17 What Are Leadership Obstacles?

Georgia had no idea that the obstacles she would face in leadership would be so many and appear so often. Yet from nearly day one of her leadership, Georgia had been dealing with obstacle after obstacle. As soon as Georgia navigated one obstacle, another one popped up, as if lying in wait for her. As her problems mounted, Georgia began to wonder whether she was cut out for leadership at all. No one of her obstacles was entirely disabling. But cumulatively, she could tell that they were wearing her down. Georgia wondered whether other leaders faced similar problems. She assumed that they did because the problems didn’t seem that peculiar. Yet Georgia also wondered whether other leaders had a different insight that didn’t perceive obstacles as problems.

Obstacles

As a leader, it’s good to know your obstacles, the many things that can block your path to leadership success. Leadership isn’t a cakewalk. Leadership brings challenges. No matter how adept you are as a leader, you will find your leadership challenged, likely by both internal and external sources and issues, inside and outside of your team or organization. Indeed, you’ll likely find that leadership not only challenges your knowledge, skills, experience, and discernment but also your mental and emotional health, and your professional and personal relationships. The measure of your leadership may thus not be in your leadership skills and attributes but instead in how you respond to the obstacles your leadership faces. Will you succumb, or will you overcome? That is the question that leadership frequently asks. And the better you know your obstacles, the more likely you may find yourself overcoming them rather than succumbing to them. 

Attraction

A leader must be careful not to attract obstacles. Leadership can involve so many variables that whatever fear or weakness the leader has will soon enough find the leader through one or more of those many variables. If, for instance, you fear division among your workforce or membership, you’ll soon find the cracks. If, for another example, you fear financial weakness, that, too, will eventually appear. If, for yet another example, you fear insubordination and a direct challenge to your leadership, then that, too, will eventually rear its ugly head. Problems probe a leader, looking for weakness. And when problems find weakness, they rush headlong in. Beware projecting your fears onto your leadership team and into your organization. Circumstances will likely respond in kind, bringing your deepest concerns right back to you like a boomerang. When you encounter obstacles, look deep inside you for the fear that brought them on. And embrace and incorporate the positive opportunity that lies within every fear. Integrate your weakness into another healthy facet of a strong, whole, and authentic leader. 

Change

In leadership, change is the only constant. Yet change is also a constant obstacle to leadership success. For complex organizations, or even for relatively straightforward and simple ones, change is a given. Nothing stays the same, not missions, markets, customers, clients, patrons, personnel, technology, suppliers, facilities, finances, or the regulatory or political environment. Even social relations, worldviews, communication norms, and the culture change. Iconic brands become relics and iconic logos become embarrassments, as fashions, tastes, preferences, ideologies, and sensitivities change. With change as their primary and constant obstacle, leaders must find within themselves the commitments and character that can provide organizational stability. Leadership itself becomes the constant and stable thing. The natural or supernatural necessity of hierarchy, with meaning and purpose themselves descending from above, becomes the organizing constant. The leader who embodies leadership’s natural, philosophical, psychological, and spiritual attributes is the stable, unchangeable thing. Make yourself a rock of a leader in the midst of constant change. 

Recession

Economic recession is one of those external threats that can seriously challenge a leader in maintaining the organization’s health and welfare. No matter what sector in which you lead, economic recession can bring swift change and challenges to your leadership. If your organization depends on sales, a sharp downturn can crater sales revenue, requiring a swift financial response, typically involving layoffs or reductions in compensation and benefits that seriously harm morale. The same can be true if your organization is in the nonprofit sector and depends on public contributions or if you lead a government agency dependent on fees and tax revenue. Prepare for economic downturns if you can, by controlling expenditures and building a rainy-day fund. Beware adding full-time employees in the good times, when you know that you’ll need to lay them off in a downturn. Try, as your organization’s leader, to smooth the ups and downs. Keeping the ship level across the swells and troughs is a big part of a captain’s job. Beware economic recession. And when you encounter one, use its opportunities to trim inefficient programs, while retaining and rewarding key members of your organization.

Compliance

Organizations exist within a web of law, rules, and regulations designed to restrict the organization’s activities to preferred bounds. The organization that violates law, rule, or regulation risks criminal responsibility, regulatory penalties, civil liability, and reputational harm. All it takes is one significant violation among a thicket of confusing and at times even contradictory restrictions, to so badly harm an organization as to potentially shut it down. Federal, state, and local regulatory agencies, with their examiners and inspectors, can investigate and sanction your organization’s employment practices, compensation measures, employee benefits, workplace safety, fundraising efforts, advertising content, sales practices, goods designs, service practices, facility maintenance, and other systems, practices, and functions. A regulatory notice and action may require you to alter, suspend, or sunset programs and operations, refund sales or fees, repair facilities, purchase new equipment, monitor and report conditions, and pay fines, among other measures. Regulatory compliance can be an ongoing and substantial obstacle to your effective and successful leadership. Maintain an astute compliance function, using knowledgeable and skilled consultants and personnel. Your leadership may depend on it.

