Workweek Newsletter {beacon}

Does this deserve another year of your money??? Let’s review its performance first! ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌
I Hate It Here
Hebba Youssef
Oct 29th, 2026
{cta_url_read_in_browser = community_base_url + "/library/" + article_id + "?utm_source=newsletter&utm_medium=email&utm_campaign=" + edition_slug + "&utm_content=read_in_browser"}{cta_url_read_in_app = community_base_url + "/library/" + article_id + "?utm_source=newsletter&utm_medium=email&utm_campaign=" + edition_slug + "&utm_content=read_in_app"}{cta_url_join_conversation = community_base_url + "/library/" + article_id + "?utm_source=newsletter&utm_medium=email&utm_campaign=" + edition_slug + "&utm_content=join_conversation" + "#comments"} {if profile.vars.member_status == "lead" || profile.vars.member_status == "unfit"} {else}{if profile.vars.member_status == "fit"} {else}{if profile.vars.member_status == "member"} {else} {/if}{/if}{/if}

In partnership with


Surprised to see me in your inbox on a Thursday?! Well, here I am!

This is a ✨special edition deep dive✨ of I Hate it Here. Every now and then, you may get one of these from me! 👏

This special edition deep dive is sponsored by Intuit.

What's a deep dive?

Deep dives are opportunities for me to collab with specific companies in the HR/People space on topics of joint interest to them, me, and even you! The sponsoring company provides invaluable input on the topic, but this edition itself is written, edited, and published by your fave gal, me!

Today, I'm discussing why your HR software deserves a performance review before it gets another year of your money.

Let's get into it!


Your HR Software Wants You Back: Here’s What to Ask Before Saying Yes

Your software wants another year of your money, but have you considered giving it a performance review first??? 🤔

Yes, that’s a serious question!

We make employees explain what they’ve accomplished and sit through convos about meeting expectations.

Meanwhile, it’s not uncommon for a system that you’re used to (that requires more workarounds than you’re willing to admit) to get renewed just because someone forwarded an invoice and that’s the way it’s always been done.

If you’re the only HR person at a company of up to 75 people, I totally understand the appeal of the status quo!

You’ve got payroll coming up, an employee asking about benefits, and a to-do list that never seems to get any smaller, even when you cross a dozen things off of it.

So your immediate reaction might be “Shopping for software? Suuuuure. Lemme pencil that in between lunch and whatever emergency has claimed lunch.”

I also understand how much familiarity offers a form of relief, because you know where everything lives, despite having to make weird adjustments regularly just to make up for your software’s faults.

But renewal commits you to another year of that arrangement! 👀

Before you approve it and move on, I think your current system deserves a lil scrutiny, and I’m going to explain why right now!

Familiarity Is Doing Some Heavy Lifting Here

There’s something especially annoying about paying for a tool and then developing expertise in compensating for its shortcomings, am I right?!

You even catch yourself doing the micro-workarounds so automatically that you barely register it anymore. 🤯

Open another tab, move the information, check it again. Your brain subconsciously files the whole thing under how this works.

Eventually, someone asks why a supposedly simple task takes so long, and you hear yourself DEFENDING the questionable process. gasp

“Oh, it’s easy once you know the seven extra steps!”

That adaptation is exactly what makes renewal tricky…you’re evaluating a system after spending months making it tolerable!

The original frustrations have become muscle memory, which makes them even harder to see.

⏪ Rewind for a second and start with the job you hired the software to do in the first place:

What did you expect it to take off your plate? Where has it delivered? Give it credit for that.

Reliable payroll deserves acknowledgment, and a useful employee portal can spare you plenty of repetitive questions.

Next, you have to examine the promises that still require your intervention. 🔎

Maybe the report leadership wants means combining multiple exports, or the “easy” workflow becomes easy after you explain it individually to every manager.

I think you should put all of those examples beside the renewal price!

According to Intuit, small and mid-market businesses rely on 7 to 25 workforce tools, with estimated annual software spending of $120,000.

Of course, your company’s bill may look very different, but the most important point is how much value that collection actually delivers.

A tool can have an impressive feature list and still demand an embarrassing amount of supervision! 🥴

Ask whoever approves the budget to consider the subscription alongside your time. Bring a specific example:

“Every pay cycle, I spend this long correcting information that should already match.”

That convo gives leadership something concrete to evaluate. It also beats just saying that your software is annoying, which doesn’t tell much of the story at all.

Would you recommend your current setup to an HR friend starting fresh???

Pay close attention to any hesitation before answering!

Why Does Your Software Need a Full-Time Chaperone?

Somewhere along the way, HR became a diplomat responsible for maintaining the fragile peace between systems.

A new hire enters one platform, while their payroll details go somewhere else.

