CEO BLOG

The Secret Art (and Science) of Writing Great Questions at Joyous - Unplugged

Ruby Kolesky, CEO @ Joyous

May 5, 2025

 

Ever felt like the feedback you get isn't that useful? TL;DR: It’s probably not the feedback - it’s the way you asked.

In other words...it's not them, it's you. Want better feedback? Just ask better questions. Sounds simple, but in reality this is much easier said than done.

Before we dive in, a little context.

Joyous makes it simple for leaders to quickly identify high-impact changes based on frontline feedback.

Our platform - and the questions we design - helps some of the world’s largest organisations uncover fast, actionable insight across areas like cost optimisation, service delivery, workflow efficiency, employee experience, accelerating change, and sales innovation.

Behind the scenes, we’ve developed a library of conversation templates and a structured, question formula. An approach based on millions of conversations and years of experimenting and refinement.

That approach is the foundation of this blog.

Why now?

Because last week we launched our AI Campaign Design Assistant. It doesn’t just craft upfront questions - it scripts full conversations, combining structured drafts with our existing dynamic real-time follow-ups.

It’s our best work, made accessible at scale.

And if you care about asking better questions - and getting better, more useful answers - I’d love to share some tips based on what we’ve learned.

1. Stop wasting everyone's time.

Three good reasons not to ask for feedback:

  • You don’t care.
  • They don’t care.
  • You don’t plan to act.

If any of those are true, then don’t ask.

As the CEO of a feedback company, you might be surprised I’m saying this. But we give this advice to customers all the time.

Feedback is a valuable resource. Please don’t waste it. Everyone’s busy enough already.

2. Get out of the 1980s with your big ol' survey.

Surveys might get you scale, but they are too long and too vague.

People talk about survey fatigue. I talk about survey trauma.

I get it though. You feel like you have to ask all those questions. Your KPIs depend on them. Management expects them. But even if it’s easier said than done, it’s still worth challenging.

We're all on a feedback journey - myself included.

To be transparent, our methodology does include an optional baseline survey to start, followed by short pulses to verify impact.

But the real goal? Getting to fast, targeted conversations.

An example of our structured approach to frontline feedback for the Operations use case



So if not surveys, then what?

  • Focus groups? Too small, even if they offer juicy insights. Also a lot of work to organise and analyse.
  • Crowdsourcing? Fun, but chaotic - a minefield of feedback you probably won’t act on.
  • Interviews or ride-alongs? Glorious, but not scalable. One data point ≠ decision material.
  • AI-Powered 1:1 Chats? Scalable, fast and actionable. Can do more harm than good if not handled with care.

Joyous is primarily focused on the last one.

3. Don't ask more than two questions at a time.

You've got between 60 seconds to 3 minutes before you start to lose people. Largely thanks to that device you're reading this on.

A Joyous campaign covers two topics, tackled over two weeks - each with a pre-designed rated statement and an open text question.

After someone replies to the open text question, an AI agent first checks if the response is detailed or vague. If it's vague, it asks a tailored follow-up - once only.

This means no need for more questions or complex branching upfront. People can simply speak their mind, and we follow their lead in real time.

The design structure of a Joyous campaign



Our data from millions of conversations confirms: Asking less (questions) actually gets you more (actionable insight).

Thanks to this approach the average Joyous conversation is wrapped up in less than 2 minutes. With enough depth to act on.

4. Stop asking bad questions. Use these five principles instead.

Poorly formed questions are the number one reason leaders get bad feedback. And you, dear leader, are probably not trained in the art (and science) of writing great ones.

Here’s what our new AI assistant builds into every campaign:

Principle 1: Identify and solve in one go.

Don’t separate problem and solution. Ask a question that gets you both - it's just more efficient this way.

Example:

  • ❌ “What gets in the way of selling [product] to customers?”
  • ✅ “What would make it easier to sell [product] to customers?”

The second one gives you the barrier and the fix.

