7 Unconventional Leadership Principles with Hubspot’s Rebecca Yang

In this guest interview episode, Rebecca Yang, Director of Engineering at HubSpot, shares her unconventional journey to tech leadership and reveals seven uncommon leadership principles that have shaped her success. From her early days in client services to leading a 50+ person engineering team, Rebecca opens up about how embracing authenticity and overcoming personal challenges has made her a more effective leader. Her refreshing take on leadership - including why micromanagement isn't always bad and why you shouldn't trust your gut with feedback - offers valuable insights for leaders at all levels.

About Rebecca:
Rebecca Yang is a Director of Engineering at HubSpot, leading the Breeze Intelligence group. She joined HubSpot in 2023 through the Clearbit acquisition, where she previously served as VP of Engineering. She's passionate about cultivating high performance engineering cultures. Rebecca's teams focus on shipping innovative, impactful customer-facing solutions.

Highlights:

• How coming out as a queer woman early in her career shaped her leadership style, particularly around transparency and authenticity
• The unique culture of engineering teams and how it allows for greater self-expression and authenticity
• Why psychological safety starts with how we handle critical feedback - both giving and receiving it
• A deep dive into Rebecca's "7 Uncommon Leadership Principles"
• How Rebecca successfully led her team through a challenging one-third reduction in workforce by being transparent about the "why"
• The importance of "Debate, Decide, Unite" in building team alignment
• Why leaders must own difficult messages rather than deflecting responsibility

Links & Resources Mentioned:

• Rebecca Yang’s LinkedIn Profile
• Stay SaaSy Blog: Don’t Create Chaos
• Dharmesh Shah's "Debate, Decide and Unite" Framework

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Transcript

Kristen: Welcome to Love and Leadership, the podcast that helps you lead with both your head and your heart, plus a bit of humor. I'm Kristen Brun Sharkey, a leadership coach and facilitator.

Mike: And I'm Mike Sharkey, a senior living and hospitality executive. We're a couple of leadership nerds who also happen to be a couple.

Kristen: Join us each week as we share our unfiltered opinions, break down influential books, and interview inspiring guests.

Mike: Whether you're a seasoned executive or a rising star, we're here to help you level up your leadership game and amplify your impact.

Kristen: \ Hello and welcome back to Love and Leadership. I'm Kristen.

Mike: And I'm Mike. 

Kristen: And today we have a special guest with Rebecca Yang. She's the Director of Engineering at HubSpot, leading the Breeze Intelligence Group. She was previously VP of Engineering at Clearbit and then joined HubSpot when they acquired Clearbit in 2023.

And she also was previously a VP of Engineering at Marchex after they acquired another startup that she was at. So she has a lot of experience with both startups and getting acquired by larger companies as well. And she currently oversees the team of 50 plus engineers, and she's incredibly passionate about cultivating high performance engineering cultures.

Thank you so much for being here, Rebecca. 

Rebecca: Thanks for having me. It's great to be here.

Mike: So are these companies acquiring the other companies just because of you? It seems like they might be. 

Rebecca: You know, it's kind of, it's, it's interesting. mean, obviously there's so much that is luck. Like there are people who work super hard for a really long time and just aren't able to find that product market fit. Or, there are leaders who, you know, even when there's signs that it's time to maybe take the exit, believe there's still more growth opportunities. And so in some ways, I think I do choose companies with leaders who me the right signals that they're there for the growth, but also pragmatic enough to know when it's time to take some chips off the table. So I think I've been lucky.

But I also have worked very hard and I want to take credit, for at least some of it, keeping companies afloat during really tough times and helping them grow.

Kristen: Amazing. 

Mike: That's a good answer. that's right. ~Well,~ luck is preparation meets opportunity.

Rebecca: That's right. 

Kristen: Well, and Rebecca, one of the things I love about your background, as an engineering leader, you have a lot of qualities that I think make you different. Like you have been in engineering a long time, but you've also worked in different functions prior to that.

You, are a woman, which unfortunately is still not very common in, in engineering leadership roles, and you're a part of the LGBTQ plus community. Like how, how do all of these different factors help contribute to you being the leader that you are today?

Rebecca: That's a good question.So I have worked in a number of different industries and capacities in the past. I think working in client services was really formative, for making me a better communicator and helping me influence in a, from a place of, let's say relative weakness and what I mean by that is when you're working in client services, you are working really closely with someone who basically, at any moment can decide that they don't like you and fire you and in the ad agency world like if a client says get Rebecca off my account I'm i'm gonna be taken off the account like there isn't any like Pip.

