start⬆Mngr handbook pt. 7: How do I make my boss happy?

start⬆Mngr handbook pt. 7: How do I make my boss happy?

First, a personal story.

After spending two years as a decent individual contributor, I was promoted to team lead. It would be the first time that I manage people. How exciting!

In my first few weeks as manager, I didn’t really do anything different, aside from having one-on-one talks with my new direct reports. I didn’t change how I interacted with my boss, and continued to hold bi-weekly meetings to report on my priorities. I let operations run as normal and only intervened when team members needed my help.

Everything seemed great at first, but after a few months, I started to feel like I wasn’t doing enough, and wasn’t growing as a leader. I had a rough sense of how my team was supposed to help advance the company, but I didn’t know if our innovation initiatives were aligned with that of other teams. Yet I didn’t want to bother my boss with my problems; I didn’t want to reveal that I felt insecure in my new position.

Every week that passed felt worse and worse. I started to feel incompetent as a manager, unsure of where I was supposed to lead my team. My boss rarely provided feedback, so I didn’t know whether my team and I were successful.

One day, I finally rallied up the courage to tell my manager: “I don’t know if I’m successful or not. I don’t exactly know what results are expected of my team. We work on a ton of projects, but I don’t know how they relate to the overall company mission. I also don’t know if I’m acting as a good leader and would like some mentorship and coaching.”

What ensued was one of the most productive conversations I’ve ever had. Turns out, my manager made the assumption that I knew how our team’s priorities related to other company initiatives, so it was never discussed with me. We took the time to clarify all of that. On the management coaching side, my boss also didn’t know I needed it as I was doing fine. We then setup a mentorship plan, and also involved another manager at the company so that I could get two perspectives instead of just one. That night, I felt relieved and re-motivated. I found clarity on what was expected of me. I was confident that my team was advancing toward the right direction, and I personally had access to two mentors to guide me.

What did I learn? That not having clarity on what my boss expects of me leads to a stressful, confusing, and unpleasant time. The more time I let pass without clarifying expectations with my boss, the more insecure I became.

Since my manager interacts with many people daily, they may assume that I know things that are actually news to me. It is thus my job to communicate what isn’t clear to me.

In part seven, I’ll discuss how to manage up and stay in sync with our boss. This will help:

  • Understand what our boss expects of us;
  • Meet our boss’s expectations; and
  • Hold tough conversations with our boss.

Recommended Reading

What does my boss expect of me?

As our responsibilities evolve, our manager’s expectation of us also evolves.

Whereas a nurse is expected to report on his/her patient’s status and health, a nurse leader is expected to report on his/her team’s performance.

As we work to understand what is expected of us, it’s a good idea to share with our manager the management system we use (if they are not already aware). This ensures that our boss knows how to communicate  expectations with us, and more importantly, how we want to be held accountable.

Once a management system has been agreed upon, we can ask for clarity on their expectations of us: What goals they want us to achieve, what weaknesses they want us to improve upon, and how they envision us growing professionally.

We can also take it a step further and request direction, support, or coaching in specific areas to help our manager understand where and how they can help. This saves them time in diagnosing how to spend their energy with us, in addition to showcasing our sense of self-awareness. And fact is, most managers won’t find the time to diagnose where we need coaching, so let’s facilitate their job and ask for it.

Here are some questions that can help us clarify expectations of us with our boss:

  • What are the performance indicators or success criteria that will be used to assess my role and responsibilities?
  • What is the preferred method to communicate updates on my progress? 
  • What is the preferred method to communication update on my team’s performance? 
  • What is the preferred method for me to give and receive feedback? 

Who is my boss?

It’s also critical to understand our manager, the person. Insight on the person provides the necessary context to explain why our boss expects certain things from us, and behaves the way they behave.

It’s thus a good idea to observe and record our perception of our boss’s motivations, frustrations, values, strengths, weaknesses, work styles, and perceptions of us, in the same way that we keep dynamic profiles of our direct reports. In addition to understanding the boss’s frame of mind, this also helps us tailor our priorities accordingly. For what’s important to our boss should also be important for us.

How do I give feedback to my boss?


It’s not natural for most individuals to give feedback to their manager. We have a tendency to expect our leaders to know more than us, to be self-aware, and to not need our feedback. We may even expect our boss to be perfect. Yet nothing could be further than the truth.

Nobody is perfect (even definition of perfect varies from person to person). Nobody knows everything. Nobody can assess their performance objectively. Nobody can be certain of how they are perceived by others.

It is thus critical to proactively give feedback to our boss, to ensure that they know how to work with us effectively, and help us achieve our full potential.

Here are some tips that can help us give feedback to our manager:

  • Develop trust: Without trust in us, a manager is rarely going to listen to anything we say. It’s thus critical to show that we understand the problems faced by the team, along with our boss’s priorities. Once trust has been established, we can begin to share feedback.
  • Agree on a feedback system: Proactively asking the manager how they’d like to receive feedback helps establish a channel where feedback can flow.
  • Be transparent with our intentions: If we are planning to communicate feedback, we should let the boss know in the beginning of a conversation.  e.g. “Would you mind if I shard a point of feedback with relation to the situation around ______? I’d love your thoughts on my interpretation of the situation.”
  • Be specific and provide evidence: To avoid any opportunity for debate about the feedback, we can take the following approach:
    1. Find and communicate non-negotiable evidence that support our thoughts and feelings around a feedback. e.g. “Earlier in the ___ meeting, you dismissed Taylor’s opinion.”
    2. Share interpretation of the observations and communicate how their behavior impacted us, the team or the company. e.g. “The quick dismissal of Taylor’s opinion makes it uncomfortable for the rest of the team to share their thoughts openly.”
    3. Share a potential solution, while giving them the benefit of the doubt that they meant no harm. e.g. ” I know that you didn’t mean to hurt Taylor or shut down her idea. There was probably a distraction in the moment. To help keep conversations constructive in the future, perhaps you could share with Taylor how she can share opinions the next time? Or perhaps educate all of us on how we can constructively share feedback?
  • End with a praise and vote of support: A vote of support to our manager helps them understand that we are trying to help improve a behavior, and not attacking them personally. e.g. “I care about this team and this company, and enjoy our relationship. I thus want to make sure that the entire team feels this way and have the same supportive and constructive relationship we have.”

It’s important to realize that managers and leaders seldom receive feedback from direct reports. More often than not, direct reports simply get frustrated and leave the organization before trying to communicate feedback. That’s a shame. To help us avoid this fate with our boss, I highly recommend the adoption of a clear feedback channel between both parties. Give your boss a chance.

Recommended reading:

Recommended exercise

Let’s pick a frustration or issue that we have with our boss and work to communicate it to him or her.

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2 Comments on "start⬆Mngr handbook pt. 7: How do I make my boss happy?"

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Frank Yue

Just spent my whole afternoon reading this blog. These articles are really helpful and i expect to read more of it in the future!


Thank you for the note Frank! Glad you’re finding this valuable.