As soon as someone changes their info, you’re forced to figure out whether or not every relevant record got the memo!

(Congratulations on your additional appointment as Director of Did That Sync? 🏆)

For one ordinary week, I highly recommend keeping a running list of the moments when software creates follow-up work.

That especially includes all the tiny 5-minute fixes, since they tend to disappear from memory while, at the same time, collectively eating an afternoon!

Next, write down what triggered each task and what happens if you miss it.

An outdated address creates a different concern than a missing document or an incorrect pay rate.

Getting specific helps you identify where admin friction could affect employees or complicate compliance.

Your diligence can keep a clumsy process functioning for YEARS! 🫩

That deff deserves some recognition, but it also deserves support beyond hoping you remember everything during a busy week.

Consider how that affects something like your onboarding process. Intuit’s recruiting, hiring, and onboarding overview video offers a useful (and kinda entertaining) starting point for reviewing the process.

Walk through your own version from offer acceptance to first paycheck while you’re at it. How many handoffs depend on you personally checking whether something happened???

If leadership asks what labor is costing right now, can you answer while decisions are still being made, or do you need payroll to finish before assembling the picture?

Visibility before payroll runs can help inform staffing discussions and budgeting. When HR has to reconstruct the numbers afterward, that opportunity shrinks.

And yes, I am well aware that replacing software takes effort!

Migration is its own unique pain, especially when the person running it also handles broadly gestures at everything else.

It’s worth estimating the changeover workload alongside another year of recurring fixes and the time employees will need to learn something new.

At the end of the day, you deserve a decision based on the whole burden.

Unfortunately, the renewal invoice captures a surprisingly small portion of it!

We’ve Decided to Explore Other Candidates

In a perfect world, I would absolutely love to see software experience the interview process it helps administer.

“Tell me about a time you successfully transferred information without making HR investigate.”

Take your time…I’ll be here all week! 😒

Renewal gives you a reason to define what good support looks like today.

It’s entirely possible that your org has grown since the original purchase.

The setup that suited 30 employees deserves another look when you’re approaching 75. 👀

Build your requirements around actual situations. For example:

An employee gets promoted…now show me how that change reaches payroll.

A manager needs to review staffing costs, so show me when those numbers become available.

Intuit’s HR automation overview is another helpful resource for thinking through workflows and documents. Use your recurring tasks to shape the questions you take into a demo!

With AI, I’m interested in the task it completes and the checking it still requires from me. A confident answer delivered instantly can create plenty of work when it’s wrong…and we’ve all experienced that at this rate.

Ask how exceptions are flagged, what you approve, and where a human expert enters the process. For complicated payroll or HR questions, getting appropriate help matters more than enjoying a conversational interface.

💡 Pro tip: Request a demo using a specific, messy scenario from your week. Sales presentations tend to feature suspiciously cooperative employees who submit everything correctly (LOL).

Check what’s included in the proposed plan, then ask about additional costs and implementation responsibilities before comparing it with your renewal.

Your existing provider can participate too. Give them the same requirements and an opportunity to explain what’s changed.

Renewing after that review can be a sound decision, but so can switching. Either way, you’ll know what earned your approval!

And please, for your own peace of mind, read the cancellation deadline while there’s still time to act on it.

A Candidate Worth Interviewing: QuickBooks Workforce

If your current system expects you to hold the operation together through sheer vigilance, Intuit’s QuickBooks Workforce deserves a place in the convo, especially if you already trust QuickBooks with your books!

QuickBooks Workforce connects payroll and HR, with automation and access to human expertise. It lives right inside QuickBooks, so you’re not bolting yet another tool onto the ones you already use, and your info only gets entered once. Its connected approach gives businesses real-time visibility into labor costs alongside their financials, helping HR bring useful info into decisions sooner.

Imagine the extra time you'd have with fewer payroll corrections and less document chasing! 💭

Maybe you'd finally work through the manager training you've postponed, or take an employee convo slowly because another admin deadline isn't pulling at your sleeve.

HR tools and expert support vary by subscription, so have Intuit spell out exactly what you'd receive, including who helps during setup and what ongoing help looks like afterward.

Ask Intuit to show how QuickBooks Workforce would handle the work you documented, and bring the awkward examples, then compare the actual proposed cost with your current subscription and the effort keeping it running.

Your software wants another year, but if you’re not 100% sure it’s earned, it’s time to start looking for a solution without workarounds. 💡

Interview Your Next System


Thanks for reading this deep dive! Reply with any thoughts you have.

XOXO, 

Hebba Youssef

LinkedInInstagramPodcast

1023 Springdale Rd Suite 9E, Austin, TX 78721

© 2026 I Hate It Here

Unsubscribe
Community home