Dear ,

In 2021, I stepped into my first HR leadership role after years of advising clients as a consultant. One of the first things I inherited was a difficult vendor relationship. Issues lingered for months. Conversations were reactive, and every interaction started with a problem and ended without progress.

Based on experience, I knew what needed to change. I set up a weekly standing meeting. The vendor was surprisingly eager to be involved. There had never been a regular cadence to review open issues, discuss priorities, or talk about what success looked like. Once that structure existed, the relationship changed. Problems resolved faster, communication improved, and both sides started working toward the same goals.

Organizations invest months evaluating software, comparing features, and negotiating contracts. Once the contract is signed though, little thought goes into how that relationship will actually be managed over the next several years.

Your vendor will be there for open enrollment, payroll issues, acquisitions, system upgrades, leadership changes, and the many challenges that come up along the way. Leaders often tell me they feel stuck with their vendor. After working on the employer side, the consulting side, and inside a technology vendor myself, I've learned the breakdown usually starts much earlier.

Here are five questions I encourage every organization to ask, before and after signing the contract.

Question #1
Does the vendor's culture align with ours? 
One of the questions I always ask clients during a system evaluation is, "Can you see yourselves working with this team for the next several years?"

Technology will evolve. Features will change. Account managers will come and go. But your day-to-day experience will be shaped by how your vendor communicates, responds under pressure, admits mistakes, collaborates with your team, and prioritizes customer success.

Pay close attention during the sales process. Are they listening more than they're talking? Are they transparent about limitations? Do they answer difficult questions directly? Do they treat your team like a partner or simply another sale? The culture you experience before signing the contract is often the culture you'll experience long after implementation.

Question #2
How will the relationship be managed after go-live? 
Many organizations treat implementation as the finish line. In reality, it's just the beginning. Set a recurring cadence with your vendor to review open issues, discuss priorities, and flag risks before they become problems. Don't wait for something to break before you talk.

Question #3
What does success look like for both sides? 
Talk about response times, escalation paths, ownership, communication preferences, and how success will be measured. When expectations remain unspoken, both sides often believe they're doing a good job while the other walks away disappointed.

Question #4
How will you separate operational support from strategic planning? 
Innovation matters and new capabilities matter. But when your team is calling because payroll isn't balancing or open enrollment files aren't processing correctly, that conversation should remain focused on solving the immediate issue. Create separate opportunities to discuss future enhancements and new products. Doing so allows support conversations to stay productive while still giving both sides time to think strategically about what's next.

Question #5
How do we know if it’s working? 
Look for trends. Are the same issues continuing to surface? How quickly are critical items being resolved? What improvements have been made since last quarter? Are both organizations becoming more proactive, or are they simply reacting to problems?

The health of a vendor relationship isn't measured by whether issues occur. Every partnership will experience challenges. It's measured by how effectively those challenges are addressed together.

That’s easier to see from the outside.

Over the years, I’ve noticed conversations often change when an independent advisor joins the discussion. The focus shifts away from defending positions or debating whose fault something is, and back toward solving the problem. We don't represent the employer or the vendor. We represent the success of the partnership.

At HCM Tech Advisory, we help organizations evaluate technology partners, establish vendor governance, and build the accountability that makes those partnerships work long-term.

Whatever stage your vendor relationship is in, I hope this gives you a few questions worth asking before your next renewal or review.

Warmly, 
Leah ❤️

Benefits X AI : Solving For The Human Variable

In our latest Benefits × AI article, we look at where AI can actually create value in an already complex benefits ecosystem. Chatbots and employee self-service get most of the attention, and that's real progress. Here's where I think the next unlock is, AI that configures systems directly from plan design rules, flags downstream impacts before a change breaks something, and surfaces the claims and billing patterns much quicker and more accurately.

As the technology evolves, the need for thoughtful governance and human expertise only grows, which we'll explore in our next issue.

Explore the full series →

 HCM Tech Advisory Happenings

Modernizing Benefits Administration Through Integrated Technology.
I recently joined Employee Benefits News to discuss Modernizing Benefits Administration Through Integrated Technology. We explored how successful benefits technology initiatives start long before implementation by understanding business needs, involving stakeholders early, and selecting technology that fits the organization. We also discussed why governance, training, and vendor management are critical to realizing the full value of these investments.

If you're evaluating benefits technology or planning for a future implementation, I hope you'll take a few minutes to watch the discussion.

Watch the webinar here→
(The discussion begins around the 6-minute mark.)

 Summer Lunch & Learn Webinar Series 

Healthcare Costs Aren't Going Down. Now What?

A practical discussion on building a smarter benefits strategy.
Healthcare costs aren't going down, but reacting at renewal doesn't have to be the norm. Join us on July 22nd at 12:00 PM EST for an honest panel discussion on how employers can build a smarter, year-round strategy for managing healthcare costs while supporting their workforce.

I'll be joined by Amy Mansfield-Nelly, Employee Benefits Strategist at IMA Financial Group, along with TALON, a healthcare price transparency and consumer navigation platform, and additional industry experts as we discuss practical approaches to healthcare cost containment, pharmacy strategies, and how employers can become more informed consumers of their own benefits strategy.

Together, we'll explore how employers can ask better questions, evaluate available solutions with confidence, and work more strategically with their benefits advisors to make informed, long-term decisions.

Where To Find Us

Open Enrollment Resource Center

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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.