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What if contract law could be taught more like practicing a sport than reading a rulebook?

In this episode, I speak with Charlyn Ho, a former Navy Supply Officer, corporate law partner, and now the founder of Rikka (incl. Rikka Academy). Charlyn shares how she’s turning years of experience into structured, practical training for early-career lawyers—blending mock negotiations, real-life analogies, and AI feedback loops to close the training gap in legal education.

Whether you're in law, education, or any profession where practice matters more than theory, Charlyn’s approach offers an inspiring model.

🧠 Topics Covered

• From military contracts to startup founder: Charlyn’s path

• Why on-the-job training still dominates legal education

• The "teaching gap" in law firms and how Rikka fills it

• What good legal training looks like (hint: examples, not just theory)

• How AI bots can democratize learning in law

• Why Rikka Academy uses mock negotiations and clause analysis

• The hidden skill of adapting to “weird” contract terms

🔧 Key Takeaways

• Law is a practice, not just a theory — Most learning happens on the job, but many junior lawyers don't get enough real-world exposure early.

• Mentorship ≠ Teaching — Many partners are great lawyers but lack the skills (or time) to teach effectively.

• Simulations are essential — Rikka Academy uses real contract examples and mock negotiations to build muscle memory.

• AI can scale what great educators do — Charlyn is building an AI-powered bot to replicate her teaching feedback, making quality training more accessible.

• Mindset matters most — Instead of memorizing clauses, Rikka teaches how to think like a contract negotiator—especially when conditions are novel or unpredictable.

📚 Resources mentioned

• Book: The Tech Contracts Handbook by David Tollen

• Blog: Contract Nerds

• Ricca Academy: https://rikkagroup.com/rikkaacademy-homepage/

• YouTube Channel: Ricca Group

💬 Favorite Quote

“What I’m trying to teach is a methodology of thinking—so that the lawyer is able to adapt to any situation, even if the book or academy didn’t teach them that specific lesson.”
— Charlyn Ho

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I recently came across a fantastic talk by Val Geisler, an email onboarding expert who shared a simple yet effective framework for email onboarding. If you've ever felt overwhelmed about what emails to send during onboarding or worried about over-emailing your list, this approach is for you. Let's dive in and make your emails more engaging and enjoyable for your audience.

What you'll learn

• How to structure your email onboarding using the Dinner Party Strategy

• Tips for creating personal and valuable emails that resonate with your subscribers

• Ways to keep your audience engaged without overwhelming them

The Dinner Party Strategy: An email onboarding framework

I love using metaphors to help ideas stick, and the Dinner Party Strategy does just that for email onboarding. Think of your email sequence like hosting a dinner party—you don't serve dinner the moment guests walk in. There's a flow and a build-up that keeps guests engaged. Let's break it down:

👋 Welcome email: saying hello

Your welcome email is like greeting guests at the door. Make it personal and friendly. Instead of the usual "Welcome to [Your Brand]," try something different to stand out. For example, Drift (acquired by Salesloft in Feb 2024) was one of the first companies where the first email had “Just saying hey" as their subject line, accompanied by a casual video message. It's approachable and sets a warm tone.

🍞 Appetizers: bringing early value

Before diving into your product, offer something valuable. This could be helpful tips, insights, or resources that benefit your subscriber. For instance, a proposal software might highlight popular templates that save time. It's about adding value without immediately pushing your product.

🍝 Main course: introducing your product

Now it's time for the main event—your product. This email focuses on how your product solves problems for your customers. It's not about listing features but relating them back to the customer's needs. Remember, it's the third email, not the first, where you delve into product details.

🌮 Side dishes: offering additional value

Side dishes enhance the main course, just like extra content enhances your email sequence. Share in-depth guides, ebooks, or courses that provide further value. CoSchedule, for example, sends comprehensive content that helps users get the most out of their marketing efforts.

🍰 Dessert: a sweet bonus

As you approach the end of a trial or promotional period, offer a little something extra to encourage action. This could be a discount, a free trial extension, or a referral bonus. It's that final touch that can prompt subscribers to convert.

📨 Return invite: keeping the connection alive

Onboarding doesn't end when the trial does. Invite your subscribers to come back or stay engaged, even if they haven't converted yet. A simple email from monday.com, for instance, offers a trial extension, encouraging users to give it another go.

🪤 Avoiding the spam trap

To ensure your emails get opened and read:

• Be useful: Provide content that offers real value.

• Be personal: Write in a way that feels like a one-on-one conversation.

• Limit distractions: Keep your emails focused with clear calls to action.

An email with a specific purpose and minimal distractions increases engagement and conversion rates.

📌 Putting it all together

Creating high-value onboarding campaigns is absolutely doable, even if you're new to it. By following the Dinner Party Strategy, you can build genuine relationships with your subscribers, which can significantly impact your business. Remember, email onboarding is all about testing and refining—there's no one-size-fits-all solution. Keep your emails straightforward, valuable, and personal. Now it's time to put this strategy to work. I'd love to hear how it goes for you!

📈 Improve your customer onboarding and activation

Check out Qurioos: Turn every user into a product expert 🏆. We transform your onboarding and activation into polished personalized experiences that drive adoption faster than ever.