There's no like feedback conversation. It's just you're out and that was something that I experienced right out of college Actually with you, Kristen. And it was, I think, so powerful because once you learn how to navigate and succeed in an environment where the power dynamics and the odds are so stacked against you, like any other conversation you have after that, like cross functional interactions, when you're all on the same team, they're just so much easier.

And so there just hasn't been an interaction I've had internally that has ever felt as difficult. And so it was like, everything was better after, cutting my teeth on,on client services?

Mike: So when you say client services, this is what they, say like software as a service kind of thing. I see

Rebecca: No, it's actually, so client services for me was working at an ad agency where we worked with clients directly on their advertising campaigns and there were points where I was actually like on site at a client's office, working in the office with them a couple of days a week, but I was never part of their team.

I was always an agency that they had hired and it's stressful. Like it's very stressful because you want to build trust. You want to build rapport, but the dynamic is complicated. And it is true that you can be fired very quickly and very easily. Okay. Or you can be asked to be taken off the account and it happens. 

Mike: So that's a complicated, it's a very political almost, landscape that you have to navigate.

Rebecca: Yeah, and,

Mike: But there's a lot of different dynamics. A lot of different interested parties.

Rebecca: Yeah, like, I mean, Kristen, you've done it for a really long time, I don't know, like, how would you phrase it?

Kristen: Yeah, I mean I think that's probably like how I would, frame it, because that is ultimately the reality of you are, you're working with somebody who has power over you, right? And I think that makes you be a lot more aware of your communication patterns, your, how you're framing things, how you're setting expectations, which then can definitely come into play in leadership as well.

Rebecca: Yeah, and I think,I've always been someone who likes to honor my impeccable agreements, and something I actually had to work through, as I moved away from client facing work more towards internal work is that how you think about deadlines is very different and how you think about expectation setting is very different, where with client services, if you say something is going to get done on a certain day, It's a pretty big deal if it doesn't get done because they might be expecting it.

They might have some other, followup action items that depend on your work and it can really cause a lot of problems for them and for the relationship with the client if you don't honor that. But internally, what I found is a lot of organizations are actually somewhat comfortable with people not hitting all of their deadlines.

So let's say that I hit maybe 85 percent of the deadlines I attempt. I think that's pretty solid. And in fact, if I was hitting every single one of the deadlines I was attempting, maybe I'm not actually pushing myself enough becauseI might not be committing to enough because when you push yourself, there's going to be times when maybe you're not going to make it. You're not gonna hit that deadline. So that was like an interesting adjustment for me I work with the 85 percent rule It's the only thing I can reason about where it's like i'm still mostly honoring my impeccable agreements .But I have a little bit of space for some failure, which means I can push myself. And of course no matter what you always have to set expectations.

So as soon as you realize you're falling in that 15%, like it's very important to reach out to whoever's expecting whatever from you and let them know. And that's something I, did in client services and continue to do today.

Mike: So it sounds to me already like you have a lot of like core operating values that like steer your, your operational principles. You use that word a couple of times now, your impeccable agreements. Can you talk about those? Is that like The Four Agreements or, you know, no, that's 

Rebecca: It might be, actually,

Mike: what are.

Rebecca: Yeah, I, um,

Mike: We talk about values and a lot on this show, so it sounds like you have a lot of very strong, core values. What are what, what what

drives the engine? Yeah.

Rebecca: So one is honoring your impeccable agreements and, or making your agreements impeccable. I actually don't know where that's from. My, my manager at Clearbit, and I talked about this a lot and it's something I think both of us valued a lot.And it's when you say you're going to do something, do it. And I think that it is. It is easy to say you're going to do something and then other stuff comes up and it gets dropped.I believe firmly that once you've made a commitment to do something, it's really important, like really important to follow through. It's how trust is built. And if you're not able to follow through there needs to be a conversation where you acknowledge that, Hey, I committed to doing this and unfortunately, I'm not going to be able to do that.

And I'm like, I'm sorry. And I'm sorry for how that's affected you. And, here's what I'm going to do in the future to try to not do that. It also means that I won't make commitments that I am not sure I can meet. So as an engineering leader, I will frequently be put in situations where I maybe on a conversation with a customer and they want me to like, promise them that I'm going to get them something by Q1, we're going to, make some change to the product.

And I, you know, I've gotten really good at being able to say, you know, I totally understand how this would be helpful for you. I can't commit to any timeline, but,we're going to look at how this stacks up against the other priorities and our product roadmap, we're going to go back and we'll, keep you informed, as things develop and it's disappointing for them.

