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Dealing with a difficult boss

Bosses can be difficult in a wide range of ways. For instance, they may constantly change their minds, be unavailable, or micromanage every aspect of their people’s work. Some might even verbally abuse employees or manipulate direct reports with promises of promotions that never materialize.

If you have a difficult boss, no matter what kind, I believe there are some basic tactics you can employ to manage the situation:

  • Understand your boss’s objectives. Identify your boss’s objectives (such as “climb the corporate ladder” or “stay put until retirement”) and determine how they differ from yours. Assess how such motivations might affect your boss’s behavior. Then use that knowledge to figure out the best strategy for supporting those objectives without compromising your own.
  • Show how you’ll support your boss. Focus on helping your boss with the tasks he or she is weakest at but take care not to criticize. Criticism in this aspect would not do you much help.
  • Head off confrontations. If your boss does something that angers you, take a deep breath and give yourself some time before responding. When you do respond, keep your manner professional. My suggestion would include going for a run or sweat it off by going to a gym.
  • Document your job requirements. List all the projects and tasks your boss expects you to do. If your boss keeps coming up with more and more things for you to handle, bring out your list. Then explain how you’ll need more staff to take on the additional to-dos.
  • Get advice from your boss’s former employees. Contact someone who used to work for your boss. Explain that you’d like his or her insights about working with and learning from your boss. Frame the meeting as a tutorial for you, not a complaint session. Keep in mind that anything you say could make its way back to your boss, so edit yourself accordingly. Avoid complaining about your boss to his/ her former employees, even if they do, since they still might be in close contact with your boss.
  • Take care of yourself. Having a difficult boss can be bad for your health. To avoid stress-related health problems, focus on what makes you happy about your job, not miserable. Choose to pay attention to the people you’re glad to see at work, and concentrate on the work you enjoy. Whenever possible, take on projects that let you spend time in other parts of the organization or with other leaders. Identify one or more mentors who can give you things you aren’t getting from your boss, like feedback, instruction, and encouragement. Try not to let this one person ruin your day, job, or career. Concentrate on the positivity and let the negative emotion come and go.

In addition to these basic strategies, you can tailor your approach to the specific type of difficult boss you’re dealing with, whether he or she is:

  • Hands-off
  • Absentee
  • Insecure
  • Self-focused
  • Micromanaging
  • Conflict-averse
  • Plays favorites


If your boss has limited knowledge of the details of the business, is uninterested in the status of your projects, and doesn’t follow up to ensure that agreed-upon actions have been taken, you’ve got a hands-off boss.

Having a hands-off boss can have both advantages and disadvantages. On the plus side, though your manager is less engaged than you prefer, you likely have significant autonomy in managing your workload and making decisions. On the minus side, you may feel a lack of support when problems or questions crop up.

Here are strategies for dealing with different kinds of hands-off managers:

Try to avoid complaining about your boss to others; it won’t improve the situation or your relationships within the organization. Instead, accept that your boss’s behavior isn’t ideal, and make the most of the freedom you have to take the initiative on your own.


If your boss is never around, seems psychologically distant, and doesn’t meet with you regularly to fill you in on critical decisions in the organization, you’ve got an absentee boss.

This disconnect could have a number of causes. Maybe your boss is busy with other projects, is feeling burned out, or has become bored in his or her current role. Whatever the reason, having an absentee boss could make it hard for you to get the information and resources you and your team need to meet business goals.

Manage your absentee boss with these tactics:

  • Schedule time together. Try asking your boss to meet with you more often or to give you more feedback. But try to do this at your boss’s preferred time.
  • Make the most of meetings. Be prepared and efficient when you do get together.
  • Keep your boss informed. Provide your boss with regular, brief reports. When something important comes up, send him or her a short note that outlines the issue.
  • Build relationships. Network with colleagues and with others outside your organization so you can exert the influence needed to advocate for your team in ways that your boss is not.
  • Get to know your boss’s support staff. You can often get responses to questions through them.
  • Volunteer. Offer to take on tasks your absentee boss doesn’t enjoy; you’ll help him or her out as well as develop your own skills.


Ideally, bosses and the people they manage work in partnership, with all parties feeling competent and confident in their position on the team and in the organization. But some managers are insecure in their roles and uncertain about their abilities. They may act defensively in response to people’s opinions or suggestions, regardless of how respectfully those are presented.

A manager who is reluctant to seek your input, ignores your ideas, or punishes you for speaking up is likely insecure. Your boss may take employee suggestions as personal criticisms and aggressively stifle good ideas because of his or her own insecurities.

