#29 JooBee's newsletter

TL;DR

🦜 Don’t choose an HR tool just because others say so

🥵 Select the right vendor: A guide to ask tough questions

❓ Your views on vendor selection

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Don’t choose an HR tool just because others say so

This is a question I avoid without context. We often rely on word of mouth when choosing tools—if it worked for someone else (or JooBee 😱), it should work for us, right?

But copying isn’t always smart. It’s like assuming you’ll love my Hoi Sin chicken and broccoli pizza (yep, really!). Sounds adventurous, but do you want that every Friday night? When it comes to HR systems, the stakes are higher—let’s figure out what you actually need.

Know thy problem: The pain and the gain

The first rule of tool shopping: know the problem you’re solving. Identify the pain points—whether it’s time-consuming performance management or a messy hiring pipeline—and define the gains you want, like streamlining onboarding or empowering managers. Once you're clear, solutions start to emerge.

But that’s just the start. When meeting vendors (and you’ll meet plenty), keep these essentials in mind to make the right choice. Here are some key considerations:

 1. Data management, compliance and security – The HR Trifecta

Data security may seem dry, but it’s essential when handling sensitive employee info. One breach can be disastrous. Ensure the tool complies with regulations like GDPR or CCPA, and has strong data protections. Always involve your legal, security, and IT teams—this is non-negotiable.

2. Scalability – Because your start-up won’t stay a start-up

Here’s where many of us go wrong: we pick tools for right now and forget that we’re supposed to be growing (hopefully quickly). HR needs change fast in start-ups, and switching systems is costly and complex. Ask yourself: Can this system support our size and complexity in 2-3 years?

3. Customisability – Your HR system, your way

This isn’t just about aesthetics or slapping your logo on the system. Check the tool’s ability to customise fields and features is crucial. For example, you might need to capture specific data that a generic tool doesn't track by default. How easily can you add custom fields or tweak workflows? This flexibility allows you to tailor the system to your needs without compromising functionality. 

4. UI/UX – Because no one should need a PhD to use your HR system

Here’s the unfortunate truth: many HR systems are built for HR, not the employees and managers who use them. Simple tasks, like finding a team dashboard, shouldn’t feel like navigating the Bermuda Triangle.

And let’s be real, no one wants to log into 47 different HR tools. Integrating with platforms people already use—like Slack—is key to driving the behaviors you want. For example, a performance tool that integrates with Slack allows managers to give quick feedback directly without needing to switch between systems. A good UI/UX is crucial for adoption—don’t overlook it.

5. Vendor support and service – A lifeline when things go south

Once upon a time, I inherited an HR system from a US-based vendor. Sounds fine, right? Wrong. I quickly learned that they didn’t offer 24/7 support, and I had to wait a painful 48 hours for a response to an urgent issue. When you’ve got an HR fire that needs putting out right now, waiting two days is two days too long. So, when you’re shopping around, check the support hours. Do they have a dedicated service team? Will they respond to your emails like they care? These things matter—especially when it’s crunch time.

6. Integration capabilities – Because no tool is an island

When it comes to best-in-class vs. all-in-one solutions, I’m team best-in-class. I prefer tools that solve a specific problem in depth, not ones that do everything just okay. If you’re the same, make sure your HR tool integrates with systems—like payroll, learning platforms, performance management, etc.

And don’t forget non-HR systems—like finance software or your CRM. Without integration, you’ll be stuck with manual workarounds (read: spreadsheets), and nobody’s got time for that.

7. Reporting and analytics – The data goldmine

One major perk of an HR system is access to rich data—I’m not just talking about basic headcount reports. However, reporting maturity varies widely between vendors. To evaluate this, ask yourself: What can the reporting do for you?

• Provide information: What happened? How often? Where are the issues? What actions are needed?

• Provide knowledge: Why is this happening? What if these trends continue? What’s likely to happen next?

• Provide intelligence: How can we achieve the best outcomes with this data?

By assessing these aspects, you'll gauge the system's reporting capabilities effectively. 

Don't copy—choose smartly

The right HR tool should fit your start-up’s unique needs and future goals—not just follow trends. Word of mouth is helpful, but avoid the “if it works for them, it’ll work for me” mindset. Focus on your challenges, think long-term, and ask the tough questions. Your future self—and your HR team, people and business—will thank you.

Select the right vendor: A guide to ask tough questions

As a Chief People Officer (CPeO) or HR leader, selecting the right vendors impacts everything from efficiency and employee experience to overall business growth. It's tempting to rely on marketing materials or word-of-mouth recommendations, but ultimately, the responsibility lies with you to ensure you're choosing the right tools for your business.

Vendor selection can be challenging, and asking tough questions might feel uncomfortable, but it's necessary. In this newsletter, I’ll explain why asking difficult questions matters and how to do it, using a scenario to illustrate which questions you shouldn’t hesitate to ask.

Why ask tough questions?

1. You are accountable for your choice
Choosing a vendor is a significant investment of time and money. Poor vendor choices can lead to headaches down the line, impacting efficiency and employee satisfaction.

