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A recent WSJ article looked back at how the 40-hour workweek became the standard in the first place and whether AI will continue to shrink the workweek (it used to be much longer). The part that really stood out was what employees say makes them switch companies.

According to the article, 41% of employees would leave their current company for a four-day workweek with fewer hours. That is somewhat expected, but the real surprise was what topped the list.

Topping the list is upskilling, with 42% of employees saying they would leave their company for one that offers better upskilling opportunities. The number one reason isn’t a shorter workweek, it’s upskilling.

The researchers defined upskilling as improving skills related to someone’s current job or the next step in their career path. In other words, employees want to grow. They want to learn advanced skills to stay relevant in a world where AI and technology are constantly evolving.

This has real implications for CTOs, engineering leaders, and companies. If talent retention is a priority, upskilling is no longer a nice bonus. It is a strategic differentiator.

Companies that invest in employee skills development get two advantages:

The signal from the workforce is loud and clear. People want real learning opportunities, real career mobility, and real support to build the skills that matter. And they are willing to change companies to get it.

This shift is reshaping the employer value proposition for 2025 and 2026. Engineering leaders who get ahead of it will build stronger teams, ship better products, and avoid the painful cycle of losing mid-career talent that feels stuck.

Now that employees have put upskilling at the top of their list, the natural question becomes: what exactly counts as upskilling today?

Upskilling is one of those words everyone uses, but it means different things to different companies. For many employees, upskilling means learning new skills that help them grow in their current role and prepare for the next one. But in engineering organizations today, the definition has become much broader.

Here is what upskilling means in a modern technical team:

1. Building new AI and automation skills
Teams want to learn how to use AI tools in daily workflows, how to build simple AI agents, how to integrate LLMs into applications, and how to automate repetitive tasks. Upskilling in AI is one of the fastest-growing areas because it keeps engineers relevant and keeps companies competitive.

2. Strengthening cloud and infrastructure skills
Cloud architecture, Kubernetes, DevOps practices, and infrastructure automation are always evolving. Upskilling in cloud skills helps teams reduce operational drag, improve security, and modernize legacy systems.

3. Growing data skills across the organization
Companies need more people who can understand data, work with analytics tools, write SQL, or collaborate with data engineering teams. Data literacy is rapidly becoming a requirement across engineering, product, and operations teams.

4. Improving core software engineering skills
Software architecture, testing practices, quality engineering, Python development, and API design are still core skill sets employees want to strengthen. Even senior engineers appreciate updated training that reflects today’s standards.

5. Closing cross-functional skill gaps
Upskilling is also about communication, tech leadership, product thinking, and system design. Many engineers want help developing broader skills to prepare them for roles such as staff engineer, tech lead, or engineering manager.

At its core, upskilling is not only about training. It is about helping employees stay future-ready in a world where AI and new technologies continually reshape job requirements.

For companies, this means rethinking their approach to learning. One-off online videos or generic e-learning courses no longer cut it. Employees want upskilling that matches their skill level, their tech stack, and the real projects they are working on.

So which upskilling formats work best?

1. Live instructor-led training
The most effective format for engineering teams. Live training allows employees to ask questions, work through real scenarios, and get explanations tailored to their actual tech stack. Teams say this is the fastest way to close skill gaps.

2. Short-format workshops
These are typically two to four hours and focus on one targeted skill. Examples include "LLM prompting fundamentals," “how to deploy with Terraform,” or “intro to analytics engineering.”

3. Multi-week deep dive courses
These are structured across two to six weeks, usually with weekly sessions. They help teams build deeper skills in areas like cloud architecture, AI engineering, or software design.

4. Hands-on labs
Labs let employees apply what they learned in a safe environment. Engineering teams love labs because they get real practice without worrying about breaking production.

5. Cohort-based learning
This format groups employees together for a shared learning experience over several weeks. It fosters collaboration, accountability, and peer discussion.

6. Project-based learning
Teams work on real internal projects or simulations guided by an instructor. This is one of the most effective ways to build applied skills because employees learn in the context of their actual jobs.

