Posted by: Dr Churchill | September 10, 2014

The Seven Deadly Sins of Leaders Entrepreneurs & Company CEOs

I am a Communications Guy through and through…

But I started early on.

I founded my first “company” when I was a kid in a cold and distant Boarding School and going stir crazy from missing my family and friends — I used my Ham Radio to communicate with the world at large. I couldn’t help it, because am a Communications kinda guy, so I started sharing this with my new friends, and then when word got out — I offered the communication service to all of my classmates who streamed up in the attic of the school after curfew, and had a talk and listen party with “hamsters” all over the world. Before Internet these things were the Internet of the day. Like pico radios that brought down the Soviet Union, these after hours, ham radio sessions were all the rage.

A veritable party for geeky kids.

Needless to say immediately after the “Authorities” got wind of this, they shut me down. lesson learned, I started my second communication company in a completely Stealth Mode and run it quietly offering an improved service. Talk to Girl Ham radio operators. I must have been about seven or eight years old but who is counting.
Since then, I’ve cofounded, financed, ventured, or Angeled, and led hundreds of companies. Some of the best continued as Consulting Clients throughout my career – from startups and small businesses to large publicly held and Global Enterprises.

Along the way I have learned a thing or two as I have managed distributed teams of employees from America to Europe and China, and most places in between.

To claim that I have seen it all it would be boastful but there you have it. At least I’ve seen a lot in regards to leadership, HR and management.

And although am not perfect – I believe the best leaders are always learning, just like everyone else – but here are seven major mistakes I’ve seen leaders repeatedly make and sink companies completely. These are killer mistakes and are almost always will destroy a company because they are like criminal character flaws for a CEO. Thankfully if I can help it, the CEOs suffering from these are usually replaced just before they drive the boat on the rocks. That is why I call them seven deadly sins, also known as the capital vices or cardinal sins, because they are a classification of vices and a strong part of Christian ethics, that has been used since early Christian times as an admonishment in order to educate and instruct Christians concerning fallen humanity’s tendency to sin.

So I’ll stick with the Christian theme in this story but because the sins are given in no particular order, as wrath, greed, sloth, pride, lust, envy, and gluttony – we’ll mix them up. Good to remember that each sin is a form of Idololatry-of-Self with Pride and Avarice being the worst examples of where the subjective self-serving behaviour reigns over the objective and rational reality of the community of the World.

1) Pride, is the old nemesis of highly intelligent people: This can be felt deeply when CEOs are micro-managing people. Especially at the C-level, leaders should have confidence to let the people they hired do their job, which often includes managing a team of their own. Hold employees accountable with specific goals and metrics – if they don’t meet them, figure out why, together. But if you have to micro manage your team (see their To Do list every day, ask the same questions over and over, etc), you’ve either hired the wrong people or you’re not focused on the bigger picture.

2) Sloth: is taking relaxation of Standards too far and taking the company to a new Low. It comes when the CEO is being perceived as “too hands-off” And although “sloth” might seem contradictory to the point above about Pride, you can’t disappear as a leader, either. There’s a difference between paying attention and ensuring everyone is meeting goals, vs stepping away and never checking in on progress towards those goals, while you are signing off electronically on your own salary receipts and Executive Compensation from your yacht in Saint Tropez. It’s not good leadership form to ask, “Is it done?” the day something is due, or even when you remember it a few days or even weeks later…

3) Wrath: is worrying all the time about everything and being angry at your people. Screaming at folks and employees and then start worrying about hurting everyone’s feelings. On the one hand, you need to lead in a positive manner, yet on the other hand, this is business. You can’t keep everyone happy, nor should you try. Screaming and causing break downs and then retreating and trying to avoid the inevitable conflict or the tough decisions due to fear of hurting someone’s feelings is a good way to lead in the wrong direction and damage people and the company irrepairably. As a matter of fact always take a deep breath before you “excommunicate” someone and before you attack the people for faults of their own or for a general organizational failure which is ultimately, failure to lead. And it rests with you…

4) Lust: is the Chief Excutive Officer’s failure to dig deep into the work while lusting for the perks and the admittedly heady compensation of the office. Failure to see things as they are by digging deep into the datastream of the company. Failure of the CEOs suffering from this cardinal sin of lust to access equitably all the employees and instead getting dazzled by the shinny monkeys out there. Lust is the idiotic failure to focus on what’s important because the CEO only sees the ones he/she cares lustfully about. Those executives in turn fail to see and are not able to check what’s working and what is not, who is working and who is not, and above all else, which way the ship’s compass is pointing at. If you know, by some special instinct – great. But if you can’t check the ship’s compass to find the true North, chances are you are a weather vane going round and round to wherever the wind is blowing you to.

