How to Win Arguments and Manipulate Managers

Everyone has a boss, and God, in his infinite appetite for cruelty, will almost certainly ensure that said individual is a dumbass. Maybe you spit on an Indian burial site and got cursed. Maybe low IQ is a prerequisite for VP titles or board seats. Who knows. Regardless, you are going to have to learn to deal with people more powerful than you. So learning how to navigate an organization is one of the most important skills for a career. Yes, it is trite and bleak and horrible, but I would prefer a colleague who can get the VP to agree with what our team wants over any other capability. 

The need for this skill is especially acute for those of us who do analysis for a living. Whether you are tasked to build a financial model, a dashboard on user data, or a flowchart of workflows, if you are semi-regularly asked, “Can you figure that out?” this guide is for you. 

These are hard-won lessons. Frankly, for most of my career I was atrocious at this. My analysis has always been good, but I sucked at translating the spreadsheets into company change. I (foolishly) thought that “data would prevail” or “management will do what the math says we should.” 

But what data is, or what “right” even means, can be strongly skewed by incentives or bias. Even though most firms should base their decisions on analytical rigor and risk-adjusted investment, they end up doing so based on hubris.

So, after nearly a decade of doing this wrong, please learn from my mistakes. These skills should be used for good (improving the company’s chance of success) but are also applicable in a more Machievellian sense, if that’s your sort of thing. To make this feel more real, I’m going to walk you through a work of analysis I did here at Every. Using it as a framing device, I’ll share three ways to use narratives, psychology, and gotcha slides to win at work.

Toro, toro, toro

I think of founders and executives as bulls in the budget shop. They’re strong and powerful and  ill-tempered and a smidge destructive. The skills that let them ascend to the top of an organizational structure very rarely include analytical rigor. Great founders and CEOs typically shine in their ability to understand and communicate stories. Their job is to rally investors and team members—with the most universal way to do so in charisma and charm. 

These are the people you need to convince, so instead of trying to teach them how math works, adjust your math to their story. 

Whenever I’m presenting an analysis, I like to start with the story of how we got to the need for this analysis to be with and why this math matters—fairly normal advice. However, I’ll take it a step further. 

Rather than rattle off the numbers along with my suggested fix, I’ll wave three red story flags in front of the executive’s eyes. Each discrete work of analysis has an accompanying story to be told. Your job is to get the bull to pick which flag to charge at. Since founders are the bulls in the arena, you either give them a target or they will just rage about willy-nilly. As you get better, you’ll be able to present all three stories, but they’ll charge the one you want every time. 

At Every, top of the funnel has always been our biggest concern. Our traffic mostly derived from people sharing our essays on social media—in particular, on Twitter. Unfortunately for us, Twitter was bought by Grime’s jilted ex-lover, who instituted algorithmic changes that have decimated one of our best sources of traffic. Since we need, like, customers, this is a business-is-on-fire situation.

I put a meeting on everyone’s calendar called “I got 99 growth problems and Twitter’s the biggest one.” When we met, I started off by showing the overall traffic decline to Every’s website. Then, I showed this chart of Twitter views volume. 

Source: Google Analytics (a product so abysmal that I can’t get the damn charts to do what I want or look how I want or show what I want. I hate I hate I hate). 

I didn’t show this because Every CEO (and my boss) Dan doesn’t know that Twitter sucks now, but because I got him to focus by waving that red flag. He has a lot on his mind (note from Dan: "for example, my lead writer says unhinged things about me in this newsletter"), so getting him to dial in is important. 

In my preparation for the meeting, I knew that I would need Dan to approve a few growth initiatives. I had done a bunch of math that showed which ones were most likely to work, but he needed to OK the new workflows. Thus, the red flags.