Top 10 Biggest Challenges to Leadership

By Sherry Cook

Updated Over a Week Ago

Minute Read

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Take a look at the biggest challenges to leadership that any leader faces. They are listed in no particular order since each can be as difficult as the next. Additionally, from discussions with past and present leaders in diverse fields, I have tried to offer a solution for each. But the intent is not to overwhelm you with advice. So I will offer one solution that has worked best for every challenge listed.

“It is better to lead from behind and to put others in front, especially when you celebrate victory when nice things occur. You take the front line when there is danger. Then people will appreciate your leadership”

Nelson Mandela

The President of South Africa was right when he said that the true measure of a leader is in her words and actions during a difficult situation. He said that when things are going well, the leader should take a step back and allow her team members to bask in the limelight.

This is the reason why being a good leader is no easy task. There is a rush of people willing to smile for the cameras during good times. Introduce a full-blown crisis to the mix, and everyone immediately looks towards their leaders to show the way. A leader’s life is rife with leadership challenges of all kinds, and the door of the coveted corner office is where the buck stops.

1. Choosing the Right Battles

Another way to describe this challenge is ‘failure to delegate.’ Today’s leader has been a proven performer in the past and usually continues to be so. That makes many leaders roll up their sleeves and wade right in at the first sign of a crisis.

A certain degree of involvement is essential to keep the troops’ morale high. But good leaders have people who are better than them in doing certain things and know when to step back. They avoid fighting all their battles themselves.

What works best?

Good leaders have the strength to change what they can, the confidence to delegate what someone else can do better, and the wisdom to know the difference.

2. Staying Motivated

Keeping the team motivated is always considered the responsibility of a leader. A team full of star performers usually punches above its weight. But who trims the hair of a barber, or who fixes a problem with the mechanic’s car? They typically have to do it for themselves. All good leaders must also make efforts to stay motivated.

A leader needs to ensure that the job pressures don’t pull him down to hopelessness. It is very well to say that the leader’s drive is enough, but sometimes it does become unbearable.

What works best?

You are taking a step back and doing or thinking of something else. How about reliving some past battles that your teams and you successfully won?

3. Prioritizing

Every leader agrees that adverse situations never come alone. They hunt in packs. There are days when the stream of bad news doesn’t seem to stop, and every crisis seems to scream for attention. This is when a leader tries to clear the water from a boat with too many leaks.

What works best?

As soon as a crisis presents itself, a wise leader would avoid the temptation to begin working on it immediately. More important than jumping into it is a level-headed assessment of how critical the problem is.

Prioritizing Challenges to Leadership

4. Developing Future Leaders

A leader’s job is complete only when she has created a second rung of top-notch leaders who can step up when needed. Unless that happens, the current crop of leaders will never move up the corporate ladder themselves. This sounds logical enough, yet many leaders face challenges in leadership development.

What works best?

An institutionalized formal succession plan doesn’t always happen. The next best way is to take every opportunity to throw a challenge at a promising team member to see how she shapes up. This also gives her a dry run for future battles. This solution needs to become a habit when things are under control. It will not work when the excreta has already hit the ceiling.

5. Leading by Example

Parents are often reminded that their children learn less from what they hear and more from what they see. This holds true for a corporate leader as well. A leader who walks the talk will gain more respect from the team, and the team will also try to emulate their actions.

What works best?

The simplest thing to do is for leaders to ask themselves if they would be willing or able to do what they were asking their team members to do.

6. Encouraging Dissent

It is very easy for a leader to fall into the trap of ‘I know what’s best for us.’ This results in missing out on several good ideas if the leader’s mind is not open to opposing views. This could also mean that possible flaws in the leader’s plan could stay suppressed, leading to undesirable results.

Leaders need to display the courage to welcome views at variance with theirs. An idea that is well thought through by the team has a far better shot at successful implementation.

What works best?

Such a leader must force herself to ask for views from team members. It is just a matter of forming a habit. Once this has happened a few times, the benefits from a healthy discussion will coax the leader to make this her second nature instead of forcing herself to accept dissenting opinions.

7. Showing Tough Love

Most leaders veer towards either one of two extremes. The first type is the goodfella, whose door is open for all and who is not given to bursts of anger if things are not done right. The other is the manager everyone loves to hate, a merciless slave driver with little human kindness.

Leadership challenges are tough for both these extremes. The nice guy is likely to be taken advantage of, or worse, not taken seriously enough. Not fair, but that’s the way it usually is. The evil boss is unlikely to get her team members to open up and show initiative. They will do just enough to avoid getting beaten up by their leader.

What works best?

The most effective persona of a leader is one that displays tough love. Very demanding when needed, but with a sincere human face if the situation demands it.

Tough Love

8. Managing Attrition

There are two aspects to managing attrition well. A leader must be able to retain good talent for the good of the organization and also be able to let people go when that is best for both sides concerned. A leader who can overcome these challenges can ensure that the best possible playing eleven takes the field.

What works best?

Timely appreciation, frequent opportunities for stretch assignments, and meaningful employee engagement are proven ways to retain good employees. Letting go of an employee can become a lot easier if the leader sincerely tries to find the concerned employee an alternative opportunity elsewhere.

9. Admitting Mistakes

Many leaders continue to push ill-conceived projects through even after it becomes apparent that they were not as great as expected. One reason is getting emotionally attached to the initiative and finding it difficult to walk away. The second and more dangerous reason is that the leader finds it difficult to admit the mistake. This refusal to cut losses and run while there is still time can often prove disastrous for the organization.

What works best?

The greatest of leaders have made poor decisions, so joining that club is not the end of the world. Accepting this would make it easier for a leader to swallow pride and roll back a wrong decision.

10. Failing to Follow Up

The number of great ideas that got lost in the humdrum of daily work is depressingly high in most organizations. The blame for that must be placed squarely on the shoulders of the leader. There is still a chance that someone would keep track and remind the leader or manager about it with big ideas. The more significant harm happens when a leader neglects to follow up on smaller instructions given to an employee or a small group of employees.

What works best?

Most leaders would have advised some of their team members to maintain a to-do list and check off items that are done. Leaders should also maintain a follow-up list of things they had instructed employees or commitments that employees had made to them.

So, what challenges to leadership do you have?

You are mistaken if you imagine this is an exhaustive list of challenges to leadership. These are the ones I picked because they are quite common, and you must have found many situations familiar.

Let me save the others for another blog. I await your comments on your own experiences of challenges to leadership as a team member or as a leader. I hope some of these suggestions will help you fight some of your challenges.

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Sherry Cook
Sherry Cook
Sherry Cook is a writer and blogger. She loves to read and write about leadership, entrepreneurship, teamwork, communication, etc. She loves running, MCU, Sherlock Holmes, and hanging out with her friends and family. Follow her on Twitter or visit her Medium Blog.
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