I would love to, it is so nice to be able to give someone what they want. So I would love to say like, Hey, yeah, we gotcha, but it's not part of my team. And frankly, like in the heat of the moment or in that moment where you're feeling like anxious is not the time to be making decisions about what's going to go on your product roadmap.

And so that has worked very well for me.

Kristen: One of the things that you provided up front is these seven uncommon leadership principles that you swear by. Before we get into those though, I'd love to just go going back to your background for a moment. Is there a particular moment or two that come to mind that you think about in your career what has really shaped you as the leader you are today?

Rebecca: Yeah. I think one thing that really, and it happened really early on in my career, was coming out of the closet, as a queer woman, was a really big deal for me. And, there's a couple of ways in which I think it, it shaped who I am as a leader. First, I think I'm probably, on the spectrum of transparency, I'm extraordinarily transparent.

Like maybe too transparent. Like I probably could shield my team from some of the stuff I say to them a little bit more. But ultimately I would rather err on that side. And I think that really did come from holding in this sort of big secret for so many years. feeling so much shame about it.

When I finally started,I have this memory of being in college and being in a room by myself and wondering, like, I had this nagging voice in my head for years. Are you gay? Are you gay? And I remember being in a room alone and wondering if I could say the words out loud, like in a room by myself.

So not even as someone else. And I couldn't like in that moment, it was so scary. The thought of saying those words out loud was so scary that I couldn't bring myself to do it. And at some point, I just had to get over the fear because I knew that if I wasn't leading an authentic life and I wasn't being my authentic self and sharing that with the people in my life.

That I was never, I was never going to be known. I was probably never going to know people. Because you have to share yourself to, to build that trust to be able to know other people. And I was going to be miserable and unhappy and I wasn't going to be satisfied in my relationships. And so, I think the other thing that helped me was just conquering something that was really scary.

That was really scary and I didn't know what was going to happen. I, I really didn't, I didn't know how my parents were going to react or my family. I, it occurred to me that I would potentially get disowned. I didn't know. and at the time gay marriage wasn't legal. So I was accepting that, society might not accept me that I might never get to have a marriage, the, legal sense. But it was still worth it. So I think that being willing to take a leap of faith, because even when it's scary, um, actually does translate to a lot of moments in business and and leadership.

Mike: I mean, that's awesome. Thank you for sharing that. When you were talking earlier, it struck me that you were a very like honest communicator, right? You were talking about telling a client, like, I know that you want this and we want this for you, but it's might not happen. And a lot of people don't want to do that.

They,it's hard to disappoint people. We're, I'm not raised with that like kind of honesty and directness. So I mean it seems like that shapes your and reading through your uncommon leadership principles. There's a lot of just clear communication in there and being like honest with yourself and honest with others and like herding cats to where you need them to go, basically. So that kind of makes sense 

Kristen: Yeah, I think the honesty transparency vulnerability authenticity seem to really Help define who you are as a leader, which is a very good leader. 

Mike: It's a very good leader, but I don't work with enough like software engineers to make any sweeping assumptions, but it seems like these qualities might not be the most prevalent in that particular workforce of hyper intelligent technical people.

How has that been for you? 

Rebecca: I love it. I think there's certain things that are so cool about leading software engineers. I think there's a lot of functions where if I, decided to just one day show up to work with a blue mohawk, I might not be well received and I honestly feel like in software engineering,

Mike: can show up with a

Rebecca: I could do that.

Mike: Yeah. 

Rebecca: I could do, I can be myself. And I love that. And I think that the people I work with are, they're wonderful. There is a wide range of personalities and that's another reason why I really like software engineering. I think that because the, like what we look for is very focused on like technical skillset, you'll get all sorts of different personalities.

We're not looking for a certain like archetype of This is how this person, communicates with customers or this is how this person, has a brand voice in their writing or whatever. it's really focused on, can you do the work? And so I've developed really close, vulnerable relationships with tons of people in software engineering.

And in some way it's actually easier because I think on average people care less about notions of what's proper. Same way I can have a blue mohawk, I can talk about all sorts of things in a way that really feels like I'm not being judged. And,I like to live my life that way. I like to, I prefer not to judge others.

And so it's great. I think it's super fun. 

Kristen: I love that. So there's like less of a barrier in some ways because people are just more direct in general. 

Mike: Well, you're hiring for a 

very specific skill set and you're willing to take, I don't know, a wide variety of personalities and it's less image based. I come from a fairly 

image based world.

