The 12 Toughest Challenges of Leadership

The challenges of leadership are inside leaders. Stop blaming organizations and others for your shortfalls and failures.

Take the bull by the horns.
You are the bull.

The 12 Toughest Challenges of Leadership:

  1. Humility during success.
  2. Confidence during setbacks.
  3. Stepping back so others can step up.
  4. Putting plans into action – Follow through. Experience shows up to 90 percent of strategic plans never achieve execution.
  5. Leading change. Leaders don’t just do things, they change things.
  6. Admitting mistakes. One contributor suggests that self-awareness and honesty are essential to saying, “I was wrong.” (See more comments on Facebook)
  7. Listening with the goal of learning.
  8. Encouraging constructive dissent.
  9. Learning from criticism.
  10. Asking for feedback.
  11. Maintaining focus on the future.
  12. Building the team.

Situational or not:

Leadership challenges always involve changing situations. You, however, are the common factor. Your ability to lead yourself is your greatest ability. Situations come and go but you are always there.

Number 12:

Leading yourself to build the team is the leadership challenge that produces the most fruit. Success depends on your ability to attract, develop, and retain top talent.

How to spot top talent?

Top talent wants to:

  1. Know where you are going so they can find alignment or not. Tell them the goal?
  2. Develop plans with you. Once they align with the goal, don’t give them the plan, develop it with them. Top talent wants a hand in making plans.
  3. Make meaningful contribution. They ask, “Where do I fit in?” They need meaningful contribution. Drifting isn’t enough.
  4. Work with others. Lone Rangers have a place but never on great teams.
  5. Rise to challenges.

Key qualities:

Determine the nonnegotiable qualities you expect from your team members. Go with their strengths; compensate for their weaknesses.

What are the toughest challenges of leadership?

What qualities do great team members possess?

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24 Responses to “The 12 Toughest Challenges of Leadership”

  1. billgncs Says:

    good point about letting top talent be involved in the planning

  2. LindaFisherThornton (@leadingincontxt) Says:

    Great list! I love the paradoxical nature of numbers 1 and 2 – Humility in success and confidence during setbacks.

  3. Karin Hurt Says:

    I do see top talent wanting to work with others… they are inspired by other top talent and eager to grow.

  4. Ken Mason (@nanolithoman) Says:

    “listen with the goal of learning” ..wow, that is golden.. How often do I find myself listening with the goal of making MY next point.

  5. Cameron Markcray Says:

    Number 11. Trying to not be consumed in the now, and focusing on the future.

  6. Marc Bacon Says:

    Dan,
    This is perhaps the most concise list I’ve ever seen.
    Lots of food for thought. I’ve nothing to add that even comes close.
    Thank you

  7. Thomas Says:

    Great post today Dan. Your insights are so valuable and easy to read. Your simplicity is profound and that inspires others top take action! Thanks for the daily zingers!

  8. MrunalAsher Says:

    Dear Dan,
    An interesting post with useful tips & the check-list to assess where do you stand on your scores as a good leader.

    Other challenges could be: any of the own trusted people’s betrayal, delayed actions in execution and not meeting the committed schedule, unexpected moves by direct competitors resulting in direct impact on business, missing the supportive power of co-workers due health or personal reasons at critical times, sudden failure of business alliances, emergence of an union and its prohibitive moves etc.

    Good successful leaders march forward with quick decisions and alternate action plans. Effective communication and transperancy are the crucial things to bring the desired changes fast.

    • Dan Rockwell Says:

      Dear Dr. Asher,
      Powerful additions, for sure. I appreciate how you bring an organizational/business emphasis to this discussion. You bring up a topic with a whole new batch of leadership challenges.

      Quick decisions and alternative action plans… now there are two ideas that need to go hand in hand.

  9. Ajay Kumar Gupta Says:

    Dear Dan,

    Humility during success is very challenging. I think, servant leaders are good at maintaining humility during success. Besides all the suggestions, I would add some challenges of leadership- challenging habits and learning habits.Generally we believe that our habits are good and acceptable but sometimes we need to see whether our thinking towards our habits are good or bad. This I say from my own experience. At present I am in Milan, Italy where I need to take care of my foods and other needs. In India, I was dependent on my family. Now, I am find it difficult to cook food for me. Though I know how to cook but unable to convince or change my habits. And the fact is that unless I change my habits, it would be difficult to survive. So, the whole point is that leaders in new environment or situation need to question their own habits and should be ready to adapt new habits .So, by this experience, I think, unwillingness to change or inability to change habits could be the toughest leadership challenges.
    The greatest qualities in team is perhaps cohesion and synergy. Each member of teach must own accountability and ownership.

  10. Margaret Says:

    the photo made me laugh out loud–love the top talent tips. Things to strive for in myself, not just to keep an eye out for

  11. Chuck Marr Says:

    Awesome reference list for leaders and aspiring leaders! One thought that comes to mind as either an additional point or intertwined throughout the current list is the importance of keeping the organizational Mission and Values visible and alive. When the formal and informal leadership of the organization uses similar terminology and can express what it all means in similar terms a stronger shared resolve for success evolves. This helps create an environment that attracts top quality people.

  12. vusbergnet Says:

    Why not total involvement? I really believe that it is a challenge for leaders as their life is usually busy.
    But the list was done really carefully… :)

  13. A Gracious Life Says:

    I find myself having problems with Challenge of LEadership #2.

  14. Pankaj Rai Says:

    Thanks to envisage and produce marvelous points to guide us during long run of leading in peaks and troughs.

  15. Sofie Sandell Says:

    Thank you, very good article!!! It’s scary to ask for feedback, but you can learn a lot from it….

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