5 Technical Red Flags Business Leaders Shouldn’t Ignore

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When you’re leading a business, keeping an eye on everything is key – especially when it comes to technology. The world of tech can be tricky for non-technical leaders, and it’s easy to overlook or ignore warning signs. But some red flags, when ignored, can cost time, money, or even the company’s reputation. I’ve seen it firsthand, so here are five technical red flags business leaders should never brush aside.

1. Inadequate Clear Documentation

Documentation is not only for technical teams; it’s for the entire business. When you examine a technical solution and note that little or no documentation supports it, that should be an automatic red flag.

Consider this. If something is going to fail, how are team members going to be able to troubleshoot? How will the next person taking over know about the system? Without well-documented code, it’s not merely technical debt; it’s about the danger of having things fall apart in the future when the original developers leave or when the software is upgraded. Lack of good documentation means you’re essentially constructing on sand where things may appear to be fine for now, but may collapse later.

As a business manager, you may or may not get into the technical docs, but ensure your tech people are on top of developing and keeping it current. If they’re not, push them to do so, because, without it, you are shooting in the dark when things get complex.

2. Over reliance on Legacy Systems

Each business has its one system that’s been in existence forever. It may have begun as a tiny, uncomplicated tool, but now it’s deeply entrenched in every aspect of what you do. The issue with legacy systems is that they easily become out of date and hard to maintain.

You may be receiving “It still works fine” from the technical team, but this is where business leaders should exercise care. Because something “works” does not necessarily make it efficient or future-proof. Legacy systems tend to have limited flexibility and security to support growth. They tend to put bottlenecks in the way, decelerate productivity, and significantly expose companies to security threats.

If your crew still clings to old systems because “it’s always worked,” pose the tough questions. Are there more secure, better options? How much will it cost to replace or upgrade? Dismissing the need for current technology can leave your business at a significant disadvantage.

3. Focus on High Turnover Among Developers or Tech Staff

If your technology team has a lot of turnover, that’s a major red flag. It’s not a matter of hiring replacements—it’s a matter of why they’re leaving. Is it burnout from having to work with aged-out tools? Or are they frustrated with bad project management? If your technical team keeps changing, that can introduce instability into your company’s tech strategy.

High turnover also leaves a knowledge void, particularly in sophisticated projects. When employees depart, they carry their experience and wisdom with them. You could experience lengthy delays as new employees ramp up, and key knowledge is lost in the process.

It’s worth talking to your tech leads to take a pulse on morale and the health of the team. If more people than usual are leaving, investigate. Is the workload unreasonable? Are they using tools that aren’t up to the task? Are expectations set too high? Getting on top of these issues can avoid more turnover in the future.

4. Fuzzy Communication Between Tech and Business Teams

Sometimes, it feels like tech and business teams speak entirely different languages. The tech team is deep in the weeds with code, infrastructure, and systems, while the business team focuses on customer needs, growth, and revenue. If there’s no clear communication between the two, things can quickly get out of hand.

Imagine this: your tech team builds a tool that they think is perfect, but when it rolls out, the business team realizes it doesn’t meet customer needs. Or, the tech team’s vision of a new platform is misunderstood, resulting in delays and frustration across the board. This happens more often than you’d think.

As a business executive, you must make sure there’s open, continuous communication between the two teams. Regular meetings, clear documentation, and open channels all play a crucial role. It’s not simply a matter of passing information back and forth; it’s ensuring everyone gets the big picture of where they’re headed and how technology can help them get there. If this connection is lacking, your technology investments might not meet your expectations.

5. Security Risks Are Ignored

Security can’t be an afterthought or something “handled later.” It has to be in the conversation from the beginning. If security problems are being avoided, or if the technology team isn’t keeping up on updates and patches, that’s a huge red flag. Security vulnerabilities can result in data breaches, loss of customer trust, and enormous amounts of money – things that no business can afford to overlook.

This is a common problem that occurs when businesses are more focused on speed or convenience than on security. Perhaps there is a push to get a product out the door quickly, and some security procedures are cut. But when you’re neglecting the fundamentals – such as encryption, data backups, and regular audits – you’re setting yourself up for much greater troubles down the road.

As a business leader, ensure security is on the top of your agenda. Demand frequent vulnerability scanning, open security guidelines, and openness about possible vulnerabilities. A breach of security can be one of the most expensive problems your company can endure, and tackling it before it is an issue is the best protection.

The Bottom Line

Business and technology have a symbiotic relationship, and you, as a businessperson, can’t afford to be ignorant about certain warning signs. You may not catch every issue, but watching for these five can protect your business from expensive errors. Whether you see poor documentation, antiquated systems, excessive turnover, loss of communication, or security threats, each of these symptoms is indicative of an underlying problem that must be addressed. The trick is to remain engaged, pose the right questions, and maintain an open channel of communication across teams. Tech might not be your strong suit, but recognizing the risks and consequences of these red flags can be a game-changer in the long term. Proactivity, not reactivity, will position your business to succeed – and avoid pricey setbacks.

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