My lovely wife keeps encouraging me to grow my hair very long. I'll have very luscious curls. I don't feel like it looks super good in a three piece suit though. So I'm not a, I'm not a zen assassin. I think you can get away with that as like a hit man or something, you know, like

Rebecca: Maybe like a,

Mike: Man bun or something. John wick. Yeah, for

sure. You look like it. I'm not 

Kristen: saying man bun to be clear. This is like two 

Rebecca: heard man 

bun.

Kristen: So 

Mike: What I can, you're saying I can get away with that in software engineering or a blue mohawk. I saw that in my. In my jujitsu, all these guys will do just the craziest. There's a lot of mohawks.

They're warriors. They don't care. You know, they're not trying to get a customer service job at the hyatt or whatever. Neck tattoos, you know, like you can be yourself. I think that is pretty awesome I do love hearing that about tech and it's like well, you're focused on the results not on the image.

Well, there you go. And that's

Rebecca: It's like the early, Mark Zuckerberg. Now he is a fashionisco, but back in the day it was like hoodies. 

I This is about I got fancy for you all like usually i'm wearing like a t shirt that I got for six bucks or a sweatshirt

Kristen: Amazing. Well, we feel honored. 

Mike: I feel jealous 

is what I feel. I

feel quite jealous. I would love to work in my Crocs and

Kristen: Oh, the Crocs. Oh, the Crocs. We won't talk about this So do you 

Mike: have engineers that show up in Crocs?

Rebecca: I mean they might because, we're fully remote. or at least the team 

Mike: Okay.

All right. Yeah. 

Rebecca: Who knows? And you, it just doesn't matter, 

right? You can, as my boss says,

Kristen: The world I live in as well, where unless I'm going on site to with a client or speaking engagement, it's all remote. So it is a little bit different. Well, I

Rebecca: my boss asked me once if I was letting, Letting the piggies hang out. Like my toes.

Mike: I was like, sir, you're going to HR on that one. We're going to, we're going to. We're gonna maybe have to address that. But I like that, you know, I don't know, I think I'm remembering a John Kennedy speech where he's like, we want people to be judged by the content of their character. Not, I can't remember the rest of it, but it's not it's not their image, it's who they 

That's how you, yeah, 

that's awesome. 

Kristen: I love it.

Rebecca: Yeah,

Mike: Beezus loves it. She's coming for her third visit, we're trying to She's, she really is Oh, there's the tail. Just 

Rebecca: got a tail. 

Mike: shot. 

Kristen: Beezus. 

Please do not knock the webcam. Beezus, no. 

Oh my god. 

Sorry Beezus. 

Mike: Beezus, you're on lockdown. 

Kristen: Welcome 

Mike: back to the Ludwin Leadership Podcast, now that cats are on lockdown. 

Okay, so we were really talking about like authenticity. 

It sounds like you live in a world where people are much more accepted than maybe in mainstream society. That's nice. I could be 

wrong.

Rebecca: Yeah. And I was a weird kid in I want to say a good way, but I, there's like a photo of me when I was like three or four years old with my two best friends and I was Batman for Halloween. And we had a princess and like a fairy. And I don't remember at that time feeling any shame or embarrassment, obviously I didn't because I showed up as Batman, but at some point, like I stopped and I wouldn't have been Batman for Halloween, even if I wanted to be.

And I think I,I want that. I want that for myself and I want that for the world.

Kristen: My eight year old niece has, for the second time in her life, a huge mohawk right now. And it's incredible. And she has no shame whatsoever. She just wears it and like everybody in herclass thinks she's so cool and I'm like this is, we need more of this. I'm 

Mike: sure I've seen a meme circulating like, be yourself, unless you can be Batman.

Then always be Batman. Well who wouldn't want to be, you know. Um, that's cool. So you, you found some, acceptance and authenticity in your life. That's what we all 

want, right? You're doing something you love, 

Kristen: Yeah. Yeah. So getting into these, these principles, I'm actually just going to read them all briefly, just since I think they're so good.

So They're 

Mike: very good. They 

Kristen: are Yeah. Don't trust your gut when receiving critical feedback. Fear not their emotional backlash. Be a chaos vacuum. Micromanagement is only bad if the job would have gotten done otherwise. Always own the message and everything is your fault. 

Mike: What about Unity and Harmony Matter?

Kristen: Oh, did I skip that one? You missed 

Mike: six. I want to talk about all of these. 

Rebecca: I mean, I would argue if your organization, if your relationships, and this is Love and Leadership, is functioning healthily, like there's a lot of feedback. There's a lot of positive feedback, and there's a lot of critical feedback. And when we talk about creating psychological safety, A big part of that, I actually think, comes from being able to deliver critical feedback in a way that makes you feel safe.

