The Lousy Leader’s Roadmap: Overcoming Obstacles to Complete Leadership

Picture yourself running a small start up with a few employees in the mid-2010s. Tired of your garage-based office, you seek a more professional space. However, traditional offices are expensive and unappealing. Enter co-working: a solution with private desks, shared areas, modern design, and a vibrant atmosphere. You just stepped into a WeWork office, seeming almost too good to be true—sadly, it was. Adam Neumann, WeWork's founder, propelled the company to a $47 billion valuation in 2019, only to witness a failed IPO, lasting reputation damage, and his own removal as CEO. But how did this happen?

Neumann was a lousy leader. He flashed wonder-boy brilliance at times, but his notorious resume flaunted extravagance, tequila-laden meetings, and the pursuit of immortality. Predictably, things soured. He personally profited around $500 million from WeWork—yet, he lost more than he gained.

We can relate to this in some measure—maybe not the aspiration of becoming deified, but recognizing our leadership shortcomings. That moment when we ponder, "I might not be the leader others think I am," or worse, "I might not be the leader I believe I am."

Complete leaders produce healthy organizations, and they embody these transformational qualities:

  • Compelling Vision: A dream with an invitation

  • Executive Presence: Behaviors that inspire trust

  • Time-Tested Character: Unimpeachable credibility

But what if you lack one? This is where lousy leadership sets in. Today, we explore three leadership profiles, revealing what happens when one element is absent.

The Wandering Companion

If you are lacking only for compelling vision, you are the wandering companion (you possess only executive presence and time-tested character). On the bright side, you are very well liked by people. You do very well in the spotlight, and people like to listen to you. You treat them well, are fair, listen to their problems, and create a great place to work.

You have simply become one of the people—you’re a peer to them, not their leader.

Over time, people lose respect for you, and you can’t tell why. You sit around the campfire with the people, when you should be off in the distance thinking about where you’re going tomorrow. Once tomorrow comes, you are asking everyone else where to go. Your primary method for decision making is “consensus.” This works great when everyone agrees, but is detrimental when there is dissent. In effect, you find yourself going in circles, wandering around, but not making progress. Most of the time, you don’t know what to do next.

Here’s the solution to the wandering companion quandary: thoughtful observation. You need to learn how to discover and communicate a compelling vision. Get yourself around other leaders who are strong in compelling vision, and ask them how they do what they do. Shadow them at a meeting. Watch how they lead and interact with their team. Emulate them in your leadership setting.

The Graceless Pioneer

If you are lacking only for executive presence, you are the graceless pioneer (you possess only executive presence and time-tested character). The positives are that you have direction, and you get there fast. You have a heart of gold—good intentions and no private agenda. But that is where things start to break down.

You unknowingly leave leave people behind—you have no tact.

Your passion gets people in the door, but your clumsiness makes them leave. When you speak, people’s bodies grow tight and tense—they don’t know what to expect. You are often confused at people’s response to you—”Why can’t they just see what I see, and follow where I’m going?” When you leave the room, people have to debrief to figure out exactly what just happened. It’s not what you do, or why you do it, but HOW you do it that gets you into trouble.

Here’s the solution to the problem of the graceless pioneer: honest feedback. You can’t merely read about executive presence. You have to see it. Find someone in your life who has articulate communication, high self-awareness, selfless listening, charitability, consistency, or contextualized appearance. Treat this person to lunch, and ask them to teach you about the one of these areas in which you struggle the most. If you're feeling especially bold, issue an anonymous survey to your team, and ask them to FORCE RANK these six factors of executive presence top to bottom—they will probably be right about the area where you struggle the most.

The Counterfeit Charmer

If you are lacking only for time-tested character, you are what I call the counterfeit charmer (you possess only compelling vision and executive presence). Fortunately, people are quick to get on the train with you. When you speak, people listen, and they buy in--big. People may even boast about following you, and your leadership can become almost cult-like—to be inside the circle is something special. You are smooth, well spoken, and invited to share your insights among increasingly prestigious audiences. Things could never go wrong for someone like you—until they do.

Your notoriety has grown faster than your character, and nobody suspects it—especially not you.

Sadly, you are headed for a scandal. There is a trap in your future, and it may cause you to lose everything. You have a big vision, and know how to captivate a group, but given the chance, you will cut corners. Occasionally you get caught, and you are great at talking your way out of it. But eventually, you will fall down a pit so deep, that even you can’t get out. If unchecked, your demise will be fast and painful, undoing decades of work seemingly overnight.

To get out of this pit, you need authentic accountability. Build a small, trustworthy, personal board of directors outside the organization. Invite these people to ask anything, and meet with them regularly—tell them where you struggle most. To go a level deeper, write your own”pre-mortem.” This is a worst-case fictitious story about your future demise—how do you fail? Come face to face with the possibility, and then re-write the story, inserting safeguards around that vice to make sure you never take the first step down that perilous pathway. Have your trusted friends ask you not just about your vice, but the safeguards you are putting in place. Very few men or women with small character, and unchecked ambitions, will survive in the long run

Conclusion

If you are deficient in compelling vision, executive presence, or time-tested character, you are not yet a complete leader. There are two pathways for you: Growing into a complete leader, or not. The difference is humility and persistence. Acknowledge you are not there yet, and pursue complete leadership through thoughtful observation, honest feedback, and authentic accountability.

Truth is, we are all lousy leaders. Yet, aspiring complete leaders can embody these qualities when it matters most. Nobody wants to end up as a failed leader. To prevent that, we must not only look behind, but also ahead. Come face to face with your lousy leadership, and commit your deficiencies to growth before they commit you to failure.

The world craves complete leaders. Let’s embark on that journey today.

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The Healthy Organization: Developing a Core Focus

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Beyond Titles: What Makes a “Complete Leader”