How to Organize Your Disorganized Boss
They're Boss for a Reason (But Organizational Skills Aren't It)
Help Your Boss Get His (Or Her) Stuff Together
He's the boss for a good reason, but that reason is certainly not his organizational skills.
Sometimes he neglects key details. His office is a mountain of misplaced files. When your boss can't find that important document, impending deadlines can make the office feel like a pressure cooker. Sound familiar? If so, help your boss manage his time and prioritize -- all the while letting him think that it was his idea.
As your boss becomes more organized, he will enhance his professional image. He will also be more aware of what is on his schedule and will develop greater command of his time. In turn, you can reap residual benefits of less stress and more efficiency.
Think of the extra time and effort required in getting him organized as an investment. By managing up, you will be managing your own career progress and professional image at the same time.
Ready to get started?
You Got This!
First Build Trust
Before you try to fix anything, you have to earn the right to do so. That means building a foundation of trust.
Lead by Example
Make sure you demonstrate solid organization skills yourself by fine-tuning your system for staying on track. Keep your own work space tidy. Show up to meetings prepared. Meet all deadlines. In addition, demonstrate your resourcefulness by having the most frequently relied upon information at your fingertips (e.g., key contacts, frequently accessed reports).
Seek to Understand
As you gain your boss' trust, also listen, paying particular attention to any feelings that are expressed. Listen for signs that your boss' poor organizational skills are causing him frustration, conflict, or even consequences in the organization. Examples include missed deadlines or meetings, lost paperwork and comments from others.
Assess the situation first before jumping in to help, and especially avoid providing him feedback which could backfire on you. (Remember that you are in an information gathering mode.) There may be a method to his madness, however ineffective, which you need to understand.
Also, no matter how irritated his sloppiness makes you, never chime in with anyone who bad mouths him. Your venting could get back to him, and such critical comments are inconsistent with your intent to help.
Building a Trusting Partnership Is a Key to Success
Provide Strategic Support
Make sure that both your role and your behavior support your boss' best performance by minimizing distractions and enhancing his efficiency.
Learn what your boss' goals are and how he is measured in the company. Be sure that your performance goals are linked with his. If you perceive a disconnect, tell him you'd like to seek clarity on how your goals can more fully support his and the organization's.
Get the Hint Gentle Reminder Tags. Help your boss remember that important document. Tags read: Looking For This?, Do This, It's Here, Take This, Don't Forget This.
Find the joy in snarkiness, bewilderness, and befuddlement. I LOVE these because they bring humor to a challenging situation.
Ask him how he prefers to receive information, both in terms of his channel (e.g., electronic, in person, phone) and timing preferences. Some people are "morning people" and enjoy diving right into their day, whereas others are slow to warm up.
Also understand how he wants interruptions to be handled, and help him to avoid those that are unnecessary. Research indicates that office employees are interrupted an average of once every three minutes.1 Given that it can take up to 23 minutes to return to the original task, it's no wonder anyone can finish what they start.
Rather than popping in to ask that quick question -- which often isn't all that quick, is it? -- try this technique. Group together several less important items, then book 15 minutes on your boss' calendar to take care of all of them in one sitting. After using this technique a few times, explain to him that your rationale is efficiency and minimizing disruptions. Discuss how it works for both of you. You might find that this is a great conversation starter regarding efficiency.
Make a Good Boss an Organized One
How organized is your workspace?
Because time is so precious, keep both verbal and written communication succinct. If the text of your email is longer than two paragraphs, consider shortening it or using another mode of communication.
Use "Reply All" Sparingly
Email chains can become overwhelming when long lists of employees volley back and forth using "Reply All." Help your boss manage his inbox by asking him to specify under what circumstances he wants to be included on emails. If you see a lot of back and forth replies, then a meeting, conference call, or the use of email voting buttons are more appropriate venues for discussion of the issue.
You might also volunteer to be a key contact person for a project so that your boss can delegate inquiries to you. This increases your visibility within the organization at the same time it helps your boss manage his priorities.
