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Ep 283 – Diane Sadowski-Joseph (Co-Founder, Clarinet)
Published 3 days ago • 5 min read
Go listento the latest episode of The Modern People Leader — where we sat down with Diane Sadowski-Joseph, Co-Founder and Head of Product at Clarinet (formerly ApplyAI), to talk about how HR teams can actually move from AI curiosity to AI execution.
If you’ve ever felt behind on AI — or overwhelmed by the sheer volume of tools, workflows, and “10x” case studies flooding your feed — this one’s for you.
Here’s what stood out most from the conversation. ⬇️
“Build AI on something — not something on AI.” — Diane Sadowski-Joseph
1. You’re not behind — you’re comparing outputs, not inputs
It’s easy to scroll LinkedIn and feel like everyone else has already automated their entire function. But Diane made a critical distinction: most teams are comparing outcomes without understanding the inputs required to get there.
For AI to truly unlock value, you need three things:
A somewhat standardized process
Clean, accessible data
A consistent problem + consistent output
“How many areas of a startup truly have that trifecta of clear process, standardized data, and consistent output and frequency?”
Not many.
AI is often marketed as plug-and-play magic. But in reality, it thrives in structured environments. If your workflows are chaotic, your data is messy, and your output constantly changes, AI won’t save you — it will amplify the mess.
The takeaway: before chasing the latest model release, ask whether your inputs support the outcome you’re expecting.
🏡 A better way to do backup care
Backup care has felt especially real for us lately. With Stephen navigating life with a newborn plus two teenage daughters, and Daniel raising a toddler - we find ourselves dealing with sick days, last-minute gaps, and those moments when childcare plans fall apart at the worst possible time. It’s also when you realize quickly whether your backup care benefit actually works… or just looks good on paper.
That’s the issue a lot of employers are running into these days. Traditional backup care wasn’t built for how families live and work today - so when employees need it most, it doesn’t show up.
That’s why more companies are switching to Wellthy Backup Care.
Here’s what that looks like in practice:
Flexible backup care for kids, adult dependents, and even pets
Access to a vetted provider network or a Wellthy expert who handles booking
Pay-as-you-go pricing so you only pay for care that’s actually used
Onsite and nearsite options for in-person teams
Backup care has changed. See the difference with Wellthy.
2. Stop chasing the latest model. Solve today’s problem.
One of the most freeing insights from Diane: the newest AI release isn’t necessarily the one that solves your problem.
“There’s a difference between the tech that solves your pain and the latest tech.”
It’s easy to fall into the trap of constantly upgrading — new models, new agents, new copilots. But most organizations haven’t fully implemented what’s already available.
Instead of asking: What’s the most cutting-edge tool?
Ask: What business pain are we trying to solve right now?
Diane framed AI adoption more like kaizen — continuous improvement — rather than a one-time “AI implementation.” Your workflow today will evolve in three months. That’s not failure. That’s iteration.
The use case implemented today beats the perfect use case you’re still designing.
3. If you don’t know where to start, automate work chores
Diane introduced a simple prioritization lens: the Five Frictions framework. But if you’re short on time, here’s the shortcut:
Start with work chores.
These are the time-consuming, low-leverage tasks that:
Drain cognitive energy
Don’t require deep strategic thinking
Often fall into the “rubber ball” category (drop it, and it bounces)
“Automate work chores first. Everyone will thank you. You will thank yourself.”
Work chores are powerful because:
The ROI is obvious (time + energy savings)
The risk is lower than experimenting on mission-critical systems
They build momentum quickly
Instead of trying to “AI-ify” your entire function, find the repetitive tasks that make you sigh every time you open them.
That’s your starting point.
📊Turn your people data into usable insight
In our MPL webinar on how HR teams are actually using AI, leaders like Jenny Molyneaux (Vercel) and Brandon Sammut (Zapier) kept highlighting the same idea: AI only matters if it makes insights usable. Teams don’t need more dashboards - they need clarity.
That’s exactly what Ask ChartHop is built for. You type a question and instantly get an answer. When we saw it at HR Tech, people were surprised by how fast it worked. Org charts, comp bands, churn risk, hiring timelines, pay equity views, headcount plans - all generated in seconds. No spreadsheets, no BI requests, no “I’ll get back to you.”
One of Diane’s client examples stood out: a fast-scaling fintech company trying to reduce time-to-hire.
Rather than brainstorming random AI ideas, they anchored everything to a business goal.
They realized hiring managers were slowing down candidate feedback. So they built a simple GPT that:
Took interview transcripts
Allowed messy bullet points from hiring managers
Transformed them into high-quality, legally compliant candidate feedback
Drafted the email for recruiting to send
What used to take days of shoulder-tapping now took minutes.
The result:
Faster time-to-hire
Higher candidate experience
Less friction between recruiting and hiring managers
“Build AI on something — not something on AI.”
That line stuck with us.
If you’re not tying AI to a KPI you’re already accountable for, you’re probably building theater — not leverage.
5. Click-cutters are the compounding interest of AI
Some of the most powerful wins aren’t flashy agents or dashboards. They’re what Diane calls “click cutters.”
These are tiny workflow improvements:
Automatically converting transcripts to Google Docs
Auto-filing documents into the right folders
Reducing copy/paste steps
Eliminating unnecessary tab switching
“Every little click is cognitive friction.”
It’s not just about saving time — it’s about preserving mental energy. The more micro-frictions you eliminate, the more strategic capacity you create.
Click cutters compound.
Individually, they seem small. Collectively, they change how your day feels.
💙 Make leave feel human - not chaotic
In one of our recent webinars, we talked about how leave is usually put into three buckets: compliance and pay, business continuity, and the very real human experience happening at home.
This couldn’t have hit harder for me and Stephen. We both recently became parents - and it showed how complex leave can be, even on a tiny team.
That’s exactly what Tilt is built for.
Tilt is a leave experience platform that manages all types of leave, nationwide - from FMLA and PFL to everything in between - while giving HR, managers, and employees clear visibility into what’s happening. It combines compliant leave management with a genuinely human experience.
Here’s what that looks like in practice:
Personalized leave plans for every employee
Role-based visibility for HR, managers, and employees
AI that automates admin and answers routine questions
Compliance-backed, expert support
It turns leave from paperwork into a people-first leave experience.
We’ve learned from the best HR leaders so you can lead like the best. Our newsletter brings you lessons from CHROs, Chief People Officers, and work pioneers who are reshaping the way we work. Through their stories, you’ll discover what’s working, what’s not, and how they’ve built their careers—giving you practical insights to shape what’s next for HR and for your own leadership.
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