To manage an insecure boss:

  • Understand the cause. Evaluate any external factors that may be causing your boss stress, such as looming deadlines or pressures from senior management. Make a point of striking a collaborative tone in your interactions.
  • Build trust. Alleviate your manager’s fears and gain his or her confidence by sharing as much information as possible.
  • Give feedback carefully. Insecure bosses find constructive criticism threatening, so before providing your manager with feedback, highlight his or her positive qualities and accomplishments. Also, reduce your manager’s defensiveness by offering your comments in private rather than in front of other team members.
  • Emphasize potential gains. If you are recommending any kind of change, underscore the potential gains. Avoid implying that your boss caused the problem you are seeking to solve.


Self-focused bosses are so career-oriented that they may see others simply as tools for advancing their own agendas. Some may even take credit for others’ achievements, or hold others back so they can get ahead.

Such bosses often spawn people problems in their teams, like low morale, burnout, and erosion of engagement and motivation. And if such team problems arise from other causes, a self-focused boss might not notice them or care about resolving them.

To manage this kind of boss:

  • Own the problem. Rather than seeing yourself as a victim, take responsibility for improving your relationship with your boss and getting your own career needs met.
  • Look for alternative explanations. Consider whether there might be other explanations for what you perceive as negative signals from your boss. For example, if your boss excludes you from meetings, it may be that he finds smaller meetings to be more efficient, not that he’s intentionally keeping information from you.
  • Suggest ways to balance people and projects. Embrace his or her goals, while offering periodic reminders and recommendations about people issues that need addressing.
  • Set an example. Treat your boss as you’d like to be treated. Or better yet, treat your boss the way that he/she like to be treated, but in order to do this, you need to understand and know what your boss like or doesn’t like.
  • Speak up. If you haven’t managed to subtly change the dynamic with your manager, engage her in a constructive conversation. Set a positive tone by indicating that you want to find better ways to support her. Also indicate how you hope she can help you in gaining new skills and experience.


If your boss constantly scrutinizes and criticizes your work, he or she is micromanaging. This kind of boss is not only annoying; the seeming lack of faith in you could make you doubt yourself and stunt your professional growth.

To deal with this type of boss:

  • Keep your boss up to date. Understand that micromanaging often stems from internal anxiety and a need to control situations—so keep your boss informed of your progress, take your ideas to him or her before sharing them with others, and bring him or her any news you hear.
  • Be reliable. Earn your boss’s trust by succeeding in dimensions he or she cares about most, such as on-time delivery of projects.
  • Seek guidance. If your boss is micromanaging because he or she has high standards or because you do, in fact, need to make improvements in specific areas of your job, treat it as an opportunity to learn from you boss.
  • Create ground rules. Agree with your boss up front about how he or she will be involved in projects, what role each of you will play, how you’ll measure success, and what the high-level guiding principles for the work will be—not the details.
  • Free up your boss. Tell your boss that he or she is better off not getting involved in the details of a project, because “Your time and effort are more important and valuable for the big picture.”


If you have a conflict-averse boss, he or she might avoid advocating for you and your team with others in the organization. As a result, you don’t get the support and resources you need. Your manager might also avoid difficult conversations, even if they’re about important issues such as serious interpersonal conflicts in your team that need discussing. As a result, such issues remain unresolved.

To manage your conflict-averse boss:

  • Make conflict more comfortable for your manager. Express disagreement using gentle language such as “This may sound like a crazy idea, but…” and ease into awkward conversations by talking about something neutral first.
  • Ask “what if” questions. Propose different scenarios to get your boss thinking about how dealing directly with a conflict could help serve business needs.
  • Strike a neutral tone. Focus difficult conversations with your boss on problem solving, not the personalities involved.
  • Provide documentation. Gather supporting evidence to help your boss advocate for resources your team needs.

Plays favorites

Maybe your boss has a favorite employee, someone who gets the most interesting assignments and special perks. She invites this person to social events, confides inappropriately in him about “problem” colleagues, and acts like they’re old friends.

Favoritism especially shown to an average performer can demoralize you and the other members of your boss’s team and cause you to miss out on valuable resources and attention. But because your relationship with your boss is key to your success, it is important to put effort into improving it.

