How to Deal With an Unstructured Boss

by Gaby Gramont

Everyone appreciates a little structure.

Unstructured boss

That’s not to say that micromanaging is the way to go, but some clarity and framework are always welcome. A lack of organization can be quite scary. For example, if you’re at your first job straight out of college, you’re used to syllabus deadlines, prompts and specific criteria for homework and exam dates. Coming into the workplace can be a little disorienting, especially if your boss likes to look at things at the “macro-level” and is very ad hoc about things. Similarly, if you’ve been in the workforce for years and recently changed to a new position where your supervisor is nothing like your past ones, you may also be experiencing stress. After all, the human mind does not like uncertainty or lack of structure!

Traditionally, we think of a boss/employee relationship as unidirectional: the boss manages their employee, period. However, that’s not the only dynamic in that relationship. In work relationships, the employee can (and should!) also manage UPWARDS. This is where you can gain some control over your work structure.

Here’s how you can manage your unstructured boss: 

First, acknowledge that everyone has different management styles due to their personality style

The way people manage others is directly related to their personality style. Some people are very idea-oriented and like to think of concepts on the broader spectrum while others like to execute and focus on granular details. One may be more visual where they like to send emails detailing important tasks – they could prefer giving verbal requests through the phone or in-person, etc. Study your boss’s management style at work. Do they typically ask you for tasks last minute? Do they ask you to do something mostly over the phone? Are they very active on Slack or Teams? Do they mainly contact you during certain times of the day?

Try to understand your boss’s strengths and weaknesses. Perhaps they come up with great ideas but aren’t able to transform those into meaningful actions. Maybe they work well under pressure and that’s why they tend to leave things until the last minute.

Suggest ways that you can work more effectively 

Instead of critiquing what ISN’T working, approach your boss with suggestions that can improve your work dynamic. Improving your work dynamic is sure to improve your ability to do your job, a win-win! Come up with ways that help you and your boss both stay organized and on top of the same things. You can say something like “it really helps me to be able to visualize all the simultaneous projects in one single timeline. Maybe we could create a calendar view that holds all of these in one place.” Something like this will let your boss know what your preferred way of working is.

Make sure to get really specific with the ideas that you suggest. There are many tools out there that provide shared spaces for co-workers to collaborate. Notion is a great example. There are multiple templates that you can use and different views including agendas, timelines, list views and more. You could create a shared Notion account with your manager and keep all your important deadlines and info there.

If they are more old-school, you can suggest keeping a document in Sharepoint that you regularly update. If that’s not up their alley, you can make a weekly email template summarizing key dates and deadlines for the week so that nothing is missed!

If they don’t give you the clarity that you need, ask for it

If your boss tends to throw out tasks in a 1:1 meeting without setting any specific deadlines, make sure to summarize the key takeaways at the end of the meeting to make sure you’re both on the same page ”So it looks like you want the finalized ad and the latest campaign analytics done. When would you like those for?” It would also be a good idea to write down the answer to those questions and send them an email at the end with the summary of the meeting so that you can both refer back to it.

If they have a bunch of ideas but no clear action items, ask questions to get the ball rolling. Lay out the steps that need to be taken to execute the idea.

For example, if they say: “I’d like us to create a new web page with all of the products we offer,” you can say “That sounds great! Which products, in particular, do you want to feature? Who in the company has the product specifications so that we can include them? Will you write the copy for this page? Do we have a contact that can help us with the coding of the page?”, etc.

Often managers like to keep it big picture and forget to give guidance to their employees. If the path isn’t there, you can map it out yourself by asking questions.

Don’t be afraid to express your doubts and concerns to your manager

At the end of the day, your performance reflects in part on your boss’s management abilities. It’s in their best interest to create an environment where you feel supported and clearly directed. Have an honest conversation and explain to them which areas you need more clarity in for you to achieve your highest potential. Chances are, they’ll embrace the initiative and be happy to hear some feedback from you!


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Posted in Job Search Tips