Setting Expectations When You Work For a Last-Minute Boss

Do you set expectations when you begin a new working relationship?

I was chatting with a friend this morning. She’s in graduate school and about to start a new semester as a TA. The professor informed her she leaves a lot of things to the last minute and likes to “fly by the seat of her pants.”

My friend, on the other hand, is a planner. She likes to know what tasks she’s doing and when those tasks are due, and she likes to have plenty of time to work them into her schedule. My Boundary Spidey Sense perked up immediately. This sounds like a dangerous combination.

Can a planner and a “seat of the pantster” work together in harmony, or is this destined to be a point of contention, frustration, and resentment?

Characteristics of Planners and “Seat of the Pansters”

You’ll often hear these terms in the writing community. Planners like to schedule their writing time, outline their work, and know where they are going and how they will get there. I’m a proud member of the Planning camp. My first book took almost 5 years, and it will never see the light of day. Subsequent books take me between 2 weeks and 6 months. They are out in the world helping people. Is this because I’m a better writer now? Well, I certainly hope so. But that’s not why I’m able to write faster. After that first year-long project, I learned how to outline. I research, plan, and create a detailed outline, so when I’m done writing each day, I look at the next day’s work and let it percolate while I go about my day. No more long periods without writing, no more writer’s block. This planning strategy follows me in all areas of my professional life.

Here are some signs you might be a Planner:

• Your calendar, with a well-thought-out schedule, brings you peace.
• Starting a project without knowing where you’ll end up makes you twitchy.
• You LOVE a good outline. Planning is part of the project, not something you have to do before you start the project.
• You can’t get enough checklists and find true joy in crossing off finished tasks.

Now, let’s look at the flip side. Pansters, also known as Doers, feel suffocated by an outline. They prefer to sit down and let the muse take them where it will. Pansters are spontaneous and often work in spurts, knocking out a lot of tasks in a short burst of energy.

Here are some signs you might be a Panster or Doer:

• You prefer to dive in and see where the project takes you.
• If you keep a calendar, it’s more of a loose “suggestion.”
• You learn best by getting your hands dirty and actually “doing” the work.
• Meetings seem like a waste of perfectly good “action” time.

It’s hard for this Planner to admit, but Doers definitely bring something to the table. While I’m overanalyzing what needs to be done, a Doer is just… well… doing it. And if it doesn’t work out the way they intended, they’ll just do it differently on the next try. However, when you find security in scheduling and you have to work with someone who leaves things until the last moment, stress levels can skyrocket.

Setting Expectations: How Can a Planner and a Doer Work Together?

First, it’s important to recognize that both types of people want to complete projects and do them well. They may have different approaches to this end goal, but ultimately, the end goal is the same. Acknowledging this is the first step to a peaceful working environment.

Next, it’s time to set expectations (ie: boundaries). There are a few different ways you can do this.

1. Communicate with your boss regarding your work style. Explain that in order to do your best work, you need to understand your role, have a clear list of tasks, and have due dates that allow you to complete the current project while still handling your everyday responsibilities.
2. Schedule a Weekly Meeting. Ask your boss to meet on a regular basis (scheduled in advance) so you can discuss upcoming projects and what is expected of you.
3. Set work hours. If your boss knows you are on the clock from 9 to 5 (or any other schedule), they will be less likely to dump a project on you at 4:30 and expect it the next day. (Less likely… but it’s not completely unheard of.)
4. Ask questions. If your boss insists on dumping last-minute tasks or changes in your lap, be prepared to ask some fact-finding questions like:
   1. When do you need this by?
   2. What current tasks of mine should be rescheduled to allow enough time to complete this?
   3. Am I the right person to do this, or would a teammate be better suited/have time?
   4. Why are we doing this, and is there another solution?
5. Consider saying No. Terrifying, I know. However, if you are not going to be able to complete the task with your normal level of quality, or if it’s not in your job description, you may want to suggest another team member who can complete it as expected.

Your work styles may never match, but hopefully, you can find a peaceful coexistence by setting expectations early on.

What If Your Boss Refuses to Work with You?

We can set boundaries all day long, but that doesn’t mean anyone is going to respect or follow them. Your boss may bend. They may see the value you bring to the table and be willing to work with you even though you are quite different from them.

Or, they may not.

Not every boss will be willing/able to change their ways. When this is the case, you have two options. Grin and bear it, or run for the hills.

1. Grin and bear it. It’s rough to hear, but if you love your job, are just working a temporary project with a Panster, or are in school and have very little say over who you’re placed with, you might just have to deal with it for the time being. One way to make it easier is to get all the work you KNOW about done sooner rather than later. This will free up your time for last-minute assignments. Also, accept that they may not get your best work. It’s painful to think of, but you might have to turn something in before it’s “perfect.”
2. Run for the hills. If this is a permanent role and a permanent supervisor, it may be time to look for another job. Your boss isn’t going to change, so unless you stop letting it bother you, you may want to find a new opportunity.

Conclusion

It’s my personal belief that Planners and Pansters can work together once some guidelines and expectations are established. What has your experience been?

If you’d like some more tips on setting healthy boundaries in the workplace and in your personal life, I’m here! I’m offering free Boundary Discovery calls to help you uncover what’s holding you back and give you the tools to move forward. Book a discovery call today, and let’s chat.

About Sheryl Green

Sheryl Green is a Mental Health speaker and author and the “How to Say No” Expert. She works with individuals and organizations to establish healthy boundaries to improve relationships, communication, and well-being. Her mission is to make the world a better place… one boundary at a time. Learn more about her entertaining and illuminating programs or contact her at 702.885.4309.

Get her How to Say No cheat sheet.