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Preparing for the AI Revolution: Leadership Challenges in Workforce Upskilling

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Preparing for the AI Revolution: Leadership Challenges in Workforce Upskilling

What if the biggest barrier to AI fluency isn’t budget or tech—but the invisible fear that learning it might quietly make someone obsolete?

As companies race to level-up their teams on AI and analytics, a startling gap emerges: the tools are ready, yet the humans behind them often aren’t.

This HR Spotlight asks the question no one wants to admit out loud: are we accidentally training our workforce to panic instead of prosper?

From mindset paralysis to patchy data pipelines, from “one-size-fits-none” courses to the terror of looking stupid in front of a chatbot, seasoned leaders expose the gritty, human hurdles that turn bold upskilling plans into half-hearted flops.

Their answers reveal a surprising truth: the fastest path to mastery isn’t more courses—it’s dismantling the quiet anxieties that keep people from even starting.

Read on!

Julia Yurchak
Senior Recruitment Consultant, Keller Executive Search

The gap between AI enthusiasm and practical implementation costs organizations millions in wasted potential.

At Keller Executive Search, we notice the fear factor can’t be underestimated – many team members resist new technology simply because it feels intimidating.

The most successful transitions happen when we create tailored, role-specific training rather than one-size-fits-all approaches. We must bridge the gap between technical skills and business strategy, ensuring AI capabilities directly support our goals.

Data infrastructure often proves inadequate, requiring us to build stronger foundations before meaningful analytics can happen.

Perhaps most challenging is cultivating the right culture – one where our teams feel empowered to experiment while maintaining healthy skepticism about AI’s outputs.

When we address these challenges with clear communication about purpose and benefits, we achieve significantly better adoption rates and ultimately derive greater value from our AI investments.

Fear Blocks AI Before Training Starts

Brian Futral
Founder & Head of Content, The Marketing Heaven

Data Discipline

Skill gains die if the data pipeline still leaks.

First, lock a cross-team squad on data cleaning, version control, and privacy flags.

Dirty columns or orphaned dashboards will turn your newly minted analysts into cynics.

Keep the pipeline open but governed with clear roles for requests and approvals. It looks dull, yet it stops the wild west chaos that burns talent.

Mindset Reset

Most staff arrive with badge fatigue from endless training videos.

I ditch the slide deck and hand them a tiny real client brief.

We co-pilot with a generative model, watch it stumble, then fix the prompt together. The aha moment sticks.

Plan for uneven progress; extroverts share tips fast, introverts may need a channel to experiment in silence.

Allow side quests where volunteers document hacks for the wider team, and you get organic playbooks that no vendor can sell.

Dirty Data Kills Skill Gains Fast

Dr. Chad Walding
Chief Culture Officer & Co-Founder, NativePath

As a leader, you are sure to deal with resistance to change.

Humans are wired to resist change, and to confuse that with learning new technical tools outside of their range of comfort can be overwhelming.

The most important thing is to get them to adopt a growth mindset.

In my practice, I always encourage small steps so the employee can learn gradually, not all at once.

This plays a role in motivation; it keeps them from quitting because of burnout.

Another challenge has to do with time and energy.

The addition of learning new skills on top of existing duties can be demanding and drain energy.

I’ve always recommended that people create very clear, achievable learning goals and weave them into their daily routines, just like I encourage slow and not aggressive nutrition or movement habits for long lasting wellness.

Burnout Crushes AI Learning Curves

Amra Beganovich
CEO & Founder, Colorful Socks

Perhaps the biggest challenge in upskilling a workforce in analytics and AI is overcoming the “intimidation factor.”

Employees see AI as too technical or worry that it will replace them, and therefore resist or disengage.

Leaders need to build psychologically safe spaces that focus on AI as a means to augment, not substitute, for human decision-making.

The second challenge is finding a balance between technical depth and business applicability.

Upskilling initiatives need to be role-specific, demonstrating how data and AI enhance everyday operations directly.

As I frequently advise clients, “Training needs to feel applied immediately, or it’s overlooked.”

And leadership also needs to fill infrastructure gaps.

Without clean, usable data and the proper tools, even highly competent workers can’t use what they’ve learned.