Here’s what to do about it:

  • Use a sounding board. If you feel that your boss isn’t treating you fairly, find someone outside the organization to talk to who can help put things in perspective. Avoid complaining to your coworkers since it won’t change things and may create a negative tone on your team.
  • Take the high road. Don’t take your frustrations out on your boss’s favored employee. That person isn’t the source of the problem. Instead, focus on your own successes. Look for ways to boost your career and your connections to others in the company.
  • Watch and learn. Observe your boss’s favorite in action and make note of how he or she interacts with your boss. You may want to adopt some of his or her behaviors but only if doing so feels authentic to you.
  • Build bridges. Create goodwill by getting to know your boss and his or her favorite better. Ask the favorite for advice on how to improve in your job. Regularly check in with your boss to discuss his or her priorities and progress you’ve made on them. Ask for more challenging assignments, and volunteer for tasks that others don’t want to take on.
  • Seek out mentors. If you’re not getting the career guidance you need from your boss, identify other managers who can provide you with feedback and coaching.
  • Move on. If your relationship with your boss doesn’t improve and you’re not getting the opportunities and guidance you want, consider looking for another job. It’s not worth staying in a situation that drains your energy and keeps you from growing in your career. Continue to contribute to the best of your abilities while pursuing other options.

If you are interested in reading more about this subject, I would recommend a book, entitled “Coping with difficult bosses”, by Robert Bramson. I ensure you that the book is an interesting read.

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Giving your boss feedback

You see your boss in a variety of settings, client and team meetings, presentations, one-on-ones, negotiations. That gives you insight into his or her strengths and weaknesses and their impact on others. You may wonder if you should share your observations with your boss.

Providing feedback to your boss is tricky. But if you share your observations in the right way, you can help him or her and strengthen your partnership. In fact, when managers don’t know how others experience them, their performance can suffer. Your input can help your boss see him- or herself as others do. As a result, your manager can make valuable behavioral changes.

In order to give your boss constructive feedback, here is what you should do –

  • Wait to be invited. Even if you have a great relationship with your boss, resist any urge to launch into unsolicited feedback. Some bosses request feedback at the end of a formal review. Or, when you first start working together, your boss may share his or her development areas and ask you to keep an eye out for certain behaviors he or she is working on. If your boss doesn’t directly request feedback, ask if he or she would like it. Do this in the context of a new project or client.
  • Don’t offer feedback if you’re uncertain how it will be received. If you’re not sure your boss wants feedback or if the subject in question is sensitive, it’s better not to speak up. Instead, look for opportunities to comment anonymously, such as through a 360-degree feedback process. Of course, if you think your boss’s behavior is putting the company or your unit in jeopardy in some way, follow the appropriate channels in your organization.
  • Share your observations. Focus your feedback on what you’re actually seeing or hearing, not what you would do in your boss’s place. Open with something positive. Then offer constructive comments and ideas for improvement.
  • Re-frame your feedback if your boss gets upset. No matter how thoughtfully you’ve prepared and delivered your feedback, your boss may still get upset or defensive. If that happens, re-frame your feedback in terms of what your boss cares about most. Point out how specific behaviors may be making it hard for your boss to achieve his or her goals. Then gauge your boss’s reaction to determine how he or she prefers to receive feedback and what topics your boss does or doesn’t want to discuss.
  • Time it right. Make sure that you give the feedback at the right timing. At times, the effectiveness of a message is not in the content but rather on the timing of the message.
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How to establish credibility

It’s a note worth taking a look at.

Credibility is the cornerstone of persuasion and negotiation. If you don’t have it, your boss may not commit time or resources to ideas you’re proposing.

Credibility can be understood like this:

Trust + Expertise = Credibility

The more trust you earn from your boss and the more expertise you accumulate, the more credible you and your ideas will become to your boss.

To earn your boss’s trust:

  • Be sincere. Demonstrate your conviction that your idea is worth your boss’s time and attention. A supervisor who sees you as sincere and committed will be more likely to trust you.
  • Follow through. Follow through on promises and commitments you’ve made to your boss. By consistently fulfilling the responsibilities you’ve taken on, you also foster your reputation for being trustworthy.
  • Welcome suggestions. Listen to your boss’s concerns. You’ll demonstrate openness to his or her perspectives.
  • Put your boss’s best interests first. When you show that you have your supervisor’s interests in mind, he or she will trust you and your ideas more.
  • Own up to your flaws. When you own up to your flaws, your boss will see you as a truthful and therefore trustworthy person. That’s because most people try to conceal their faults.
  • Open-minded attitude. Be open to constructive feedback as you go along with your daily work and show effort in addressing your weakness and feedback that you received.

