In the last three months alone, we’ve watched HR teams sprint toward their first real AI win. Some moves come straight from the C‑suite: “Become AI‑first, stat.” Others are grassroots, fueled by teams tired of copy‑pasting the same answer for the hundredth time. Wherever the pressure comes from, the simplest starting point keeps bubbling up: automating repetitive employee questions.
This is Winslow’s #1 mission, and we built our assistant to do exactly that so HR can get back to the work only humans can do.
The employee question avalanche everyone knows too well
Whether you’re a two‑person team or a 100‑person department, answering repeated questions can swallow nearly half the week.
- Surveys show that HR pros lose up to 50 percent of their time tackling déjà-vu questions about policies, procedures, and benefits.
- Manual look‑ups, approvals, and document hunts add another layer, leaving engagement projects to gather dust.
- Employees feel the drain too, burning 30–90 minutes a day just digging for basic info.
We’re all in the same boat—and that’s why Winslow is the perfect place to start.
AI was practically built for this job
Generative AI is, at heart, a text wrangler, and employee questions are made of text. With Winslow, you can ask it for policy details, and it doesn’t blink.
- Digests dense docs in seconds. Trained on billions of words, large‑language models could breeze through handbooks, SOPs, and vendor PDFs.
- Keeps track of context so you don’t have to. Carry‑over rules, eligibility windows, edge‑case exceptions, all recalled in a heartbeat.
- Turns legalese into plain talk. Section 12.4(b) becomes “You can roll over up to 40 hours of PTO.”
- Handles a hundred ways to ask the same thing. Typos, half‑sentences, emojis—no problem.
- Improves with every nudge. Quick edits or thumbs‑ups fine‑tune future answers.
- Leaves the final call to humans. Review flows and audit trails keep HR in the driver’s seat.
If AI is a Swiss‑Army knife for language, repetitive Q&A is the first blade that pops open.
Zero‑to‑launch over lunch
Good news: this isn’t a moon‑shot project. Installing Winslow is more like a coffee break.
- Aim the assistant at your source of truth. Upload or link the docs you already trust.
- Flip the HRIS switch. Read‑only access is enough for personalized answers. Learn more about our HRIS integration here.
- Meet employees where they already ask. Slack, Teams, Outlook, Gmail—take your pick.
- Stay on guard rails. Keep approvals on while you build confidence, then loosen as accuracy climbs.
We’ve seen teams redirect live questions to an AI draft the very same afternoon they install it.
What happens when your HR team gets back half their day?
Reclaiming hours isn’t just nice, it’s transformative.
- Coach managers instead of triaging emails.
- Launch that DEIB initiative waiting in the wings.
- Dig into workforce analytics that shape next year’s hiring plan.
- Spend lunch actually at lunch.
Generative AI’s upside is measured in trillions, but for HR, the metric that matters most is time.
Rallying Cry for HR Leaders (and a SHRM Meetup)
We see the world through Winslow‑colored glasses, sure, but only because we’ve watched HR teams light up when they get their Thursdays back. Automating repetitive questions is the quickest, clearest path to that feeling.
If you’ll be at SHRM San Diego next week, swing by our booth. No hard sell—just a 15‑minute live demo and a conversation about how you’re fighting the question avalanche. Let’s turn busywork into breathing room, together. And you could win a free year of Winslow for your team. Book your demo here!