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Customer onboarding is crucial for driving success and retention. Yet, gaining leadership recognition and support for onboarding initiatives can be challenging. Let's explore the hurdles in securing leadership buy-in and practical strategies to demonstrate onboarding's value while aligning it with broader business goals.

Challenges in gaining recognition for onboarding

Onboarding is often viewed as a secondary or reactive function—a cost center rather than a revenue driver. This misconception leads to insufficient investment and support from leadership.

⚙️ Connecting onboarding to revenue metrics

Leadership typically focuses on new revenue and churn rates. Onboarding teams need to show how their efforts influence these areas. Effective onboarding reduces early churn and accelerates customer activation, directly impacting the bottom line.

📌 Establishing and owning key onboarding metrics

Without concrete metrics, it's challenging to prove onboarding's impact. Many teams lack data on how long it takes customers to get up and running or how many succeed or fail during onboarding.

💬 Aligning onboarding with business objectives

Understanding and aligning with the company's broader goals is essential. Onboarding should support key objectives like customer growth, expansion, and retention.

🗣️ Proactive communication and advocacy

Onboarding teams can't wait for recognition—they need to advocate for themselves. This involves consistently communicating wins, sharing insights, and demonstrating how onboarding contributes to overall success.

🙌 What leaders can do to invest in customer onboarding

Leaders play a pivotal role in empowering onboarding teams. By actively supporting and involving themselves, they can enhance the team's impact.

Key takeaways for leaders:

1. Join onboarding calls: Participate in customer calls to gain firsthand insight into the onboarding process and challenges.

2. Include onboarding leaders in strategic meetings: Ensure they have a seat at the table to provide input and align strategies.

3. Open communication: Encourage onboarding teams to share their metrics, challenges, and successes openly.

4. Align goals and metrics: Work collaboratively to set goals that support overall business objectives.

⬆️ Conclusion

Securing leadership support for customer onboarding requires a strategic approach that highlights its direct impact on revenue and customer success. By owning key metrics, aligning with business goals, and proactively communicating their value, onboarding teams can transform perceptions and gain the recognition and resources they need.

For leaders, investing in customer onboarding isn't just about reducing churn—it's about fostering long-term customer relationships and driving sustainable growth. By empowering onboarding teams, leaders unlock significant value for both customers and the organization.

📈 Improve your customer onboarding and activation

Check out Qurioos: Turn every user into a product expert 🏆. We transform your onboarding and activation into polished personalized experiences that drive adoption faster than ever.

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In the world of SaaS, customer onboarding can be a make-or-break factor for user retention and satisfaction. There's an ongoing debate between adopting human-led onboarding or relying on in-app solutions to guide customers. Let’s see how both approaches can complement each other.

🎩 1. The myth of the perfectly intuitive product

One of the biggest misconceptions in onboarding is the belief that a product can be designed so intuitively that users don’t need human assistance. While product teams strive to create seamless experiences, the reality is that not every user will engage with or understand even the most well-designed features in the same way. Adult learners vary in how they absorb information, and relying solely on pop-ups or guides often falls short of ensuring full adoption.

🤖 2. Why in-app onboarding alone isn’t enough

In-app onboarding can be an excellent tool for driving feature usage and increasing activation. However, many companies make the mistake of assuming that this approach will solve all onboarding challenges. In reality, in-app solutions only work when they’re highly targeted and relevant to the user’s specific needs. A generic tour or pop-up often fails to tie back to the user’s goals, which is where the approach starts to break down.

⛰️ 3. Understanding leadership’s role in onboarding decisions

Often, leadership or engineering teams push for a completely in-app approach, believing that a perfectly designed product eliminates the need for onboarding teams. This mindset can stem from a reluctance to acknowledge that their product isn’t as intuitive as they hoped. However, removing onboarding teams without a robust in-app alternative tends to overwhelm support teams with questions, ultimately harming the customer experience.

👤 4. The importance of human touch in onboarding

There is a common belief that product-led growth models eliminate the need for human touch in onboarding. While these models are efficient for some aspects of user acquisition and activation, they still require human-led components to ensure long-term success. Enterprise customers, in particular, often expect hands-on support, even when they’re comfortable with the product itself.

🔔 5. Maintaining and evolving in-app onboarding

One of the challenges of relying on in-app onboarding is that it requires constant maintenance. Product features evolve, user goals shift, and new issues arise—making it crucial to continuously update in-app guides, prompts, and training materials. Relying solely on in-app onboarding without regular updates leads to outdated information and frustrated users.

🔗 6. How human and in-app onboarding work together

The most effective onboarding strategies integrate both human-led and in-app components. In-app tools can handle the repetitive, instructional aspects of onboarding, such as guiding users through features. Meanwhile, onboarding teams can focus on more strategic conversations, helping users align product usage with their business goals.

🚀 7. Scaling onboarding without losing the human element

As companies grow, scaling onboarding becomes a challenge. It’s tempting to look for ways to reduce headcount by relying more heavily on in-app solutions. However, rather than eliminating onboarding teams, the focus should be on making them more efficient. By offloading basic tasks to in-app tools, onboarding teams can dedicate more time to strategic guidance and higher-value activities.

