How To Deal With The Asshole At Work

emoticon angry
How many of us feel when dealing with difficult people.

There’s always going to be that one guy or lady who is a complete jerk. You know who I’m talking about. The one who’s been around forever and no one knows why they’re even still employed. The one who is totally ego driven, who manipulates others to get what they want out of a project in order to “look better” and are only driven by job security.

How do you deal with someone like this while attempting to apply design thinking or lean startup practices to your organization? I’ve outlined my process below.

There’s Always Going to be an Asshole Anywhere

Let’s face it: wherever you work, there’s always going to be someone who is difficult to work with. Hopefully this person isn’t your boss or supervisor, otherwise you may want to look somewhere else for work. 

Think the Bigger Picture

I stress on this point big time and this may be the most important point: always keep the triad in mind of the customers, the company and the team. Never compromise the customer, your company or the team for any decisions you support or participate in. That’s how empires fall. Empires are built by people and grow from people, not by knocking them down for someone’s selfish whim. We don’t want our empires to crumble, right? Right.


If you’ve got a meeting coming up with the asshole in it, build your strategy. This is a good best practice tool anyways. Generals always prepare for battle by having a strategy. Gather data, bring sketches for a product or new interface, bring your ideas and be open.

Go Into Every Meeting Coming Out the Winner

In every meeting that you’re at where the asshole is attending, always come out the winner. I don’t mean that you, as in your ego, come out as the winner. You’ve got to win for the empire by being an advocate of the customer, your company and the team. Have the eagle eye approach of a general, such as George Washington or Ulysses S. Grant, who could keep their cool in the most dire of life-or-death circumstances. Both generals were able to navigate what seemed to be impossible odds in order to come out triumphant.

Stay Cool, Calm and Collected

Whatever happens at the meeting with what the difficult person says, keep your cool, don’t let him or her get under your skin, as it’s not about you, it’s about the customer. If that person presents something that you know is far fetched, use the switch and bait approach: “that’s a great suggestion, but how does this help the customer? I appreciate your contribution, as you’re right in one way, but….” Look for something that they say that might be truthful or at least acknowledge that they’re contributing. Egotistical people just want their ideas to be heard, so even slight praise usually satisfies them and then you can get everyone at the meeting to question their suggestion by bringing it back to the larger picture: the customer.

If asshole is insistent, and the meeting starts going in one direction, throw back the idea of doing an A/B test (if it’s a digital app) or user experience testing various prototypes (if a product). You can’t argue with data and most people, including the boss, will buy into facts because they are proven.

Everyone’s got an ego, and you have to make sure that yours stays in-check during the meeting. Winners don’t throw tantrums: they rule with confidence wherever they go. And remember that the meeting may not go in the direction you thought. Usually, even better ideas are generated at a meeting. I’m totally ok with my team and I coming up with new ideas because they’re usually better than what I could come up with on my own, as we all contribute with different perspectives, strengths and weaknesses.

Summarize and Write It Up

After the meeting, provide a report backed by data, with a one page summary at the beginning of the report. Also make sure you put the one page summary in your email as well. Your boss doesn’t have time to read through pages of reports. They need the elevator pitch summary in order to make a quick decision, as they have a larger perspective than yours on the bigger picture of the company, the market, etc.

Get Top Down Buy In

To win, you’ve got to get buy in from the top. When you’re boss is the guy or lady who makes the final decision, you’ve got to make sure that they’ve got your back and support the decision. Otherwise the plan fails at the meeting and you’re a loser. When you lose, you let the customer down. If that does happen at work, go back to your desk (this is when you can let off steam—we’re humans after all) and then you can approach your boss and say “you know, I’ve been thinking about X which seems like a good idea, but I did some reasearch on X and actually Y may be a better approach.” That’s when you present your one page summary with a stack of data (if your boss requests it) in order to get the buy in. There’s more than one way to skin a cat.

Be The Best Version of Yourself

Sometimes it’s not enough to win. Ryan Holiday summarizes this in this quote from Ego is the Enemy: “Your potential, the absolute best you’re capable of—that’s the metric to measure yourself against. Your standards are. Winning is not enough. People can get lucky and win. People can be assholes and win. Anyone can win. But not everyone is the best possible version of themselves.”

Live your life with integrity by being the best version of yourself at work, in life, in general. Always strive to do better, greater work by pushing yourself out of your comfort zone. That’s when true progress happens. At the end of the day, you’re looking at yourself in the mirror. When looking at yourself, ask “did I live by by standards today? Did I do my best?” If yes, pat yourself on the back and keep striving to live by your standards. If not, identify what went wrong and vow to make a change. You’ll have another chance tomorrow to work at it. 

How do you deal with the asshole at work? Please post in the comments.

Tools and resources

Ego is the Enemy by Ryan Holiday:

The Obstacle Is the Way by Ryan Holiday:

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s