Leadership: Managing Up to Your Boss in the Workplace | Monica Thakrar | Skillshare

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Leadership: Managing Up to Your Boss in the Workplace

teacher avatar Monica Thakrar, Organizational Consultant and Coach

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Taught by industry leaders & working professionals
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Watch this class and thousands more

Get unlimited access to every class
Taught by industry leaders & working professionals
Topics include illustration, design, photography, and more

Lessons in This Class

    • 1.



    • 2.

      Understanding Your Boss


    • 3.

      Communicating and Trust Building


    • 4.

      Anticipating Your Boss' Needs


    • 5.

      Influencing Your Boss


    • 6.

      Final Thoughts


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About This Class

Improve your working relationship with your boss with Organizational Consultant and Coach, Monica Thakrar! 

We’ve all had bosses where we have had to navigate working through some tricky situations. While it can seem tough, there are some very practical ways to understand and get to know your boss so that you can be an asset to the team and be able to raise issues with them that they may not be seeing. Join Monica as she walks you through the tools to better examine your own role in being able to navigate working most effectively with your leader. 

Together with Monica, you will:

  • Understand who your boss is
  • Communicate and build trust with your boss
  • Anticipate your boss’ needs
  • Influence your boss

Whether you are an entry-level or mid-level employee, this class will help you become more savvy in working with leaders and those to whom you report. 


Monica’s class is designed for all students to participate and enjoy.

Meet Your Teacher

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Monica Thakrar

Organizational Consultant and Coach


Hello, I'm Monica. I am an organizational consultant and coach based in Washington DC. I have 18 years of experience working with medium and large scale corporate and government clients leading large scale change, teaching leadership classes focused on soft skills such as  emotional intelligence, conflict resolution, presentation skills, and mindfulness. I also am an executive coach helping leaders gain skills and grow in their leadership journey.  I am most passionate about helping leaders and organizations grow into their fullest potential. Sample clients include Marriott, NASA, MedStar, National Science Foundation, and Columbia University.