Lastly, ongoing learning is essential—AI changes at a pace that requires multiple training sessions.

Leaders need to inculcate learning into the culture and incentivize curiosity.

Intimidation Stalls AI Upskilling Hard

Monica D. Higgins
CEO, FuturProof™

The biggest practical challenge I urge leaders to prepare for when helping their workforce level up on AI and analytics skills is mindset.

At a recent HR conference I spoke at, I asked: “Who here is actively using AI tools like ChatGPT, Claude, or Gemini at work?” Nearly 80% said no.

That shocked me since AI literacy is the new spreadsheet fluency. It’s the new digital divide, and that divide is growing.

What stood out was that the people in that room were smart, ambitious, and driven. Yet, many were quietly intimidated.

Some feared using AI would make them look lazy or incompetent. Others didn’t know where to start.

The issue wasn’t technology. It was a mindset.

To shift mindsets, leaders should:
– Focus on small, real-world wins
– Build AI skills directly into the flow of work
– Let people execute to learn

When they use AI to solve real problems in their actual roles, confidence grows—and so does capability.

Mindset Gap Trumps Tech Gap

Joe Sagrilla
Faculty, CEO & Principal Consultant, University of Texas

A practical challenge leaders must address is making AI both safe and easy to use from the outset.

Too many confusing rules or barriers create friction, discouraging adoption or driving employees to use AI on personal devices for work—a risky trend already documented.

Unlike traditional top-down tech rollouts, AI adoption is fundamentally bottom-up: individual employees design use cases and drive innovation.

This means companies must upskill teams in data and systems literacy—what I call a “digital mindset”—so they can continually adapt to new, evolving AI tools.

Crucially, strong incentives are needed: consider offering breakthrough rewards, like a bonus equivalent to a year’s salary, for employees who develop transformative automations.

Without meaningful incentives and reassurance, employees may hide innovations out of job security fears.

Leaders must foster a culture that rewards innovation and consistently demonstrates that automation is celebrated, not penalized.

Reward Bold AI Wins Big

Damon Kelly
CEO, Enlighten Designs

My thought is that AI and analytics require distinct approaches to workforce development, with AI representing a far greater shift in mindset and skill.

At Enlighten Designs, we’ve supported Microsoft’s Data Journalism Program and other customers in mastering analytics through data storytelling.


Analytics is fundamentally about uncovering insights and effectively communicating them transforming raw data into narratives people can understand and act upon.

AI, however, demands a deeper, cultural shift.


Leaders must first help their teams overcome any initial apprehension around AI by emphasizing human-AI collaboration.


Practically, this means guiding teams to utilize generative AI by defining clear personas aligned with specific roles or problems, providing ample context, and training the AI with unique, relevant information.


AI should be approached as a copilot like an employee whose suggestions you evaluate critically, rather than handing over complete control.

I encourage other leaders to proactively address the human elements of AI adoption, ensuring their workforce feels supported, confident, and in control.

Human Fears Outweigh AI Limits

Jennifer Wu
Senior Vice President Global Human Resources, Team Lewis

Everyone’s Starting from a Different Place:

Teams have different levels of comfort and experience with AI and analytics.

Leaders should assess baseline skills and provide flexible, tiered learning opportunities.

Create an environment where everyone can progress at their own pace.

Explain The Changes: Introducing new tech to your teams can be intimidating.

The best place is to start with the “why” and the benefits of upskilling.

Measure Impact: Sure, tracking training attendance is easy.

The hard part is measuring how new skills then translate into business outcomes.

Leaders should create clear objectives for upskilling initiatives and review progress regularly.

At TeamLewis, one of the ways we are addressing these challenges is by creating our own proprietary AI platform, SideKick.

Our intuitive, accessible platform, SideKick helps demystify AI for our teams.

We’ve taken the opportunity to identify key individuals at all levels who are driving the transformation.

This means AI isn’t just a top down or market dictated requirement. It’s becoming part of the everyday workflow.

One-Size Training Fits Nobody

Martha Carlos
Principal, Blue Orbit Consulting

Within my team we started with the most straightforward use cases – transcription and summarization.

It’s one of the simplest ways to use AI on video and conference calls and also often illustrates what the tools are great at and where they make mistakes.