To demonstrate your expertise to your boss:

  • Research your ideas. Find out everything you can about ideas you’re proposing. Talk with knowledgeable individuals. Read relevant sources. Collect pertinent data and information to support and contradict your ideas. That way, you’ll be well versed on your idea’s strengths and weaknesses.
  • Get firsthand experience. Participate in cross-functional teams. You’ll gain new insights into particular markets, products, or business processes. You can then draw from this knowledge and experience in presenting ideas to your boss.
  • Cite trusted sources. Support your proposals with knowledge gained from trusted sources within or outside your organization.
  • Prove it. Launch small pilot projects to demonstrate that your ideas deserve serious consideration.
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Listen and ask questions with your boss

Effective two-way communication is vital to managing your relationship with your boss. The ability to listen to what your boss is saying and how he or she is saying it is just as important as conveying your own message clearly and succinctly. By being attentive to the explicit and implicit messages your boss is communicating, you can ensure that you and your manager are in alignment on tasks and priorities.

During every encounter with your manager, let him or her know about any questions you have and any areas requiring clarification.

Listen actively to your boss’s responses by:

  • Offering verbal feedback (“I see” or “I know what you mean”) and nonverbal feedback (nodding or smiling) to indicate your understanding
  • Paraphrasing what your boss is saying to check that you’ve understood correctly
  • Withholding judgment of whatever your boss is saying, to show interest and empathy

Also use questions to:

  • Be proactive.
  • Find out what kinds of information your boss wants from you, how often, when, and in what format
  • Gather new insights about your manager’s priorities, expectations, concerns, and viewpoints
  • Show interest in your boss’s business objectives
  • Check for agreement on critical points
  • Continue building trust and rapport
  • Verify or clarify information your boss has imparted to you

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Asking boss for what you want

Many people feel uncomfortable approaching their bosses to discuss salary, promotions, and professional development opportunities. But unless you do, you are unlikely to get what you want. By discussing your needs, you open the door to a win-win situation: You gain something in terms of your career progression, and your boss and organization benefit by motivating and retaining a valued employee. You will never get what you never asked for.

To conduct a “here’s-what-I-want” conversation with your boss:

  • Prepare your case. Collect information to support your request, whether it’s from online salary surveys or company benefits packages. Document your accomplishments, including your and your team’s recent performance. And show how any professional development opportunities will benefit your organization by providing you with valuable new skills. *
  • Take a collaborative approach. Link your request to your boss’s needs. Ask open-ended questions, such as “How can we make this a win for you?” Listen and ask follow-up questions, but be sure to circle back to your request.
  • Understand the context. During the conversation, collect data to inform your negotiation strategy. For example, if you’re planning to ask for a promotion within the next year, ask what skills and experience you’ll need to be eligible. You might learn about new areas your organization will be focusing on—something that could help guide your professional development plan.
  • Use “what if” responses. One way to build on your boss’s responses to your request is to prepare “what if” scenarios—specific actions you could take in different situations. For example, if your boss says you need more cross-functional experience before you can advance, you might reply with “what if” ideas for how you could get that experience. These might include collaborating with another department on an upcoming project or participating in a one-day role swap with a peer in another functional area.
  • Be open to a Plan B. Even if you make a strong case, there may be circumstances that cause your boss to reject your request. If so, explore other ways to meet your needs. For example, if your boss can’t give you a raise for budgetary reasons, he or she might be open to alternatives such as extra vacation, more job flexibility, or paid continuing education.
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Your boss expectation of you

I’m sure that almost everyone at some point in their career life wondering about their bosses expectation of them. At a minimum, your boss expects you to –

  • Produce. You need to create the expected results your boss has to answer for. You can do this by achieving your team’s goals such as: reach sales targets, improve productivity, reduce costs, or meet deadlines.
  • Collaborate. You should be working with colleagues across the organization, including getting involved in cross-organizational projects, to support your boss’s and the company’s priorities.
  • Be reliable. This means fulfilling your commitments, including achieving goals on time. Basically, just get your job done.
  • Share information and ideas. Your boss counts on you to share good news, such as positive results from an experiment, as well as bad news, such as delays or mistakes in a project. He or she needs both kinds of information to make smart decisions. Your boss also wants you to share your ideas to spark innovation.
  • Resolve your team’s difficulties. You should be ready to step in if one of your direct reports falls behind with his or her commitments, if an interpersonal conflict develops, or if a crisis erupts.
  • Stay current. Pay attention to the news. What happens in the world affects what happens with your team, your company’s marketplace, and the organization’s competition. Also, know what’s going on with your organization’s customers and competitors—how they’re changing, and how technology and world events are affecting their plans.
  • Brilliant at basic. This mean that you are fully competent at your job function regardless of your age, work experience and educational background.
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Your boss’s boss

Your boss advocates for you and supports your career development. But he likely still has to get the approval of his boss for your pay increases and developmental opportunities. To better understand your role in the organization and advance in your career, it can be helpful to establish your own relationship with your boss’s boss.