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Level: All Levels

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1. Introduction: Have you ever wondered how to navigate working with your boss, whether you have a difficult one or one that you like? Well, you are in the right class. [MUSIC] Hello, my name is Monica Thakrar and I'm an Organizational Development Consultant and Coach based in Washington DC. I have 22 years of experience doing a mix of leadership training, executive coaching, and change management consulting for commercial and federal clients. This class is all about managing up to your boss through the following key steps. First, understand who your boss is, second, communicate and trust-building with your boss, third, anticipate what your boss needs and finally, influence your boss. I'm really excited to talk to you about this very important topic, as we've all had bad bosses where we've had to navigate working through some tricky situations. I know I had to navigate many different bosses in my 10-year corporate career prior to becoming my own boss. Now, I work with hundreds of managers who have dealt with these problems themselves or with their employees managing up to them. While it can seem tricky, there are some very practical ways to understand and get to know your boss so that you can be an asset to the team and be able to raise issues with them that they may not be able to see. The project for this class will be a working document where you can answer questions about your boss, that will give you much more insight about them, understand their style, as well as how to anticipate what their needs are. Finally, it will include a space to plan how to raise an issue and influence them on that topic. I'm excited to walk you through this class today so that you can become more savvy in working with leaders and those to whom you report. Let's get started. [MUSIC] 2. Understanding Your Boss: What does it take to manage up? Well, the first step in being able to effectively build a great relationship with your boss and thereby influence them, is to learn more about who they are. By getting to know your boss, you can understand them better and learn what is truly important to them. By doing that, you're gaining an understanding of who they are, how they operate in the organization, as well as what is important to them and why. Some things to think about when getting to know your boss better are the following. What are their priorities? What are their strengths? What keeps them up at night? What is important to them, and how are you making sure you find that out regularly? If your boss does not set up a weekly or regular meeting with you or your team, ask for them. Spend some time getting to know your boss over coffee or lunch. Get familiar with what is going on for them so that you can understand how they operate and what their focus is on. Just like with anyone else, the more we care and show that we care, the more that person is going to want to work with you. It also helps you to get to know them as a human being so that you can build rapport and thereby a good working relationship with them. This means getting to know a bit about their family and their interests outside of work. Relationships are all about trust, insight, as well as understanding. By getting to know your leader and what is really important to them, you gain valuable tools to help to influence them when needed. An example in my own situation, my own life, I worked for a woman who was one of my senior leaders in my organization when I was back in the corporate days, sometimes we would grab lunch or coffee and just talk. I got to know a little bit more about her husband who had some health issues. I got to understand that she really valued education and teaching. That's why she really loved spending a little bit more time with me and mentoring me. But getting to know that really helped build our relationship and how we worked together. Look in your class project workbook and answer the questions there about your boss. If there are questions that you cannot answer, consider setting up some more time with them or use time in your regularly scheduled meetings to be able to ask them some of these questions in order to get to know them better. As we get to know them better, we can determine what things we can support them on, spearhead or take on for them. 3. Communicating and Trust Building : The second step to managing up is communicating effectively with your boss and building trust. You can build up your relationship with your boss by understanding how they like to be communicated to and how they like to be interacted with, and adjusting your style to do so. For example, do they prefer to communicate in person, via phone, via video conference or text, or something else? Is there a time of day that they are at their best? How do they like to be briefed - very high level and outcome-oriented or very detailed and specific or somewhere in-between? By understanding the communication needs of your boss, you can get them to hear you better. As communications professionals say, the best way to be heard by anyone is to communicate in the way that the other person can hear you. That means tailoring the way that you speak to how the other person would like to hear it. This does not mean changing your entire personality, your way of being, but it does mean adjusting your style in some ways, especially in important moments in order to be heard. In the behavioral assessment called DiSC, there are four different styles, dominant, influencer, steady, and conscientious. Each of these styles have a different behavioral focus, but also prefer to be communicated to differently. If you can understand which style your boss is, then you can adjust your style to meet their communications needs. Let's go through each of the four behavioral styles and how they like to be communicated to. First, the dominant is very results-oriented and outcome-focused and likes to be communicated to the bottom line upfront. The influencer is highly optimistic and social and likes to be communicated to first by connecting to them as a person, rather than just business. Ask them about their weekend or their family before launching into work topics. The steady one prefers teamwork, steadiness, and cooperation, and in communications, likes to take things slow, so don't come on too strong or expect a decision right away. Finally, the conscientious one is very analytical, quality-focused, and into facts and figures. Make sure you have all of the details ready when speaking to them as they will want data to be able to move forward. A way to understand what style your bosses is really by looking at them while you're communicating. Are they glossing over when you are getting into so many details and don't really pay attention? Or are they rushing you when you are focused so much on going through all the facts and figures? Do they really stumble when you've asked them to make a quick decision? Thinking about things like that, understanding those four styles can be really beneficial. As you can see, with each of these four styles, you can tailor how you communicate based upon how your boss typically likes to receive information. Therefore, you'll be much more effective. The other way to connect with your boss is to make sure to build trust with them. As Stephen M.R. Covey says, the son of Stephen Covey in the book, the Speed of Trust, trust is built in three different ways, character, competence, and communications. Character trust is being honest, having integrity, and following through on the things you say you're going to do. Competence trust is being able to do the things that you say that you're going to do. That means being good at the work technically and being able to get it done. Finally, communications trust is that you're open, transparent, as well as timely in communicating things to people, especially to your leader. For you to build your relationship of trust with your boss, be sure to show these three characteristics to them so the trust can be there. While for some leaders, trust will come over time and with verification, for others, it will come quickly and remain there by continuing to show these three characteristics. Overall, by