⬆️ Conclusion

While it’s tempting to dream of a future where all onboarding is automated, the reality is that products—and the people who use them—are complex. A well-designed in-app experience can handle certain aspects of onboarding, but it will never fully replace the need for human support. The most successful companies are those that find ways to integrate both approaches, ensuring that customers not only know how to use the product but also achieve the goals they signed up for in the first place.

In the end, onboarding is not just about learning to use a product—it’s about setting the customer up for long-term success.

📈 Improve your customer onboarding and activation

Check out Qurioos: Turn every user into a product expert 🏆. We transform your onboarding and activation into polished personalized experiences that drive adoption faster than ever.

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Hey everyone! I recently had an awesome chat with a customer about setting up an LMS (Learning Management System) without breaking the bank, and I just had to share it with you all.

So, imagine you're just starting out and need to organize your educational content. You don't want to invest in a full-scale custom LMS yet. This customer told me they used Google Drive to create a free LMS and it worked wonders for them. It gave them a way to structure their content and really understand what their learners needed before they made the leap to a custom system.

Now, I know what you're thinking – a Google Drive LMS isn't the same as a professional LMS. And you're right, it's not. But it's a fantastic first step. Here’s why:

1. Organizing Your Content: Google Drive lets you create folders and subfolders to neatly organize your materials. It's like having a digital filing cabinet, making it super easy to keep track of everything.

2. Private Video Hosting: This is a big one. Instead of uploading videos to YouTube as unlisted (which isn’t really private), you can upload them directly to Google Drive. This way, your videos are truly private and only accessible to those you share them with.

3. Flexibility with Integrations and Reports: Google Drive is incredibly flexible. You can use Google Slides, Forms, and Sheets to create custom reports. And if you want to get fancy, tools like Zapier or Make.com can help you integrate and automate processes, making your life so much easier.

4. Cost-Effective: Best part? It’s free! For small teams or organizations just getting started, this is a no-brainer.

The customer I spoke to found that by starting with Google Drive, they could effectively plan their content and understand what worked best for their learners. When they were ready to invest in a custom LMS, they knew exactly what they needed.

So, if you're in the early stages of creating an LMS, give Google Drive a shot. It’s a practical, cost-effective way to get your content organized and gather valuable insights into your learners' needs. And when you’re ready to go big, you'll have a clear idea of what features to look for in a custom LMS.

Let me know if you have any questions or if you’ve tried this yourself. I’d love to hear your thoughts!

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🤣 Who doesn't want yet another e-learning module...

AI image of the week, created with Canva AI Image Generator.

🎥 Video script prompt for ChatGPT

If you need to create videos, you might want to use ChatGPT or something similar to write the script. Here is a smart way to structure your prompt, by @Scott Millard from Videospark.

🗣️ Three types of feedback to improve your courses

By James Clear, author of Atomic Habits:

“My friend once said my feedback (about writing) always falls into three categories:

1. Make it shorter.
2. Make it more appealing.
3. How could it apply to more people?"

🥽 VR for language learning….?

The last thing I would expect to learn using a VR headset was language! It seems people are searching for this as it’s the top trending search across the VR learning topic.

📢 The concept of “learning in public”

In 2019, Shan Wang (known as Swyx) published an article about learning in public that resonated with many people. I’m a big fan of this concept, and this newsletter is part of my learning in public.

“Whatever your thing is, make the thing you wish you had found when you were learning. Don’t judge your results by “claps” or retweets or stars or upvotes - just talk to yourself from 3 months ago. I keep an almost-daily dev blog written for no one else but me.”

🚨 Before you start building a course…

Kirsten Campbell-Howes, a learning design mentor shared her take on how to start building a course on the newsletter. She covers ✅:

1. How to define learning outcomes
2. How to understand your target audience of learners
3. How to avoid common pitfalls when designing a curriculum

👩 10 image generators for your courses

From the Trends.vc newsletter:

• ​HeadshotPro • Professional business headshots by Danny Postma​

• ​Photo AI • Create beautiful AI photos without using a camera by Pieter Levels​

• ​Secta AI • Turn selfies into professional headshots with AI

• ​Aragon AI • The most realistic AI headshot generator

• ​InstaHeadshots • Turn your selfies into professional business headshots by Magic Studio​

• ​1PhotoAI • Generate beautiful AI photos from one selfie by Ken​

• ​Try it on AI • AI headshots for your LinkedIn, resume, social media and more

• ​Simplified • Generate professional headshots without breaking the bank

• ​BetterPic • Professional headshots with your phone selfies and everyday photos

• ​HeadshotsMaker • Professional headshots in 2 clicks by Vadym

🔍 Random

Reddit’s Instructional Design community is in the Top 3% subreddits!

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😂 AI generated image of the week

I used Koala for this one and the prompt was:

A person who needs to change jobs, and it assigned to a new team where he has to get re-trained and learn new skills.

💬 Internal mobility and learning -vs- Laying off

Some companies reduce their costs by laying off staff. Other companies find new roles for their existing staff and enable them to add more value. This increases the need for training and supporting those who suddenly are in a new team with a new role. Learn how they did that at Zapier. Also, check out this article from Raconteur.

