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Development
9
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AI coaching for individuals: when no one is developing you

Career stalled, reviews vague, peers moving ahead? What AI coaching changes for individual contributors who have to run their own development. Start free.

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Performance
The coaching frameworks every leader should know
Performance

The coaching frameworks every leader should know

GROW, SBI, Situational Leadership: the three coaching frameworks every leader should know, when to use each, and how AI coaching applies them.

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Why generic AI assistants aren't safe for employee coaching
Privacy & Trust

Why generic AI assistants aren't safe for employee coaching

Employees are coaching themselves with ChatGPT, Claude, Gemini, and Copilot. Their prompts are admin-accessible by design. Here's the architectural fix HR can trust.

What AI coaching changes for managers
Development

What AI coaching changes for managers

You were promoted, but nobody coached you through it. What AI coaching changes for managers across retention, feedback, and the conversations that matter.

AI coaching for individuals: when no one is developing you
Development

AI coaching for individuals: when no one is developing you

Career stalled, reviews vague, peers moving ahead? What AI coaching changes for individual contributors who have to run their own development. Start free.

Where coaching actually happens - Work Tech Weekly
Company & Product

Where coaching actually happens - Work Tech Weekly

Aaron Ward on Work Tech Weekly: why coaching belongs with every employee, not just the lucky 5%, and where the real conversations actually happen.

The cost of inconsistent managers across your org
Retention

The cost of inconsistent managers across your org

Manager variance shows up in your engagement scores, exits, and L&D budget. What inconsistent managers cost across the org, and how to compress it at scale.

Executive coaching, for everyone
Accessibility

Executive coaching, for everyone

Executive coaching used to require a title and a budget most people never had. Here's why we built Huckleberry to make it something everyone can own.

What is AI coaching? A working definition for buyers
Company & Product

What is AI coaching? A working definition for buyers

What 'AI coaching' actually means, the nine questions to ask any vendor, and how to tell real coaching from a chatbot with a friendly tone. A buyer's guide.

The conversation that doesn't happen
Readiness

The conversation that doesn't happen

HR leaders told us the real problem is the hard conversation that never happens. Why coaching solves it, at a price that finally reaches everyone.

Coach the team, not just the manager
Development

Coach the team, not just the manager

Developing the manager doesn't develop the whole team. What changes when every person gets a coach of their own, and why architectural privacy makes it work.

Huckleberry raises US$1.2m to bring AI coaching to everyone at work
Company & Product

Huckleberry raises US$1.2m to bring AI coaching to everyone at work

Huckleberry raised US$1.2m in pre-seed to bring professional AI coaching to everyone at work, grounded in voice feedback from the people you work with.

AI coaching for executives and founders
Development

AI coaching for executives and founders

You had a coach. Your managers and high-potential ICs didn't. What scaled AI coaching does for the layer that will be running your org tomorrow.

Where coaching fits in L&D
Development

Where coaching fits in L&D

L&D delivers knowledge; coaching delivers transfer. Where continuous AI coaching fits in the stack, what it isn't replacing, and three plays to run.

Your assessments, finally put to work
Development

Your assessments, finally put to work

DISC, Big Five, StrengthsFinder: most assessments end up in a drawer. How Huckleberry turns them into living context that sharpens every session.

How we measure coaching quality
Company & Product

How we measure coaching quality

Most AI coaching asks you to take quality on faith. How Huckleberry scores every session against a rubric informed by the ICF Core Competencies.

Launching Huckleberry: a professional AI coach live from Transform 2026
Company & Product

Launching Huckleberry: a professional AI coach live from Transform 2026

Aaron Ward sits down with Samara Jaffe at Transform to launch Huckleberry. The 10-minute interview includes a live product demo and the founder's origin story.

Feedback is critical to better coaching
Company & Product

Feedback is critical to better coaching

A founder essay on why traditional 360 feedback fails, and what changes when feedback finally has somewhere useful to go: a coach who knows you.

How Huckleberry handles legally sensitive coaching territory
Privacy & Trust

How Huckleberry handles legally sensitive coaching territory

How Huckleberry handles FMLA, ADA, and protected-class conversations. The architectural guardrails, the in-session pivot, and what to bring to counsel.

I was skeptical of AI coaching. Here's what changed my mind.
Company & Product

I was skeptical of AI coaching. Here's what changed my mind.

A working coach was skeptical of AI coaching. Real stories on trust, safety, and what changed his mind about how Huckleberry deepens human coaching.

The coaching frameworks every leader should know
Performance

The coaching frameworks every leader should know

GROW, SBI, Situational Leadership: the three coaching frameworks every leader should know, when to use each, and how AI coaching applies them.

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