Having Difficult Conversations

"It's so unsafe for your manager to turn to a young woman on the team and say, 'Here, let me give you feedback on your physical appearance, and how it affects your competence and how you're perceived in the workforce.' That the vast majority of them will just never do it because there's no winning... but then that person never learns the rules of the game."

"The number one company value from my startup... was to be kind and candid... we, as founders, realized that we often would be nice and it wasn't actually the right thing to do. We would delay the difficult conversations and we were not candid... think of being candid as an act of kindness."

"Hope for the future is so important. I know this is going to be challenging for you to hear, not going to promote you, but I want you to know this. It's really important to me that you're able to succeed in your career here, and so I want to continue to help you find opportunities to build your skills and to advance."

"No one wants to make anybody upset, but through that upset on the other side of that, can often be a whole new possibility and a whole new revelation, and actually a lot of joy and freedom. I think that we forget about all the other possibilities that come out of difficult conversations and we just land on these really uncomfortable parts."

"Matilda, I want to chat with you about the way you're interacting with your peers. So what I'm hearing from them is that you're missing deadlines on a regular basis and not letting them know you're missing the deadlines, and that also you're not fully keeping your team up to speed. And so they're kind of confused running around. Now, we both know that the most important way you can be successful here and also achieve your goals is to make sure that you are working with your peers in a way that's consistent and that they can count on you and you can count on them."

"Matilda, part of your job is to be able to create these documents and I appreciate that you do them on time. What I've observed is that they can often be not as structured as I'd like them to be and they also lack a conclusion. So what I'd love you to do is look at these three or four examples of some folks who are doing them really well and see if you can model your writing on theirs."

"Let's pause for a second because I'm feeling the energy has changed and I can see that you're getting a little bit heated by what I'm saying and I want you to know that I have no intention of upsetting you. I just want to be able to talk to you about the things that are going to help you in your career."

"Matilda, I know this is going to be challenging for you to hear. I know you were hoping to get that promotion, but I want to let you know that we are going to actually be looking for an external candidate. I want to give you a few thoughts about why. First of all, in discussing this with my peers, I'm realizing that we need someone who has done this role multiple times in the past and has that experience."

"I need you to know that this is very important. I need you to fix this within the next 30 days. Otherwise, I'm sorry to say, we're going to have to find a way to part ways because I can't keep this going with you. I know you have it in you to change. I value all you bring to the table, but if you don't fix these things, we're not going to have a future together."

"Matilda, we talked about this multiple times. The last time we had this conversation, I told you I needed you to make these changes. You haven't made these changes and we're going to part ways. So I have here, Sarah from HR or whatever, and we're going to talk through the logistics of that."

"I hear what you're saying and I understand. Nevertheless, this is what's going to happen. And obviously, the words that you can use for that might be different... I heard you and your input, trust me, was incorporated into the decision, nevertheless, this is the path we're going to take."

"I try to let myself just feel the things that I'm going to feel. ... Then once that's passed, whether that's a few hours or a few days, don't react. Don't try to say, "Oh, I don't believe this." Listen. And then ask myself, okay, well where is this feedback coming from? Why am I getting this feedback?"

"I will say this very directly to people, I care so much about you and I'm giving you this feedback because I want you to be successful and I want you to be able to reach the pinnacle of what I know you can accomplish. ... then it makes the other person much more receptive to hearing whatever you have to say."

"I'd say I just sit them down and I would say, 'Look, you're a really good director of engineering because you do a great job at managing the team, get the products out, all that. But you're not really a CTO because to be a CTO, you have to be effective with other parts of the organization... if you want to get good at that, I'll help you. I'll work with you on it, but if you don't, I'm going to have to hire a CTO at some point because obviously I need that.'"

"you've got to be able to tell them the truth in a way that you probably don't tell most of your friends the truth... all the most important things I've said are things that I've said to CEOs that they did not want to hear. And that's what the leadership is about."

"Being kind isn't that. Being kind is like, 'Hey, how can I deliver this feedback in a way that is actually productive and helpful, in a way that is going to help them and not cause them just to feel bad and helpless?'"

"She could have the most profound disagreement with somebody in the world... and she would respond. She would say, 'Fascinating. You have to tell me more about why you think that.'"

"She pulled me into a room and gave me talking to a little bit about holding my team to as high of a standard as I have. If someone wasn't meeting my expectations, what was my plan to manage them out of the company..."

