Many leaders learn a lot from hardship or a bad boss, even if they learn what not to do as a leader.

Customer Journey Series: Carrie
Carrie is a finance executive who came to coaching during a career transition. Over the years that followed, she navigated new roles, organizational change, layoffs, difficult bosses, and periods of uncertainty.
Her journey explores self-leadership, resilience, confidence, and learning to take ownership of her own growth.
Each post in this series examines a real coaching conversation or leadership challenge from Carrie’s journey.
This is the fourth post in Carrie’s series.
The next year, Carrie faced her biggest challenge of all. There were layoffs. About 2000 people were let go, and her team was broken up. Half of her team was let go. Thankfully, she was retained.
A consulting company was hired to manage the reorganization, and within a few weeks, they re-assigned her to a different division where her skillset didn’t match at all.
Her new boss was formerly from the consulting company. This was supposed to be a perk of an assignment for him.
But he turned out to be a bully of a boss. He started commuting at 5:30 AM, and she would get up to 20 emails before 8 AM demanding to know this or that. He would continue to send demanding emails until midnight, and often on weekends too. He seemed haphazard in what he might focus on at any one moment and was unpredictable.
He would come into the office yelling. He was negative and discouraging for everyone. She noticed how often he was judging people, telling them what they should be doing and that their work was not satisfactory.
When You Have a Bad Boss
The entire experience was demoralizing. She went on the company website and started applying for other positions, anything to get out of this division.
Carrie was the main breadwinner for her family and was grateful she had not lost her job.
“For my own sanity, I have to make the best of what I have,” she said, trying to salvage what she could of her attitude.
Carrie became a sounding board for a lot of the other teammates who were equally unhappy as she was. She had come from a more senior position than most of them, and they trusted her.
She listened, empathized, and encouraged them to do the best they could so they could move out of this division. They would be judged by their performance. Even if they don’t like the work or the boss, it was in their best interest to do their best for the company.
Sometimes the team would solve problems in spite of the negativity, and the boss would take the report up to his superiors and take credit for the solution. Still, they all kept their heads down and did their best.
Even the boss recognized Carrie as a leader. He noticed other people coming to her for advice. Finally, the boss asked her: why do people come to you and not me?
She raised her shoulders in a shrug. He saw the power of encouraging and developing others, but he was stuck trying to gain power through intimidation and control. It was all he knew.
Carrie had come a long way since those early sessions when she first worried about being unapproachable
After a few months, it was clear that he was having a hard time keeping track of where projects were. He had four different work streams that he was trying to manage.
One day, he called her into his office and admitted: “I’m drowning here. I need help,”
She became his de facto personal assistant and helped him organize the projects and create score cards and progress milestones.
But even after she started helping him out, he continued to yell at her often and demean her.
She continued coaching once a month during the year, just to feel validated and to help her keep her spirits up. She told me more than once it was the hour she looked forward to most.
Most leaders learn a lot from hardship, and this was no different. I helped Carrie see what she was learning, even if she was learning what not to do as a leader.
- She learned about the effects of bad leadership, the emotional contagion of how a boss’s bad mood can ruin everyone’s day.
- She learned that leadership is not a title but an attitude that means helping and encouraging others to be their best.
- She learned about burnout and how to pull back effort in order to make time for herself. She established boundaries by not returning emails after 8 PM or before 8 AM.
- She learned how demeaning micromanaging is. Being told what to do made her feel disrespected and treated like a child. She didn’t want to feel resentful at work, but she did.
It was a year of just surviving under the worst circumstances.
To help her maintain her spirits, I offered three suggestions:
- At the end of each day, write down 3 things you did well or got done that day.
- In the morning before work, write down 3 specific things you are grateful for, even if it just the weather or your dog.
- Remember every day: You are good at your job. You are not the problem.
I reminded her: Thousands of people were let go. Even though she was sidelined, she wasn’t let go. Someone valued her and they just needed time to reorganize and build that function back.
Sure enough, around October, a senior manager reached out to her to say he was putting a team together and she would be perfect for it. He encouraged her to apply.
Continue the Journey
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