Note: While reading a book whenever I come across something interesting, I highlight it on my Kindle. Later I turn those highlights into a blogpost. It is not a complete summary of the book. These are my notes which I intend to go back to later. Let’s start!

  • Your job, as a manager, is to get better outcomes from a group of people working together

  • Chris Cox Manager Evaluation Framework:

    • Half of what he looked at was my team’s results—did we achieve our aspirations in creating valuable, easy-to-use, and well-crafted design work?
    • The other half was based on the strength and satisfaction of my team—did I do a good job hiring and developing individuals, and was my team happy and working well together?

  • A manager’s day can be sorted neatly into three buckets: purpose, people, and process. The why, the who, and the how.

    • The purpose is the outcome your team is trying to accomplish, otherwise known as the why. The first big part of your job as a manager is to ensure that your team knows what success looks like and cares about achieving it.
    • The next important bucket that managers think about is people, otherwise known as the who. Are the members of your team set up to succeed? Do they have the right skills? Are they motivated to do great work?
    • Finally, the last bucket is process, which describes how your team works together. You might have a superbly talented team with a very clear understanding of what the end goal is, but if it’s not apparent how everyone’s supposed to work together or what the team’s values are, then even simple tasks can get enormously complicated. Who should do what by when? What principles should govern decision-making?

  • If you are wondering whether you can be a great manager, ask yourself these three questions.

    • Do I Find It More Motivating to Achieve a Particular Outcome or to Play a Specific Role?
    • Do I Like Talking with People?
    • Can I Provide Stability for an Emotionally Challenging Situation?

  • The best outcomes come from inspiring people to action, not telling them what to do.

  • Leadership is the particular skill of being able to guide and influence other people. Leadership is a quality rather than a job. Leadership is not something that can be bestowed. It must be earned. People must want to follow you.

  • Questions to ask your reports:

    • What did you and your past manager discuss that was most helpful to you?
    • What are the ways in which you’d like to be supported?
    • How do you like to be recognized for great work?
    • What kind of feedback is most useful for you?
    • Imagine that you and I had an amazing relationship. What would that look like?

  • Other Questions to ask include:

    • What does it mean to do a great job versus an average or poor job? Can you give me some examples?
    • Can you share your impressions of how you think Project X or Meeting Y went? Why do you think that?
    • I noticed that Z happened the other day. . . . Is that normal or should I be concerned?
    • What keeps you up at night? Why?
    • How do you determine which things to prioritize?

  • Here are some things to do during 1-1s:

    • Discuss top priorities: What are the one, two, or three most critical outcomes for your report and how can you help her tackle these challenges?
    • Calibrate what “great” looks like: Do you have a shared vision of what you’re working toward? Are you in sync about goals or expectations?
    • Share feedback: What feedback can you give that will help your report, and what can your report tell you that will make you more effective as a manager?
    • Reflect on how things are going: Once in a while, it’s useful to zoom out and talk about your report’s general state of mind—how is he feeling on the whole? What’s making him satisfied or dissatisfied? Have any of his goals changed? What has he learned recently and what does he want to learn going forward?

  • Here are some of my favorite questions to get the conversation moving during 1-1s:

    • Identify: These questions focus on what really matters for your report and what topics are worth spending more time on.
      • What’s top of mind for you right now?
      • What priorities are you thinking about this week?
      • What’s the best use of our time today?
    • Understand: Once you’ve identified a topic to discuss, these next questions get at the root of the problem and what can be done about it.
      • What does your ideal outcome look like?
      • What’s hard for you in getting to that outcome?
      • What do you really care about?
      • What do you think is the best course of action?
      • What’s the worst-case scenario you’re worried about?
    • Support: These questions zero in on how you can be of greatest service to your report.
      • How can I help you?
      • What can I do to make you more successful?
      • What was the most useful part of our conversation today?
  • Say things like the following when you don’t know the answer:
    • “I don’t know the answer. What do you think?”
    • “I want to come clean and apologize for what I did/said the other day. . . .”
    • “One of my personal growth areas this half is . . .”
    • “I’m afraid I don’t know enough to help you with that problem. Here’s someone you should talk to instead. . . .”

