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The Rough Notes Company Inc.



May 27
13:49 2021

Management by Coaching

By Kimberly Paterson, CEC


Overcoming the destructive behavior that can end a promising career

Sarah is a hard worker, always the first to arrive and the last to leave. Her track record for quality, productivity and technical expertise made her the obvious candidate to take over the leadership of her department. At least that’s what the senior team thought.

Six months into her tenure, Sarah is failing miserably. Self-conscious and awkward, she’s unable to speak with authority and command the respect she needs to succeed in the job. Her team rarely turns to her for advice and her counterparts in other departments avoid her. Afraid to delegate, Sarah is assuming more than her share of the work and is on the fast track to burnout.

Employees who suffer from “never feeling good enough” function at a fraction of their capacity. … [T]hey don’t rise to the top, embrace challenging assignments or share their best thinking. The individual and the organization both pay the price.

Sarah feels like an imposter in her new role. Fearful of being found out, she keeps to herself and avoids interaction whenever possible. Her fellow managers are older, more outgoing and seem so self-assured. Most of her direct reports have been in their jobs for years. They’re a tightly knit group that makes Sarah feel like an outsider.

Michael is smart, young, personable, and ambitious. He has many of the characteristics of a top-notch sales professional. Management sees real potential in him and is investing heavily in his success. So far, the effort isn’t paying off. Michael is great at opening doors but he’s awful at follow-through. He procrastinates developing his sales presentations, and when finished they’re often filled with mistakes.

While the underlying behavior pattern manifests differently in Sarah and Michael, both suffer from “never feeling good enough”—one of 12 discrete behavior patterns that lead to career troubles. According to James Waldroop, Ph.D., and Timothy Butler, Ph.D., directors of the MBA Career Development program at Harvard Business School, the ways people fail in their careers are quite limited. They fail in the same ways and get fired for the same reasons, from one industry to another, from the lowest levels to the highest.

People who suffer from “never feeling good enough” believe they don’t deserve to be where they are. Their lack of self-esteem leads them to undermine themselves. Common tactics include: staying in their comfort zone, procrastinating, not taking initiative, avoiding growth opportunities, holding back on contributing, and other forms of self-sabotage or self-limiting behaviors. Their feelings of inadequacy are often invisible to others and sometimes to the individuals themselves. The behavior pattern impacts a surprising number of people.

For some, the pattern is pervasive and impacts all areas of their lives. For others, it’s situational. Consider Arun, a seasoned sales professional, well respected and liked by clients and colleagues. His “not feeling good enough” is situational. He’s highly confident with clients that he sees as equals—people his age from similar blue-collar backgrounds. When faced with an Ivy League-educated CEO from a wealthy family, he can hardly get a word out. A graduate of the local community college and the son of non-English speaking janitorial workers, education and wealth trigger Arun’s feelings of “not being good enough.”

Arun manages his discomfort by avoiding people he perceives as better than he. He rationalizes that he’s sticking with a successful formula. In reality, Arun is good enough to handle larger, more complex accounts that generate far more income. He’s staying where he believes he belongs and is limiting his potential.

How the organization is impacted

The organizational impact of an employee who “never feels good enough” is not as apparent as some of the other behavior patterns or Achilles’ heels that derail careers. Their behavior seldom results in lost clients, a dip in morale, other employees quitting or quality suffering.

The cost to the organization is high. Employees who suffer from “never feeling good enough” function at a fraction of their capacity. Afraid to venture beyond what feels safe and familiar, they don’t rise to the top, embrace challenging assignments or share their best thinking. The individual and the organization both pay the price.

The sales professional with better follow-through could be closing twice the deals. The sales professional who had the confidence to tackle larger accounts could significantly increase the revenues generated.

Root cause of the behavior

The behavior pattern of “never feeling good enough” generally goes back to childhood. The roots are deep enough to overpower our most basic drive to grow and reach our full potential. From growing up in the shadow of an older sibling who was the smart, successful one to the harsh, judgmental parent who could never be pleased, the messages received in childhood shape the adults we become and how we see our place in the world.