Employ Consistent Labeling
Agree on consistent labeling in the email status line for confidential, action-needed, and similar items. For example, draw attention in the status line to items that need special handling (ACTION REQUIRED by date) or those that are CONFIDENTIAL. Consider using built-in email system reminders to help with deadlines. For best results, ask to include the entire team on the conversation so that everyone is on board with the labeling structure. Then, apply it across the department.
Help Your Boss Share Information
In staff meetings or other appropriate venues, prompt your boss to share what is going on elsewhere in the company by simply asking him. He may otherwise forget. You will appear eager and interested in the company while helping him to do his job. That's a win/win!
Present Solutions, Not Problems
When you present a problem to your manager, avoid simply "dumping" it on him with the expectation that he fix it. Instead, present the problem along with three solutions. (More than three solutions is overwhelming, however.)
One solution should usually be to do nothing because let's face it: staying the course is an easy option. A second solution can be one that is ideal or expensive. The third is a compromise or more reasonable solution. This should be the one you are advocating. Be ready to discuss advantages, disadvantages, and the financials associated with each solution you present.
Manage Your Time and Help Your Boss Manage His
Help your boss with time management using the following tips:
Create and Share a Calendar
Help your boss create a calendar that he can share with the team. Update it and refer to it often as projects and other due dates approach. Ask questions that reference the calendar (e.g., "I see that the Chairman's report is due next week. Would you like me to pull the numbers for you so we can start working on it?") He should also have access to calendars of his subordinates, and calendars should be linked. This can be done with ease electronically.
When you have important discussions with your manager, integrate due dates, dates for status checks, and progress milestones to keep you both on track. Stay organized by keeping all notes of meetings that you have with your boss in one notebook.
Follow up any key discussions with email verification of agreements you make with him. Honor any time-bound commitments, and hold your boss accountable for his end as well.
If your boss frequently runs late to meetings, offer to prepare an agenda. Email her the bullet-points several hours prior to the meeting and remind him how he will be needed in the meeting. Use automatic meeting notice reminders in the email system to assist attendees in being timely.
Conquer Disorganization Together
Divide and Conquer
Divide and conquer your boss' mess using the following pointers.
Label, File, and Store
Well organized people have a mantra: "A place for everything and everything in its place." Develop a system of folders, bins, or file drawers that works for your business. For example, use color coding based on project type or topic. Where relevant, prominently include the date to help you purge out-of-date files later.
First organize your own files, then request permission to tackle some of the common files (perhaps with the help of teammates). After you receive compliments for your efforts, offer to help your boss with some of his files.
Adopt the "One Touch" Rule
As new items come across your desk or email in-box, resolve to touch them once rather than allowing them to accumulate. Either read, respond, dispose of the item, or direct it to an appropriate file. As you gain success with the technique, resolve to share your learnings with your boss.
Yes, Change Is Possible
The Soft Sell
Small Changes and Buy-In
Making changes in small increments and getting her buy-in as you go along will work wonders. You may find that he asks your coworkers to adopt your new efficiency techniques.
Don't Be a Know-It-All
Rather than telling him how to organize, try asking if you can help him or suggesting that "we" try something new. No one wants to be schooled by a sassy-pants, event if that person is right. Try these lead-ins when suggesting something new:
- "How about if I help you ..."
- "I bet we can figure out how to ..."
- "I've learned ..."
- "One thing I have found is ..."
- "What do you think if ...?"
- "Would you find it helpful ...?"
Since your boss is not naturally organized, he will need your encouragement. Don't expect change overnight. Encourage him and celebrate small successes, and keep working at it.
Locations with Names Associated with Poor Organizational Skills and Losing Things
1The Wall Street Journal. "Workplace Distractions: Here's Why You Won't Finish This Article." Last modified December 11, 2012. http://online.wsj.com/article/SB10001424127887324339204578173252223022388.html#project%253DDISTRACT1212%2526articleTabs%253Dinteractive.
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