Ever tried dealing with a large company, only to get stonewalled? You're talking to a black box that repeats “Sorry, that’s against policy” or “I can’t do that”

But if you can open up that box the picture changes. The moving pieces become visible. Watch how each one ticks, and you’ll start noticing the systems at play.

Leaders design incentives to be armor plating for the company, protecting its interests. They work well for the most part, but all plating has seams.

The Dangerous Professional finds those seams and slips between them.  They'll dodge gatekeepers and dance around policies, doing whatever it takes to get the job done.

Bypass the Gatekeeper

Companies setup divisions with the job of managing all the incoming complaints. You know them as customer service.  Depending on whether you’re that company’s customer or their product, customer service’s role varies from “keep them happy with minimal effort” to “get these people off our backs.” They’re the ones companies want you to contact.

When customer service isn’t being that helpful, look for someone else to complain to. Like the CEO.

Jeff Bezos is famous for reading all customer emails sent directly to him. When a complaint lands in his inbox he forwards it to one of his reports with just a question mark added: ‘?’. Whenever anyone gets this email they drop everything and scramble to solve that customer’s problem. The customer service department doesn’t have that kind of clout.

I witnessed this at Microsoft. The VP got a complaint and forwarded it down to his direct report.

Which got forwarded down again. And again. And again. Each level adding one more manager’s weight. Propelling it faster and faster and faster till it smashed into my team’s inbox at critical velocity. All hands on deck!

Why did  this work? Look at what’s happening behind the scenes. Your message went to someone with just enough time to say "This might be important, I’ll delegate it to the relevant team." And it gets fast tracked through the chain of command

A funny bit of management psychology comes into play here: If your boss’s boss’s boss tells you to “look into this please,” it jumps to top of your priority list. Usually folks don’t bother to ask if it should be prioritized higher or lower than the large pile already on their plate.

Achievement unlocked: Teleport to front of line.

Dance around the Rules

Many businesses have departments tasked with nothing but creating rules other departments must follow. Some of those rules get really weird:

Once I was going on a business trip to help with a conference. My company had instituted a hotel budget of $250 per day. But this was a BIG conference. Hotel prices were jacked up, and only the sketchiest places met that price point.

The cheaper hotels were 30 minutes away, but then I’d blow the budget for uber rides. I asked if I'd have to cancel my conference trip.

Manager: “There’s not actually an uber limit”


I booked that distant hotel and took an uber everyday. Now here’s the kicker: the hotel + uber cost more than what I would have paid if I had gotten a hotel walking distance from the venue. But that’s too complicated for the finance department to write formal rules around. Imagine if they prevented people from getting a ride when it was really needed!

Thus the current policy was born.

It gets better. When you see the policy’s red lines drawn out, you can dance around them like Danny Ocean’s crew navigating a laser maze.

Good sales reps know this and use it to push deals through. Patrick McKenzie offers an example:

"Suppose you are selling a $100k product to a director who has $100k budgeted for it. You do the dance. Purchasing says they need a 10% discount because We're Big Enough To Always Demand One.

Three days later you submit the following: $100k invoice, discounted 10%, for 1 year of SaaS services. Comes out of software budget. $12k invoice, discounted 10%, for 1 year commitment to professional services. Comes out of consulting budget.

Purchasing is *extremely* likely to approve this."

Did the company hire people who couldn’t do basic math? Of course not.

They pay people who know where their time will be most valuable. Writing a policy that covers 95% of situations will take them 10 hours and saves the companies $XX millions of dollars. Writing policies to cover the remaining 5% will take ten times as long and only offer a tiny fraction of the savings. The cost/benefit analysis doesn’t work out.

If you learn what was left in that missing 5% you'll have the advantage.

Remember there is no “company.” All of the company’s decisions are actually individuals acting within their own set of incentives. The “company” is what emerges when those individual incentives interact with each other.

You don’t have to fight the entire company.

There is no company

Hidden incentives exist in your own company too. Is a team resisting doing something you’re asking for? Learn why. Find the fulcrum point. New paths will emerge.

For example, I used to struggle with people not responding to my emails when I tried to get their approval on a change I was making. “People are busy,” my manager explained. “Instead say, ‘I’ll be making this change on Thursday unless you object before then.’”

I started doing that.

The objections were rare. The complaints, non-existent.

What Makes Them Tick?

You get the best results when you adapt your approach to the person you’re facing

Now replace "person" with "team" or "department"

The sentence remains true

Figuring out each team's incentives can take some detective work. But once you understand them you’ll learn what makes each group tick. As you get better at this you’ll find yourself able to collaborate with others much more effectively and Get Stuff Done.

Now since you reached the end,  you might also enjoy my article Interview Advice that got me offers from Google, Stripe, and Facebook. I share insider tactics I learned over 13+ years to get offers from multipe tech companies companies like at Google, Facebook, Stripe and Microsoft.

Interview advice that got me offers from Google, Microsoft, and Stripe
“What would you say if I asked you to design me a service capable of responding to thousands of user requests every second and latency was critical?” “Umm...that you have to solve this problem at work. But you’re out of ideas, and are looking to interviewees for suggestions”

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