❓ Video production: $3000/minute to $___/minute

Video and image generation is a crucial part of learning programs. Costs typically vary between $1,500 and $10,000/minute. A reasonable approximation for a 5-minute video is $3,000/minute.

How much will AI impact this?

According to Bain & Co. (the global consulting firm) for films with limited visual effects where production is closer to $500k/minute, the cost saving would be in the range of 5% to 10%, including cutting 4 weeks off production time.

For learning & training videos: It’s too early to even estimate.

🗣️ Improving your copy (so your GPT can do the same)

Copywriting is super important in learning. Yet most of us are bad at writing.

“Most people write copy like they are writing instruction manuals. They got lost in explaining how the sausage is made and no one cares. And even worse they use that same robotic copy in the content they create.

By Greg Isenberg (An advisor for Reddit, TikTok / 373k followers on Twitter/X)

Here is Greg’s list of 18 things you need to focus on to improve your copy:

⚙️ Tools

Koala: Claims to be 8X faster in image generation.

Gamma: Build epic decks just from text.

Castmagic: Upload a recorded conversation - It generates all the social and other content for you to tweak and publish

💡 Cool stuff

Harvard Business Review: Voice Recognition Still Has Race and Gender Biases

New York Times: Chilly at Work? Office Formula Was Devised for Men

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📶 Stat of the week

A 2021 survey of 800 Gen Z found that 76% believe learning is key to success in the workplace. Was it just because they are younger than other generations and they have more things to learn, or is it a generational shift?

👥 Learning communities are bad. Can we fix them?

Gina Bianchini, CEO & Co-Founder Mighty Networks, a popular community learning platform thinks we can.

“Today, we’re spending an average of eight hours a day consuming content.

Content that creates the illusion of connection without the real thing.

And it’s making many of us miserable.”

Read the full article here

🎮 Adding games to your training

Genie, claims to be the first generative interactive environment that allows you to create simple interactive games like this in a few clicks. Would you add a game to your course or training? I will add one for sure.

“The model can be prompted to generate an endless variety of action-controllable virtual worlds described through text, synthetic images, photographs, and even sketches.”

🧠 Top priority for remote workers: Improve skills

On the latest We Work Remotely report (surveys 2000 remote workers) the #1 priority was learning new things! I'm not sure what the priorities are for in-office workers.

🎙️ Podcasts in training?

Pew Research published a report showing the most popular podcast categories in the US and it got me thinking. Audio/podcasts are rarely used in learning and training and I think it’s probably because people listen to podcasts for entertainment, not for work-related things. Also, a 2021 study found that podcast listening happens mostly outside work which makes sense: 49% at home, 22% while driving, 11% at work, 8% while exercising.

😂 Random joke

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🦸 The age of the ✨ super-instructor ✨

I predict GenAI will enable any expert to become a ✨ super-instructor ✨ → Learning & development will become largely automated → The top 3% of learning & development professionals will become strategic advisors working with ✨ super-instructors ✨, and everyone else will change jobs.

We already saw experts teaching at General Assembly and Maven (example below) but I think the ✨ super-instructors ✨ will replace every single course created by L&D:

😱 Create a learning tool in 5 minutes

Amjad Masad, the founder of Replit (a popular developer tool) gave a speech on TED AI 2023 showing how anyone can chat with an AI bot and build a software product in minutes. What is the future of learning software?

Watch it here on ted.com

The magic number: ✨ 40 hours of training ✨

Back in 2013, IBM reported:

“When preparing for a project, teams receiving 40 hours of training per member met their significant project objectives three times as often as teams that received 30 hours of training or less.” From The Value of Training report

What will that number be with AI?

Get the full report

🔁 Spaced repetition + AI

In the 1800s, psychologist Hermann Ebbinghaus found that we typically lose 80% of the knowledge we’ve learned within a month! It’s inevitable: when we take on information that we don’t consider critical, the knowledge gradually degrades over time. (Source: Valamis)

Training without spaced repetition looks like this👇

If you use spaced repetition, it looks like this:

How will training change if we live in a world where we don’t need to memorize as much knowledge given AI will be our second brain?

🎞️ OK Sora

Open AI launched Sora where you generate videos by simply describing the content using text. Just think how that impacts 💥 learning and training video creation💥

⚙️ Cool tools

These recommendations are from Vaibhav Sisinty, founder of growthschool.io

Humata: AI assistant for working faster with documents.

Claude AI: AI assistant for various tasks from sophisticated dialogue and creative content generation to detailed instruction.

Uberduck: Text-to-speech singing and rapping vocals for creative agencies, musicians, and coders.

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💬 Onboarding chatbots anyone?

Already from 2019, Akamai (9000+ employees, cloud technologies) built Avi, a chatbot that helps new hires navigate the onboarding process and complete their certification.

• Boosted completion rate 📈: New hires who used Avi were 58% more likely to complete their Technical Primer Certification, plus it took 20% less time.

• Increased impact 💪: 80% of users reported feeling confident with HTTP concepts taught in their certification training.

But the real question is → how many companies are using onboarding chatbots now?

