Companies that consistently avoid dissecting failures, like lost deals, demonstrate a cultural aversion to learning. They prefer chasing new opportunities over improving. For employees in such an environment, this systemic refusal to learn is a major red flag indicating limited growth and a need to seek opportunities elsewhere.
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When interviewing salespeople, the biggest red flag is blame. Strong candidates demonstrate humility and self-reflection by taking ownership of lost deals and analyzing their own shortcomings. Weaker candidates deflect, blaming the product, competition, or other external factors, signaling a lack of coachability.
Even a top-tier sales professional has a career pitch win rate of just 50-60%. Success isn't about an unbeatable record, but a relentless focus on analyzing failures. Remembering and learning from every lost deal is more critical for long-term improvement than celebrating wins.
When evaluating senior candidates, don't view a failed entrepreneurial venture as a negative. It often indicates valuable traits like risk-tolerance, scrappiness, and resilience. These leaders have learned hard lessons on someone else's dime, making them potentially more effective in a new organization.
People have an extreme aversion to acute pain. They will accept any level of chronic pain—like a company slowly bleeding out over five years—to avoid the single, difficult conversation or dramatic change required to stop the losing. This explains the long, slow death of many companies.
Even the best coaching will fail if the company culture punishes desired behaviors. A 'firefighter syndrome' culture, which rewards heroes who solve last-minute crises, will undermine coaching aimed at fostering proactive problem-solving, rendering the investment useless.
Hyper-growth and strong sales create a positive, winning culture that solves many problems. However, this success can become a blind spot, causing teams to ignore critical underlying issues that may later prove detrimental, as seen in the Zenefits story.
Keeping an employee in a role where they are failing is a profound disservice. You cannot coach someone into a fundamentally bad fit. The employee isn't growing; they're going backward. A manager's responsibility is to provide direct feedback and, if necessary, 'invite them to build their career elsewhere.'
A company's culture isn't its mission statement; it's the worst behavior it's willing to accept. High-integrity employees will leave a toxic environment, while transactional, self-serving employees who tolerate anything for a paycheck will stay. This selection process causes a continuous erosion of culture.
Contrary to the popular trope, you learn far more from success than from failure. It's more informative to see how things are done right than to analyze what went wrong. To accelerate your career, you should prioritize joining a winning team to observe and internalize successful patterns.
A powerful way to gauge cultural fit is to identify who is succeeding within the organization. Then, honestly assess if you respect them and their methods. If the path to "thriving" is paved by behaviors you don't admire, it signals a fundamental misalignment and may not be a game you want to win.