Here is some tips on how to get to know your boss’s boss:

  • Interact. Greet your boss’s boss when you see him/her. But make sure to be polite and appropriate, don’t seem to be pushy.
  • Reach out. Communicate with your boss’s boss when opportunities arise; for example, send a congratulatory email if he/she gets a promotion or award. Make the email personal, not a gimmick to show off to your fellow colleague.
  • Ask for advice. Get your boss’s okay to email his boss (copying your manager on the message) to ask for advice. For instance, maybe you’d like suggestions on courses you’re thinking of taking or professional organizations you’re considering joining. Make your own boss look good in these emails by writing something like, “Michael thought you’d have some good ideas about this.” For example, ask for honest feedback.
  • Extend invitations. If you’re giving a presentation or your boss is leading an important meeting, ask your boss if it’s okay to invite his boss.
  • Pass along praise. If you receive praise from a customer or other key stakeholder, send it along to your boss. Your manager will likely pass it along to his boss, since your success makes your boss look good too. This is what I called ‘shared success’.
  • Volunteer for a cross-functional team. Leading or taking part in a cross-functional effort helps you contribute to the larger organization—and that makes you more visible to your boss’s boss.
  • Fix a problem. Find a way to make an improvement that furthers your organization’s goals or supports a core value. Share the results with your boss and his boss.
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Extra benefit of managing your boss

Among other benefit in addition to getting you the information and guidance, insight, resources, and development opportunities you need, effectively managing your boss helps you:

  • Make difficult decisions. Your boss will be better able to support you by providing advice, drawing on his or her knowledge of how things work in the organization, and seeking insights from higher management.
  • Navigate change. If your organization is experiencing major change, such as acquiring a business or adopting a new competitive strategy, your boss will be more likely to help you navigate through the inevitable turmoil.
  • Boost your effectiveness. Your boss can increase your influence within the organization, buffer you from office politics, and work with you to arrive at solutions to problems facing your team or company.
  • Get the most from available resources. Your boss can support you in getting the expertise and resources you need to achieve your goals and in making good use of them.


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Tips on managing long-distance boss

At times, especially in a multinational organization, you will experience a case of long distance relationship with your boss. Partnering with your boss when you are in separate locations presents a different set of challenges than when you are in the same building. When your main means of communication are electronic, whether email, phone, or video call it can be difficult for the two of you to stay aligned.

So, here are some tips for staying in step with a boss in a different location:

  • Be disciplined about holding regular meetings. Once you have created a meeting schedule, protect those times. Ensure that you and your boss don’t fall into the habit of postponing or canceling them.
  • Determine norms for communication. This includes which communication channels you and your boss will use and how you will use them. It also means having explicit agreements concerning response times for queries how quickly you should expect a reply from your boss and vice versa.
  • Establish clear and comprehensive metrics. By setting up ways to measure and report on the results of your activities, you ensure that your boss has a good sense of where things stand on your team.
  • Schedule periodic face-to-face meetings, if possible. This is especially important early in your relationship. In-person connections can go a long way toward establishing mutual trust.
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What managing your boss is?

Managing your boss is one of the essential skills in the corporate world, one of the skills which I deemed quite difficult to master. Therefore, it would require some time to look into.

A boss or supervisor is someone who assigns work, provides motivation, and typically oversees direct reports’ performance.

In many organizations especially those with matrix structures or project-based teams an individual may report to multiple bosses, including ones in different time zones or even different countries. In all cases, learning to manage your boss or bosses is essential to your mutual success and to the success of your team, project, and organization.

Managing your boss can be defined as the process of taking the initiative to:

  • Build a strong working relationship based on mutual respect and understanding
  • Consciously work toward mutually agreed-upon goals
  • Collaborate to make decisions that benefit both of you as well as your organization

Managing your boss isn’t:

  • Political maneuvering
  • Manipulation only for the sake of advancing your career
  • It is not ass-kissing.