Division

Another obstacle that leaders can face involves division in their leadership team, workforce, or membership. Divisions can arise over the choice or design of programs, the undertaking of new initiatives, the conduct of operations, or the allocation of budgets. Divisions can also arise over organizational commitments and how the organization expresses them. Divisions can also arise between departments, units, and branches or locations. A divided organization becomes difficult to lead. Major and minor decisions start to cut both ways, with one side favoring and the other side disfavoring the decision, as for or against their separate interests. The unit or faction becomes more important than the whole of the organization. The leader cannot turn this way or that way without one side or the other perceiving a sleight. Everyone starts to walk on eggshells, and the organization’s productivity and innovation slow as engagement falls sharply off. Division within the organization can be among the most difficult of obstacles to face and overcome, requiring constant reminder to focus the whole organization on its uniting mission. 

Conflict

Conflict within the organization can be a related obstacle. The conflict may not necessarily be between two ideologically divided and warring sides, as the prior paragraph suggested. The conflict may instead be over a one-time incident involving just two individuals or a handful of individuals within the organization. The conflict may, for instance, be over a promotion that one candidate received while the leader passed over another candidate, or over the assigned use of a room, piece of equipment, or other resource. The conflict may, for other examples, be over a rude remark or other insult between colleagues or a romantic workplace relationship gone sour. Or it may be over perceived inequitable treatment in assignments and rewards. Once conflict emerges, it can be hard to address and tamp down. An organization’s members can hold long grudges that throw mud in the gears of productivity, engagement, creativity, and morale. Leaders do well to identify and address conflicts quickly and equitably so that they do not congeal into bitterness and resentment, poisoning the workplace culture.

Insubordination

Insubordination toward the leader, managers, and supervisors can also become a leadership obstacle. A leader faces one set of problems when an organization’s workforce or membership divides or conflict arises between two individuals within the organization. In those cases, the relational problems are horizontal, between individuals or groups at the same level of hierarchy and authority within the organization. In those cases, fair and equitable treatment of colleagues is the solution and rule. A leader, though, faces a different challenge when a lieutenant or other individual within the organization defies the leader. In that case, the relational problem is vertical rather than horizontal. And in that case, the solution has more to do with the need for leadership to communicate the rationale justifying the disobeyed directive to the subordinate and to hold the subordinate accountable. Don’t ignore insubordination, unless it involves an immaterial detail. Insubordination can spread quickly. Insubordination from one individual can quickly become disrespect for directives among other individuals. Confront insubordination head on. Inquire of the subordinate the grounds for the insubordination, to ensure that you address any just grounds. Explain the rationale, and then hold the subordinate accountable.

Vitality

A leader’s vitality for the difficult role can also become an obstacle. The constant stress and demands of leadership can wear on an individual. An embattled leader’s mental and emotional health may soon decline, characterized by anxiety, depression, poor concentration, moodiness, withdrawal, and isolation. Physical health issues may later follow, caused or accompanied by sleeplessness, stomach upset, hypertension, and weight gain or loss. A leader who has lost natural energy and vitality faces an especially difficult challenge in maintaining leadership performance. Leadership is hard enough when the leader is healthy. Leadership can become intolerable when the leader is unhealthy, whether due to the role itself or to other causes. If you find yourself losing vitality for your leadership role, make adjustments swiftly. Address your work-life balance and your personal health including diet, exercise, rest, relaxation, and medical checkups and care. Ensure that you are delegating enough responsibility to capable individuals, to appropriately lighten your leadership role. Rely on mentors, and get psychological and spiritual help as necessary.

Humility

A leader’s pride, arrogance, self-aggrandizement, and hubris can also become obstacles to sound leadership. Leadership brings status and honor. Leaders also get strokes. Subordinates may flatter leaders unduly in pursuit of their own interests. Leaders can easily fall prey to over-confidence, to believing too much of themselves. Sound leaders remain humble, recognizing that their success depends heavily on others and on circumstances aligning. Sound leadership is servant leadership, supporting and encouraging others, providing others the resources and guidance to lead the organization forward, and giving others recognition, reward, and credit for organizational successes. Prideful leadership, by contrast, claims credit where credit is due to others, discouraging those others and turning them toward resentment. Arrogant leaders dismay and embarrass their leadership team and their managers and members. Leaders who exhibit hubris overextend the organization, accept more risk than warranted, miss the warning signs of impending disaster, and set the organization up for failure. Beware pride, arrogance, and over-confidence.

Reflection

What are your current obstacles in your leadership? What obstacles do you anticipate may soon appear? What obstacles concern you the most, and why? What obstacles, by contrast, do you feel that you can most easily navigate? Is your leadership team ready to adapt to change? Do you have a strong regulatory team to avoid regulator action? Do you know your regulatory risks? Is your organization showing cracks of impending division? Can you undertake an initiative now to head off a potential division you foresee? Do you have simmering conflicts between individuals or groups within your organization that you need to address before they break out into open disruptions? Do you have hidden or open insubordination going on within your organization, undermining your leadership? If so, what measures can you take to quickly address and resolve it? Is your vitality for your leadership role still strong, or do you need to make adjustments? Are you exhibiting pride or hubris, preparing your leadership for a fall? 

Key Points

• Leaders can face frequent obstacles standing in their leadership way.

• Beware that your fears do not display weakness that attracts obstacles.

• The shifting ground of change can be an obstacle to steady leadership.

• Economic recession can present substantial leadership challenges.

• Regulatory actions can become substantial obstacles to leadership.

• A broad division within the organization can challenge leadership.

• Small conflicts within the organization can poison the well of morale.

• Insubordination is another obstacle that can spread quickly.

• A leader’s vitality for the role can also become an obstacle from stress.

• Pride is a natural obstacle arising out of leadership privileges.

Read Chapter 18.