This has saved our team countless hours of notetaking and creating summaries, and increased accuracy in some areas while generating awareness of AI’s lack of context in others at times.

One of the biggest challenges for everyone is not just using tools but recognizing that AI will impact every aspect of work and roles, and we win by figuring it out now rather than getting left behind.

Normalize AI Through Practice

The HR Spotlight team thanks these industry leaders for offering their expertise and experience and sharing these insights.

Do you wish to contribute to the next HR Spotlight article? Or is there an insight or idea you’d like to share with readers across the globe?

Write to us at connect@HRSpotlight.com, and our team will help you share your insights.

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Upskilling Mantras: Leveling Up Your Workforce

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Upskilling Mantras: Leveling Up Your Workforce

Upskilling workforces in AI and analytics is pivotal for 2025 competitiveness, yet practical challenges abound, with 46% of leaders citing skill gaps per McKinsey. 

This HR Spotlight article compiles insights from business leaders and HR professionals on key hurdles to prepare for. 

Experts highlight mindset shifts, fear of displacement, data quality issues, and ethical concerns like bias. 

They stress fostering curiosity through real-world applications, tailored training, and human oversight to bridge gaps. 

By addressing resistance via empathy, ensuring tool relevance, and promoting continuous learning, leaders can transform challenges into opportunities, boosting productivity and adaptability across industries from healthcare to consulting. 

Read on!

Casey Cunningham
Founder & CEO, XINNIX

One of the biggest practical challenges leaders face when helping their teams level up on AI and analytics is making it feel real and relevant. It’s not just about training—it’s about sparking curiosity.

I encourage leaders to create space for people to share how they’re already using AI—at home, at work, anywhere. Personal use often translates into professional impact.

I also challenge leaders to ask their peers how they’re approaching this. You don’t have to figure it all out alone. Chances are, someone else in your organization is already a few steps ahead. Learn from them.

And finally—ask AI! Use it to create grocery lists, build menus, fix issues—get people playing with it. When they see what it can do in everyday life, they’ll be more open to using it professionally.

The goal is to normalize it. The moment they experience that “wow,” the resistance fades. Now they’re in.

Spark Curiosity for AI Adoption

Mary Rizutti
Practice Leader, HR Advisor & Outsourcing

Challenges in AI and Analytics Upskilling

While AI is changing so many aspects of business, with change comes challenges. There is clearly and expectedly a learning curve in this space. Companies are facing the challenge of a workforce that has had limited to no exposure and/or training in AI.

To work effectively with AI, a combination of technical and soft skills is needed. Technical skills such as knowledge of programming languages like Python, Java, R and C++ are commonly used in AI development.

Individuals with backgrounds in computer science, data science, artificial intelligence, robotics, mathematics and statistics and software engineering may possess skills upon which they may rely to begin to understand large language and algorithm model development, as well as prompt engineering (the ability to optimize prompts for AI tools), as an example. may be acquired through self-study.

It’s important for companies to assess the current workforce to help them understand which employees might be suited to support an AI integration process. One initiative many companies are undertaking is to perform a skills analysis on its workforce to identify those in-house who possess the capability to engage in identifying areas where AI may be appropriate.

Companies should also be prepared to deal with the challenge of identifying the application for AI within their companies. Some questions they should consider include: How far down the road should we go with AI? Are there controls in place to test and trust AI’s output? Do we have policies in place to monitor and provide guardrails for individual usage?

These challenges call upon leaders to not only possess, but to also instill and encourage keen problem-solving skills among their teams, to create ethical awareness around AI biases, privacy concerns and the responsible use of AI.

Fostering an environment of continuous learning, adaptability, curiosity, communication and collaboration needs to be a deliberate focus for leaders to enable their companies to travel the AI journey that is ahead.

Assess Skills for AI Integration

Danielle Pickens
Chief Program Officer, Urban Schools Human Capital Academy

One key challenge for education leaders is preparing their workforce to effectively adopt AI and analytics. This goes beyond technical training as it requires a mindset shift toward data-informed decision making.

Educators are the heart of schools, yet many lack exposure to AI tools and face time constraints, making targeted professional development critical.

Leaders must ensure equitable access to technology to prevent deepening disparities, while addressing ethical concerns like data privacy and bias.