And I, I will say that a lot of these uncommon leadership principles are things that do not come naturally to me at all. Like they're principles I swear by because I need to keep remembering them because it's hard because I've messed up.AndI am a deeply insecure person at times and sometimes.

When I get critical feedback, the person delivering it might strike a nerve, hit something that I'm very insecure about, that is deeply hurtful. And they probably don't know, or maybe they do, but assume best intent, they don't know that like, this is something that I have years of built up anxiety about, and they've just called me out for it. All they're doing is saying their truth. And I have developed a habit of like, when someone's giving me critical feedback, I can feel it, I can feel it physically and emotionally. When like it's hit a bad place like I almost started to get like a tunnel vision and like my ear. Like I almost shut down like 

Mike: Yeah. You have a 

physiological 

reaction. Yeah.

Rebecca: it's very like fight or flight and you know, there's a part of me that just wants to get out of there and there's a part of me that wants to tell them all the reasons why they're wrong.

And I actually have a sort of rehearsed response, which is thank you for feeling safe to give me this feedback. And frankly, it doesn't matter who is giving it to me. Thank you for feeling safe to give me this feedback. Do you mind if I chew on it for a little bit? And I can get back to you. So, I don't, I don't try to like, accept it and respond to it in the moment if I know I'm not going to be able to.

And then I pause, do whatever I need to do, let time pass. And then I can come back and I always circle back and I always try to look for what's true in the feedback instead of focusing on all the reasons why it could be wrong.And I know for me personally, it's really hard to give feedback to others. 

Mike: I was going to ask you about it. People underestimate how difficult it is as a leader to give difficult. It's so hard. It's so hard. Like we all want to be liked. Well, for the most part, 

But for the majority of us, it's really uncomfortable. So I love your first part of that. Like, thank you for feeling safe to give me this feedback. Yeah, That's acknowledging like the person doing this is also very human. 

Kristen: Yeah. 

Rebecca: Yeah, it is. I think, I think the hardest thing about leadership is the facing of your own emotional demons. I think that emotional intelligence is super, super important. We've talked about it before, and I know you talk about it a lot.The sort of next leadership principle I swear by, which is fear not their emotional backlash, I think is something I have to keep reminding myself, because I am a very empathetic person.

It's not something that's been hard for me, but what ends up happening often is I'm so good at anticipating how people will react to different things or decisions that it can actually start to create a sort of decision paralysis where I'm avoiding making a decision that needs to happen or I'm avoiding giving critical feedback because. I think giving critical feedback is hard because most people don't respond well to it. Like,

and it is, it sucks. I wish everyone in the world could go through, like, feedback training then,

Mike: 

mean, they could.

We could do that. That could be part of our culture of teaching these things. You know, like. If we're just 

Rebecca: that would be 

great.

Mike: now, like that would be great. 

Kristen: Well, and part of the problem is we did an episode on this relatively recently on giving feedback. But a lot of the like traditional models for giving feedback are not really taking in a good understanding of like emotional intelligence and, understanding that, everybody's, almost everybody's going to have that emotional reaction to getting feedback.

It's very common to get defensive. like, how do you set people up for success and how do you, acknowledge that, like, when you say, like, don't be afraid of the emotional reaction and, like, how can that not stop you from making the decisions or giving the feedback that needs to happen, but also, like, acknowledge it.

Mike: And, you know, understand this is a part of the process instead of being afraid of it. Well, I love what she said. She's like acknowledge your team's feelings without becoming entangled with them. That's really tough And then like your job as a leader you sum it up very well. You have to continue to do what's right for the mission. And you know, you will be viewed by many people as outcasts mean or unfeeling or this person doesn't get it and you have to accept that kind of judgment that you and feelings that you're going to get from people and still plow forward to whatever your mission is.

And if you don't accomplish that, you won't keep your leadership position and you don't belong there in the first place. And that's a really lonely kind of feeling sometimes, and not becoming entangled in them. I mean, that's, that's a lot of therapy right there, you know, that's hard. That is 

Rebecca: it really is.

Mike: It's

Rebecca: I've thought about this so much, especially like the past few years. There's just been a lot of moments that have been tough. I was at a company where we laid off a third of the team. And I think where I've landed is if, in order to be a good leader, you have to be empathetic and you have to be emotionally intelligent.

And you also have to do really hard things that make people sad. Then the job of being a leader. inherently is going to be very emotionally draining and difficult if you're good. And if you're able to completely turn those feelings off, you're probably going to miss out on some of the positives that come from practicing emotional intelligence.

