Pause, review gaps, and reset priorities BUT don’t ignore the issues. Sometimes a reset is what keeps things from getting worse; stay objective, document what’s off track, and tackle it step by step until it’s right.

All in all, switching systems isn’t just a tech project, it’s a people and process project. And for small employers, the margin for error is smaller. You can’t afford to waste the money you have or six months on a system that doesn’t stick.

But the good news? When you go in with your eyes wide open: realistic timelines, clean data, internal alignment, and a plan to fix broken processes, a great implementation is absolutely possible.

If you’re planning your own implementation (or stuck in the middle of one), let us know. We’ve got the scars, the spreadsheets, and the toolkits to help.

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