Prevent Your Achilles’ Heel From Becoming Achilles’ Hell

Achilles Heel

Your Achilles’ Heel can guide you on a path to Achilles’ Hell. Or, you can master it and become a better leader, partner, parent, and friend. Let me explain how this works.

If you’re human, you have flaws. And there is probably one big one that can screw up your career or, at the very least, limit your potential for great leadership and/or big promotions. We call this the Achilles’ Heel in homage to a mythical Greek warrior who was invulnerable in battle except for his foot. I describe the Achilles’ Heel as a set of habits wired into your brain and body that limits your repertoire of leadership behaviors. In other words, it constrains your degrees of freedom.

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Fortunately, the latest neuroscience teaches us that these habits can be rewired even well into adulthood. The leaders I work with accomplish this through deliberate practice and rigorous self-observation. This takes courage and focus, but the result is greater energy to respond to complex decisions and challenges.

How would you describe your Achilles’ Heel?

Here’s my hunch: you have a very good idea of the behaviors that get you into trouble. One or two dozen performance reviews have taught you that. But do you know what is behind these behaviors? Wouldn’t it be nice to have a better understanding of the thought patterns and habitual emotional reactions that produce these behaviors so you can nip those habits in the bud?

No, not really, Amiel. That sounds unpleasant. Pass the beer nuts.

Let’s assume you’re willing to muster the courage to delve into these inner experiences. Let’s say you are up for honing in on what makes you tick—and that you might actually appreciate what you get out of this. How might you learn about your Achilles Heel, and what would you do with the new understanding?

A Brief History of the Achilles’ Heel

Before we go there, I’d like to provide a very brief history of the Achilles’ Heel concept in leadership. In the late 70s and early 80s, researchers at the Center for Creative Leadership (CCL) identified a set of leadership derailers. If you’re a train speeding down a track (rather than a Greek warrior entering battle), these are the factors that can throw you off track. It was wonderful research, and it had several significant upshots for organizations.

  • Take the time to identify leaders’ derailers. Then do something about them. At that point in time, leadership derailers generally weren’t on organizations’ radar. First, because the concept hadn’t been invented and, second, because in the United States companies had experienced a remarkable period of growth without significant global competition since World War II. I don’t think it’s a coincidence that the CCL study happened shortly after the United States stopped being the only economic game in town
  • Go beyond the simple reward strategy of promoting managers up the chain. To teach managers the lessons they needed to lead on a larger level, CCL suggested employing lateral moves. For example, if you have an operations manager with solid results and great potential who is lousy at listening to others, put them in a customer service management role where the job itself forces them to practice listening.

As robust and practical as the CCL’s research was, it had far less impact on managerial practice than the researchers had hoped. The happened for two reasons:

The rise of competencies

The notion that leaders have a single big potential derailer was trounced in the marketplace by the concept of competencies. When your organization asks you to do a 360, the result is a report that lists anywhere from 15 to 100 different competencies. A bunch are strengths. A bunch are weaknesses (or “development areas” or “opportunity areas”). This is all fine and good, but the sheer number of items detracts from the focus on a single Achilles’ Heel. When I work with leaders who have received a 360, my first task is to help them find the signal in the midst of all this noise.

The strengths-based approach

The other competition to the notion of Achilles’ Heel is the growth of the strengths-based school of leadership development. If you’ve taken the StrengthsFinder instrument, you’ve been part of this school. Personally, I can’t imagine coaching leaders without an understanding of their strengths. And I would agree that leveraging your strengths is a wonderful way to develop. Where the strengths-based school goes overboard, in my opinion, is in its insistence that people always develop best in their area of greatest strength. This may be true for many first-line employees, but it is not for managers. Here’s why: the complexity and pressure of their roles—coupled with their wide span of people they affect—is incompatible with an unattended Achilles’ Heel. High performers get hurt and leave. Or stick around but lose passion for work. Low performers retaliate or find new justification for working below standards. And the leaders’ own career can suffer.  So my take—grounded in research and my own experience—is that leaders develop best in both their area of greatest strength and their Achilles’ Heel. (Quick aside: for strengths, my favorite instruments are StrengthsFinder 2.0, created by the Gallup Organization, and the VIA Survey of Character Strengths. The latter is available for free by registering on the University of Pennsylvania’s Authentic Happiness web site. There are also many excellent books on this topic like Now, Discover Your Strengths, Strengths-Based Leadership, and Go Put Your Strengths to Work.)

Identify Your Achilles’ Heel

The Enneagram

As for identifying your Achilles’ Heel, there are a number of instruments and tools you can use. My favorite is one with an unusual name: the Enneagram. It’s a model of nine personality types. Each type describes a deep and fundamental pattern of making sense of experience that drives what you pay attention to and what you ignore. Remember the listening filters from the last chapter? Each listening filter is an expression of a particular personality type. As we’ve seen, if you’re not attentive to it, it can get you into all sorts of trouble. That’s one reason I joke that the Enneagram describes nine potential paths to Achilles’ Hell. Fortunately, the Enneagram also shows the nine roads to great leadership precisely by helping you get free from the constraints of your Achilles’ Heel. Rather than putting you in a box, it shows you the box you put yourself in every day—and how to escape it.

The nine Enneagram types are known as The Perfectionist, The Helper, The Achiever, The Individualist, The Investigator, The Loyal Skeptic, The Enthusiast, The Challenger, and the Peacemaker. My favorite books about this topic, Personality Types and The Wisdom of the Enneagram, both by Don Riso and Russ Hudson, describe how each type has Unhealthy, Average, and Healthy manifestations. In other words, just identifying your type doesn’t tell you immediately “how you are.” You also need to assess your relative level of health within that type.