🔌 Automating evaluations and feedback for 1-on-1s

Watch here how a custom AI solution can analyze recorded one-on-one sessions (feedback, mentoring, coaching..etc.), score the session's quality, and give immediate feedback to the coach/mentor.

The use case I found is built by Gianni Mazza at Third Space Learning for one-on-one tutoring sessions between a tutor and a student. If you add sentiment and tone analysis, this process can have epic outcomes.

Steps:

1. They tried building it using ChatGPT 4, but it didn't work.

2. They combined a Python script to run it + an NLP library to analyze the language used by the tutor + an open-source model to create actionable suggestions for tutors, and it worked.

3. They now have to focus on making it operational at scale and cost-efficient as they want to run this to 10k one-on-one sessions per week.

🧐 There is a GPT for everything - including L&D

In case you haven’t checked the OpenAI’s library of custom GPTs recently, now there is a GPT for everything. I searched for "'training” and I got GPTs for dog training 🐶, astronaut training 🧑‍🚀, humor training 😂, and more.

Some GPTs are hyper-valuable!

Like the CustomerEd Strategist & Growth Advisor created by Jim Conley, ex-Director of Partner Education @ Twitter/X, ex-Global Lead for Scaled Creator Development @ Youtube. Give it a try!

🗣️ Quote: "Always ask, but never expect”

By James Clear, Author of Atomic Habits.

“Always ask for what you want. Many people are happy to help—if the request is direct and specific. In a surprising number of cases, something remarkable is possible if you have the courage to ask.

Never expect people to say yes. Everyone is busy and balancing multiple priorities. Your request is not their responsibility. When you're told no, move on lightly and freely. The world is full of opportunity."

⚙️ Cool tools

Colossyan: The AI video platform for workplace learning (just raised $22m).

Kaiber: Turn text, videos, photos, and music into stunning videos.

Apple has recently unveiled MGIE. Users can simply describe desired edits in natural language, and watch as the AI seamlessly brings their vision to life.

😂 Random joke

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🔗 7 embedded learning examples

Productivity

Platforms where teams create and manage their work.

1. Notion - Watch here how Notion expert Marie Poulin creates and tracks online learning for 😲 2200+ learners with 100+ lessons, through Notion templates.

Note: I’ve personally experienced a new hire onboarding & learning path built on Notion and IMHO it was much better than LMS-based onboarding paths I’ve seen.

Community

Platforms where teams and companies gather to discuss and connect.

2. Circle - a popular community platform, offers a powerful learning management feature set for creating and tracking learning paths within a community-first product.

HRIS

Platforms where HR teams manage payroll, benefits, compliance, time and attendance, etc.

3. Gusto - one of the most popular HRIS tools, offers several LMS integrations as well as their own Gusto Learning which includes basic compliance training programs.

4.​ Rippling​ - another very popular platform that started as an HRIS and now expanded into IT and Finance, offers a fully-fledged LMS​ along with learning automation that brings team members back into learning paths.

Employee experience

The platforms for managing onboarding (beyond legal and payroll), understanding employee happiness, setting and managing employee goals, and career development paths for employees.

5. CultureAmp​ - a popular experience platform, offers a feature called Skills Coach​ which integrates micro-learning in tools like Slack, Teams, and email.

6. Leapsome​ - another popular platform - offers a wide range of learning features including live training. They also partnered with Dutch course provider ​GoodHabitz​ to make it easy for Leapsome customers to use their courses covering 65 competencies.

Risk management

Platforms that help companies reduce security, privacy, compliance, and other risks.

7. Haekka - a popular platform in this space, delivers security and privacy training to employees directly inside Slack, right when it’s required.

What’s next?

Learning is evolving, we’ll see a lot of ‘new’ ways to create and manage learning like the example below, where someone is trying to understand how to do that on Asana, the popular project management tool.

📮Popular from Linkedin

📽 Are you spending hours creating videos?

1. ​HeyGen​ — AI videos of you. Upload a few videos of yourself and the script, and let the AI create videos of you talking, just by uploading text. Surreal! 🤯

2. ​Video.AI​ by Microsoft Azure — Auto-extract meaningful snippets from your videos. It uses various machine learning algorithms to understand which parts of your videos are more important.

3. ​Descript​ — When you’re creating videos for your courses, you often need to edit stuff out eg pauses or entire sentences you didn’t like. You can do that by editing the text, and it automatically removes the related seconds from the video.

🎙 Podcast nuggets

​Damien Yee​ (Singapore) Chief Learning Officer at ​Epitome​, interview with Sonia Sant (Singapore)​. Full episode here.

• 🤖 AI Integration in L&D: "So I see AI not as a singular Band-Aid, but rather in all the different functions that we see in the organization."

• ✍ AI for Content Creation: "You can use AI to kind of do the research for you, create templates to up your Lesson plan."

• 🎛 AI for Customization and Personalization: "It is potentially possible that you can generate more customization, personalization for the learner, and I think that part is exciting.”

• ⚖ Guidelines and Ethical Considerations: "Before we even go there, there's a need for organizations to decide how they want to participate with Generative AI. What are the guidelines internally?"

