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You and Your Boss: 2 Essential Questions to Help You Both Succeed


Fri Nov 09 2018

You and Your Boss: 2 Essential Questions to Help You Both Succeed

Imagine you and your boss have been working together for a long time and things are running fairly well. You know each other’s styles, preferences, and communication needs. Then, wham! You learn your boss is moving on to a different position. You freeze. Your stomach tightens. You ask yourself: “Who will be my new boss? What will they be like? What will they expect from me?”

Or, imagine a different scenario where you and your boss don’t get along. Every morning as your alarm goes off, the depressing realization hits you that you must face your boss again. Ugh! Stress flows through you as you prepare for another day of tension and misery. You ask yourself, “Why can’t I have a different boss?”


Of the dozens of executive coaching sessions I have each month, the above scenarios are not uncommon. Most people have some degree of apprehension or frustration about working with and for their boss. This is only natural, since your boss plays such a major role in your life. A good relationship with them can make your work life very enjoyable, but a poor relationship can make your life miserable—and probably their life as well.

If you want a stronger and more productive working relationship with your boss, there are two specific questions I encourage you to ask.

First Question: How is your boss evaluated?

The person to whom your boss directly reports is obviously very influential in their life. Your boss’s performance is carefully watched by their boss. Consider the following three components that influence how your boss is evaluated:

Evaluation Component 1: Accountability

Understand the aspects of your boss’s overall job that they are held accountable for. You can be sure that these are the primary considerations influencing how their boss evaluates them. Consider the role you play in impacting your boss’s performance in each of these areas.


Evaluation Component 2: Metrics

Ask your boss how the various aspects of their job are measured. Some will be fairly straightforward and easy to measure, while others are more subjective. Knowing these metrics will enable you to help them achieve the performance they are measured against.

Evaluation Component 3: Pressures

Often the greatest pressures your boss will face are related to schedule parameters and budget constraints. Understanding these will enable you to better relate to your boss and support them more fully. You will recognize what keeps them awake at night as they worry about meeting deadlines and budget limitations.

Actions You Can Take


The more you understand these three evaluation components, the more you can directly help your boss accomplish their goals. And, consequently, the more your boss will appreciate and value you, because you are helping them perform well, which elevates their reputation in the eyes of their boss. Ask knowledgeable people in your organization what they know about your boss’s boss. Learn about their style and expectations. Identify how their goals align with the organization. This will open your eyes to the daily life that your boss experiences in working for their boss.

Second Question: What is your boss’s style?

Every boss has a unique style they have developed over the years. This style is the result of their personality traits, personal preferences, and the many positive and negative experiences they have had throughout their career. Once you understand your boss’s own unique style, you can better respond to it.

Here are six key style components that will help you discover and define your boss’s unique style:

Style Component 1: Communication

To succeed with a boss, communication is a primary factor. Few aspects of a work relationship surpass it in importance. It is essential that you learn and adhere to your boss’s preferences around communication. Identify how they prefer to communicate, and under what circumstances and times. Consider the primary communication vehicles—emailing, texting, phone calls, face-to-face conversations. What are they most comfortable with? Also learn if they are a reader or a listener. Do they like to come well-prepared to a meeting, or process it in the moment? Discover your boss’s comfort level with each of these options; then, you will be able to adapt and adjust your own style to best meet your boss’s preferences.

Style Component 2: Decisions

Your boss’s style of making decisions has a major impact on your job. A clearer understanding of it creates a more workable relationship with them. Some bosses tend to use an authoritative approach. Others like a consultative or collaborative one. Consider how they prefer to make decisions. Do they generally seek consensus, or follow their own ideas? Are they fairly quick to make decisions, or are they more analytical and thoughtful? What role do they prefer their people play in the process? How do they support and communicate the final decision? Knowing answers to these questions will enable you to better understand the role you and your fellow team members play in formulating and supporting your boss's decisions.

Style Component 3: Work Schedule

Everyone has a personal predisposition about how and when they work. Ask your boss about their schedule preferences. This knowledge will help you better understand, respond to, and support them. For example, some tend to be morning people. Others are at their peak later in the day or evening. Find out what works best for them. Identify when your boss prefers to have meetings. Some like set agendas, others are more comfortable with free-wheeling discussions. Many bosses are action oriented; others prefer longer discussions over several meetings. Find out how action items are assigned and the typical follow-through pattern.

Learn when your boss prefers alone time to catch up on work assignments and projects. Do they prefer early morning for uninterrupted “in-the-zone” time? What are their views about an open-door policy? What about weekend work time for emailing or calls, or late-night emails and the expectation of a reply? All these data points will dramatically help you be more supportive and understanding of your boss’s idiosyncrasies.

Style Component 4: Delegation

Delegation is a critical method by which successful leaders accomplish their goals and develop their people. Learn what your boss prefers in terms of delegation style. Are they available for questions and follow-up? Do they generally give the why behind the task and show how it fits into the bigger picture? Do they leave the how up to you? Have an open discussion about what frustrates them when delegation doesn’t work the way they envision it. By being more aware of their delegation philosophy, you will be better prepared to deliver and complete tasks that are delegated to you—and it will minimize frustration, rework, and confusion.

Style Component 5: Preferences

Learn your boss’s preferences on a variety of topics. This includes social boundaries with their direct reports, and how open they are about life outside of work. Explore their preferred balance of work life with personal life. Talk with your boss about their preferences around being available to you—about your career, giving feedback regarding your performance, and your taking the initiative on future projects. Knowing your boss’s own preferences will enable you to support them and have a far better understanding of what to expect from them.

Style Component 6: Annoyances

No doubt we all have things that really bug us at work. Your boss is no different. Learn what gets under their skin. Consider the behaviors that have potential for backlash: drop-in conversations, socializing with employees after work, attire in the office, and office gossip or politics. Observe any of these behaviors demonstrated by your boss, and alternatively, their reaction toward what they consider to be others’ annoying behaviors. What is their tolerance toward tardiness, and formality versus casualness? Being more aware of their annoyances will help you avoid being an irritant to your boss and allow you to be more supportive and adaptable.

Actions You Can Take

Have a heart-to-heart chat with your boss to explore how they are evaluated, along with their preferred style around communication, decisions, work schedule, delegation, preferences, and annoyances. The more clarity you have with these aspects, the more likely you are to establish a comfortable and successful professional relationship with them—enabling you both to succeed.

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