Most leaders, most organizations, and most families operate at an Average level of health. This means there is a lot of room for growth. To give you a taste of how this works, here are quick-and-dirty summaries of three different Enneagram types that I’ve lifted from Personality Types.

  • Type One: The Reformer. The key motivation is to be right, have integrity, and be consistent with their ideals. At the highest level of Health they “become extraordinarily wise and discerning…Humane, inspiring, and hopeful. [At an Average level,] dissatisfied with reality, they become high-minded idealists, feeling that it is up to them to improve everything…They point out how things ‘ought’ to be…Become orderly and well-organized but impersonal, rigid, emotionally constricted…highly critical both of self and others… [At an Unhealthy level they] make very severe judgments of others, while rationalizing their own actions… [They are] condemnatory, punitive and cruel in order to rid themselves of whatever they believe is disturbing them.”
  • Type Six: The Loyal Skeptic. The key motivation is to have safety and security. At the highest level of Health they “become self-affirming, trusting of self and others [which] leads to true courage, positive thinking, leadership, and rich self-expression… [At an Average level they] start investing their time and energy into whatever they believe will be safe and stable…Constantly vigilant, anticipating problems… [They have s]trong self-doubt as well as suspicion about others’ motives… [At an Unhealthy level they] become clingingly dependent and self-disparaging with acute inferiority feelings…Feeling persecuted, that others are ‘out to get them,’ they lash out and act irrationally, bringing about what they fear.”
  • Type Nine: The Peacemaker. The key motivation is to have serenity and peace of mind. At a Healthy level they are “optimistic, reassuring, supportive: have a healing and calming influence—harmonizing groups, bringing people together. A good mediator, synthesizer, and communicator… [At an Average level they] become self-effacing and agreeable, accommodating themselves, idealizing others and ‘going along’ with things to avoid conflict…Become passive, disengaged, unreflective, and inattentive… [They p]ractice wishful thinking and wait for magical solutions… [At an Unhealthy level they] do not want to deal with problems: become depressed and listless, dissociating self from all conflicts. Neglectful and dangerously irresponsible.”

I trust you won’t try to identify your type from these brief descriptions. That requires more thorough exploration. Instead, I invite you to notice the wide variation in motivation between just these three types. They are very different!

That’s the great thing about pinpointing what makes you tick: it suggests very specific practices for becoming a healthier version of your personality type and therefore increasing your odds of practicing great leadership.


Another useful tool for working with your Achilles’ Hell is the Hogan Development Inventory (Hogan) which identifies “the dark side of personality—qualities that emerge in times of increased strain and can disrupt relationships, damage reputations, and derail peoples’ chances of success.” Hogan measures personality along 11 scales like Excitable, Skeptical, Leisurely, and Colorful. I don’t use Hogan because it gives leaders an enormous—and, in my opinion, overwhelming—amount of data. It’s also expensive for clients. However, many trusted colleagues of mine use it regularly. What I appreciate about Hogan is that it consciously builds upon the Center for Creative Leadership’s pioneering research on derailment by making the derailers identifiable.

Heal Your Achilles’ Heel

What do you do after you’ve honed in on your Achilles Heel? Both the Enneagram and Hogan provide a wealth of answers. Here are my suggestions:

  1. Learn your unique path to Achilles’ Hell. As you consider each outer practice of great leadership, ask yourself, “How might my Achilles’ Heel get in the way of successfully taking on this practice?” For example, as someone who identifies with Type Six (The Loyal Skeptic) on the Enneagram, I find that my pattern of seeing what could go wrong puts me at risk of the following: putting a damper on conversations for possibility by pointing out risks, turning against others when I fear I cannot trust them, getting stuck in complaints, taking my assessments to be the truth, assuming some relationships will never improve, only telling stories that confirm a pessimistic view of the future, getting distracted from listening by worst-case scenario thoughts, and asking mediocre questions because I’m afraid the great ones will blow people away
  2. Observe. Observe your Achilles’ heel in action. What triggers it? How does it operate? To make this practical, pick one meeting or event each day to observe yourself. Mark it on your calendar. When you step into the room or pick up the phone or look at the monitor, start paying attention to yourself. When are you heading in the direction of Achilles’ Hell. What are you doing or saying at this moment? After the meeting or event is over—or at the end of the day—jot down your observations in a journal. At the end of the week, look back at your journal entries. How many different paths to Achilles Hell have you taken? By getting to know these paths inside and out, you can recognize them next week and self-correct.
  3. Practice. Take on new inner practices that elevate you to the healthier levels of your personality type (in the case of the Enneagram). For me, a Type Six, this includes what Martin Seligman calls universalizing the positive and particularizing the negative. When something positive happens, like 4,000 people listen to one of my podcast episodes, I have two options. Option A is to particularize the positive by telling myself, “I got lucky” or “That was an easy audience.” Option B is to universalize the positive by thinking to myself, “I’m a good interviewer.”  Universalizing the positive reinforces my sense of competence and confidence and therefore erodes negative thinking. A similar principle applies when something negative happens. Let’s say I trip on a flight of stairs, something I used to do a lot in high school and recently did at home (I’m fine). Option A is to universalize the negative by calling myself “clumsy.” Option B is to particularize the negative by thinking, “oops, slipped, no biggie.” Particularizing the negative reinforces my resilience and builds a sense of myself as a capable person.

As my podcast guest Sean LeClaire says, “You are not the water you swim in, only the water you drink.”

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