Aaron Ward sat down with Steve Smith on Work Tech Weekly at Transform 2026 to talk about why coaching belongs in the hands of every employee, not just the lucky 5% at the top, and where the real conversations are actually happening when work goes home.
Aaron Ward, CEO of Huckleberry, sat down with Steve Smith on Work Tech Weekly at Transform 2026 in Las Vegas. The full conversation, plus the bit that's been on my mind since.
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There's a line from this episode I keep coming back to.
If you're not having good coaching conversations with your team at work, that doesn't mean those conversations aren't being had. They are. With a spouse over dinner. With Google at midnight. With ChatGPT in a private window the next morning.
And the answer your team is getting back? It's not necessarily the right one for them. It's almost certainly not the right one for your business.
That's the gap Huckleberry is built to close. The 36 minutes I spent with Steve walks through how, and why now, and what changes when every person in your business has a real coach in their pocket.
Below: the bits worth pulling out, plus timestamps if you want to skip around.
Huckleberry, as a product, was not possible a year ago.
What's changed is voice. Real-time voice AI that can hold a coaching conversation, remember what you said last month, and stay grounded in the context of your actual job. Memory plus voice plus context is the unlock. Without all three, what you have is a glorified search bar.
We all learned how to talk before we learned how to type. In a couple of years we'll look back at "type into a box and wait" the same way we look back at faxing. Talking is the natural mode. Writing was always the workaround.
Seven years ago I got my first executive coach. It changed me. Better leader. Better colleague. Better husband. Better father.
The thing is, to qualify for it, all I had to do was be a 40-something CEO of a venture-backed SaaS startup. That's who gets coaching.
What about everyone else? What about me at 25, the version of me who needed it most?
For decades coaching has been a luxury good. Reserved for executives, paid for by corporate budgets, available at $300 to $500 an hour. The 95% of professionals who've never had a coach are the ones who'd benefit from it most. They're the ones figuring it out alone, breaking, and only sometimes recovering.
We built Huckleberry so the answer to "who gets coaching?" is "everyone." At the start of a career, not the end when they're broken. At $20 a month per employee, not $500 an hour for the lucky few.
There's a reason real coaching is built on confidentiality. People don't open up to someone who can be subpoenaed by HR.
Most "AI for HR" tools fail this test the moment you read the docs. ChatGPT Enterprise has admin transcript access. Copilot has compliance APIs. Every prompt your team types is auditable, exportable, and a data risk if any of it touches a real situation, a real colleague, a real complaint.
Huckleberry is architecturally private. Not a policy. A design decision. Your manager cannot read your sessions. HR cannot. The company cannot. There is no compliance API, no eDiscovery path, no admin override that lets the wrong person read the right person's coaching. That's the only design that lets the conversation actually happen.
The average manager went from 12 direct reports to 15 in the last two or three years. The HR team that supports them is shrinking at the same time. The 1:1s are turning into status updates. The growth conversations are being pushed to next quarter. The hard feedback is going unsaid.
Then someone resigns. Then a Glassdoor review goes up. Then HR is in the room solving for something that should have been a coaching conversation eight weeks earlier.
Most managers aren't bad at this work. They're stretched past the point where 1:1 quality is humanly possible. AI coaching is the only lever I've found that actually moves on this. Not because it replaces the manager. Because it gives every employee a place to think out loud, prep the hard stuff, and grow in real time, without waiting on a slot that may never open.
When Huckleberry is working inside a company, the signal is simple. People are having tough conversations more often. Those conversations are going better. People are growing in their roles. They're staying. They're getting promoted.
For an HR leader watching the dashboard, every coaching session is roughly two hours of recovered productivity. Not because we billed against a 1:1, but because the conversation that needed to happen got the right answer the first time.
For a CFO, the avoided cost of a single retained mid-level manager pays for the platform across a thousand seats.
For the employee, it's the coach that the most successful people you know have always had. Now it just costs $25 a month, or zero if their employer is one of the businesses already running it.
One of the lines Steve pulled at the close of the episode, in his words better than mine.
If you have a good experience at work, you're going to go home, you're going to be nicer to your kids, you're going to be nicer to your spouse, you're going to pet the dog. Good things come out of that.
That's the whole thing. Make work better, and a lot of other things get better with it.
Work Tech Weekly Episode 13 with Steve Smith of RepCap, recorded live at Transform 2026.
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Or skip ahead:
Huckleberry is a voice-first AI professional coach for every person in your team. It's private by architecture, knows you and your company, and replaces the executive coach that used to cost $500 an hour.
Three things. It remembers you across sessions, so you're not starting from scratch every conversation. It has context about your team, your role, and your company through HRIS integrations and 360 feedback. And it's architecturally private, with no admin access, no compliance API, no path for anyone in your business to read your sessions.
Yes. End-to-end encrypted. Not a policy promise, a design decision. There is no admin transcript access, no eDiscovery path, no compliance API. Individual conversations are never visible to managers, HR, or the company.
Free tier with 30 minutes of coaching a month, no credit card required. $25 a month for individuals with unlimited coaching. $20 per seat per month for teams of five or more, including HRIS integrations and team insights. Compare to a human executive coach at $300 to $500 an hour.
Go to gethuckleberry.com and sign up. Everyone gets 30 minutes of coaching a month for free. If your company wants Huckleberry for the team, book a demo.
Aaron is the co-founder and CEO of Huckleberry. He was previously the founder and CEO of AskNicely, a customer feedback platform. He's based in New Zealand and is, in his own words, a recovering accountant.
Huckleberry is the AI professional coach that you can hire for every person in your team. Voice-first. Architecturally private. Built around the way coaching actually works.
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