How we failed an employee – and almost lost everything


Opinions expressed by Entrepreneur contributors are their own.

While vision is important to success, execution matters more. Startups can be subject to multiple points of failure—people, products, competition, and legal challenges, to name a few. These issues can be interconnected, adding to the difficulty of overcoming them. Ours is a cautionary tale about key man danger.

After recently going public, we were building for our next step of growth. As I waited in traffic on my way back from my run, my thoughts turned to the upcoming annual general meeting (AGM) set for May next year.

It was starting to rain when Elena broke the silence, “KK, are you off the phone? Zisis (our CEO) is calling me. I glanced at her and replied, “No, it should be, why?” noticing the dots of rain that landed somewhat heavier.

Looking at my phone, I noticed it was on, but on silent mode. I could see a bunch of messages, namely, “It's urgent.” She gave me her phone. Zisis, breathing rather heavily, said “Hey man, I'm sorry we can't wait. We have a serious problem.”

My heart rate increased. As the adrenaline surged for all the wrong reasons, the skies had turned noticeably dark and the rain turned to hail. He continued, “(Our CTO at the time) demands $10 million by tomorrow, or he'll delete the code, post all the internal conversations online.”

As I processed this, the sound of the hail intensified. Subconsciously, I figured we could pay it, but it would crush us. “20 minutes; I'll call you back,” I replied as I drove home, zombified and broken.

Getting out of the car, I was engulfed in hail. As I reached my study, impulsive thoughts flooded my mind. “Do I go extrajudicial here? Shame it globally?” Alas, calmer heads would prevail as the team and I huddled over the hours to come up with a plan B.

Negotiating with a metaphorical gun to the head was one sine qua non. Our solution involved informing stakeholders of the situation and rebuilding the codebase in Europe. We would take the opportunity to refactor the code and remove technical debt. Finally, a police report would be made and referrals would be denied. Not a cent would be paid under duress. While writing our response, we received an unexpected message from the CTO himself. He retracted his threats and asked for a phone call. Had our silence given him pause for thought?

Looking out the window, I saw a ray of sunlight breaking through the cloudy sky.

Although relieved, I was still confused by his actions. The next day, our CTO appeared on the call quite calmly. He explained how he was at the end of his relationship and just wanted a proper exit. A fair question I thought, considering how much effort had gone into it. What bothered me was the finality of his decision. His threats weren't just a flash in the pan. The reasons behind them had been incubated over the years.

After deeper introspectionhere's what i learned.

Related: Identify and stop rogue employees before they become a security threat

1. Cultivate real relationships

This incident was a victim of OWN war. Whenever a new product idea was envisioned, it was our CTO and his loyal team who had to bring it to reality. Line after line, they coded away, adhering to deadlines and debugger audits. They suffered in silence hoping that scaling would happen. It didn't – at least not on their timeline. Over the years, mental exhaustion set in.

Zisis would travel to the satellite office several times a year. He would spend a few days with the team there and work on business process improvement and problem solving. The more time we spent together as a team, the more I believed our expectations were aligned. But every year, as our CTO would wait for Zisis at the airport, he must have wondered why I never took the time to meet him. Did I not appreciate it enough?

The truth is, I did. But I didn't invest the time in that relationship, prioritizing firefighting elsewhere in the firm.

Cultivating relationships it is not just a simple phrase or noise. Your employees require vision and RELATEDnot just a salary.

2. Don't let closeness – or the lack of it – fuel resentment

After the pandemic, going to the office became a thing of the past. Of course, telecommuting can bring some productivity benefits according to some the studies. Other studies indicate that these benefits are not necessarily validated by employers.

If you're a startup, having your tech team in another country is a recipe for disaster. Time zone differences, delayed communications, lack of human contact and cultural differences are just a few points of failure.

When your key assets share the same premises, problems can be addressed quickly. In our case, it was a proverbial death by a thousand cuts; anger was drinking in silence for many years, but the distance created cognitive dissonance in my mind. I failed to see the problems before it was too late.

Related: The 4 managerial pitfalls of telecommuting (and how to deal with them)

3. Be careful with your words

Three months before the threats, I Skyped Zisis in the middle of a critical code issue affecting our users, “What's the point of our testing process? Just get rid of (our CTO's name) next time…”

Call it karmic justice, but this comment was relayed to him as part of a larger “forward” message by mistake. I can't imagine the shock and disappointment he felt when he read it.

I learned – the hard way – to eliminate histrionics in electronic communication channels. Second, I learned not to write anything in any online medium that I wasn't comfortable seeing printed on the front page of Financial Times.

4. Always have a plan B

When we received the threat, our headquarters in Cyprus was still under construction. We didn't have any senior technical leaders other than our CTO. We never felt the need – a painful miscalculation.

If you can afford it, a part-time job that monitors your key technology personnel is advisable. Today, we pay to hire said resource for audits, codebase backups, and interview assistance. This person also steps in in case of an emergency – and boy, have we had our fair share since then. The system is now, however, engineered to have no single point of failure and is battle-tested.

Consider Plan B as insurance. No business works without it.

Related: Don't wait for disaster to strike – these 5 preventative measures can protect your business from all types of risk

5. Invest in soft skills

The relationship may not be linear, but there is an inverse correlation between coding talent and interpersonal skills. The more time spent with code instead of people, the more emotionally detached he grows.

At first, we would hire purely for technical expertise. Now, our hiring process is more comprehensive. No one person in a tech startup has more theoretical power than the CTO. They encode your dreams, but can erase them at will.

Invest in emotional stability. The main danger to man is not just something you put as an afterthought in the “risks” section of your deck. It's very real. As humans, we are all flawed in different ways. So hope for the best, but beef up your defenses in case the “bad actor” in all of us rears its ugly head.



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