I asked a client the other day when faced with hiring two salespeople, are you thinking of taking the asshole or the nice guy?
They immediately defaulted to the nice guy but saw the disapproving scowl on my face and went with the asshole. In their situation it was probably the right call. But it is not always the right call, and the problem I see repeatedly is that having genuine sales confidence and swagger often does not even get a look in.
People have said to me all my life that I must be great in job interviews given how good I am at sales. For twenty years I have been saying no, they are the opposite. Sales is all about the other person. An interview is all about me.
There is a greyscale tightrope that every salesperson needs to walk constantly. Not enough asshole and you lose deals. Not enough nice guy and you are insufferable.
The Hubris Problem
The dictionary defines hubris as extreme, excessive pride or arrogance.
The overconfident loud sales guy is easy to spot and easy to understand. When salespeople have a good month they fill with pride, overestimate their ability, and start to reek of arrogance. Too much confidence and you apply urgency at the wrong moment, come off as pushy and sleazy, and the deal walks out the door before you even know it has left.
Assholes are genuinely difficult to have in a team. Hard to manage, hard to interact with, and corrosive to culture. Everyone else is trying to build harmony and good salespeople are trying to ram more work down everyone’s throat.
Recently a young guy reached out on LinkedIn, said he wanted a job and thought I was the best in the country and he wanted to learn from me. Good stuff. I asked what he valued himself at. He said he brings trust and relationship building. I said no, I am asking what dollar amount you think you are worth. He replied north of three hundred thousand base and very healthy commission.
It was great that he answered high. But he overvalued himself. A few years of experience wanting senior leadership money, plus mentorship and training throughout. He is not going to generate the six million in sales required to justify that base, let alone the commission.
But the money is the simple problem. The real problems are these. He thinks he already knows everything. He will lord it over other staff and clients. He will be impossible to motivate because there is no way he will grind. He is not drinking his own champagne, preaching relationship-based trust selling while sliding into my DMs on LinkedIn. And the main problem is he thinks he is the main character. Sales is not about him. It is about the customer.
The Humble Problem
So hire nice guys, right?
No. That’s even worse.
Humility describes having a modest, low estimate of one’s own importance. Nice guys are just as painful.
Nice guys hide behind a social mask. They agree with everything the client says. They mimic, they accommodate, they go the extra mile, they are basically cheerleaders on the sidelines of a contact sport. They are terrible negotiators. They concede everything. They will not cold call because it feels rude. They will not ask the hard questions. They do too much and they do not worry about getting paid.
Nice guys do not get promoted. They work hard on all the wrong things, get stuck in average, and end up resentful. They spend a lot of time supporting the client but are not involved in the actual game. They will tell you with genuine surprise that the competitor was awarded the contract three months ago.
One of my mentors used to get genuinely angry when I was too passive. He explained it like this. When someone asks what ice cream you want and you reply oh anything is fine, you think you are being pleasant and easy to deal with. To senior people you are being a pain in the backside. Now the burden is on them to know you well enough to order for you. Your passive attitude just created more work for everyone else. In a negotiation it is so much easier to deal with an asshole. At least they are honest and tell you what they want.
The Chameleon
Both are the answer. Neither is the answer.
In a modern sales environment I look for people who score very low in agreeableness on the Big Five personality framework. I had a major argument with a job posting platform about this. Their algorithm keeps sending me nice guys. I told them I want convicted felons, disgraced cops, and the criminally insane. They said they could not do that because their entire algorithm is designed to promote agreeableness, minority group representation, and past experience at big logos. None of which I want.
The mastery is to balance between hubris and humility. Know your value. Know your vector in every situation. Be comfortable in a Google boardroom and equally comfortable talking to the bloke on the shovel, but know exactly what level of confidence is required in each.
Be the chameleon.
Step one. Dress at the same level as your client or slightly better.
Step two. Speak at their level. Their intelligence, their role, their pacing, their vocabulary, their enthusiasm.
Step three. A friend of mine said to me before I went into basic training, do not be top of the class and do not be bottom. Just disappear into the middle. Finding the balance between humility and hubris is one of the rare cases in sales where you want to be average. Then moderate from there based on the prospect. If they are loud and aggressive, move toward that. If they are quiet and thoughtful, move toward that.
I am constantly fighting this battle with the narcissistic controlling asshole inside me, and he is constantly fighting with the nice, sweet, caring nice guy.
The deal goes to whoever wins on the day.
If you want to build a sales team that understands this balance and hires for it deliberately, that is the kind of thinking we bring to outsourced sales and fractional sales management at Outsold. More at www.outsold.com.au/blogs.
Focus Keyphrase: sales hiring problems Secondary Keyphrases: outsourced sales Australia, fractional sales management Australia, sales recruitment problems, sales coaching services, sales management consulting Meta Description: Are you hiring the asshole or the nice guy? Jamie May on why both are wrong, why both are right, and the greyscale tightrope every salesperson needs to walk to actually close deals. Slug: the-asshole-and-the-nice-guy Tags: sales hiring problems, outsourced sales Australia, fractional sales management Australia, sales recruitment problems, sales coaching services, sales management consulting, why salespeople fail, sales culture, sales performance improvement Category: Sales Culture
Jamie May is the Managing Director of Outsold, an Australian founder-led sales agency specialising in outsourced sales teams, fractional sales management, and B2B lead generation across Sydney, Melbourne, and nationally.