2. Challenge the sales pitch
Any good vendor will have honed their pitch and will present their product in the best light. However, beneath that shine, there may be limitations, gaps in service, or nuances that might not align with your unique needs. It's your responsibility to dig deep and ensure that what you're getting is truly the best fit.

3. Clarify implementation and future needs
Ask tough questions to understand how the solution will scale and adapt to your start-up’s growth. Ensure it addresses real-life challenges, not just demo scenarios.

A vendor selection simulation with Cecily, Founder of Harriet

I sat down with Cecily Motley, the founder of Harriet, to ask those tough questions. Think of it as a friendly grilling session, where you’re not just looking for the glitz but also delving into the gritty details—because, let's face it, the devil is in the details.

A friendly grill session with Cecily with my CPeO hat on🤠

🔢 Understand the basics: What exactly does Harriet do (in layman’s terms)?

Cecily: Harriet delivers HR support in your pocket, so every employee, whether working at a desk or in the field, can access round-the-clock support. We sync all your existing HR data (Google Drive, Notion, or Confluence as well as your HRIS and L&D systems)) and surface it in Slack, Teams, or even WhatsApp. There’s no data migration needed; we sit on top of what you already have.

Takeaway: This may sound basic, but trust me, you want the vendor to explain it in the simplest terms. If they can't, that's a red flag. 🚩

🌎 Real-world challenges: What happens if my HR data is incomplete or inaccurate–how will you handle that?

Cecily: You’re not alone—most companies are in that position. We’ve built a product to address this. During onboarding, we perform a “policy gap analysis” and show you what's missing, what conflicts, and what needs updating. We give you a worklist, and our platform constantly updates by syncing with your live documents—whether in Google Drive, Dropbox, or elsewhere.

Takeaway: Ensure vendors can address the “messiness” of real-world scenarios. You want to know—are they just there to deploy software, or are they actively solving a problem?

🎯 AI accuracy: Can Harriet provide incorrect information, and how do you prevent AI hallucinations?

Cecily: "We take AI hallucinations very seriously. We have worked hard to make them a never event and  cross-check answers using multiple different models. If Harriet isn’t 100% confident, it flags the question and escalates it to a human rather than risking an incorrect answer. Additionally, HR teams can fine-tune the AI’s responses based on feedback, ensuring even greater accuracy over time."

Takeaway: AI-powered tools risk "hallucinations," where the AI produces incorrect but convincing information. Given how sensitive HR information can be, ask vendors how they manage and prevent hallucinations.

🚧 Long-term reliability: How do you keep the tool updated after the initial implementation?

Cecily: Harriet automatically syncs with your current documents, so whenever you change something in Google Drive or your HR system, it’s reflected immediately in Harriet. You don’t need to worry about manual updates in multiple places.

Takeaway: Look for tools that require minimal manual updates.

✅ Reality check: What if employees still bypass Harriet and come to HR with their questions?

Cecily: That’s normal, but we’re not trying to sever that relationship. Harriet is there to answer simple, transactional questions quickly, so your team can focus on high-value tasks like employee relations or strategic initiatives. We find that over time, employees prefer using Harriet because it’s faster.

Takeaway: Expect gradual adoption; the tool should simplify processes over time.

✂️ Customisation: Can Harriet’s tone of voice be customised to fit our company culture?

Cecily: "Yes, Harriet’s tone can be adjusted to match your company’s communication style—whether you prefer a formal, factual approach or something more upbeat and conversational. This ensures the tool feels integrated with your brand."

Takeaway: Ensure vendors offer a certain level of customisation to align with your culture.

😎 Differentiation: Why should I choose you over similar tools in the market?

Cecily: What sets Harriet apart is its vertical focus. While other AI tools are generic, Harriet is built specifically for people operations. We solve the unique challenges HR teams face, like delivering real-time, localised information, know how to handle sensitive questions, and free up your people team by handling repetitive inquiries.

Takeaway: Vendors should clearly differentiate themselves from competitors. Look for a clear answer that aligns with your business needs.

💁🏻‍♀️Ask for help: I don’t have time to build a case for Harriet—can you help?

Cecily: Absolutely! We’ll help you outline the ROI, from improving employee retention to saving time on HR admin tasks. We’re happy to work with you to quantify the value Harriet can bring to your start-up.

Takeaway: A confident vendor should assist in making the business case.

☠️ Risk mitigation: What if this doesn’t work out?

Cecily: Harriet’s got a money-back guarantee after the onboarding process, so if it doesn't work, you can part ways with no hard feelings​. 

Takeaway: Be sure to ask about exit clauses and guarantees—because a long, messy breakup with a vendor is never fun.

😯 Avoid surprises: I don’t like surprises—how will pricing change if my start-up doubles in size?

Cecily: We offer flexibility. For example, we include a 20% headcount fluctuation in our contracts, so if you grow by 20%, your pricing remains the same. If you exceed that, we’re transparent about additional costs upfront.

Takeaway: Clarify long-term pricing structures. If a vendor is vague or evasive, it’s a red flag. 

Asking tough questions is your right as a buyer. Don’t hesitate to grill vendors; your business and employees will benefit from your diligence. Go ahead, ask away!

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