Difficult People

A CEO at a mid-size tch firm asked me why salespeople can be so "Difficult". I immediately laughed out loud because every single SUCCESSFUL salesperson I have ever worked with, has been a total and complete pain in the ass.

I believe that successful salespeople are always pushing the limits of an organization's standard operating procedures. That energy is exactly what I am looking for. There are real misconceptions attributed to salespeople. Here is why I think organizations should target "difficult" salespeople.

A successful salesperson has no patience for bullshit. For example, the company may publicly communicate that they are "Customer First", but if that axiom is not honored and held dear by the leadership team, there will be conflict. The successful salesperson will fight for their customer and push back on leadership to follow through on the promise of the brand. A salesperson is a representative of the brand, if they have any integrity, they will voice their frustration on their client's behalf. People buy from people with integrity.

A successful salesperson does not care if they are liked by you. First of all, the prevalent salesperson stereotype is an extravert personality that is overly friendly and accommodating. They buy dinners and are masters of small talk. This may be enough for transactional sales and order taking roles, but complex enterprise sales environments require deeper analytics and problem-solving skills. The venerable doofus salesperson stereotype needs to die. Secondly, the stress level of anyone in sales is very high. Five seconds after the contract is signed, someone is asking about the next deal. It is never ending. That grind may make some of us less amiable at times.

A successful salesperson is motivated by money. The cold reality of a salesperson's career is to execute contracts consistently, make commissions, OR be fired. Most organizations don't keep the lowest performing salespeople. Sales is by far the riskiest role in every organization. The Economy sucks, who cares, your fired. Your biggest customer just went bankrupt, who cares, your fired. You lost the deal because finance overpriced the contract, who cares, your fired. This is the system that they are in, and not all variables are under their control. The ones that survive, are smart savvy earners that hedge their risks effectively. They want to be paid on time and will ask for more. Money is the carrot held in front of them. Don't be dismayed when they reach for it.

A successful salesperson is always breaking process. I am a huge fan of process. Process is a social contract that establishes accountability and responsibility for work to be completed. If I do "A", someone else in the organization is obligated to do "B". If the process is well defined and agreed to by all parties, things can get done. It can be beautiful. That being said, a successful salesperson doesn't care about how well the process is designed. Customers create challenges that are unforeseen and do not fit into the square hole we have cut. A good salesperson will find loopholes and backdoors to bypass things that take too much time to execute. Where there is a will, there is a way, and that is good for the company. It balances our strict reliance on order and predictability. A little chaos is the flavor of life.

Good salespeople tend to have strong opinions, are passionate about their work, and fight for what they believe in. This should not be interpreted as a difficult employee. This energy is what most organizations need to drive growth. Hiring salespeople is always challenging to find the right fit for any organization. The propensity to overvalue likability and extraversion behavior traits is a red herring that should be avoided.