  • Recognition for hard work, valuable skills, helpful advice, or good values can be hugely motivating if it feels genuine and specific. Furthermore, people are more likely to succeed when using their strengths

  • Before any project tell your report:
    • What a great job looks like for your report, compared to a mediocre or bad job
    • What advice you have to help your report get started on the right foot
    • Common pitfalls your report should avoid
      • In your first three months on the job, I expect that you’ll build good relationships with your team, be able to ramp up on a small-scale “starter” project, and then share your first design iteration for review. I don’t expect that you’ll get the green light on it right away, but if you do, that would be knocking it out of the park. Here’s what success looks like for the next meeting you run: the different options are framed clearly, everyone feels like their point of view is well represented, and a decision is made.
    • Give Task-Specific Feedback as Frequently as You Can
      • As the name “task-specific” implies, you provide this kind of feedback about something that someone did after the fact. For example, after your report presents an analysis, tell her what you thought she did well and what could go better in the future. Be as precise and as detailed as you can.
      • Example: That research report you shared yesterday was excellent. The way you succinctly summarized the most important findings at the top made it easy to process. The particular insight about X was really useful.
      • Quick note about the presentation you gave this morning: I noticed you went straight to the proposal without explaining how you got there. This made it hard to assess why it was the best path. Next time, try spending a few minutes walking through your process and what alternatives you considered.
    • When you zoom out and look at many examples of task-specific feedback for a report, what themes emerge? Does he make decisions quickly or slowly? Is he a process wizard or an unconventional thinker? Does he gravitate toward pragmatic or idealistic solutions?
    • Asking this question about themes helps you reflect on your report’s unique strengths or areas of development as shown in his patterns of behavior.
  • When you give behavioral feedback, you are making a statement about how you perceive that person, so your words need to be thoughtfully considered and supported with specific examples to explain why you feel that way. It’s best discussed in person so the receiver can ask questions and engage in a back-and-forth with you.
    • Example: When people ask you questions about your work, your tone is often defensive. For example, when Sally left a comment on your code, you replied with “just trust me.” This disregarded the substance of her feedback and made you appear less trustworthy. Your recruiting skills are top-notch. Candidates often say they leave a conversation with you feeling more inspired than when they began. You also have a keen sense for suggesting the right people for the right roles. For example, you identified John for Project X a year ago, and now he’s thriving.

  • On 360* feedback: Every quarter, for each report, I send a short email to a handful of his or her closest collaborators asking: a) What is X doing especially well that X should do more of?, and b) What should X change or stop doing?

    • Example Feedback after a 360* review:
      • Your peers give you a lot of props for how you managed the budget crisis. This was important and difficult work, and your calm demeanor, excellent listening skills, and rational arguments helped the team get to a good outcome. One of the consistent themes from your 360-feedback is that your plans need more rigor. An example is how you left out the edge case of senior discounts in your pricing proposal, which resulted in incorrect projections. This pattern of small errors across your work is starting to undermine your credibility.

  • EVERY MAJOR DISAPPOINTMENT IS A FAILURE TO SET EXPECTATIONS

  • Nobody likes being taken by surprise with bad news.

  • “If the first time he hears that he’s not meeting expectations is during his performance review, it’s going to feel terrible,” she said. She went on to explain that because our reviews are meant to summarize performance from the past six months, if Albert was indeed not meeting expectations for most of that time, I should have told him that much earlier.

  • Following are some examples of how setting expectations early can preempt future disappointments.
    • Your Report Has Made It Clear That She Wants a Promotion
      • You don’t think it’s likely to happen within the next six months. If you wait until the next performance review to tell her, she’ll have spent months wondering if she got the promotion and then be disappointed.
      • Instead, if you say right away, “I understand that you’d like to work toward a promotion, but here are the gaps I’m seeing . . . ,” you’re showing that you want to help her reach her goal. Spell out what your promotion criteria are. Over the next few months, coach her and give her frequent feedback on how she’s doing relative to those expectations. That way, she’ll never have to wonder.
    • You’ve Just Assigned a Challenging New Project to Your Report
      • Because this project is high stakes, you’d like to keep a close eye on how it’s going. If you frequently drop in and ask for an update or give unsolicited feedback, you risk making your report feel disempowered. He’ll be constantly checking over his shoulder, paranoid that you’re just around the corner.
      • At the same time, you don’t want to wait a month before reviewing the work. If it’s not heading down the right track, you’d like to know sooner rather than later.
      • Here, setting expectations helps with both problems. At the beginning of the project, let your report know how you’re planning to be involved. Be explicit that you’d like to review the work twice a week and talk through the most important problems together. Tell him which decisions you expect to make, and which he should make.
      • Managers who pop in out of the blue and throw down new requirements can breed resentment with their team (just Google the term “Swoop and Poop.”) But managers who proactively lay out what they care about and how they want to engage in projects rarely encounter those tensions.
    • Your Team Has Set a Goal to Launch in October
      • Let’s say your team learns in June that they’re unlikely to be ready in October. Would you prefer for them to tell you shortly before launch or right away?
      • I don’t know any manager who would choose to know later. At that point, a lot more work will be wasted—money spent on marketing, press plans that need to be redone, sales forecasts that are no longer accurate. Plus, you’re going to wonder why your team didn’t tell you sooner—was it incompetence or was it deceit?
      • If you’re informed in June, then you have more options. You could decide to put more people on the project or cut features to hit your October goal. Or you could accept the delay and point everyone toward a new launch date.
      • And yet, your team may resist telling you directly, “We don’t think we can make the October goal.” They might believe they can still turn things around. Or they might fear getting into trouble. By setting expectations that you’d like to hear about any concerns with the launch date as soon as possible, you establish that it’s safe to talk about problems even in the early phases.
      • It’s impossible to expect perfection. We are only human. Failures will occur, projects will miss deadlines, and people will make mistakes. That’s okay. But when these things happen, readjusting expectations as quickly as possible helps people recover from errors with grace. You demonstrate care and maturity when you preempt bigger issues down the road.
      • Whenever you find yourself deeply disappointed, or disappointing someone else, ask yourself: Where did I miss out on setting clear expectations, and how might I do better in the future?