• 🧠 Adaptation and Critical Thinking: "Don't think that what you're doing now is still going to be relevant and you just start thinking about what is the relevancy that you bring to the organization and start from there to kind of craft your new role."

​Andrés Peters,​ Chief Learning Officer at ​Maestro Group​, interview with 360Learning. Full episode here.

• 👩‍🎨 Artisan-like: "My role is just to help individuals do their jobs more artisan-like and with much more pride."

• 👨‍💻 Changing environment: "The company shifted from live to virtual training and is now transitioning to self-paced learning."

• Kirkpatrick's 4 levels of learning evaluation: "We also have added in these additional questions (unexpected learnings and missed expectations) that I think most learning organizations don't tend to ask, but we feel like they're really impactful to us."

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Kaz Ohta is the ex-VP Technology at Arm (7,711 employees) and CEO of Treasure Data (Customer Data Cloud unites operations, service, sales, and marketing teams around the same unified customer profiles).

1. Why you shouldn’t train customer success teams to sell

Customer success team members should focus on activation, customer needs alignment, and churn prevention.

If they try to upsell, cross-sell, or expand the account in any way, the relationship with the customers becomes more transactional. Churn risk increases as customers start seeing them differently.

🙌 This is why it’s crucial to separate the expansion function from the customer success function.

2. How to train your enterprise customer onboarding team

• Value engineering framework: Treasure Data uses it to understand how they can create value for customers fast once the 6-9 month implementation is done.

• Focus on low-hanging fruit: In their case, they use the customer data that lives on their platform to create quick wins by helping customers optimize existing costs and cut unnecessary costs.

• Joint plan: In order to ensure you have defined goals with customers, enterprise CS teams should be trained to build a shared plan with the customer that outlines what the goals are, how we’ll get there, and what success looks like.

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🎩 Customer: “Obviously this is a hat”

Modern teams that work on customer onboarding and success should be seen as revenue functions, as they enable revenue for customers that don’t know how to get value.

🔢 What is your north star metric?

1. Onboarding aligned with customer needs

🏥 Commercial health

• Are your customers set up to renew or expand?

• What things need to happen during onboarding to ensure you’re ready for this when the time comes?

🔚 Outcomes

• Are you delivering business value?

• Do you have an agreed way to measure qualitative and quantitative outcomes?

🔊 Customer sentiment

• Do you and your customers agree on the right way to solve problems?

• Are you able to support the way they wish to get help from you?

🤝 Key relationships

• Are you actively nurturing champions and economic buyers?

• Do you have nurture relationships with 2+ people in case someone leaves?

📋 Feature completeness

• Does your product have the right features?

• Does your roadmap align with customer needs?

⚙️ Technical health

• Does your product work for the customers?

• Does it have technical limitations that act as bottlenecks?

2. Onboarding aligned with the C.A.R.E framework

• Convert: What training/education is needed to convert prospects?

• Activate: What is an activated customer for you and what training/education is needed to get them there?

• Retain: What knowledge do your customers need to stay with you?

• Expand: How can customer education help with expansion?

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Brian Balfour is the ex-VP Growth at HubSpot and founder of Reforge (on-demand and live learning for product leaders and teams). He has experienced HubSpot’s growth from the early days and in this Churn.FM episode, he offers valuable insights on how teams should think when it comes to customer onboarding.

1. Why customer training fails to match the key moments

According to Reforge, products should focus on 3 key moments in a customer journey:

• The setup moment

• The aha! moment

• The habit moment

To understand those moments, you need to do qualitative analysis for being able to answer:

• What the habit looks like?

• What that journey to reach the habit is?

🚨 Most customer success teams don’t have the resources and/or processes in place to think and act in that way.

They deliver initial onboarding materials and 1-2 calls and they consider the customer onboarded, when in fact they are not there yet.

Working from a conversion point forward doesn’t allow you to understand the destination you’re trying to get the customers to. Because of that, customer training is often focused exclusively on setup and not on activation.

✅ The successful way to approach this is to work backward by looking at successfully activated customers and understanding what events led to this. This way the customer training can focus on the series of events and behaviors customers need to go through.

2. Train customers by leveraging their existing habits

There are products where you’re tapping into a pre-existing habit and products where you’re creating a new habit. The latter is very difficult as generally humans and organizations stick to their existing behaviors.

Ask your customers about their behaviors in relation to the value you’re aiming to offer them and map the customer training onto the habit pattern that makes sense for your team: Daily → Weekly → Monthly → Quarterly → Every 6 months → Annually.

3. Train customers with the right use case(s)

If you look at customer training where the customer ended up churning fairly fast, you’ll realize that some of those failures happened because the customer’s use case wasn’t the right one for your company at that given time, and some were because customer onboarding failed.

Every product and service is built for a specific type of use case. Customer success teams as well as other teams in the company need to be aware of who that is.

Each use case is pulling the customer onboarding and activation flow in different directions and it creates chaos. You’ll be able to layer additional use cases on top of the main one over time.

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🧠 Why everything is about to become Duolingo-like

Adaptive learning is a concept we hear for 10 years but few products and organizations managed to make it work.

