Opinions expressed by Entrepreneur contributors are their own.
Why does traditional training fail tech teams? It’s jarring to know that 78% of organizations abandon projects partway through because they didn’t have employees with the necessary IT skills. Today, skill gaps are considered the biggest barrier to business transformation.
Here’s a reality check: 39% of existing skills will be outdated by 2030. For firms, this number translates to lost revenue, delayed projects and weakened competitiveness.
These growing skill gaps are making it harder to innovate and retain top talent. To stay ahead, these firms need to lean into their agility and rethink how teams learn and grow in real time.
After leading cross-functional technology through 25 years of rapid industry shifts, I’ve seen what works. Two practical strategies have consistently helped mid-sized tech firms build stronger, future-ready teams without massive budgets.
Related: 5 Ways to Create a Culture of Innovation
Strategy 1: Let your team learn by doing
Engineers don’t learn best by sitting in classrooms; they learn by building real solutions.
Stretch Projects: Stretch projects provide the perfect opportunity for your team to learn new skills while also delivering on your roadmap. They’re like sprints, but learning is done on the go. One of my teams had to fix a crashing application, and in the process, they learned how to use Docker. It was chaotic, but the learning was real.
Microlearning: In my experience, pairing these with microlearning sessions keeps teams engaged without derailing deadlines. These could be quick tutorials by senior engineers or docs tied to the project’s needs. This model mirrors the iterative nature of software development itself: test, fail, refine, repeat. You’d be amazed how fast your team grows.
Balance: Remember not to rush; stretch projects are great for learning, but be mindful of burnout and disrupting workflows, which may challenge smaller teams with tight deadlines. Limit stretch projects to 20% of the workload, balancing with regular tasks.
Here’s the playbook you can start with:
- Begin by auditing your team’s skills. Create structured opportunities for engineers to apply new skills hands-on.
- Assign stretch projects tied to sprint deliverables.
This will help you with faster deployment cycles, improved innovation and stronger retention of technical skills.
Strategy 2: Get your team to share the know-how
But learning by doing is just one piece; teams must also learn from each other.
About 80% of executives and 72% of IT professionals say their organizations often invest in new technology without ensuring employees are properly trained to use it, a gap I’ve bridged with peer-learning sessions.
Knowledge Sharing: Some of the best learning happens when your team comes together to swap ideas. I saw a serverless API project stall because engineers lacked AWS training, and stretch projects helped us fix that fast, because I had experienced engineers overseeing it.
When knowledge sharing becomes a cultural norm, mid-market firms transform training from an external activity into a core competency. Over time, this keeps your team sharp and ready to take on emerging challenges.
Peer learning: Provide a platform to your team by implementing monthly workshops where everyone shares what they’ve learned. Peer learning is a great way to keep this institutional knowledge alive and build a team that can think beyond just the code. It’s a simple approach that lets mid-sized firms like yours stay nimble and deliver top-notch work without the big budgets of larger companies.
Institutional knowledge: While technical upskilling is vital, peer learning also plays a key role in retaining often-overlooked business-critical skills that can quietly erode with turnover. In fact, LinkedIn data shows that companies with high turnover often lose key capabilities like business strategy and project planning.
To put this into practice, try these:
- Build a culture of peer-to-peer learning.
- Host monthly knowledge-sharing sessions,
- Encourage team collaboration on real projects
You can try platforms like Coursera, GitHub Learning Lab, Pluralsight and AWS. Free resources like video tutorials, open-source community and online learning forums are invaluable for upskilling.
These will mean faster skill-building, stronger team collaboration and a more agile workforce.
How to make it stick: reward growth, not just delivery
Now, here’s the important part. Hands-on and peer-driven learning creates momentum, but without recognition or growth opportunities, even engaged teams can lose steam.
Career Growth: Gen Z employees (17%) are the most likely to stay because of upskilling opportunities, compared to Millennials (9%), Meanwhile, 67% of employees say they would leave their company altogether if there were no opportunities for internal mobility.
If mid-sized firms can’t provide these kinds of opportunities, engineers will look for them elsewhere not just for more money, but to stay relevant and keep progressing in their careers.
Cost of Turnover: Hiring a new IT employee takes 10 weeks in the U.S., compared to 9 weeks globally, and costs over $8,000 more on average than an upskilled one. You want to keep your best people? Align learning and development with their career growth. That’s why investing in your current engineers is faster, cheaper and more effective.
Incentives: Make it your top priority to encourage your talent to pursue certifications in high-demand areas like AI, DevOps and cloud security. It is always good to celebrate their achievements. Offer them tangible rewards such as summit invitations, speaking opportunities or passes to major tech conferences that show that they are making a difference. Recognition matters.
Try gamifying it with hackathons, 15-minute coding challenges or building a cloud-native prototype. Tech teams love those!
Early on, my team started small. An AI prototype took one sprint and transformed our skillset. We went on to build AI-specialized teams as we grew.
These “DIY” upskilling approaches allow firms to bypass the rigid and expensive learning models enterprises often rely on.
The two strategies use an often-overlooked advantage mid-market firms possess: agility. But when paired with a strong reinforcement mechanism, these two strategies can help you build a culture where learning, collaboration and recognition fuel long-term growth.
Related: How Brands Can Turn Rewards Programs Into Long-Term Loyalty
Next steps for tech leaders
Despite the so-called saturation, AI and ML remain new, with only 8% of companies scaling AI at an enterprise level and using it in their core business strategy
So, this quarter, pilot a stretch project to start with an automation tool, a cloud-native application or an AI-driven feature, maybe a chatbot?
These steps will pinpoint skills your team needs now, ensuring you stay competitive. In my experience, the firms that prioritize upskilling today will shape technology markets of tomorrow and tomorrow is not that far.
Conclusion
With 40% of organizations already planning to reduce staff as some skills become obsolete and 50% aiming to transition staff into new, growing roles, I see upskilling not just as a defensive move against market disruption but also as an offensive strategy for radical growth.
By encouraging fearless innovation through stretch projects and tying skills acquisition to tangible career rewards, mid-market tech teams can scale with limited resources.
Do this correctly, and by 2026, I see your team nailing data tools and automation, building solutions that stand out. My passion for creating great software keeps me hooked on this approach, and I’m betting you’ll see the difference if you start now and get your team learning.
I ask that you see skill-building not just as a milestone but as a journey. It will help you build a learning culture where capability grows and sticks.