And so I think there's a lot of like mindfulness and, I love the term dispassionate empathy because you have to be able to both feel it and also be able to look at something objectively. 

Mike: I love the next one too. Be a chaos vacuum. Do you want to talk about that?

Rebecca: Yeah, there's a, there's a blog post I really liked from a blog called Stay Sassy, but essentially, in the blog post, the author says, any room or Zoom that you join should have more certainty and a firmer plan by the time you leave it. Good leaders can walk into a situation where people have lost track of their goals and get everyone on a clear path forward.

And I think this is another, I mean, all of these are difficult. This is another one that I think at times has been hard for me, and I think it's actually a very common one that is hard for engineers. And the reason why is to be a really good engineer, you almost have to be a borderline conspiracy theorist in terms of all the ways your system can go wrong, right? Like when you think about security vulnerabilities, or you think about edge cases, how, like how something might break, you're thinking about like, even if it's like point 0001 percent of traffic that is going to go this other way, like that can take your system down. Or that can like end your company. And so there's a lot of detail and time spent on these details.

And as a leader, you sort of have to do the opposite. You have to get out from like the trees, look at the forest and be able to quickly notice when people in your team are going down rabbit holes and help pull them back out, help them disqualify, like things that are just not important.Finding the signal in the noise and it's also how you communicate like I think leaders can have a tendency to come in and I've heard the term, you know, add swirl like they'll come in with a question in the 11th hour that potentially derails the project. I think leaders have to be really thoughtful when they come in.

Like, should I be asking this question is now, like, how important is it for me to do this? Is this gonna like make or break, whatever it is where we're trying to do? Is it in line with the mission or can I just like, let it go? And I think that is super important.

Mike: Yeah, absolutely. I've definitely been a part of those times and yeah, some leaders create a lot of chaos and they don't even necessarily realize the impact it's having on their team. Well, I think some of that is like a lot of leaders you feel like they need to add more value and they you can try too hard.

You can well, I have to have all the good ideas I have to be the smartest person. No leadership very much is like exactly what you wrote here. It's like cutting through the noise simplifying and a uniting people toward, an actionable goal. And that's a skill. That's an actual skill. You can learn it, you can practice it.

But you know,it's kind of counterintuitive. Yeah. You know? 

Kristen: Yeah. The episode that will air the week before this is on What Got You Here, Won't Get You There by Marshall Goldsmith. And he talks a lot about that. Like sometimes it's don't add too much value because it can create chaos situations. 

Mike: A lot of time it's your ego, right? Like I have to go in, I have to know everything. I have to. No, you just cross a few things off the list and be like, let's focus on that. Those two things. That'll get us there. Yeah. I like this one too. Micromanagement is only bad if the job would have gotten done otherwise, Super smart. Yeah.

Rebecca: yeah, that one. I. I definitely have fallen short on in the past wherelike the opposite and a lot of these are in tension with each other right being a chaos vacuum and avoiding creating chaos means not micromanaging or jumping in when it's not necessary. But I think where I have fallen short also is seeing the signs that something is off, going off the rails and my team actually needs me.

But sometimes you ask, like, oh, do you need help? And they don't say yes.

Mike: No one says yes.

Rebecca: No one says yes. Um,

Mike: be seen as needing help. I don't. I don't. Don't ask me. This is genius. The key is to adjust your management style based on individual capabilities and gradual grant autonomy as they grow. That is money right there. Yeah.

Rebecca: Yeah. I mean, and sometimes it's sort of like, fear not their emotional backlash. Like when you step in to help, like often you will get pushback. People will say like, she's a director. Why is she involved in this? Like usually directors aren't involved. And in the moment, I hear the feedback, I understand it.

But I've also gone through enough iterations of projects and planning and trying to, hit some sort of deadline that I can tell if something isn't on track. And I know that even though it's gonna, impact someone's ego, they might feel annoyed. They might think that I'm inappropriately micromanaging them. Everyone's gonna be better off if we're able to succeed and, have not done that in the past and projects have not succeeded. And frankly, it's worse for everyone. It's worse for the person. It's worse for the business and our customers. It's worse for me.

Kristen: Yeah. Well, and this is ultimately about like giving people the support they need in order to be successful, right? Which sometimes looks like what people would call micromanagement, which has a really bad connotation, but it's actually around like, what do people need to be successful in recognizing that? Which is hard. Cause yeah, cause you said they don't usually ask for it. 

Mike: 

Rebecca: Yeah, and you wanna,

Mike: Oh, sorry, please.

