Brian Friedman on how to have the worst experience of your life

Published on January 2, 2019

Firing an employee is never easy, and in the close-knit fabric of a startup, it’s exponentially more challenging.

To this day, firing my first employee at Loopd remains a top contender for “worst experiences of my life.” Despite the difficulty, it is also one of those defining moments where a distinct leadership style and strong company culture proved critical.

A firing shifts the tectonic plates of company infrastructure, and questions arise about your people skills and foresight as a leader. On a practical side, it opens a painful gap where a critical role is left unfilled, increasing everyone’s workload and wasting emotional energy that could be better spent elsewhere. It can also cause collateral damage and a negative ripple effect inside and outside of the company.

Despite all these potential negatives, a firing handled well can demonstrate how resilient you, your team, and your mission truly are.

The best way to prevent firing an employee is to never hire them—but this is easier said than done.

After a few poor hires, I began to identify unhealthy personality types during job interviews. By asking some leading questions and speaking to references about job candidates, I stopped hiring these people in the first place. But occasionally I had a critical need for a specific skill set, and my choices were limited. In these instances, I needed to weigh the likelihood of their potential toxicity against the urgency of my need for their competency.

From my experience (i.e. mistakes), I outlined a few potential employees I would definitely not hire:

The “no show” employee: This employee is like the office phantom and either shows up only sporadically or is chronically late. Interestingly, these people are very knowledgeable about the number of sick days, personal days, and vacation days available. During the job interview, this person may ask first about the number of personal days allotted and then flatter you by mentioning how this compares favorably with past employers. He/she will likely mention a two-week vacation that is already scheduled in the next three months and therefore requires this as a condition of employment.

If you hire this repeat no-show offender, you will quickly start receiving calls about an unscheduled doctor’s visit, car trouble, or a million other excuses for missing work. Initially, you will be sympathetic and tolerate this behavior, but it won’t take long for your sympathy to run thin and for these excuses to be a constant distraction and waste of time.  

The “customer-unfriendly” personality: This employee has a pervasive air of superiority over the customer. He/she assumes that customers are always less intelligent and less experienced and speaks down to them in public. In some cases, this employee will boast to the customer about having worked successfully with larger, better known companies (or even competitors). Unsurprisingly, this will cause some customers to cancel an order unexpectedly or fail to renew without explanation. If you’re lucky, the customer will circumvent this employee and complain to you directly, but this is not always the case.

During the job interview, candidates with the “customer-unfriendly” personality will readily devalue customers, referring to them negatively with descriptions like “ignorant,” “misinformed,” “brain-dead,” or “out-of-date.” Other times, they avoid referring to customers in specifics and simply lump them into a general description of “the market.” To avoid hiring these problem individuals, ask for references and specifically dig into this person’s past interactions with customers. Take the reference check further, and try to contact these customers directly.

The “blame-game” personality: This employee is a master evader of responsibility. He/she takes credit for everything going well, and points the finger at everyone else when it does not. This employee is surface-level friendly, but is always making sly comments about the failings of other employees. In a team setting, this person is quarrelsome and constantly finds fault with the ideas and opinions of others. This causes a predictable souring in office relationships and team productivity.

Only a mild exaggeration.

The blame-game personality creates a toxic environment where deadlines are missed, products fail to meet expectations, and customers complain. Identifying this personality type during a job interview is tricky, if not impossible. A better way to sniff it out is to look at his/her LinkedIn page for the number of employers, duration of employment, and absence of promotions. When checking references, be sure to ask specifically if this candidate is a team player who celebrates the success of others and is a “fun” person to have in the office.

Companies are the sum total of the people working there, and hiring any one of these three types of employees could bring down the whole organization. If you must hire someone who is a bad cultural fit but has the technical knowledge you need, be sure to document his/her actions, track performance, and proactively build your case for termination. This may sound extreme, but in my experience, any startup with one of these problem personalities will suffer the potentially irreparable harm of poor sales, weak products, and high staff turnover.  

Depending on the age of the startup, this can either be a debilitating wound or a fatal blow. While a more established company can weather the damage of a toxic employee, a newer startup simply can’t survive if it leaves the problem unchecked for too long.  In older companies, the threat of a bad employee is amplified as he/she is promoted and tasked with hiring people. Toxic people often hire similarly toxic people, and the problem only compounds.

In order for your team to be successful, you need to hire employees who are relaxed, collaborative, and oriented to the needs of others. Companies define culture on paper, but employees establish what that culture means in practice.

Brian Friedman, 27, is a columnist at Grit Daily. He is a Millennial entrepreneur who has lived the full life cycle in California’s Silicon Valley from a blank sheet of paper to a successful multi-million-dollar exit in under three years. During this short time, he secured over $2.5 million in angel and venture capital financing, grew his team to more than 10 full-time employees, opened offices in San Francisco and Taiwan, and sold products and services to Intel, Cisco, Castrol, Box and other major global brands. Brian is currently the Vice President of Digital Innovation at Aventri, the leader in cloud-based events management software. Previously, Brian was the CEO and cofounder of LOOPD, the emerging leader in offline analytics that utilized socially smart wearables and actionable metrics to help marketers understand, target, and interact with customers.

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