7. Self-paced online content
Useful for foundational knowledge or when employees need flexibility. The main limitation is that self-paced content rarely closes skill gaps on its own. Most companies pair it with live training.

Duration matters a lot in engineering. People want training that is long enough to be useful but short enough to fit into the sprint cycle. Here are most common upskilling durations companies use:

1. Micro-training sessions
30 to 90 minutes
Used for small topics, tool overviews, or AI quick wins.

2. Half-day or full-day workshops
4 to 7 hours
Great for focused, high-impact training with hands-on work.

3. Short courses
1 to 2 weeks
Often used for topics like Python, SQL fundamentals, cloud basics, or AI productivity skills.

4. Deep technical programs
4 to 6 weeks
Best for advanced roles like cloud architect, data engineer, or AI engineer. Employees learn progressively and build real mastery.

5. Long-term development tracks
3 to 12 months
These combine multiple courses, labs, and coaching sessions. Companies use this format for staff-level growth or major role transitions.

One misconception is that longer training always equals better training. In reality, most skill gaps can be closed with programs that run between two and six weeks, especially when the curriculum is tailored to the team’s actual needs.

If the format is wrong, employees lose interest. If the duration is wrong, managers won’t approve the time. If the content is too generic, teams do not develop real skills.

Upskilling works when it fits into the flow of engineering work and respects the reality of sprint commitments. The best programs make it easy for employees to learn without slowing down delivery.

This is also why engineering leaders are turning away from generic online courses. People don’t want to sit through hours of videos. They want short, interactive, live learning experiences that help them build practical tech skills they can apply immediately.

The next question is: which companies are actually doing this well?

The companies that consistently rank highest in upskilling share a few common traits. They invest early, they invest across the entire workforce, and they tailor training to actual business goals. A few examples stand out:

Accenture
Accenture upskills tens of thousands of employees each year in cloud, cybersecurity, and data engineering. Their training programs are designed around real client projects, keeping learning practical and aligned with business outcomes.

Amazon
Amazon invests heavily in cloud, data, and AI training, mainly through programs linked to AWS certifications. Their “Career Choice” program funds employee learning paths, and their internal cloud training initiatives helped thousands of employees move into higher-skilled technical roles.

Google
Google invests in technical upskilling through internal engineering courses, cloud training, and leadership development. They also offer Google Career Certificates externally, which have helped shape the broader upskilling market.

IBM
IBM focuses heavily on AI, automation, and cloud skills. Their internal AI academy has become a model for enterprise AI training programs. Large parts of their workforce have gone through upskilling programs that help them shift to new AI-driven roles.

What these companies share is not just big budgets. They treat upskilling as a strategic capability, not a perk. They focus on real skills, real career mobility, and real business impact.

For more company upskilling examples, read LinkedIn’s top 50 best large employers to grow your career.

Smaller organizations may not be able to invest as much, but they can still create world-class upskilling programs. The key is to customize training and make it easy for managers and employees to request the support they need. This is where TryTami helps.

Upskilling should not require a huge HR team, a long vendor search, or endless back-and-forth with training providers. Most engineering leaders simply want a fast way to get high-quality training for their teams that actually matches their tech stack and aligns with their goals.

TryTami’s AI Learning Coordinator makes this possible.

When you tell TryTami what skills your team needs, it instantly recommends a tailored course outline and matches you with the best instructor to teach it live. Whether you need AI skills, cloud architecture, Python development, data engineering, or DevOps training, TryTami designs the program around your team’s real-world needs.

TryTami also handles the logistics for you. It schedules the sessions, confirms instructor availability, and manages the attendee list. Instead of spending weeks coordinating training, you can launch a customized course in minutes.

The result is simple. You close skill gaps faster, your engineers stay engaged, and your company becomes a place where people feel supported in their growth.

Upskilling may be the number one reason employees would leave. It can also become one of the strongest reasons they stay.

If you're ready to offer a better upskilling program, we would love to show you how it works. Request a demo of TryTami’s tech training platform:

Until next Tuesday,
Kelby, Dean, & Dave