Are you the organized one dealing with a disorganized boss? I often get questions from audience members at presentations and clients about how to work with someone who is disorganized. The frustration is real, but there are a few ways to handle a boss whose organizational skills are lacking. Try one of these five tips:
1. Stay Organized and Take Initiative
When your boss struggles to stay organized, it’s up to you to utilize your good organizational skills to counteract it. Take the initiative to set up systems that work for you. Create detailed to-do lists, break down tasks into manageable chunks, and set clear deadlines. Don’t wait for your boss to outline every step—be proactive about figuring out what needs to be done and when. Additionally, documenting key decisions, instructions, or changes in project scope ensures that nothing gets lost in the shuffle, giving both you and your boss a reference point to return to if needed. Documenting everything also gives you back-up in case of a misunderstanding! (And if a disorganized office comes along with the disorganized boss, check out my free e-book, The Ultimate Guide to Organizing Your Office for some timely advice on how to help!)
2. Communicate Clearly and Concisely
Clarity is key when working with a disorganized boss. Since they may be juggling multiple priorities, your communication should be straightforward and to the point. When discussing tasks, outline what’s been done, what’s pending, and any decisions that need to be made. Provide brief updates and ask for any specifics that will help you prioritize work better. When yet another project gets dumped on you on top of an already overloaded schedule, clearly and definitively ask what should be prioritized and what can be pushed ahead for another time. When receiving instructions, ask clarifying questions right away to avoid any confusion down the road. Being clear and concise reduces misunderstandings and ensures everyone is on the same page.
3. Set Up a System for Follow-Ups
It’s common for disorganized bosses to forget or overlook important tasks. To minimize this, set up a system for follow-ups. Regular check-ins, whether they’re weekly meetings or informal updates, can help ensure that things are on track. Tools like Asana, Trello, or even a shared Google Calendar can provide visibility into what’s been assigned and what still needs attention. Don’t hesitate to send polite reminders when needed—just a simple “checking in on X project” can jog their memory and keep things moving forward.
4. Be Flexible and Adaptable
The reality of working with a disorganized boss is that things often don’t go according to plan. Deadlines might shift, projects might take unexpected turns, or urgent tasks may arise without warning. Flexibility is essential here. If priorities change, be prepared to pivot quickly and reassess your workload. Again – communication is the key. Check in again on priorities and remind them of what you’ve been asked to prioritize before so you can clarify what needs to be done, even on the fly!
5. Set Boundaries and Manage Your Stress
While it’s important to be helpful, it’s REALLY important to set boundaries to prevent burnout. (If you struggle with boundary setting, check out the free boundaries workbook from BlissMoreStressLess.com.) Disorganized bosses might ask for last-minute requests or try to shift priorities without warning. Without boundaries, your work-life balance can suffer. Be clear about what’s possible given your current workload, and don’t be afraid to assertively communicate when you’re at capacity. Equally important is managing your own stress. Find strategies to decompress and keep a positive attitude, whether it’s through exercise, hobbies, meditation, or other forms of self-care. Remember,
“Taking care of myself doesn’t mean ‘me first.’ It means ‘me, too!’” (L.R. Knost)
By staying organized yourself, communicating effectively, setting up follow-up systems, being adaptable, and managing stress, you can navigate the challenges of working with a disorganized boss and keep that ever-elusive work-life balance in check!