Rebecca: you wanna, you wanna give them enough slack that they can try something and maybe fail in a very, controlled way. so it, it is hard to find the balance, for sure.

Mike: Yeah, that's,You know, I was thinking of it like teaching a child, well, I don't have children yet, teaching a child to tie their shoes, right? First,you do it for them, then you put your hands on top of theirs, and as their motor skills develop, you gradually apply less and less,control of their hands, and then they're doing it themselves, and they think, oh, I learned to do this all on my own.

Okay, perfect. I, I don't need the credit. I don't need you, right? That's the goal, right? But yeah, it's you know, you sit you down here at number seven and jump a little bit. You say everything is your fault. That's extreme ownership, right embracing total accountability. But to go back to the micromanagement part people are like we believe in decentralized leadership and coaching and development and things like that but if somebody's not getting the job done It is absolutely your job to go in and micromanage and ensure that they can. You know, you're only going to do that as long as you need to and if you need to do it You For too long, you probably have the wrong person, but it is absolutely your responsibility to adjust your leadership style to, to get the, most out of all of your people.

That is not something I love number seven. That is not something I will get out of a lot of leaders where they're willing to take total accountability for everything. 

Kristen: But not need to take all the credit, but take all the. 

Mike: Oh, I want the credit. 

Kristen: Well, that's a whole other, that's a whole other topic, but yeah, I mean, I also love how that like accountability feeds into your principle of always own the message, which is so important.

And you talked about going through difficult situations where, especially where you had to lay off a third of your team, like how, how have you seen this, play out?

Rebecca: Oh gosh. I mean it, I literally get like a pit in my stomach thinking about this because I've messed up, a few times. I think that you want, you wanna be liked, but sometimes you have to do really hard things, andI truly believe that when, as a leader, especially in a complex organization like you are the, you are representing the company mission, the company strategy and principles, operating principles, andyou can decide which company you want to work for, you don't get to sort of go rogue on the principles. And what I mean by that is, if your company decides to lay off a third of the team, if the, the board and the leadership, and maybe you decide to lay off a third of the team, it is completely unacceptable to, make it seem like you're not in agreement with that when speaking to your team or complaining about, the decisions coming from up top.

And I've seen it so many times. I think it's actually one of the most common mistakes 

Mike: So common. 

Rebecca: That leaders make. 

Mike: Yeah, I've done that. I want to pass the buck. Oh, this is coming from upstairs. Don't be mad at me. it's really hard to be like the bad guy. Yeah,

Rebecca: It's really hard, but I have seen it enough times where when delivering critical feedback, if you, as the person delivering the feedback are not owning that message. It doesn't have the same impact like I have measurably seen what happens if you deliver feedback. Let's say you have an engineer on the team who's just not performing and you go to that engineer and you say, you know, my boss thinks you're not doing a good job.

And like, I don't know that I agree, but like, my boss really doesn't think you're doing a good job. So, like, can you do a better job? That is so much less effective than, like, I believe that there are some ways that you can improve and I am aligned with this and it is hard. It is really hard. I have seen like night and day differences in terms of how people make turnarounds.

When you give them feedback like that, it just completely dilutes the message. It dilutes the power of you can't own it.

Mike: I believe Brene calls that courage, right? Like that. It takes courage to, to, own the message. Yeah. 

Kristen: Yeah.

Yeah. And sometimes you may not agree with it, but. Yeah, when it comes down to the next level. Yeah, that is very hard to do, but very important. 

Mike: So talk about the next one, unity and harmony matter.

That's not easy. How do you make that happen?

Rebecca: It's sort of expecting everyone else to own the message too. Right. So unity is important for a team's success. You know, you hear the phrase, are we all rowing in the same direction? And if, you know, one person's rowing forward, another person's rowing right. Another person's rowing left or whatever. Like you're not gonna, you're not going to go anywhere.

And you're just going to kind of like spin around in circles or go aimlessly. And, you know, our HubSpot CTO, Dharmesh Shah, he has a framework called Debate, Decide, Unite. And I think at least nowadays, we've gotten really good at debating. Like I think that I, at least I've seen a lot of tech organizations, like we have created space where people can openly debate ideas.

I think we're less good at deciding. Like there are a lot of decisions that go unmade for a very long time, but eventually decisions do get made and communicated sometimes very directly, sometimes implicitly or like tacitly. And I would argue they should be communicated directly, but I digress.

