Six Keys to Successfully Working With Your Boss


I have been working with a senior executive for several years who possesses a remarkable skill of successfully and consistently working with his bosses.  Being curious to learn his secret, I interviewed him to learn what he does. He shared with me the following six keys that he uses in building strong relationships with them.

As you read through these six keys, consider the extent that they apply to the relationship you have with your boss.

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, and then follow through. Learn their preferences in sending and receiving information so you can gauge your methods of communicating with them as follows:


My graduate professor was the guru of management, 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 when you get the best results from them: through oral briefings or written summaries.


Within a typical 24-hour cycle, all of us tend to have times that are more productive than others. Discover when your boss’s peak energy phases are: early morning, mid-morning, or late at night. Once you discover this about your boss, you can choose when to share information with them—depending upon the content and emotional elements of the subject.


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.

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. The first step in building this trust is to follow through with your commitments. Develop a solid reputation of reliability through your actions–not just your words.

Trust in relationships is so vital that I am going to share with you some age-old advice. Do what you say you will, and be consistent. Be upfront with bad news and don’t fudge the truth. When mistakes are made, especially if you made the mistake, 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 others can count on. Trust is the foundational element of any relationship. Building trust or maintaining trust comes down to how you choose to respond to any given set of circumstances. A poor or careless choice is not one worth damaging a trusting relationship.

3. Learn their goals and priorities

In order to work successfully with your boss, it is imperative you understand the immediate goals they need to achieve in order to be successful in their role as a leader.

When you make it a point to know how your work enables your boss to meet their goals, you will know how you can support them and anticipate their needs.

Pay attention to what your boss is held accountable for by their boss so that you understand their agenda. Knowing how your boss gets evaluated provides you insight into how to prioritize your own work.

Just as you would like your boss to know your career and professional development goals, it’s equally important that you take the time to get a sense of where they want to go. Knowing this means you can understand their long term goals and it will help to make sense of their reactions to certain time pressures or commitments.

4. Clarify their expectations

Knowing your boss’s clear expectations of you is imperative. Being on the same page with your boss determines your success or failure. Too often I have found that people assume that they have clarified assignments with their boss, but in the end, each had a different view. Assumptions are dangerous. Clarity is essential.

To quote my son, business psychologist, Dr. Peter Stewart, “The definition of frustration is when expectations are unmet.” Minimize or eliminate frustration on both your, and your boss’s part, by seeking clarification in what they expect of you.

In addition to clarifying their expectations of you, pursue clarification in potential problem areas. For example, ask your boss where your boundaries are so that you minimize the risk of turf wars with your peers. Other potential problem areas include schedules, budgets, and methods. Ask the questions needed to ensure the two of you are in full agreement.

5. Listen to them

Your boss needs you to listen! If you fail at this, then you invite 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. Studies on communication suggest that 80% of all communication represents everything that is nonverbal including reading eyes, face, tone, mood, pace, urgency, dress, body language, energy, and many more signals that indicate your boss’s emotional state.

Zero in on what your boss is saying and how they say it. As you talk to them, pay close attention to these reactions. Do the same in meetings. Close observations of their nonverbal cues will provide you with a much more accurate understanding of your boss.

In addition to paying attention to all of the non-verbal communication that is happening, show your boss you are listening by using active listening skills. To do this, take a moment to summarize the points they have made and then ask any clarifying questions to get the details you need. Make sure you have the full picture–especially if you are getting information on something that is your responsibility.

6. Value their time

The one limiting resource that we all have is time. Respect your boss’s time by being selective in taking it. Many bosses have shared with me their frustrations in dealing with high maintenance employees or unnecessary drama.

In general, strive to be concise and time-conscious. Use your emotional intelligence and non-verbal communication skills to sense their mood. You may have caught them at a time where they can talk casually with you, or you may have interrupted them when they are working against a tight deadline or agitated for some unknown reason. 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. By knowing 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 seen as 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 very productive.

Critical Questions to ask yourself:

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

  • How many of these six keys do you use in understanding your own boss?
  • Which of them do you feel you need to work on?
  • As you coach a colleague, note which of these six keys would help them be more effective with their boss?