Seven Deadly Leadership Sins that Derail Your Career

In my executive coaching practice, I often work with gifted, capable leaders who repeatedly get passed over for promotion. They move up the ranks from individual contributor to frontline manager and (maybe) a manager of managers.

But then they get stuck.

An open door to a more senior position remains out of reach, and, unfortunately, no one tells them why. Perhaps because the executives making these decisions don’t know why themselves. They just have a sense about it that can’t be put into words.

As I’ve tried to unravel this mystery, I’ve come to see seven reasons for leaders getting stuck. I refer to these—with apologies to Thomas Aquinas—as The Seven Deadly Leadership Sins. They will, most certainly, derail your career.

1. A Compulsive Need to Win

I work almost exclusively in the sales side of businesses. The typical career trajectory for a leader in sales travels from being a salesperson to being a frontline sales manager. In both roles intensity and competitiveness are essential, either as an individual contributor or the leader of a team of individual contributors.

But all that changes when this leader begins to interact cross-functionally with the rest of the organization. Competitiveness that shifts from winning every deal to winning every argument sends a shiver down the spine of colleagues in the company. That shiver says stay away from this person. At. All. Costs.

Any leader—not just a sales leader—who doesn’t tame a compulsive need to win ends up moving laterally throughout the organization, burning bridges and derailing their career. If this is you, refocus your energy on big, company-wide wins, not personal wins. Work patiently to achieve long-term objectives. Think years, not months and quarters.

And, finally, grow up. A mature adult doesn’t need to have the last say in every conversation. Let stuff go. Lots of stuff.

2. Adding Too Much Value

Adding too much value is a term coined by Marshall Goldsmith in his book What Got You Here Won’t Get You There (the ultimate book on career derailment). It’s the tendency of leaders to have something to say about everything, to be an endless fountain of ideas and insight.

That’s what leaders do, right? Provide ideas and insight. An endless fountain of ideas and insight, however, sucks the oxygen out of the room, even when that input is supremely positive.

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Consider this statistic. We know that the appropriate ratio of positive comments to negative comments in healthy human relationships is 5 to 1. But the same research study discovered that when positive comments reach a ratio of 8, 9, or 10 to 1, people don’t believe them. They feel like they’re being lied to and tune everything out.

Too much of any good thing is a bad thing. It makes a leader look needy. Effective executives show restrain with their words, seasoning conversations like salt.

3. Inability to Inspire Internal Commitment

For too many managers, leadership is a transaction. I do something for you. You do something for me. That’s all well and good if human beings were robots. But we’re not robots. We’re emotional creatures who need to be motivated, inspired, and energized to do the things we do.

Transformational leaders take a different approach to people. They listen and learn from them. They encourage and support them. They even love and care for them, receiving love and loyalty in return.

Mere transactions get you only so far as a leader. Transformational leadership, however, taps the reservoir of purpose and passion that lies deep within a person’s soul. The commitment that comes from this emotional connection sparks a flame that becomes a raging fire of world-class results.

In short, deeply connect with the people you lead, and you’ll unleash a passion that produces great performance. Transformation!

4. Failure to Develop One’s Own Voice

Two of the best-selling authors of the last century (and perhaps of all time) are Dr. Seuss and Stephen King. Their voices are very different, one whimsical and the other super creepy, but neither author woke up one day writing the way they did. Their voice was cultivated over time until it became the full expression of who they were.

The same is true for leadership.

Knowing who you are at the core of your being, how you solve problems, and how you relate to people defines your leadership voice. It allows you to stand out from the crowd and be heard. A failure to develop your voice leaves you like the thousands of authors who publish books every year that never get read. What a waste!

Too many leaders naively think that if they put their head down and do good work, people will notice them and promote them.  I’m sorry to inform you, all that does is make you disappear. Just the opposite occurs, however, when you know your leadership voice. It empowers you to speak with authenticity and authority. It deepens the followership of your people and positions you for the right kind of promotion.

5. Inability to Hold Others Accountable for Results

Nice but never hits the number.

I can’t tell you how many times I’ve heard this statement about leaders who are beloved by others but always behind in performance. Inevitably, I discover that beneath this pleasing exterior is an addiction to pleasing people. When this addiction exists, it’s next to impossible to hold others accountable for results.

The answer to this problem, of course, is not to become a jerk, but to learn how to lean in and have difficult conversations without anxiety.

The way I frame this to people pleasing leaders (which I can also be myself) is that it’s loving to be clear. It’s kind to speak with candor. Why? Because it helps people become the best versions of themselves. If done in a respectful manner, what could be more loving and kind?

This approach is what Jim Collins refers to as The Genius of AND. The Genius of AND cares about relationships and the issues at hand. Both at the same time. It creates safety for people to share their heart and speaks with soundness and clarity. It embraces humanity and honesty, love and truth. It’s nice and hits the number.

6. Repeated Emotional Reactivity

The sixth deadly leadership sin is repeated emotional reactivity to people and circumstances. Not the occasional moment of frustration we all experience, but regular volatility.

Emotional reactivity comes in two varieties: implosion and explosion. Implosion occurs when we stew in our own juices, emotionally reacting internally with bitterness, malice, and resentment. As Nelson Mandela once said, this is like taking poison and expecting it to kill our enemies. It only kills ourselves.

Explosion is a killer as well. This occurs when we emotionally react externally with outbursts of anger and accusation. Leaders who act this way get what they ask for—forced compliance—but not what they want—respect and followership.

Leaders who respond repeatedly in either of these ways (or a combination of both), inject anxiety into the blood stream of the organizational system, making it less responsive and less resilient. Fear paralyzes. It does not empower.

Leaders who allow their emotions to own them and not the other way around derail their career. Except when…

7. Toleration of Talented but Toxic Team Members

Except when the leader above them tolerates their toxicity.

This is the final of the seven deadly sins. It’s not being emotionally reactive yourself but allowing others on your team to be emotionally reactive and looking the other way.

I see this so much in my work: an effective leader who tolerates a toxic team member. Maybe that person is a friend, or maybe they possess a skill set that’s hard to replace. Either way, the rest of the organization comes to believe that this person’s behavior is perfectly fine and acts that way themselves (or leaves the organization).

Tolerating toxic team members sends a message that you value talent over anything else. And that’s a very dangerous message to send because it destroys the most valuable asset of your organization: culture.

Confront toxic people without fail. But do it in private. No one likes to be humiliated in public, no matter how toxic they are. Give them one opportunity to change. Then another. Then be done. Everyone in the organization will thank you for your courage and the culture will thrive.

Winston Churchill once said that Russia was a riddle wrapped in a mystery inside an enigma. The same could be said for leaders who keep on getting passed over for promotion.

I hope I’ve unraveled some of this mystery for you. Identify which of these seven are holding you back and invest in yourself by working with an executive coach to help put them behind you forever.

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