For example, in most companies, employee training is still done like in 2005 → watch a video, read a PDF, and then do a quiz. Yey! You now have a new skill 😐

Most progressive organizations have implemented a skills map or skills matrix where learners see relevant modules they should complete to hit a goal. But that’s just a smarter way to bundle learning resources, it’s not adaptive learning.

Duolingo is probably the first company that made true adaptive learning work at scale (to my knowledge) and it revolutionized the way we learn languages (and the way we certify language skills).

With the explosion of AI, adaptive learning is becoming dramatically simpler. A trained AI model can detect patterns for personalizing the learning path for each learner.

A few examples:

• Kinnu (who just raised $6.5) is attempting to create a personalized learning engine to learn anything.

• Amira Learning offers a personalized reading assistant that suggests corrections to students “in-the-moment”.

• CanopyLAB offers a social learning platform enhanced by AI and they’re currently working on adaptive assessments, automated qualitative feedback, and automated grading.

👓 More reading

• Examples of adaptive learning platforms

• More examples of AI-based adaptive learning tools

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⬇️ What’s happening with US apprenticeships

Apprenticeships are not that popular in the US:

• US: 0.3% of the overall workforce has completed an apprenticeship in 2022.

• Switzerland: 70% of high school students participate in apprenticeships.

Apprenticeships grew 103% in 10 years 📉 but the growth rate is dropping post-COVID.

• 2019 → 12% growth

• 2020 → 3% growth

• 2021 → 2% growth

• 2022 → 5% growth

• 2023 → 1% (Jan-Jun) growth

🪖 Solider students

The largest apprenticeship program in the US is run by USMAP (United Services Military Apprenticeship Program) and it represents 110k (18%) of the 581k apprentices. Service members improve their job skills while on active duty at no-cost and without requiring any off-duty service hours to complete it.

Aside from the USMAP, the 2nd largest vertical is construction:

⚖️ Man-prenterships

According to the ILO (International Labour Organization), apprenticeships have a gender-based bias even in countries with relatively high gender equality such as Denmark, UK, and Germany.

Various factors influence this:

• Lower pay for women

• Culture and traditional gender roles

• Self-limitation and self-selection

• Sexual harassment and gender-based violence

• Family responsibilities

The same applies to the US where apprenticeships are clearly male-dominated unfortunately:

In terms of ethnic origin, there doesn’t seem to be any major difference, apart from the Multiple-Race group where they seem to be more popular:

💰 Funding

$150-175m/year: The Congress and three Presidential Administrations have supported increased allocations of about $150-175 million per year for the registered apprenticeship system.

$99m: The U.S. Department of Labor, Employment and Training Administration awarded $99m in grant investments to 28 grantees for the H-1B Apprenticeships: Closing the Skills Gap grant program in February 2020.

$121m: Apprenticeship Building America grants for Registered Apprenticeships.

👓 More reading

• Wikipedia: Apprenticeship in the United States

• Apprenticeship.gov

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In this episode, I interviewed Steve Karam, ex-VP Global Customer Enablement at Ellucian. Before that, Steve was VP Global Experience and Enablement at Delphix. He currently runs a scholarship fund and he teaches financial literacy courses to at-risk and disadvantaged youth in his area.

📖 What you’ll learn

• Steve’s learn, sharpen, scale framework

• Best practices in learning and enablement

• Hacks for improving learning engagement

• How to structure learning teams

👨‍💻 Contacts

Where to find Steve Karam

• Email: stevekaram@gmail.com

• Linkedin: https://www.linkedin.com/in/stevekaram/

• Twitter: https://twitter.com/YaySteveK

Where to find Akis Laopodis

• Website: https://www.qurioos.com/

• Newsletter: https://insights.qurioos.com/

• Linkedin: https://www.linkedin.com/in/akislaopodis/

🔥 Key moments from the interview

(04:22) Steve’s learning framework: Learn → Sharpen → Achieve

(05:25) What learning could use from the gaming world: Achievements

(07:05) ChatGPT’s new feature: Share bot conversations for co-learning

(08:33) What milestones matter when we learn

(10:30) Why the status quo is the greatest bottleneck

(12:20) Why attaching outcomes to learning objectives is key

(13:42) We don’t need more learning content, we need a librarian

(15:10) How to challenge perception around “how learning should be done”

(16:04) Why people take pride in what they do and forget the other side

(19:55) How to build learning teams for ensuring we understand the learning impact

(26:53) Use online communities as communities of practice

(29:53) How a learning “Hunger Games” session worked for them

(33:30) How learning experience designers and instructional designers need to work together

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🧑‍✈️ Why growth leaders don’t work for learning and education providers?

Earlier this week I wanted to contact growth leaders that work for education and learning providers and something weird happened. I searched on Linkedin:

("head" OR "VP" OR "Vice President" OR "Chief") AND "growth"

and I got roughly ~3m profiles.

Then I filtered the list down using the 3 main education-related industries on Linkedin’s industries list, and there were probably 5 people that were relevant…

The rest of the profiles were growth leaders that work for edtech companies like Chegg (Christina Lee, VP International Growth) or software vendors that sell to K12 and higher ed.