AI should be seen as a support, not a substitute, for human judgment. It all starts with a strategic, empowered Human Resource team ready to lay the foundation for continuous learning.

By prioritizing upskilling and fostering an open culture, schools can begin to leverage AI to improve efficiency, accessibility, and ultimately, student outcomes.

Bridge Tech, Human Judgment Gap

Drew Wiard
Owner, Clear Sky Properties

Everyone has varying ability levels. Some people learn new tools quickly, while others require more instruction. Training must adapt to these variations. The most effective learning is experiential, using real-world examples.

Understanding data ideas is one thing, but applying them to transactions and property management is quite another. The aim is to close that margin. In addition to teaching theory, I concentrate on demonstrating how analytics enhance decision-making.

Confidence is fostered by promoting inquiry and allowing others to grow from their errors. The team tries new things when they feel encouraged. We can maintain our competitiveness in a changing market with such a mentality.

Overcome Varying Team Abilities

Marco Dewey
CTO, Jazzberry

Prompting is your team’s new secret weapon. Everyone thinks these AI tools are just plug-and-play. Drop in a question, get an answer.

The real power of these AI tools isn’t in their ability to answer a question, but in their diversity in what they can do with that question. AI tools are not a set-in-stone algorithm, they are a dynamic algorithm that can give you custom results if you know how to prompt it.

Leaders need to train their team on the art of prompting. Prompting can be unintuitive, but it will make more sense to your team if you educate them on how these models work under the hood.

Think of prompting as a new kind of literacy, and do not be afraid to experiment; only you know what will work best for your team.

Master Prompting for AI Power

Oliver King-Smith
CEO, SmartR AI

Leaders preparing to upskill teams in AI and analytics must tackle three thorny realities. First, overcoming “grunt work paralysis”—even skilled analysts waste weeks on manual tasks like data cleaning or merging NHS trust mappings.

Tools like SCOTi® AI automate this drudgery, freeing 70% of time for strategic work. Second, bridging the “plain English gap”: Employees shouldn’t need coding skills to ask, “Why did margins drop?” Assistive Intelligence that answers conversational queries (with charts/stats) democratizes data access.

Finally, securing buy-in for “messy data” journeys—teams often stall waiting for “perfect” data. SCOTi’s Schema Sense reverse-engineers chaotic databases and even scrapes missing dimensions, proving ROI while fixing infrastructure.

Compliance remains non-negotiable: Ensure tools like SCOTi operate on-premises/air-gapped for sectors like healthcare or defense.

The real win? Treating AI as a collaborator, not a crutch—it’s why teams using assistive tools see 2x faster insights and 50% higher stakeholder trust.

Automate Drudgery, Free Strategy

Wesley Kang
Founder, Realtor1099Cafe

Honestly, running a tech forward real estate firm showed me how emotion drives adoption more than logic ever could.

People fear status loss more than technology itself and my veteran agents worried AI would erase their market expertise until we reversed the power dynamic. Now they lead our AI testing program, finding new ways to blend human insight with machine analysis.

I’ve also seen that fear hits hardest when AI touches money directly and through countless training sessions, I noticed how quickly agents embrace AI for basic tasks but panic when it approaches their commission structure. We solved this by guaranteeing base pay during the learning phase which let them experiment without risking income.

In all honesty, I believe successful AI adoption starts with protecting people’s sense of value.

Reverse Power Dynamic Fears

Paul Monk
Chief Strategy Officer, Alpha Development

AI technology is developing at such a pace that it will quickly become universal, with little to differentiate the tools used by competing organizations. Most of the value of AI will be delivered in the quality of data, and how each workforce is upskilled & motivated to engage with these new tools.

We initially categorize a workforce into two broad groups – the FOBOs (Fear Of Missing Outs) and the Resistance. FOBOs are anxious to be given access to AI tools & training, while the Resistance try to justify why AI is not applicable to their role, team, or business area. Both need to be acknowledged & engaged by any plan to upskill on AI and analytics.

Upskilling & reskilling for AI should be delivered just like any other transformational learning program – it requires business leader support, active learning, and the opportunity to practice & embed new skills following any formal training.

