Archives for the ‘Careers’ Category

16 Deadly Sins of Business

Who wants to work for a loser?

I discovered the 16 Deadly Sins of Business eight years ago when I was doing a lot of work with startups.

Written by Emory Winship, an angel investor in New York City, the 16 Sins were his early-warning system. If he saw a company commit one of the 16 Sins, he knew he might end up working with a real loser.

I only wish I knew the 16 Sins earlier in my career. I wouldn’t have to make excuses for the two loser-jobs on my resume.


How do you know you’re working for (or interviewing with) a Loser?

Separating Winners from Losers is tougher than you think. Loser-companies are masters of disguise. You’ve got to scratch below the surface to find out what’s really going on.

That’s why I love The 16 Sins. They go to the heart.

Here’s what you have to do:
  • View the original 8-page PDF for a complete explanation of each of the 16 Sins. [it's a Google doc so it should open in your browser perfectly]
  • Use my questions (below) in your interview. If a client (or prospective employer) can answer my questions, it’s likely you’ve found yourself a Winner.

1. Elephant in the Boardroom

What is the most pressing issue facing the company right now, and how is management addressing it?

2. Blinded by the Light

How does the company seek out independent perspectives on its products and services? And what does it do with this knowledge?

3. The Mouth That Roars

How much of the marketing budget is allocated to making it easier for sales people to sell and customers to buy its products and services?

4. 42

In one sentence, who is your profile customer?

5. Too Big to Think Small

How does the background or experience of the leadership team map to the current needs of the company?

6. Cowboys

Describe how strategic decisions are made and how often strategy changes.

7. Say When

How does the firm plan for growth? What systems are being developed now, in anticipation of growth?

8. All in the Family

Describe the role of the outside board of directors (or board of advisers)? What oversight and authority do they have?

9. Swiss Watch

How often does management “fire itself” with the intention of building competitive products and business models in order to maintain its sharpness. (see Andy Grove’s book, Only the Paranoid Survive, for more).

10. Who’s on First

How do analytics drive company decisions, performance?

11. Dead Right

How easily does management make difficult decisions? How do they avoid analysis-paralysis?

12. Opportunity Only Knocks Once

They say marketing’s job is to build an ever increasing base of repeat customers—in what way is the firm building a repeatable system like this? And what’s the customer profile at the core of your system?

13. Blue Angels

How often does the company independently assess SWOT? What do they do with the recommendations?

14. White Knight

When you divide revenue between your cash cows, problem children and rising stars, what percentage of the rising stars are outgrowths of current business operations and what percent are in unrelated fields, markets?

15. Patron Saint

Sorry, I couldn’t come up with a question for this one. Maybe you can suggest one or two.

16. More Money

What would happen if your budget was cut by 50%? What would be the last thing to go? What would be the first?


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