Then I tried picking the two industries that are closer to professional learning. Still, nothing. There were probably 11 people that were relevant… 🦗

And to clarify what I mean, here are a few good examples:

Mark Mashaw is the VP Growth & Marketing at Campus Org (Series A $29m) which is a modern community college that offers online, hybrid, and on-site degrees.

Maurey Bond is the VP Growth at Acacia University, an online university from Arizona.

Douglas Trudeau is the VP Growth, Sales, & Marketing at Bonfire Women, a virtual talent development training program for women.

Carson Bruno is the VP Growth at Coro Southern California, a non-profit leadership training organization.

Also, where are the women? I had to search a lot to find women in growth leadership positions.

Geet Kaur is the VP Growth at TALSMART, a sales training organization.

🧐 “The head of growth vs agency dilemma”

Neal from Demand Curve sent an email a few days ago debating whether it’s better to hire a head of growth or outsource to an agency.

I had the same experience with Neal:

Growth is an in-house motion. EVERY single successful team I know have a growth lead that is part of the team, lives and breathes the mission and the value prop of the organization and pushes very specific KPIs across various channels and areas of opportunity.

My gut feeling is that education, learning, and training organizations don’t see that and they either rely on an in-house marketing team (☝️ note: growth isn’t marketing, it uses marketing), or they outsource to some agency that handles marketing in a productized way, which leaves a lot of money on the table.

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🤖 Do your learners need an AI chatbot?

Chatbots have been around for quite a few years. With Large Language Models (LLMs) like the one used by chatGPT, the value they can offer to learners and instructors just multiplied by 1000x.

👌 AI chatbot use cases for learners

Aside from language learning, testing, and assessment, AI chatbots are used for:

🤝 Learner recruitment: Like in the example below from Purdue University, AI chatbots can answer FAQs from prospective learners, ask prospects open-ended questions, and persuade prospects to enroll.

🗺️ Learner onboarding: Builds the learner profile, aligns their goals and expectations, and reminds learners of the remaining onboarding steps.

Below is an interesting example of an onboarding chatbot (video) from the learning platform RiseUp:

🪞 Personalized learning: There are a lot of use cases where learners enjoy using chatbots for getting help. It’s a completely new situation, as now AI-based bots can support individually an unlimited number of learners at the same time, with adaptive feedback.

🚧 Project-based learning: Research has shown that education chatbots can enhance the learning outcomes of group learning as well.

Other examples:

• Standford English Learning Program: A chatbot for diagnosing English proficiency levels.

• Kasetsart University: A chatbot for learners of the Entrepreneurship Program that mimics private sessions with successful entrepreneurs.

👌 Where should learners interact with chatbots

For chatbots to work, they need to be embedded at the point of need. This can be a learning platform, a messaging/communication tool where learners interact, or the learner community (eg community platforms like Circle or WeSchool, the learner forum, or some version of what used to be the intranet).

Here is an example of a DialogFlow implementation in Moodle:

And here is another example of a chatbot implementation in Canvas by Instructure:

If the chatbot needs to be available on a social/communication tool like Slack or Microsoft Teams, given those tools have special APIs for this, you’ll need to build the relevant integration. More on this here: How to build an AI chatbot on Slack

More reading:

• 18 of the Best AI Chatbots for 2023

• 5 examples of successful AI chatbots in education

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💎 How Gen Zers learn

They are 11-26 years old today and those finishing school or working view work-related learning differently.

🛠️ Hard skills: 12% more time learning hard skills than other generations on Linkedin Learning. Their top 10 courses in 2021:

🙌 Raise or Promotion: 67% expect it when learning new skills at work.

🧭 Self-directed: almost half of them prefer independent learning ↓

📱 Mobile: they strongly prefer learning on mobile devices BUT according to Brandon Hall Group, only 6% of all online training is mobile-ready or optimized for mobile devices.

🍫 Bite-sized: Their average attention span is 8 seconds. (Millennials have 12 sec.)

🎧 Is audio learning a thing?

Apart from podcasts and audiobooks, people learn through audio courses. (I’ll leave podcasts aside as they are not a structured form of learning)

🤔 Why are we talking about this:

• A group of learning experts believes there are 3 main learning styles a) visual b) kinesthetic and c) auditory → a student learns most effectively by listening.

• Another group of experts believes there is no such thing. Their research suggests that these are only preferences (as in "I prefer to learn by listening vs. reading”) but this doesn’t translate to better learning outcomes.

• Finally, a researcher called Dr. Albert Mehrabian published the 7-38-55 rule which suggests that communication has 3 levels: verbal / non-verbal / body language, and that humans understand:

  • 7% of the meaning from the words that are spoken.

  • 38% of the meaning from the way that the words are said.

  • 55% of the meaning is in facial expressions/gestures.

🌐 Where can you learn through audio:

• Full audio courses: Listenable, Omnicourse, Pimsleur (language learning), Upskyld, and Knowable (acquired by Medium in 2021).

• Book-based audio courses: Audible Courses by Amazon, Blinkist Learning Paths, Headway, Deepstash.

📚 What can you learn through audio: There are audio courses on almost any topic you can think of. From what I’ve seen, they tend to be mostly non-technical topics.

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