  • The mark of a great coach is that others improve under your guidance.

  • The question that should always be in the back of your mind is: Does my feedback lead to the change I’m hoping for?

  • Strive for at least 50 percent positive feedback so she knows what she’s doing well—“You made a particularly keen observation” or “You showed a lot of empathy in that interaction.” If you hear something positive from a colleague, pass it along. Or, if you have a suggestion for improvement, even if it’s small, tell her that as well—“You said a lot in that meeting, which made it hard for others to get in a word.”

  • Devote a single 1:1 every month to just discussing behavioral feedback and career goals

  • The best way to make your feedback heard is to make the listener feel safe, and to show that you’re saying it because you care about her and want her to succeed. If you come off with even a whiff of an ulterior motive—you want to be right, you’re judging her, you’re annoyed or impatient—the message won’t get through.

  • When you do have critical feedback to share, approach it with a sense of curiosity and an honest desire to understand your report’s perspective. One simple way to do this is to state your point directly and then follow up with, “Does this feedback resonate with you? Why or why not?”

  • At the end of a conversation, when you’re not sure whether you’ve been heard, there are a few things you can do. The first is a verbal confirmation: “Okay, let’s make sure we’re on the same page—what are your takeaways and next steps?” The second is to summarize via email what was discussed. Writing can clarify the points being made as well as be reread and referenced in the future

  • How do you ensure that your feedback can be acted upon? Remember these three tips.

    • Make your feedback as specific as possible.

      • Use clear examples that get at the why so it’s easier for the recipient to know what you mean.

      • Example: You lost the room when you shared seven goals for the review instead of just one or two. It’s hard to remember them all, so the priorities felt unclear. At the end, you showed three different directions for where we could go from here, but you didn’t give us your recommendations or how to think about the pros and cons of each option. As a result, people were confused about the next steps.

    • Clarify what success looks and feels like. Even if your feedback is specific, heard, and understood, it can still be hard for the other person to have a clear picture of what they should aspire to.

    • Suggest next steps. Often the easiest way to help your report translate your feedback into action is to share what you think the next steps should be. Be clear about whether you’re setting an expectation or merely offering a suggestion. Also, beware of overdoing this—if you’re always dictating what should happen next, you’re not empowering your team to learn to solve problems on their own. A softer approach is to ask your report, “So what do you think the next steps should be?” and let them guide the discussion.

    • Example:Can you do another pass on this report with the changes we discussed today, and I’ll set up the next review for Thursday? One suggestion that might help you with your next presentation is using the rule of threes—no more than three goals, three sections, and three bullets per slide. Given what we just talked about, what are your next steps?

  • A template on opener for tough feedback:
    • When I [heard/observed/reflected on] your [action/behavior/output], I felt concerned because . . . I’d like to understand your perspective and talk about how we can resolve this.

  • Own the decision. Be firm, and don’t open it up for discussion.

  • Whatever the skill, don’t be afraid to ask, “Hey, I’m really impressed with the way you [do X]. I’d love to learn from you. Would you be willing to grab a coffee with me and share your approach?”