5) Greed is accumulating assets — therefore liabilities and not knowing how to pare down the company to make it fit and healthy. So what do you do? Do you take the necessary steps to find out why something is working or isn’t? With all the data available in business today, smart leaders understand to dig in and analyze it both when things are great and when they’re not so great to keep going forward. Stop accumulating divisions, making M&A deals and acquiring companies, if you cannot digest them and make them work well for you and for the acquiring company. Eventually Your Company will be a target for Takeover. So the lesson here is for the company to stay lean, mean, and hungry. This allows you to repeat winning formulas, and understand the downfalls of your organization so that you can lead to improvement. This includes staff, resources, money ideas and all the combinations therein. It alos makes you a less “juicy” target for acquiring predators. And please don’t be naive enough to think you’re an organization with no downfalls and your culture is better than the acquiring or acquired company.

6) Envy is all about wasting money. I particularly see this in startups without a well defined product or a path to monetization, but with a couple of VC commitments and an Angel round under their belt. The moment they hit the cash machine that the VC term sheet represents for them — they go nuts. Parties and a boat type car are the first draw expenses these Startuppers are famous for. And they follow with a down payment on a chateau style house if they can help it. They envy the perks that Google offers to it’s employees and they start offering massages from Thai girls in the office when all they have is a couple of months of burn-rate to get them through. Especially after said startups close funding, and go from bootstrapping and skateboarding to the office, to buying expensive cars for the founders on credit, I walk away from them immediately. Although, I’ve also seen plenty of it in large enterprises where checks and balances get more difficult to track through multiple layers of spending. It’s always the special sickness of “Envy” that causes founders to believe that they are really hot shite and deserve the same perks as those large Corporate CEOs who manage thousands of people. It never fails to surprise me how many startup CEOs, specifically, don’t really track where the money goes, and if the spending is wise in relation to where the company is in its lifecycle.

7) Gluttony: It’s easy to get caught up in the visceral items – marketing, events, sponsorships, branding – cool business cards, hiring a big name PR firm, or sponsoring a popular tech publications’ startup event. These are all things I’ve seen (especially first time) founders get excited about because it brings cache and (temporary) attention, and makes things feel “real.” But are those the items that are going to close customers for you early on? Are they helping you to develop a better product?

And I added a bonus for You who read this far. Here is an old vice from the old and stricter Christian Doctrine because it is necessary to have it in our arsenal of sins to avoid:

8) Avarice: Failure to discern. There’s a difference – a big one – between what a startup should be spending on vs a decade-old company with a solid customer base and revenue stream. Good leaders shoot down the more “fun” ideas in the early stages, and keep their teams focused on what’s going to bring in the right elements to the company – and continue to apply that insight during each of its lifecycle and growth stages.


The other overriding Sin not spelled out in the Christian educational cannon or in the religious arena, is the leader’s Bad Communication skills, and his failure to listen and relate well. This is a Big One.

Leaders listen. Leaders have to listen and to record everything. Leaders have to remember and leaders have to communicate clearly. Too many leaders think they don’t need to communicate clearly because everyone should just know what they want. This doesn’t work in personal relationships, and it sure doesn’t work in employer/employee relationships, either. Be clear, be concise, be consistent.

And repeat.

Don’t always talk in parables, or metaphors, and platitudes. It doesn’t make for Good Leadership. As a matter of fact it doesn’t make sense either. people will be always wondering what you meant Two Thousand freaking years later but next quarter results will surely suffer.

Some say that this is the reason Christ was crucified because He did not make it clear to his disciples that he needed to pray in Peace at the Mount of the Olives. He gave them a nifty metaphor about Officers of Peace, and they misunderstood his command, and sent for the Cops to keep the peace.
The rest is History…

It’s absolutely mind boggling how bad leaders can slow down the progress of a company simply by not speaking clearly their commands and by not listening to their followers. They sink the ship with Mumbo Jumbo… So instead of talking about Second Comings, please make it right the First Time. Capice?

And listen to your people carefully and satisfy the little needs and wants they have early on before they become major grievances. Case in point … Judas Iscariot, who wanted some “dough” and a raise, and Jesus failed on both occasions to deliver some measure of satisfaction to Iscariot, who went elsewhere to sell his “Inside Information”

The Inside Information in the wrong hands was the “kiss of Death” delivered to Jesus Christ, with the known apocalyptic results.

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