September 22

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Navigating a Challenging Boss: Practical Strategies for Success

By Leon Rawitz

September 22, 2023


A coaching client found himself growing increasingly frustrated with his error-prone General Manager.  The GM’s primary responsibilities included acquiring new business, generating re-orders from existing clients, and providing the accompanying Order and Shipping Documentation to the Distribution Team, for fulfillment.

However, the submitted paperwork was consistently mistake-ridden, demanding one to three hours of corrective action, multiple times a week.  Thanks to the diligent efforts of the Distribution Team, the company safeguarded its reputation for error-free, on-time customer deliveries, an accomplishment for which the GM was quick to take sole credit.

What would YOU DO in this situation?  Here’s what I proposed.

Unlocking Solutions: The Interplay of Proof and Targeted Questioning

With knowledge of my client’s previous interest in law, and his exceptional score on the Law School Admission Test (LSAT), I encouraged him to consider two powerful tools attorneys use in court—EVIDENCE and TARGETED QUESTIONING—to achieve the desired outcome.

I recommended that he approach the situation respectfully, presenting concrete examples of the errors he encountered (the evidence) and their potential negative impacts.  This included everything from inventory discrepancies to scheduling conflicts, shipping errors, late deliveries, and dissatisfied customers.

Just as an attorney would do, I suggested he ask targeted questions aimed at finding collaborative solutions to increase productivity, improve accuracy, and create exceptional customer experiences.

Fostering a Culture of Team Recognition

 In the event the boss continues to take exclusive credit for the team’s accomplishments, I advised the client to initiate a private conversation.  Ask HOW the boss was able to achieve such exemplary performance and encourage him to acknowledge others in the presence of the company CEO.

If this approach fails, step up in a public setting and credit the deserving individuals responsible for achieving the company’s high Customer Satisfaction Scores.  Great leaders focus on the team’s success, never their own.  It inspires trust and earns the respect of team members.

The EQ Advantage: Leading with Emotional Intelligence

One essential trait of effective leaders is Emotional Intelligence, especially for individuals who, like my coaching client, wear their hearts on their sleeves.  When confronted with challenges, reacting too quickly or harshly can impede progress and potentially destroy careers, regardless of their aversion to those who avoid taking responsibility and instead, blame others.  This underscores the critical importance of emotional management.

One of the best examples of Emotional Intelligence in action can be found in the below video clip of Steve Jobs addressing an antagonistic questioner.  It’s an invaluable teaching tool and one I had my client review to help him deal more effectively with his problematic boss.  Let’s break down the brilliance of Steve Jobs’ response.  https://bit.ly/48mPZV5

A Play-by-Play Analysis of Emotional Intelligence in Action… by Apple Founder Steve Jobs

1.     Restraint

Once the questioner concludes his condescending remarks, observe how Jobs takes time to collect his thoughts, demonstrating remarkable restraint.

2.     Avoid Making the Other Person Wrong

Notice how Jobs refrains from justifying Apple’s choice in software or proving his critic wrong.  Instead, he acknowledges that the questioner may be right in some areas and that the alternative platform likely has advantages of which Jobs is unaware.

3.     Vulnerability

Most impressively, Jobs displays vulnerability by acknowledging how his infatuation with technology led to repeated mistakes.  He ultimately realized that the path to building great products was starting with the customer experience—their desired end goal… and working backward from there.  Humility is a hallmark of emotional intelligence.

Managing a difficult boss is a test of your leadership and emotional intelligence.  You don’t need a title to lead—effective self-leadership is within your control.

How have you dealt with difficult bosses in your career?  Please share your thoughts and experiences in the comments section below.  Your insights will undoubtedly help others facing similar challenges.