"I feel that you don't care and I feel you're being insensitive are not feelings, and that's where we make our biggest mistakes when it comes to feedback."

"Stay on your side of the net... stick with the two realities you know because we get in trouble the minute we start thinking we know the other person's reality."

"The formula is when you do insert behavior, I feel pull out the vocabulary of feelings and I'm telling you this because, or I'm hoping the outcome of you knowing this is."

"Address it while it's still small and then it won't get big. That's why we call it talk about a pinch before it becomes a crunch."

"What did you hear me say? One of the most powerful things you can do when somebody responds in a way that feels very unexpected and out of whack with what you just said is go back to, 'What did you hear me say?'"

"Say the thing you think you cannot say... I think that I've come to believe that often your biggest strength, one, is also your weakness, but two, is something that you don't know is a big strength because it's almost like breathing."

"One is, ask a question. Right? A question is not threatening... The next trick is you own it. This is your observation, this is your perception. This is not a judgment. I am not saying, 'Lenny, I think you really botched that interview.' That's not useful. If I said, 'Lenny, you know what? I wonder if you missed an opportunity in that interview.'"

"Radical Candor and Dare to Lead, to be honest, are the ones I recommend the most. Because I do a lot of coaching new managers and helping them learn how to manage. And those are the first two I start with, because they're so good."

"I called both of them individually and I said, 'The way you are operating is not meeting our leadership expectations. If you do not change, you cannot be part of this organization anymore. I believe you can operate differently. I do.'"

"You love good relationships with people, but you don't want to make them unhappy so you don't tell them the truth basically about things that are difficult to hear... the company's conflict avoidant, so we're not telling the truth and then making a bunch of predictable mistakes."

"Where if I'm asking myself the question, 'If this person on my team came to me and said, "I'm leaving today. I have a different opportunity and I would like to take it," would I do everything I could to keep them at Netflix?' If not, then I should be having that tough conversation about, 'Should you really be here? Are you in the right role?'"

"When something's not meeting expectations or really showing up as excellence, I think it's a combination of both giving the feedback on that and being direct about it and being specific about what would it take to get this to the bar that I am expecting... And then the third and probably most important thing is help them fill that gap."

"I struggled for years with feedback to generate the intended outcome... As soon as I started closing the gap and realized I need to try harder to think about the story arc of this feedback, that becomes clearest to me how to do it when I have the intended outcome in mind."

"The first thing I did was I owned it. I said, 'Yes, it's not working. It's my fault. I will deal with it.' I took ownership. And the second thing I did was start updating him very proactively and saying, 'Here's where we are.'... I was buying life one hour at a time."

"I was teaching the Xs and Os of being a CEO, basically: hiring, firing, having hard conversations, managing a board, fundraising, selling, all the things you would imagine that a young CEO would need to know."

"My famous questions include things like, what am I not saying that I need to say? ... What am I saying that's not being heard? And then, of course, what's being said that I'm not hearing?"

"Since I'm coach executives, let's do an executive example, so conflict avoidant executive. I don't want to feel the out of control in this that I do when people argue. I don't want to feel that level of out of control, so I am going to be conflict avoidant. I'm going to avoid conflict. Every way that we go to avoid a feeling, becomes the way that, that feeling gets invited towards us."

"if you manage to get them to take the risk to give you the feedback, your answer has to be enthusiastically grateful. That's the key... externally, I'm like, 'Hey, thank you,' and I mean it. I think that's the key that most people don't focus on."

"Feedback really, in my mind, ideally, should be a daily practice... what is the best tool for us to get better? It is feedback."

"The first tip on getting feedback or delivering hard feedback is first go and actually establish that our relationship is one in which we value each other's contribution... Start by saying, 'Hey, really excited to work with you. I feel like our best collaboration is I want you to help me get better.'"

"If I sit down with you and I say, 'Lenny, I'm so nervous right now. I want to give you some feedback and I'm really worried that it's going to impact our relationship... but I also feel like it's just going to help you to hear it if you can.' That does so much of the work of... It's humanizing."

"Sometimes a win-win thing is to just say, 'Look, it's not working, and I respect and value you so much that I know you want to do something that you can be proud of and you can grow in... and right here, what we got, this isn't it.'"

"I walked into the room and there were five of them seated around the table. They had a pack of papers in front of them and they went on taking turns quietly reading from the papers all the things that they saw that I was doing wrong and all the things that they didn't like about me... luckily, thank goodness I had the sense to just listen and not respond in that way."