Once new skills have been acquired, the focus should shift to monitoring application of AI within upskilled teams – including keeping a close eye on “disengaged augmentation” i.e. when an employee working with AI augmentation disengages from their responsibilities and inappropriately allows the AI to complete the task end-to-end.

Ensuring that employees understand their role in augmentation, and are recognized & rewarded for delivering this, is crucial for delivering real change in AI and analytics skills.

Engage FOBOs, Resistance Groups

Dan Gower
Product Studio Lead, Sketch Development Services

I work at a software consulting company that helps enterprises adopt AI. One challenge we keep talking about is that AI was trained on a massive amount of material, and it’s not only the good stuff.

It’s getting better fast, but right now, we have to assume that whatever AI is doing is informed by average work. In other words, check it as you would if an aggressively average employee produced it.

Verify AI Outputs Vigilantly

The HR Spotlight team thanks these industry leaders for offering their expertise and experience and sharing these insights.

Do you wish to contribute to the next HR Spotlight article? Or is there an insight or idea you’d like to share with readers across the globe?

Write to us at connect@HRSpotlight.com, and our team will help you share your insights.

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Improving Workforce Skills: Optimal Training Methods and Delivery Formats

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Improving Workforce Skills: Optimal Training Methods and Delivery Formats

On-the-job training is pivotal for building skilled, engaged teams, yet traditional methods often fall short in delivering real-world impact. 

This HR Spotlight article compiles insights from business leaders and HR professionals on the most effective training formats and methods for their workforces. 

From immersive bootcamps and case studies to shadowing and micro-learning, these experts share what works, driven by past challenges like disengagement and knowledge gaps. 

Their strategies emphasize hands-on application, immediate feedback, and cultural fit, offering a blueprint for organizations to enhance retention, productivity, and adaptability in today’s dynamic business environment.

Read on!

Corey Harlock
Founder, KeyHire Solutions

Over the past decade, I’ve worked with all kinds of companies, from manufacturing to tech to hospitality, and I’ve learned that finding the right person for the job is about a lot more than resumes and interviews. 

I talk with small business owners across the country in my KeyHire Small Business Podcast, and one thing that keeps coming up is this disconnect between hiring and expectations. 

A lot of companies hire someone with minimal experience, don’t really train them, and then wonder why they’re not performing at a high level.  

Here’s what I’ve found: if you’re hiring based on potential, that’s great! But you’ve got to invest in that person by building a solid, structured training program. Think: job shadowing with a high performer, clear KPIs, weekly check-ins, progress benchmarks, and hands-on coaching. If that kind of training isn’t something you can commit to right now, then the better move is hiring someone with the experience to hit the ground running. 

Experienced candidates can provide faster ROI and make an immediate departmental impact. Whichever decision, you just need to be honest about what your business can support.

Hire For Potential, or Hire Experience

Wes Wakefield
Founder & CEO, Pro Coffee Gear

We have landed on live machine troubleshooting demos and interactive digital checklists as our go-to training methods.

Back in the day, we had techs fumbling through repairs because written guides were too vague, and one-size-fits-all classes left them bored or confused.

So, we switched to real-time problem-solving such as diagnosing a leaky group head on the spot and paired it with step-by-step checklists on tablets, flagging common pitfalls like over tightening bolts. It’s turned chaos into confidence, and our crew’s never been sharper.

Live Demos Build Confident Techs

Marcus Denning
Senior Lawyer, MK Law

The obvious truth is that traditional training programs often fail to engage employees in meaningful ways.

Would you rather watch a training video that feels like a lecture or tackle a real challenge with immediate feedback?

After struggling with disengagement in lengthy training sessions, we changed to a mix of micro-learning and on-the-job coaching.

According to a survey by LinkedIn, 58% of employees say micro-learning helps them retain more information. This method allows employees to apply what they learn instantly and gives them the support they need when they need it.

Micro-Learning Beats Traditional Training

Christopher Pappas
Founder, Earning Industry

Traditional onboarding sessions led to information overload, so we switched to learning in the flow of work.

Instead of front-loading everything in the first week, we use just-in-time training, where employees receive short, task-specific lessons at the moment they need them.

For example, customer service reps now access quick reference guides and video walkthroughs embedded in their workflow. This reduced ramp-up time by 40% and allowed employees to learn without disrupting productivity.

