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7 Questions to Understand “The Boss” and Advance Your Career

A crucial component in evaluating your own career is to understand your alignment (or lack there of) with your immediate Team Leader (I.e. your “Boss”). Below are seven questions, adapted from a Fast Company list, that will help you focus in on that alignment.

If you find yourself in alignment with your Team Leader, great! If not, then you really have to ask yourself – do I want to change and adapt for the greater good of my organization, or do I want to move on?

7 Questions to Help You Understand “The Boss” and Your Career

road to denali 7 Questions to Understand The Boss and Advance Your Career

1. What is your Team Leader (i.e. “The Boss”) trying to accomplish? What are his/her goals?

Start with truly understanding your Team Leader’s overall goals, either stated or implied (through their actions).

2. Is your team leader ambitious or content? What kinds of problems most worry your Team Leader? What kinds of victories most please your Team Leader?

Understanding these questions are key to understanding your potential for growth within your organization. Put bluntly, a Team Leader who is a small thinker, and content with her status, will not have as many opportunities for you to build critical experience and new skills. By understanding what things worry and please your Team Leader, you’ll get a true sense of how she views the world.

3. Why is your Team Leader the Team Leader? Why was your Team Leader picked for the job?

This question will help you understand the history behind how your Team Leader arrived at her position, and how the more senior executives feel about your Team Leader’s value to the organization.

4. If your Team Leader is ambitious, is it about substance, recognition, or both?

Understanding what drives your Team Leader’s ambitions will help you clearly assess your room for growth. A Team Leader who cares about the personal and professional growth of her team will open more opportunities than one who is solely focused on recognition.

yosemite 7 Questions to Understand The Boss and Advance Your Career5. What does your Team Leader need from you, and how do you plan to do it?

Next, get a crystal clear explanation of what your Team Leader needs from you. Dig deep here and understand not just her tactical project needs, but the personality traits that she wants to see you demonstrate.

6. What do you want out of your current position? Is this compatible with your Team Leader’s goals and ambitions? Do your goals advance your Team Leader’s ambitions, or conflict with them?

This is where you need to take an honest, objective look at what you want out of your career. Next, determine if when you achieve your goals, your Team Leader’s ambitions will also be met. If this won’t happen, you should re-evaluate your goals, your position, and/or your career plan.

7. Are you more ambitious than your team leader?

If you have a disconnect between your ambition and your Team Leader’s ambition, you might run into issues in the future. However, if you feel you can see beyond your own ambitions, and learn as much as possible from your Team Leader, new opportunities may also present themselves later.