In many organizations, HR tech stacks are a chaotic patchwork of bolt-ons, knee-jerk purchases, and legacy systems that no longer reflect how people actually work. They were often bought in a hurry to solve a moment-specific need, keep up with compliance, or react to a trend. What’s left is a fragmented system with poor integration, frustrating UX, and low adoption.
In an age where AI, automation, and productivity-enhancing tools are shaping everything from recruitment to performance management, this disjointed approach just doesn’t cut it anymore.
If there’s one strategic move HR leaders must get right in today’s environment, it’s this: Rebuild your HR tech stack with purpose, not panic.
And here’s the truth: you don’t have to (and shouldn’t) do it alone.
Bringing in a Transformation or HR Tech Stack Specialist is not a luxury – it’s a smart investment. But hiring the right person is only half the equation. To make this project truly successful, you need to ask the right questions.
Top 5 Questions to Ask Your HR Tech Transformation Specialist
1. “What’s our long-term vision – and how will our tech enable it?”
This goes beyond today’s pain points. A good specialist will help you align your future org design, workforce planning, and culture goals with a tech ecosystem that scales, adapts, and evolves with your business.
2. “How do we balance AI, automation, and human connection?”
You’re not just building for efficiency – you’re building for people. Ask how AI can enhance (not replace) human interaction, and how the system will adapt to changing expectations from Gen Z and Gen Alpha workers.
3. “Where are our biggest risks right now?”
Whether it’s data privacy, underutilized platforms, or manual processes masquerading as ‘tech-enabled’, a great specialist will diagnose not just the visible gaps but the underlying cracks in your infrastructure.
4. “How do we get stakeholder buy-in and user adoption?”
The best stack in the world is useless if no one uses it. Your specialist should have a plan to bring your people along – from early engagement through training to ongoing feedback loops.
5. “What does success look like – and how will we measure it?”
Beyond implementation timelines, ask about clear KPIs for productivity, adoption, and ROI. A real expert will help you track what matters and pivot when needed.
Bonus Tip:
Make sure they can speak the language of both IT and HR – translating complex integrations into actionable strategy, and HR outcomes into scalable tech choices.
If you’re looking to find someone who can own and deliver this transformation, we can help. Reach out to us at Intuitive TA. We know the right people to get you from A to B… and beyond.
