Subscribe to our mailing list!

Get weekly updates of the shows by staying connected.


Actually we won’t spam you and keep your personal data secure

Time Management

How to deal with a bad Boss?

By  | 

Maybe you’ve been lucky in your career and have only had great bosses, but eventually you may run into a bad boss. Don’t despair!  You are not doomed, and you don’t need to leave your job.  Instead, you can view this as an opportunity to learn a valuable life skill: how to manage your manager. Luckily, this skill will bless you for many jobs to come and might even help when you become a manager yourself.  In this interview, you’ll get the very best ideas from the best-selling author, Bruce Tulgan’s book,“It’s Okay to Manage your Boss” on how to deal with a bad boss.


Step 1: Set up a recurring time to connect with your manager

This may not be as easy as it sounds for managers who are always on the run.  These managers are constantly overbooked, and overwhelmed.  Once you are able to nail down your manager, Bruce demonstrates in the interview how you would “pitch” the idea of a recurring meeting with your boss.

The key is to convince your manager that it will be time well spent.  If you can grab thirty minutes, that’s great.  Minimally, try for 15 minutes every week.  If your boss is often travelling or it’s impossible to meet face-to-face or impromptu, then worst case try for email communication.  But even before you send an email, make sure to check your manager on his or her communication preferences (e.g. email length, format, and what things they want to decide face-to-face).

Step 2: Create the stellar weekly meeting

Your goal during your weekly meeting is to make your communication super-efficient and your agenda clear.  Often, this requires some pre-meeting planning.  Before your meeting, think about the projects you have been assigned and cue up status and questions.  If you are at the start of a project, it’s helpful to give your manager a broad overview of your plan.  For example, let’s say your boss has asked you to roll out a new holiday promotion in ten coffee stores. Your plan may look like the following:

Agenda: Go over high level plan.  Get feedback. Review where you need help (questions, red/yellow flags).

  • Business goal: Business goal of driving impulse holiday sales and introducing company’s NEW Holiday Coffee.
  • Promotion Details: Roll out new holiday promotion (free bag of Holiday Espresso Roast coffee for any $50 purchases) to hit all 10 regional stores by Nov 10th.
  • Develop work-back schedule with key milestones: Learn best practices from Jack Smith, who ran a similar promotion last year. Confirm $15,000 budget with Sam Grady from Finance group and discuss any constraints and financial targets for success. Work with Alexa from editorial and advertising group to identify steps and schedule for creating marketing materials given a Nov 10th launch date. Work with general managers of regional store managers to nail down where and when materials are needed and employee training needed for the promotion.
  • Come up with plan/milestones and deliverables 2 weeks from today to review with your manager.
  • Yellow Flags (heads up that something may present a problem): Alexa on maternity leave.
  • Red Flags (you already know there is a problem): Sam Grady mentioned in the hallway that they are cutting budgets for last quarter of the year.

The above just serves as a very high level three bullet list plan.  Most managers don’t like being overwhelmed with details.  However, you may have a manager who wants more details. If so, ask your manager what details they want in the future (e.g.- spreadsheets with financial analysis, email exchanges, etc.).  About 50% of the managers want a chance to review something in email before you meet so they can be prepared to answer questions. Make sure to send your email agenda about 2-3 days in advance.

Step 3: Ask good questions

Once you have your agenda, then make sure you ask the appropriate questions you need answers to in order to move forward.  Below is a laundry list of sample questions from Bruce Tulgan:

Pick 1-4 Questions to ask in each meeting.  Here are some good overview questions:

  • Are there any new priorities? What has shifted and changed, and what adjustments and course corrections do I need to make?
  • Are there any problems that you should anticipate? Possible solutions?
  • How do I need to change or adjust my resource plan?
  • How do I need to reprioritize my to-do list of concrete actions?
  • (if relevant) Has the checklist to ensure quality control for every concrete action changed as a result of this shift in priorities?
  • What other priorities should I be focused on as of right now?

And there’s more

The questions you may ask may vary by project.  Bruce provides a comprehensive list of the questions above don’t seem to fit your needs:

  • Are there any additional business goals?
  • Is there a particular way (order, process) that would be more efficient?
  • Are deadlines accurate?
  • How often and when are best times to check with your boss on this project?
  • Do milestones outlined have clear steps, guideline, and process? What is missing?
  • What level of detail does your boss want going forward? If you have drafts or sample of your work in progress at regular intervals, do they want to see or approve them?
  • Any other adjustments needed on current plan?
  • What does an ideal execution of this project look like?
  • What other information does your boss need?
  • What other type of details may you need to know about: work space, supplies, materials, equipment, transportation, maintenance?
  • What are resources may you need to know about (training, money, space, skills, workarounds, tools and resources)?
  • What other people should you contact either internally or externally for a successful project? Who needs to cooperate? Which people are generally obstacles and how to get around a potential snafu? What is the best way to reach them? Who do you ask for what when and how?
  • If resources are needed- Find out process, cost, and turnaround time to for obtaining that resource.
  • What are possible problems you may encounter and workarounds if Plan B is needed.
  • Get accurate/honest feedback about your performance and course-correction.
  • How to grab time with your boss if they are never available?