Culture also plays a role. Some cultures stress modesty and discourage pride and personal achievement. Japanese famously live by the phrase “The nail that sticks up gets hammered down,” a severe warning not to see yourself as, or aspire to be, the exceptional performer who stands out. It’s much safer to be a member of a team of equals.

Here in the United States, Critical Race Theory is sending powerful messages to children that will impact their self-image. For some, the messaging will link race, success and achievement with guilt, and for others, race will be connected to a legacy of victimhood. Both messages feed feelings of “not being good enough.”

How to spot it

What are the signs and symptoms of employees who suffer from “never feeling good enough”?

  • Think they are the only. Everyone else knows how to play the game but them. It’s just they who are insecure and anxious. They are alone in their struggle. They believe that what is difficult for them comes easily to everyone else.
  • Lack consistency. They flip back and forth. One minute they’re hitting the gas pedal hard, then just as they start gaining momentum, they hit the brake equally hard. They’re full of drive and ambition, then self-doubt takes over. This stop-and-go pattern dominates their career.
  • Hold back in meetings. They avoid contributing at meetings. Some will zone out in the meeting to avoid the discomfort of feeling like they don’t belong. Once they’ve lost the thread of the conversation, they fear saying something that’s already been covered. When challenged on their lack of participation, they’ll tell you they really didn’t have anything to say. Inside they fear their ideas aren’t important enough or they might say the wrong thing.
  • Make dumb mistakes. These are obvious and visible errors guaranteed to call the individual’s judgment into question. For example, one manager fired the business owner’s brother’s son who was interning with the company for the summer. She did it without ever talking to the owner.
  • Procrastinate. People who fear they’re not good enough will often avoid challenging tasks rather than risk failure. It’s better to be chastised for not doing something than to be seen as a failure.

How to coach

People with the Achilles’ heel of “never feeling good enough” have three choices: 1) rise to the challenge and address the lack of self-esteem that holds them back; 2) sabotage their career by getting demoted to where they think they belong or 3) limit their potential and stay stuck in a job that makes few demands.

If you opt to coach an employee who you believe struggles with “never feeling good enough”:

  • Consider what it is about this person that makes you think this is an issue. Identify actual events and actions that you’ve observed. Look for patterns over time, not a single incident. Be specific.
  • Talk to the person about what you’ve noticed. Share several examples that illustrate the behavior and show it as a pattern. Communicate your concerns about how this may impact the person’s career. Stay focused on the behaviors. For example, “I’ve noticed you don’t speak up at meetings,” or “You avoid calling on larger accounts even though you’ve got the technical skills,” rather than focusing on opinions, like “You seem to lack confidence.” Be curious and ask the person what they think is behind their behavior. It’s essential to understand whether the person sees the problem or it’s a blind spot for them. Once you’ve talked about the issue, ask the person what they may want to do and what support they may need.
  • If a direct conversation doesn’t feel right, gradually increase the frequency of positive comments about their work and contribution. People who lack self-esteem have trouble receiving positive feedback. The more specific you are, the less likely they are to dismiss it. When you’re evaluating performance, be honest. If you only give positive feedback, people will begin to question how genuine it is.
  • Concentrate on one or two of the behaviors that are undermining the person’s performance. With Michael, the sales professional who was losing accounts due to his poor follow-through, helping him see why he procrastinates would be a good start. His problem isn’t time management; it’s fear of failure. He’d rather be chastised for sloppy last-minute proposals than be seen as a failure as a producer.
  • Gradually expand the comfort zone. For example, with someone like Sarah, the failing department manager, let her test her wings and build her leaderships skills by managing several projects before promoting her to department manager.

“Never feeling good enough” is one of the toughest behavior patterns to break. It’s rooted in attitudes about the self, which are established early in life.

It is seldom changed for good. It may lie quietly in the background for months, but then a stressful situation like a promotion, losing a major deal or divorce triggers the self-doubts again.

With patience and commitment, you can help valued employees reach more of their potential.

The author

Kimberly Paterson, Certified Executive Coach and Master Energy Leadership Coach, is President of CIM (, CIM works with organizations and individuals to maximize performance through positive lasting behavioral change. Her clients are property & casualty insurance companies, agencies, and brokers. She can be reached at Follow Kimberly on and

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