  • Examples of what one-week and six-month notes look like:
    • THOUGHTS ON MY WEEK:
      • Recent feedback I heard: Through my Q&As, I’m hearing a lot of praise for our design team culture, which is awesome. On what we could be doing better, the top theme was clarifying expectations for career growth. I’m taking away that we need to get more buttoned-up on how we talk about assessing performance and promotions.
      • Recruiting for next year: In our planning meeting, remote office growth came up as a big theme. We will need to train more interviewers and make sure our debriefs are consistent across offices. I’m counting on all of us to be heavily involved, and we’re getting a plan together for what that looks like.
      • Strategy for Project X: I worked with Team Y to prepare our proposals for the upcoming review. This came a long way in a few short weeks—shout-out to Elena in particular for her great work here.
      • Understanding research needs: In my 1:1s, I’ve been hearing asks for more research involvement. I have a better sense of what we’re looking for now, and David and I will share a staffing plan in the next two weeks.
    • GOALS FOR THE NEXT SIX MONTHS:
      • Build out my bench: Fill three open roles to ensure that every product has a strong leader.
      • Evolve all product reviews to start with clearly defined people problems so we have a common basis for evaluation.
      • Become an expert in hiring great research leaders.
      • Get rid of status updates in my 1:1s: Use that time to have deeper conversations with my reports.
      • Don’t bring work home with me: Focus on being more efficient in the office.
  • One exercise I do every January is to map out where I hope my team will be by the end of the year. I create a future org chart, analyze gaps in skills, strengths, or experiences, and make a list of open roles to hire for. You can do something similar by asking yourself the following questions:
    • How many new people will I add to our team this year (based on company growth, expected attrition, budget, priorities, etc.)?
    • For each new hire, what level of experience am I looking for?
    • Which specific skills or strengths do we need in our team (for example, creative thinking, operational excellence, expertise in XYZ, etc.)?
    • Which skills and strengths does our team already have that new hires can stand to be weaker in?
    • What traits, past experiences, or personalities would strengthen the diversity of our team?
    • Having a thoughtful, one-year-out organizational plan lets you stay ahead of hiring needs and gives you a handy framework for evaluating candidates so that you won’t fall into the trap of saying yes to the next person who comes along.

  • To help you get started with your team vision, ask yourself the following:

    • Assume you have a magic wand that makes everything your team does go perfectly. What do you hope will be different in two to three years compared to now?
    • How would you want someone who works on an adjacent team to describe what your team does? What do you hope will be your team’s reputation in a few years? How far off is that from where things are today?
    • What unique superpower(s) does your team have? When you’re at your best, how are you creating value? What would it look like for your team to be twice as good? Five times as good?
    • If you had to create a quick litmus test that anyone could use to assess whether your team was doing a poor job, a mediocre job, or a kick-ass job, what would that litmus test be?

  • To create a shared vision of what’s important, ask yourself two things. The first is, What are the biggest priorities right now for our team? Then, talk about those with your reports and discuss how they might play a role. Ask yourself the second question: Are we aligned in how we think about people, purpose, and process?

  • The rule of thumb for delegation goes like this: spend your time and energy on the intersection of
    • what’s most important to the organization
    • what you’re uniquely able to do better than anyone else.

  • To understand your team’s culture jot down your answers to the following questions:

    • UNDERSTANDING YOUR CURRENT TEAM

      • What are the first three adjectives that come to mind when describing the personality of your team?
      • What moments made you feel most proud to be a part of your team? Why?
      • What does your team do better than the majority of other teams out there?
      • If you picked five random members of your team and individually asked each person, “What does our team value?” what would you hear?
      • How similar is your team’s culture to the broader organization’s culture?
      • Imagine a journalist scrutinizing your team. What would she say your team does well or not well?
      • When people complain about how things work, what are the top three things that they bring up?

    • UNDERSTANDING YOUR ASPIRATIONS

      • Describe the top five adjectives you’d want an external observer to use to describe your team’s culture. Why those?
      • Now imagine those five adjectives sitting on a double-edged sword. What do you imagine are the pitfalls that come from ruthless adherence to those qualities? Are those acceptable to you?
      • Make a list of the aspects of culture that you admire about other teams or organizations. Why do you admire them? What downsides does that team tolerate as a result?
      • Make a list of the aspects of culture that you wouldn’t want to emulate from other teams or companies. Why not?

    • UNDERSTANDING THE DIFFERENCE

      • On a scale from one to nine, with nine being “we’re 100 percent there” and one being “this is the opposite of our team,” how close is your current team from your aspirations?
      • What shows up as both a strength of your team as well as a quality you value highly?
      • Where are the biggest gaps between your current team culture and your aspirations?
      • What are the obstacles that might get in the way of reaching your aspirations? How will you address them?
      • Imagine how you want your team to work in a year’s time. How would you describe to a report what you hope will be different then compared to now?