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Six Keys to Successfully Working With Your Boss

Thursday, August 1, 2019
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I have been working for several years with a senior executive who possesses a remarkable skill to successfully and consistently work with his bosses. Curious to learn his secret, I interviewed him to learn how he builds and fosters these strong relationships. His response—the six keys shared below.

Key 1: Keep them informed. No surprises!

Never surprise your boss. Your job is to keep them in the loop with everything important to them. Ask them the extent that they wish to be kept up-to-date on each major project or delegated task then follow through with that communication. Learn their preferences for sending and receiving information, so you can gauge your method of communication. There are a few pieces to communicating with your boss:

How? My graduate professor was management guru Peter Drucker. He taught me that bosses are primarily “readers” or “listeners.” Knowing this will determine how you relate to them and how you keep them informed. To help you learn if they are more of a reader or listener, observe if you get better results through oral briefings or written summaries.

When? Within a typical 24-hour cycle, everyone tends to have times that are more productive than others. Discover whether your boss’s peak energy phase is early morning, midmorning, or late at night. This answer, as well as the content and emotional elements of the subject, will determine when you share information with them.

What? Find out the degree of detail they prefer when being briefed. Some bosses only want to know general overviews. Others have a much greater need for detail. Learn this about your boss to keep them fully and accurately informed.

Key 2: Consistently be honest, truthful, and reliable.

Earning your boss’s trust is indispensable. When your boss knows they can count on you, the most critical, engaging, and career-building work gets sent your way. Build trust by following through with your commitments and developing a solid reputation of reliability through your actions, not just your words.

I am going to share with you some age-old advice: Do what you say you will and be consistent about it. Be upfront with bad news and don’t fudge the truth. When mistakes are made—especially if you were the one who made them—let your boss know in a timely manner so alternate plans can be put into action. Your trustworthiness, reputation, and integrity are essential elements of your personal brand. Be steadfast in your resolve to be known as a person that others can count on.

Key 3: Learn their goals and priorities.

To work successfully with your boss, it is imperative you understand the immediate goals they need to achieve to be successful in their role as a leader. When you know how your work enables your boss to meet their goals, you will be able to support them and anticipate their needs. Knowing how your boss gets evaluated gives you insight into how to prioritize your own work. When you understand their long-term goals, you will be able to make sense of their reactions to certain time pressures or commitments.

Key 4: Clarify their expectations.

Knowing your boss’s expectations of you is imperative and will determine your success or failure on the whole and on individual assignments. Too often I have heard stories of employees assuming that they had clarified assignments with their bosses, only to find out later that each had a different view, leading to misunderstanding and frustration. Assumptions are dangerous. Clarity is essential.

To quote business psychologist Peter Stewart, “The definition of frustration is when expectations are unmet.” Minimize or eliminate frustration in the workplace by seeking clarification of what your boss expects of you.

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Key #5: Listen to them.

Your boss needs you to listen. If you fail at listening, you’re inviting a communication breakdown. Aside from taking in the information your boss shares with you, successful listening includes the essential skill of carefully tuning into their nonverbal signals like expression and tone of voice. Zero in on what your boss is saying and how they say it one-on-one and in meetings. Pay close attention to their reactions. Close observations of their nonverbal cues will provide a much more accurate understanding of your boss.

In addition to paying attention to nonverbal communication, show your boss you are listening by using active listening skills. Take a moment to summarize the points they have made and ask clarifying questions to get details.

Key #6: Value their time.

The one limiting resource we all have is time. Respect your boss’s time by being selective in taking it. Strive to be concise and time conscious. Use your emotional intelligence and nonverbal communication skills to sense their moods. Before you take up much of your boss’s time, recognize if you have caught them at a good time.

One way to accomplish this (while valuing your own time) is by asking how much your boss wants to be in the loop during each phase of your job. When you know their goals and priorities you will have a better grasp of what to keep them informed on—and, as a bonus, you will know which pieces of your project are the most critical.

Applying these six keys will take you much closer to enjoying the healthy and positive relationship you need to work with your boss effectively.

Self-Check

I suggest you assess each of these six keys one at a time to determine how well you are doing. Leverage those that you are confident with and take some time to talk over the remaining keys with your boss and figure out how to apply them to your relationship. That conversation usually proves to be productive.

Consider how you would answer these questions about your relationship with your boss:

● How many of the six keys do you use to understand your boss?

● Which do you think you need to work on?

● As you coach a colleague, note which keys would help them be more effective with their boss.

About the Author

John Parker Stewart is the founder and CEO of Stewart Leadership, which he started in 1980. He is globally recognized as a leadership coach, consultant, educator, speaker, and team performance specialist. Under his guidance, Stewart Leadership is recognized internationally for its feedback assessments, training tools, and solid, results-focused coaching services designed to guide teams and individuals to adapt, grow, and reach new levels of performance.

John has coached and trained tens of thousands of leaders worldwide including CEOs, presidents, military, government, and business leaders resulting in significant, measured improvement in individual and team performance.

John has published several articles, manuals, workbooks, and the three book award-winning Stewart Leadership Series. His title book, Lead Now! A Personal Coaching Guide for Results-Driven Leaders, won the National Indie Excellence Award for the best leadership book published over the last five years. His 52 Leadership Lessons is also nationally recognized.

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