The best training? The one employee doesn’t feel like they’re talking.

Learning in the Flow of Work

Vukasin Ilicn
Serial Entrepreneur, Digital Media

After building three businesses, I’ve found that our ‘shadow-then-lead’ approach with immediate feedback cycles outperforms traditional training methods hands down.

We pair new team members with veterans on actual client projects—first watching, then gradually taking control while getting real-time guidance.

We developed this after seeing a painful disconnect between classroom training and real work.

New hires who aced our formal programs would freeze when facing actual client challenges.

Last year, when we shifted to this experiential model with one of our content teams, they became client-ready in about a month instead of the typical three months.

The magic happens in those daily five-minute feedback conversations. When someone makes a mistake handling a client request at 10 AM, we address it by 10:30—not during Friday’s review meeting when the lesson’s already cold.

Learning by doing with immediate course correction simply sticks better than any manual or training video we’ve ever created.

Immediate Feedback is Key to Training

Christian Bullas
Owner & Director, Senior Home Care By Angels

At Senior Home Care By Angels,I believe the most effective on-the-job training methods are shadowing, mentoring, and scenario training that are hands-on.

New caregivers learn best by shadowing experienced staff, watching real interactions, and taking on duties progressively with guided support. This supports confidence-building, compassionate care, and an easy transition into our model of individualized caregiving.

One of the things we’ve overcome over the years is ensuring that training is not just procedure-driven—it’s learning the human aspect of care.

Caregiving is not about going down a checklist; it’s about building trust and being adaptable to address unique needs. That’s why role-playing real-life scenarios and ongoing coaching are a critical part of our training.

By coupling formal training with hands-on experience, we provide caregivers with both the technical knowledge and emotional intelligence to provide the high-quality, personalized care our clients demand.

Hands-On Training is Key to Caregiving

Justin Fox
Digital PR & Outreach Manager, coursesonline

From my experience the most effective approach to training are methods which place an emphasis on why we opt for a certain approach, rather than just getting team members to memorise an approach without question.

This way they are encouraged to think creatively and point out any gaps that they see in our current approach.

Therefore we like to utilize case studies, to put our new employees in the shoes of their predecessors and have them work out the same issues but with their own methodologies. Will they think the same way and reinforce the idea that we already adopt best practices? Or will they find a way which we didn’t think of? Either way the result is beneficial for us to build up our collective institutional knowledge.

Training the “Why,” Not Just “How”

Sahil Kakkar
CEO & Founder, Rank Watch

Case studies provide real-world business insights. Employees analyze scenarios to develop problem-solving skills.

Practical examples enhance critical thinking abilities.

Decision-making improves through exposure to past successes. Learning from real cases refines strategic approaches.

Previous methods lacked real-world application, and employees struggled to connect theory with practice.

Case studies bridged the knowledge gap, and exposure to industry challenges built confidence. Analyzing real cases significantly improved business decision-making.

Case Studies Bridge Theory and Practice

George Burgess
Serial Entrepreneur, Modern Day Talent

At Modern Day Talent, we’ve designed our upcoming SDR training initiative as an immersive, one-week bootcamp in Cape Town.

This intensive, in-person format creates an effective environment for developing sales talent. By bringing candidates together in a collaborative setting, we develop both technical proficiency and team cohesion.

Previous remote training approaches showed limitations: reduced knowledge retention, less peer learning, and increased early-stage turnover. We found that technical skills transfer is only one component of successful onboarding—team cohesion and resilience are also important factors.

Our bootcamp model addresses these challenges by engaging candidates in practical scenarios while building peer relationships. Participants learn essential skills—from CRM navigation and cold calling to objection handling and active listening—in a collaborative environment.

This prepares professionals with both technical competence and the resilience needed in sales environments. The in-person training format improves knowledge retention and employment satisfaction.

Immersive Bootcamps Build Sales Team Cohesion

The HR Spotlight team thanks these industry leaders for offering their expertise and experience and sharing these insights.

Do you wish to contribute to the next HR Spotlight article? Or is there an insight or idea you’d like to share with readers across the globe?

Write to us at connect@HRSpotlight.com, and our team will help you share your insights.

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