I think we're the worst at uniting. And what I mean by that is once a decision is made,we can't continue to re litigate that decision over and over again, like our team needs to say, okay, can I get behind this? Is this something I can live with? Not every part of your organization is going to be something that you love, but hopefully enough of it is inspiring you and motivating you that you want to continue to work there.

But if you like cannot get behind a decision that's been made and you just don't see a path forward, like the worst thing you can do is just stick around and complain and talk about how much you don't like the decision. It's like the ultimate toxic workplace like behavior. 

And

Mike: I feel like you're talking about the American political landscape. 

Rebecca: Maybe,

Mike: Well, it is. I, I thought, I thought that statement is genius, right? Debate, decide, unite. We're great at debating, not as good at deciding, and pretty terrible at uniting, and, and, and. Um, But I like, Well, yeah, but I like how you frame it around,getting people, aligned toward a common goal.

And if you're not rowing in the same, my, my current organization likes the movie, The boys in the Boat for because it's a literal, description of that allegory where it's like, I don't know the 1937 like Olympic rowing team and they're all have to row together in the same directionbut it it really matters like if they're if their timing's off if they're not headed in the same direction if their goal isn't the same which is simple across the finish line in the least amount of time Any other agenda than that is taking us away from the success and you know, so how do you get people on board with that?

Message or the meaning or the direction? Do you have any best practices for that? 

Rebecca: Yeah. I think that communicating the why is super important, and it's part of why, like, transparency is important. I've noticed a tendency, and I think some of it is you just have to, but there's a tendency to use corporate speak and jargon to explain tough decisions.And I think people can kind of read through it because they'll think about like, logically, like, does this make sense, and it doesn't always make logical sense.

And so there's just confusion about like, why did this decision get made? Like, I mean, I think layoffs, are a good example. So at Clearbit, we had a one third layoff.Our CEO at the time, Matt Sorenson was super direct with the team. He was like, we are not winning right now. Our churn rate is so bad that if we didn't do this layoff, like we're not going to continue to exist as a company and we need to turn things around.

And yeah, that's, you know, that's intense and scary, but it also was like a really like beautiful moment where we came together as an org to keep our company alive. And it was like a galvanizing force. And we actually did turn around our retention rate and we ended up getting acquired by HubSpot. So it was like a really beautiful, powerful experience.

And I honestly think if he had said like,gosh, this layoff really sucked. And, I didn't want to do it, but the board made me, 

I don't know, or like, I mean, like, or made up some other reason, like I, you know, Oh, we're just responding to market forces.

Mike: Well 

Rebecca: Uh,

or something like, 

Mike: big very common 

Kristen: when people very common

Rebecca: That's not inspiring.

Like, okay. If, if, if we're just responding to market forces, then nothing about, there's nothing for me to change except I can continue to just cross my fingers at the market gets better, right? There's nothing I can do, but if we're not winning and we've lost sight of, you know, what our customers need, that's actually very actionable.

Um, so I, I have found that to be very, very powerful. 

Kristen: No, I love that. There's multiple things that are happening in that response. It's acknowledging that, yes, this sucks. So you're not like trying to pretend it doesn't. But you're not like sitting in that either. You're using it as a way to unite people around a common goal. And you're being like transparent and really inviting everybody to be a part of it.

Like there's so many good examples within that. So I love that. Amazing. Well, we could, we could talk for so much longer on, on this stuff, but, we unfortunately don't, don't want to produce a three hour podcast, even though Mike would love to. I explained to him early on that's not really. 

Mike: No one wants to hear three hours of me, especially my wife . 

Kristen: But yeah. Thank you. Thank you so much for being here, Rebecca, and for sharing these principles.

I think it. It's so impactful. There's so many lessons in here that people can take away and I'm sure our listeners are going to get so much out of it. So thank you so much. 

Um, For our listeners, we will have the link to her LinkedIn profile in the show notes so you can follow her there and thank you guys so much for listening and we will see you next time. 

Mike: Rebecca was awesome having you. I love your stuff. It's really great.

Thank you for being here. We really appreciate it.

Rebecca: I love your podcast. It's been great. I'm super excited to keep following. 

Mike: on. 

Kristen: The Love and Leadership Podcast is produced and co-hosted by me, Kristen Brun Sharkey and Co-hosted by Mike Sharkey. Please rate and review us on Apple Podcasts, Spotify, or wherever else you get your podcasts. We can't stress enough just how much these reviews help. You can follow us on LinkedIn under Kristen Brun Sharkey and Michael Sharkey and on Instagram at loveleaderpod.

You can also find more information on our website, loveandleadershippod.com. Thank you so much for listening, and we'll see you again next week.