"Why don't you go to training to learn how to have difficult conversations? Because there's some great training about having difficult conversations... these are all really, really important factors that start to come into play."

"I work with a lot of founders who are not the sort of classic control freaks. They're super nice and their teams love them and they love their teams. So for them, it can be really hard to deliver hard feedback, to deliver negative feedback and even more to actually create consequences."

"I love radical candor, for example, where I try to go a step further than radical candor is to not just say, 'Hey, here's my feedback. Just wanted you to know.' But to say, 'And I want something. I would like to see an outcome.'"

"And it's basically when you want to give someone feedback, the template is when you do a behavior, I feel a feeling, and she's big on like say actual feeling word not like, 'I feel like, or I feel that,' blah, blah, blah. And step three is, 'I'm telling you this because...' and then what you want them to change."

"Radical Candor is just what happens when you care personally and challenge directly at the same time. And I think it's probably best understood by what it's not because we all fail on one of those two dimensions or both of them multiple times a day. So you can think about it as a two by two framework. On the vertical axis is care personally, the horizontal axis is challenge directly. What happens when we remember to challenge directly, but we forget to show that we care personally. That is what I call obnoxious aggression"

"I can tell when you do that thing with your hand, then I'm going to have to be a lot more direct with you. When you say um every third word, it makes you sound stupid."

"You want to be humble, you want to be helpful, you want to do it immediately. You want to do it in person or at least synchronously. If you can't do it in person. You also want to praise in public and criticize in private, and you don't want to give people either praise or criticism about their personality. So if you want to remember all that, it's HHIIPPP, two H's, two I's, kind of three P's depending on how you count."

"you want to use sort of context, observation, result, next step. So context, in the meeting, observation, when you said um every third word, it makes you sound stupid. Next step, go to the speech coach. Also is important for praise, in the meeting context, when you offered both sides of the argument, observation, result is it earned you credibility. Next step is do more of that. So you can call it CORE"

"if I didn't fire Bob, I was going to lose all my best performers because not only had it been unfair to Bob not to tell him, I also had been unfair to everyone on the team. And they were frustrated. Their deliverables were late because his deliverables were late. They weren't able to do their best work because they were having to spend so much time redoing his work."

"if you find your employee looks sad or mad, if they look sad, pause and say, 'I feel like maybe I didn't say that in the best possible way. How could I have said it differently?' And so that means you're going up on the care personally, dimension, but you're not going the wrong way on challenge directly."

"One of those things that we did two years ago was we had to architect a layoff, and we had never done a scaled layoff before. We had to lay off 10% of the company to save the company... It's a complete dumpster fire. It's a nightmare. I'm getting bashed in the press, on Twitter. Everyone is shooting at me."

"There's a more robust structure I talk about in the book called The 4 Is... The first I is information. You're just setting the playing field so the person knows what you're giving the feedback about. The second is impact, and this is impact on you, the feedback giver. The third is the invitation that you make, and then the final is the implications or consequences."

"An apology to me, I have a AAA... It's three steps, acknowledge, appreciate, and amends. So I have to acknowledge what I did. ... Then I appreciate. 'I can imagine my doing that made you feel bad...' The amends part is, 'I will work not to do this. In fact, I will wait till you're done...'"

"Fundamentally, the most selfish thing you can do is withhold feedback from someone. When you think a thought that would help someone improve and you avoid giving it to them because it would make you uncomfortable. Well, you're optimizing for your own comfort, and it's fundamentally selfish."

"The biggest marker that I've seen between a botched layoff and a successful layoff is at the moment someone hears that they no longer have a job, did they hear it from their manager in a one-on-one? If that's when they heard it, it'll be okay. But if they heard it in an email, in a group chat, in any kind of thing where they were sitting next to or they're hearing it along with other people, it wasn't personalized, it wasn't one-on-one, that is terrible."

"I believe that fear is actually giving you bad advice and I think you're predicting that if you do this A will happen. Well, I'm predicting that if you do that, the exact opposite will happen."

"I at times feel anger and I act on that anger and I don't even realize I'm in anger... she said, 'I perceive you to be in anger.' So it's an I statement and it's simply what she's perceiving. There's no judgment. That was able to punch through my anger and then I woke up and went, oh, and then I stopped and just didn't act until I was able to shift out of anger."

