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Leadership Thought #400 – 25 Ways Leaders Get Themselves in Trouble

July 16, 2022

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Even talented leaders run into self-imposed challenges sometimes.  No one is immune from errors in judgment or flaws in action.

Leadership isn’t easy, or everyone could do it.  Some talented people make it look easy, but we often don’t see all the effort that goes on behind the scenes to make it look this way.   Most leaders struggle at some point and must learn some difficult lessons as part of their journey.  Experience can be the best teacher if you are open to learning.  I’ve observed the following twenty-five ways (in no particular order) that leaders tend to get themselves in trouble:

  1. Not creating a formal decision-making process to address strategic and other critical issues – winging it rarely works.
  2. Being ignorant about basic financial management and as a result making bad economic decisions.
  3. Too much emphasis on growth at the expense of profit and cash flow.
  4. Taking on too much debt too quickly.
  5. Making overhead investments they cannot afford.
  6. Under-investment in the parts of their business that drive revenue.
  7. Burdening their company with income/wealth expectations that it cannot support.
  8. Under-communicating with their bank and other creditors or investors especially when things get difficult.
  9. Failing to properly understand and manage the risks inherent to their business model and all businesses in general.
  10. Having no flexibility built into their staffing model.
  11. Promoting people based on loyalty rather than competence.
  12. Not making sufficient investments in training, especially for new supervisors/managers.
  13. Taking far too long to fire people who are problematic for their organization.
  14. Making hiring decisions far too quickly.
  15. Holding family members in the business to a different (lower) standard than everyone else.
  16. Punishing and/or avoiding people who give them bad news.
  17. Getting too caught up with new ideas at the expense of fully executing what already exists.
  18. Not creating a consistent meeting and reporting structure with their key personnel and sticking to it.
  19. Becoming too enamored with technological solutions to every problem.
  20. Over-reliance on one or a small group of customers to drive top-line results.
  21. Not creating a systematic way to dialogue with their customers/business partners on a regular basis and acting on this feedback.
  22. Being too slow and mostly reactive when responding to changes in the competitive landscape.
  23. Creating too much dependence upon themselves as the hub of all important things instead of allowing others around them to step up and take initiative and assume responsibility.
  24. Getting too far removed from the front lines of their business and relying solely on others to keep them in the loop as to what’s actually going on.
  25. Thinking they don’t need an Executive Assistant and can manage their administrative responsibilities themselves with technology.


I could produce many more items, but this list is a good place to start.  I encourage you to assess where you currently stand against each of these issues and begin making changes as needed.  It would also be helpful to include your key people in this discussion and get their input as well.

Struggles and challenges are inevitable in business.  However, self-created problems only make the journey that much more difficult.   If you are honest with yourself, much of your woes fall into this category.  The good news is that you can usually do something about it once you have clarity.  I forget where I read or heard this quote, but I’ve always liked it, “the key to success in business and life is to get better problems.”