communicating in the way your boss can hear you and exhibiting trustworthy behaviors, you can build up your relationship with them and become a go-to person. Ultimately, that will pay off in being able to manage up and provide input to your boss when the need arises. Take out your class project worksheet and jot down answers to how your boss likes to be communicated to and which style you think they are in terms of the DiSC profile. Jot down how you might need to tailor your communications approach as a result. Also take time to think through where you are showing up in terms of trust with your boss, and where, if at all, you may have some work. 4. Anticipating Your Boss' Needs: Our third step in learning how to effectively manage up is beginning to anticipate the needs of your boss. By implementing the first two steps, understanding them, and communicating and building trust with them, you will already have taken a huge step in knowing how your boss works, and what makes them tick. In this step, you will now work to take some of the burden off of your leader by being proactive and starting to take actions off his or her plate. Think ahead a few steps on a project, and begin to implement or do some things before your boss asks for it. Build a strategy for something new that your boss is thinking about, and present it to them as a first draft. Open up possibilities of something new that he or she wasn't thinking of yet, but you thought would be aligned to his or her purpose. Being proactive versus reactive is a great way to build influence with your boss. I had one employee who is always thinking two steps ahead of me on training courses by creating surveys, preparing things I could look at, and turning things around quickly so that my trust levels of her really increased. As a result, I knew that she was a go-getter, and could get things done. Also, the more she anticipated what I needed or what the program needed, the less I had to think or worry about those things which was a huge asset. Being proactive builds confidence, and trust in your leader that you are able to problem-solve, and don't have to be monitored a lot. In fact, it provides some relief for your boss in terms of what they need to do. They will appreciate you and look to you as a trusted team member. Other ways to be proactive, are to continually be learning about the business you're in, and what your boss and team are working on. Continually looking for ways to enhance how your job is being done, and how your boss or team's work is being done can be a great way to add value, show your initiative, and show your boss you're trustworthy, and a team player. This will also set you apart from others as your boss will see you as someone who is going above, and beyond. Here is a five-step process to being more proactive. First, be curious, seek out knowledge, learn, and be open to new information. Next, get to know people in other functions within your organization. When you develop a curious mindset, you will want to reach out to people, and colleagues of different backgrounds, and expertise. Third, ask questions, successful proactive people are intentional about gathering information. Fourth, connect the dots, once you obtain information, you have to figure out how the information works together. Proactive people connect the dots to uncover what could happen in the future. Finally, make a conjecture, and then test it, once you gather information to help you think towards the future, you might arrive at a theory about what may occur, consider testing out your idea. Take out your workbook, first jot down where you're strong on this list above of those five items. Next, jot down what area you need to work on, and what are some ways that you can do that. Finally, think of some things that you can be proactive with at work, to help your boss out, and write those down. 5. Influencing Your Boss: The final step in managing up is influencing your boss. Now that you are showing your value through being proactive, taking work off of your boss's plate, and really understanding and communicating to your boss in the way that they can hear you. You've built up the ability to influence them in different areas. With your boss trusting you, they are much more open to hearing your ideas, suggestions, as well as feedback on things. When your boss sees that you understand them and are working to make the team and his or her job easier, they will be much more open to receiving ideas from you. How can you influence your boss? Well, there are a couple of ways. The first is influence based upon information or data that you are seeing in the organization that may need a change. For example, when I was a manager in a consulting company doing change management work, I noticed that my own team members were nervous about a change that we were going through ourselves as a team. My boss who was a senior-level person and the one I mentioned before was not aware about this nervousness due to her seniority and I was able to bring her information that helped her to then take action and put together a session to walk us through how to handle the change. Being a mid-level leader, sometimes we hear things that senior level people do not. Raising it to them is helpful and good for the overall team dynamics. The second is seeing issues and raising them with suggested solutions. Being able to be proactive again, by offering solutions for problems you're seeing or hearing about is again, a great way to manage up to your boss. It shows your resourcefulness as well as strategic and creative thinking skills. Identify a problem and when you present to your boss, be sure to share some data or emotions on why the change is needed so that your boss has a business case on moving forward. Data or emotions are two great ways to make a business case, either appealing to the head or to the heart of your boss, depending on how they best receive information. With one boss in the past, I was able to identify gaps in courses that we had in terms of training for our people. Once I gather the information from our training evaluations, I was able to then suggest different courses that we should offer to our students based upon the gaps that we were seeing. These are great ways to be able to influence your boss and be able to share information in order to try to influence them in the direction you are suggesting. While they may not always make the decision you are looking for, they are open to input from you and will likely talk through why they did not make the decision in the direction you are suggesting. In your workbook, write down a situation you would like to influence your boss about. Begin to think about how you would raise it to them. Would it be with data or with emotion? Write down the situation as well as the recommended solution or solutions you would like to take to him or her. 6. Final Thoughts: I know these tips and tricks have worked so phenomenally in my own life. Having many, many bosses over the years, I've had to really implement this by getting to know them, anticipating their needs, and really making this work has really helped me as I work with different leaders across the board, back in corporate and even now in my own business. I also talk to a lot of leaders who spend a lot of time talking about managing up. A lot of these solutions around data, emotions, and bringing solutions have been really impactful when they're actually trying to build that relationship because they realize they're taking a lot of things off their boss's plate by bringing the solutions to them. Now you know the fundamental steps of managing up to your boss, understanding them, building a relationship with them through communications and trust, being proactive, and influencing them. I hope you have found this to be a helpful class and can take the planning workbook that you have created along the way to begin to take the necessary steps to manage up to your leader effectively. Remember, building up the relationship is key to managing any situation. For it is the person that matters the most. I look forward to any comments or questions that you may have in the discussion section of the class. I will be happy to answer anything that's on your mind. I look forward to seeing you in another class soon.