"The reason people are bad at this is because they think that they're hurting the person who they're letting go... Decision is one thing, implementation is completely and utterly separate. That's the same thing here in letting someone go. But if you let them go kindly and humanely, the key is, in my opinion, you become their agent, like Michael Ovitz, the CAA agent. You help them find their next job actively."

"I start it off, 'Hey, this is going to be a difficult conversation. I want you to take a few seconds and prepare yourself. You are not going to enjoy this.' What I found is that the way the amygdala gets triggered is often because of surprise. So, if you give someone just a few seconds to mentally prepare, then the amygdala often doesn't get triggered nearly as hard."

"You actually want to cut deep because cutting two times or three times creates PTSD in an organization. It's trauma one, trauma two, trauma three. Now they're like, ah, it's just going to keep happening."

"The big one for me is Radical Candor... you need to care personally and challenge directly. If you're only doing one of those things, you're not giving feedback in an effective way."

"I actually pulled them aside and I said, 'Hey, we need to move a lot faster. This is where we need to get to by X. We're a growth team. We need to prove wins out early.'... I think in that conversation what's important is also saying, 'I believe you can do all these things and I'm doing this to support you.'"

"If you have feedback to give someone else, I think you can start by asking, 'Hey, do you have feedback from me?' And kind of taking the feedback first so then that person feels like, 'Okay, maybe I have my way of seeing this situation. Let me communicate that and get off my chest.'"

"Firing people is as important as hiring people. Getting good at identifying when someone does not belong or someone is not going to work out is actually a skill."

"I'd never fired anyone before I joined Intercom... and realized it always works out for both sides. And the nicest thing to do is to do the harder thing. It's actually the nicer thing to do. People are relieved in this example."

"Actually, the goal of any conflict is to create mutual understanding."

"I'm going to give you a framework that I like that many of my clients use. It's from Marshall Rosenberg's Nonviolent Communication. It is a book and a framework. So it's four steps. The first step is observations... The next step is feelings... The third step is needs... And lastly, the step is to make a request."

"There is always something that we're doing to contribute to the conflict, even if it feels like the other person is insane... Entering any conflict conversation with humility, and curiosity about the other person's experience, is critical."

"The problem was not that the team was not right. The problem was that the CEO did not make hard decision. Making hard decisions is hard... In a small place like a startup, the hard decisions will always go to the top. Now, if the CEO does not make that hard decisions, the result is always the same. The top performing people would leave."

"I have a framework called strategy, not self-expression... the goal is behavior change. So if that's the goal, trim everything else that you were about to say that does not actually contribute to that goal and only keep the part that will make the person want to change."

"When you are extending yourself, you're not nice. It's not always nice or like, it sometimes is having hard conversations. It's knowing that, oh, there's a human, they know I care about them. So when the feedback is coming like raw, they know that it's in their best interest because I've shown enough times that I genuinely care about the person behind the role."

"What we put into place is something we call Fight Club. I'll probably get in trouble for talking about Fight Club. The first rule is you don't talk about Fight Club. But it's 30 minutes every week, and it's just for myself, my engineering, and my design leader; and we get together, and we know that we're going there to have a conflict."

"Convey this feedback as situation, behavior, impact. The situation is on Tuesday in that meeting at 3:00. Behavior, you interrupted me while I was saying this thing. Impact, made me feel like you weren't listening to me... it's a subjective observation. It's not what the camera recorded, it's what you experienced."

"I had to let go of people over Zoom. I couldn't even meet them in-person. I still remember when I actually finished my speech and I told them, 'This is the last day,' now, I literally shed a tear in front of everybody, because I was like, 'Man, this is hard. This is really, really hard.'"

"Spending time and longer time in careers with people and then holding them to a high standard means that they accomplish very often things that just they didn't imagine they could. To me this is the most wonderful thing to see... hearing from someone that you respect that 'Hey, I think you had it in you to do this thing significantly better because I think you probably saw fairly early in the project this sort of path A path B. You chose path B potentially out of convenience even though you knew that wasn't the right thing. And I actually expected better of you'... that's hard to hear, right, because it's right. But it's also extremely valuable, right?"

"The number one thing that a product leader on the product leadership team needs to do is drive accountability with others in the product leadership team... When you go back and you work with your team, always have the lens are you improving things."

"Every offsite that I do with my leadership team, usually there is a one to two hour session where it is feedback to Varun, and I actually do it openly... I want to show my vulnerabilities to everyone, that I am not perfect."