The Questions Every Employer Should Be Asking

The best opportunities often begin with curiosity, thoughtful questions, and one meaningful conversation.

Dear ,

Where Curiosity Can Lead

The beginning of August has always felt bittersweet, especially after the kids finished preschool.

It marks the end of summer. The slower mornings, the more relaxed schedules, and the brief pause from the constant rhythm of school, sports, and activities.

But honestly, August is also my cue to get back to the routines that help me feel my best. Morning walks become part of my day again, life settles into a rhythm, and I find myself feeling a little more intentional. As much as I enjoy the slower pace of summer, there's something refreshing about this new season.

This summer, my 16-year-old set a goal of finding an internship. We talked through a few ideas to help him get started, but from there it became his journey. He spent the summer introducing himself to people, asking questions, and looking for opportunities to learn. Before long, one of those conversations led to an internship.

Watching him, I was reminded that opportunities rarely begin with having all the answers. They begin with being curious, asking thoughtful questions, and having the courage enough to start a conversation.

Asking Better Questions

As I was thinking about the challenges employers continue to face with rising healthcare costs, I found myself asking a lot of questions. I’ve been in many conversations recently where the topic keeps coming up. But the biggest question is what can employers do differently to continue offering competitive benefits while managing those costs.

Those questions led me to bring together a panel of experts for our recent webinar, Healthcare Costs Aren't Going Down. Now What?

As we prepared for the discussion and shared ideas during the webinar, it was clear that the issue isn't a shortage of ideas for managing healthcare costs. There are plenty of innovative solutions and approaches available today. The challenge is knowing which questions to ask, which assumptions to challenge, and which strategies are right for your workforce.

Ultimately, employers don't need to have all the answers. They do need the right advisors around them who are willing to challenge assumptions, ask thoughtful questions, and explore solutions they may not have considered before.

These were the ideas that stood out for me.

Key Idea #1
Be the steward of your health plan
You don't have to be the expert on every topic, but you do need to lead the strategy. That means understanding your organization's goals, knowing your workforce, reviewing the right information, and making thoughtful decisions throughout the year.

Key Idea #2
Let data guide your decisions
The best benefits strategies start with understanding your workforce and reviewing the right data. Data tells the story of how employees are using their benefits and where opportunities exist. Better information leads to better decisions.

Key Idea #3
Build the right team around you
Healthcare costs don't have one simple solution. The strongest outcomes come when employers surround themselves with trusted advisors who bring different perspectives, challenge assumptions, and work toward the same goals.

As we head into one of the busiest times of the year for HR and benefits professionals, I hope you'll make time to stay curious, challenge assumptions, and start one more conversation. You never know where it might lead.

Have a wonderful August.

Warmly,
Leah ❤️

More Influence Than You Think

Many employers are looking for ways to better manage healthcare costs while continuing to support their workforce. Our latest blog shares six ideas to help HR leaders make more informed benefits decisions, better understand their workforce, and strengthen their overall benefits strategy.

Benefits x AI: Solving For The Human Variable

Last month in our ongoing Benefits x AI series, we explored why AI doesn't eliminate complexity in benefits, it only changes where the complexity lives. As intelligent systems become more capable, the question becomes less about what AI can do and more about how organizations govern an ecosystem where systems, vendors, regulations, and technology are all evolving at different speeds. Stay tuned for the next article where we’ll look at governance across the benefits ecosystem.

HCM TECH ADVISORY HAPPENINGS 

I recently joined Brent Skinner at HR.com to discuss the five foundational steps organizations should take before evaluating HR technology. If you're planning a system selection or simply want to strengthen your approach, I hope you'll take 25 minutes to listen.

UPCOMING EVENTS & COMMUNITY

HR Leaders Roundtable

HR can be an isolating role. Our HR Roundtable brings together peers to step away from the day-to-day, exchange ideas, and learn from each other in a confidential setting. We have honest conversations about the challenges HR leaders are navigating today, while learning how others are approaching them.

A special thanks to Caitlyn Hernandez, Employee Benefits Consultant at USI Insurance Services, for sponsoring this month's HR Roundtable.

WHERE TO FIND US

Worldwide Employee Benefits (WEB) Network – Atlanta Chapter

Moderating a discussion on how AI is reshaping benefits administration & employee experience. We'll discuss how technology, data, & decision support are helping employers create more personalized, informed, & efficient benefits experiences.

September 17 | 11:30 A.M.
Details coming soon

HR Tech 2026

Moderating a roundtable discussion on Managing Buying Decisions and how HR leaders can approach technology investments through financial modeling, business case development, and understanding the long-term costs beyond the software.

October 20 | 11:30 A.M.
See more details

PAST WEBINARS 

A discussion on rising healthcare costs and what we can do

Learn how to prepare a CFO-ready business case

ARE YOU READY FOR OPEN ENROLLMENT?

Is your Open Enrollment plan on track? This OE Readiness checklist ensures you've covered every critical step before enrollment begins.

Looking for a deeper dive? A series of expert guided articles on the hidden risks and common breakdowns that can derail a well planned open enrollment season.

Short read: Even well-planned Open Enrollment cycles can easily go off track due to unexpected missteps.
We discuss four key hidden pitfalls every HR leader should watch for in this HR Executive article.

Prepare your team for Open Enrollment. Our Open Enrollment Masterclass is designed for employer and broker teams responsible for planning, managing, or supporting Open Enrollment. Through practical, team-based training, you’ll improve planning, strengthen collaboration, and help deliver a smoother enrollment season.

LATEST INSIGHTS

HERE TO HELP

At HCM Tech Advisory, we help organizations make better HR technology decisions by bringing together HR, benefits, systems, and implementation experience. Whether you're selecting a new platform, preparing for implementation, or trying to get more value from the systems you already have, we help you understand where you are today, identify gaps, and build a path forward with clarity and confidence.