Principle 2: Keep reading age low.

Keep it simple and short, aiming for Grade 6 or lower. Avoid jargon, acronyms, adverbs, and passive voice. This reduces the risk of confusion, especially for non-native readers.

Example:

  • ❌ “What out-the-box alternatives should we evaluate to drastically increase the effectiveness of our sales offer for E2E fiber?”
  • ✅ “What changes could make our end-to-end fiber sales offer more effective?”

The first is 19 words, Grade 15, and very hard to read. The second is 13 words, Grade 6, and clear.

Fun fact: this blog reads at Grade 5.

Principle 3: Ask one thing at a time.

Compound questions confuse people and muddy results.

Example:

  • ❌ “How can we improve our sales process and training?”
  • ✅ “How can we improve our sales process?”

Otherwise, they might only answer one part - and you won’t know which, making it hard to analyse.

Principle 4: Make it safe to answer.

Don’t put people on the spot. Ask about the thing, not the person.

Examples:

  • ❌ “I understand the training.” (self-judgment)
  • ❌ “The trainer is easy to understand.” (risks targeting someone else)
  • ✅ “The training is clear.” (neutral and safe)

Principle 5: Keep the conversation flowing.

A good campaign design flows like a real conversation.

The initial messages should be in natural language and each question should follow logically from the last. This makes the interaction for the person responding more comfortable.

Example:

  • ❌ Rated Statement: “The sales process is clear.” Open-Text Question: “How can we improve our sales training?” (slight topic shift = requires mental adjustment)
  • ✅ Rated Statement: “The sales process is clear.” Open-Text Question: “What could we do to clarify the sales process?” (logical follow-on = brain already focused on topic)

5. Use our AI Assistant.

Shameless plug? Maybe. But it’s worth it. And honestly, I'm just bloody proud of us.

Start a draft campaign in the Joyous template library using the Campaign Assistant


Here's how it generates high-quality questions (and a full campaign draft) in seconds.:

  1. You describe your purpose, topics, and audience.
  2. It finds the closest matches in our extensive campaign template library.
  3. It drafts a full campaign: natural intro messages, rated statements, open-text questions - all aligned with Joyous best practices.

We use either a GPT-4o or Gemini 2.0 Pro prompt (like ice-cream we let people pick their fave flavours).

We optimise the output with a process called RAG (retrieval augmented generation). In plain English: it only pulls from our proven campaigns, so it doesn’t go rogue or get weird.

A draft preview from the campaign assistant


This isn’t generic AI. It’s purpose-built. Using our structured approach, domain expertise, and conversation insights proven and refined over many years.

Is This A Closing question? ✅

I hope the next question (pair) you ask your team unlocks truly useful feedback for you!

In a world of constant change and stretched teams, leaders struggle to meaningfully engage frontline teams in ways that drive real impact.

As a result, change takes longer, costs more and often fails altogether.

Rather than using AI to replace humans, Joyous uses AI to help leaders make sense of critical human thinking. We run one-on-one conversations across the frontline, surfacing actionable insight and delivering a prioritised action plan - fast.

And yes, we make it just as easy for you to share the plan and the outcomes back to those who gave feedback.

If you’re not already tapping into this - the real insight hiding in plain sight - ask yourself: can you afford not to?

Ruby Kolesky
CEO @ Joyous
 

Ruby is a comedian-turned engineer, previously leading product at two global tech companies, she has been CEO at Joyous for 4 years. Her passion for making a positive impact on people’s lives is perfectly matched with the mission of Joyous to make life better for people at work.

She enjoys working across all parts of the organization and is passionate about product direction and data science.

She is the co-author of Joyfully, a book about shared leadership, modern organizational structures, and a new way of working. Her second book Pathways, is a guide to help woman and other under-represented people get a job in technology in six months or less.

She was the Winner of the Product Category for Women Leading Tech Australia 2022 and a finalist in the Inspiring Individual Category of the HiTech awards in 2023.

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