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The Good and Bad of Leadership Challenges

“One can choose to go back toward safety or forward toward growth. Growth must be chosen again and again; fear must be overcome again and again.” – Abraham Maslow

All leaders, regardless of the industry and company they are in, face challenges. These challenges are written into the ‘code’ of leadership positions. They are part of the business environment in which you operate. And they are part of the human condition in which you exist and live. While there are plenty of external forces that can throw obstacles in your path, some of the greatest challenges you will face are your own internal struggles. All leaders have weaknesses and make mistakes. We grapple with questions of conscience. Did we do the right thing? Have we acted with integrity and consistency? Does our leadership bring out the best in others or diminish them?

Yet, it’s often difficult for those in a leadership position to admit that they might have personality traits, mindsets, or behaviors that interfere with their ability to reach their goals. And that’s if they are even aware of those aspects of themselves that might be holding them back.

Part of good leadership is learning to accept the reality of the things we can see in ourselves that could be holding us back, and working to change them. The willingness to be vulnerable and ask “how can I be a better leader?” is a good first step on the road to becoming one, and this is where a leadership coach comes in.

What Holds Good Leaders Back?


Even the best leaders suffer from a lack of confidence from time to time. It’s surprising how many very capable executives we work with confess that they suffer from imposter syndrome – that feeling that one is not worthy of the position they hold, a fraud. This insecurity and lack of confidence that can make you over index on your behavior – for example, being too aggressive in some settings, and too passive in others. Creeping doubt has an insidious way of keeping you from being proactive (“I’m afraid to make a mistake or fail”), from driving your vision (“Is this even the right direction?”) and from feeling like a leader (“Who will follow me anyway?”). Your insecurity can be slowly crippling to your daily performance, like a thousand paper cuts, or cause you to make one bad business decisions that could make your initiative or plan crumble like a house of cards.

Being Overly Defensive

While feeling defensive is a natural response to being criticized, letting it influence your leadership through your words, thoughts and actions is a tell-tale sign of leadership maturity, or rather, its absence. Defensiveness is like wearing a pair of noise cancelling headphones while locking yourself into a room. It places a barrier between you and your team members, and inhibits your ability to hear feedback – a rare commodity which you receive less and less of as you move higher up in your organization. It is this increasingly rare feedback that is most valuable to you as a senior leader. An emotionally intelligent leader knows she needs to be even more intentional about encouraging others to share their perspectives, even if those perspectives are critical of the leader herself, listen carefully to what feedback she is hearing and show she’s open to receiving it.

Lack of Decisiveness

Decisions big and small require decisiveness, often with very little time to consider them. Two types of problems exist to which leaders must respond and make decisions on – complicated and complex. Theodore Kinni, in his MIT Sloan Management Review piece, The Critical Difference Between Complex and Complicated, describes complicated problems as “hard to solve, but addressable with rules and recipes, like the algorithms that place ads on a Twitter feed.” Complex problems, according to Kinni, “involve too many unknowns and too many interrelated factors to reduce to rules and processes.” Technological disruption or innovative business models can both create complexity that makes decision-making more difficult.

Not all decisions will be complicated or complex. But whether decisions are easy or hard, in every case, at some point, you just have to make the decision and live with it. It’s important to learn to make a decision when necessary and understand that living with the consequences is part of being a leader.

Inability to Address Conflict

Most people prefer to avoid conflict. Office life includes having to deal with personality differences, bringing up and discussing difficult topics, and navigating through strongly held points of view, often in opposition to each other. Unfortunately, great leaders cannot lead effectively without addressing conflict as it arises within the workplace. They push off addressing conflict at their own peril, increasing the risk of damaged relationships, missed deadlines and eroded trust.

Some of the reasons managers shy away from addressing conflict stems from wanting to be liked, being afraid of hurting others and finding it difficult to say anything negative. The side-effects of conflict avoidance are often high turnover, a dysfunctional working environment, strained communication, a loss of productivity and impaired teamwork.

Fear of Showing Vulnerability

Strong leadership requires vulnerability. Why? Because fundamentally, a team can’t function without trust, and vulnerability is a core human expression that can foster trust in others. People who are comfortable showing more of their authentic selves at work inevitably start to build more trusting, mutually supportive relationships with their colleagues.

It’s important to understand that vulnerability does not mean being weak. A vulnerable leader is comfortable with not having all the answers, engages perspectives and thoughts of their people and doesn’t have to be the first with an idea or the first one to answer. Vulnerability which leads to greater trust fuels the strongest relationships and can transform performance to help bring more success to an organization.

Everyday opportunities for vulnerability can be simple, yet powerful – asking someone for help, taking responsibility for something that went wrong at work or reaching out to someone who has just had a loss in their family.

Having to Know and Do It All

Talent recruiters talk about the ‘purple squirrel,’ that candidate who brings all the desired experiences, skills, and personal characteristics that perfectly match the job description…and simply doesn’t exist. Just like purple squirrels, there is no ‘every leader.’ You can’t know or do it all, and admitting you need help doesn’t make you a bad leader. It shows you’re human and have weaknesses that go along with all your strengths.

When you don’t know the answer to something ask someone who might. When you’re not sure how to do something, seek advice and have somebody show you. When you need help, ask for it. There’s strength in being vulnerable and using all of the resources at your disposal in order to make the right decisions.

At Copperbox, we have the tools to help you look inward to discover: What are your values? Your strengths and areas for development? What’s working well for you? What are your challenges? How do you react in specific situations? What could you do better?

Having the courage to look within and do the hard work of self-reflection is the ultimate opportunity to be a great leader. We can help.

Wayland K. Lum is the Founder and Managing Director of Copperbox. You can learn about Wayland’s work with leaders at, and connect with him at

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