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While dealing with disorganized employees is difficult, by applying strict rules and providing guidance the challenge can be addressed in an orderly manner. Recommendations on how to implement the desired changes will be addressed in the third blog of this three-part series. How to deal with a disorganized boss is far more difficult.

Understand your boss

We are all very complex creatures. We all have strengths, weaknesses, fears. Carry out a full SWOT analysis of your boss. Make it a project. Think strategically. Why is this important? Nobody likes criticism and being approached negatively. Focus on the positives. It could be that your boss is talented at designing new products, dealing with customers and investors and simply dislikes paperwork. Find out what makes him/her tick. The most common feedback is that the boss ‘wears too many hats’ or ‘juggles too many balls’. Quite often they are excuses for not delegating and managing resources properly. The blog ‘The cost of being disorganized’ covers the different patterns of behavior commonly seen from a disorganized boss.

Offer solutions

One of the biggest misnomer of all – constructive criticism – is to be avoided at all cost. Don’t criticize, don’t complain, don’t add more problems. Offer a solution to one of the problems that affect you both. Present it in a way that shows that you seek approval for a task that will lessen his/her workload and improve the company’s performance. Build a rapport with your boss. Prioritize: choose a task which you believe will be a success. Remember that trust is earned. As you deliver results, it becomes easier for the boss to say yes but do it one at a time. If too many requests are made, the safe decision is to say no.

Be succinct

Don’t submit long reports or emails. Use executive summaries. Keep your meetings short. Don’t assume that your boss does not understand what is going on. There is no link between being disorganized and intelligence. Some of the most brilliant minds in the world belong to disorganized people. Prepare for the meeting(s). If figures/results/spreadsheets/budgets are part of your proposal, make sure that you understand and can defend every number.

Put it in writing

If your proposal is accepted (if chosen carefully, it will be successful), put it in writing:

  1. Thank your boss for his/her time and confidence in your ability to deliver
  2. Outline the task, actions and timeline
  3. Be clear. Clarity is better than complexity
  4. Set a date when you will provide feedback or confirmation of success
  5. Display your leadership skills

Treat your boss as a customer

Approach your boss as if he/she is a valued customer. You would not complain to a customer and treat them disrespectfully. You cannot complain but your boss can complain to you. Use it as an opportunity to provide a solution. Listening is a disappearing skill. Be a good listener, show empathy and offer your help. Become the ‘go to’ person that your boss relies on. This will place you in the unique position of taking charge and making a change for the better.