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What Makes a Great Manager with Heidi Craun

• Laura Khalil • Episode 74

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This week’s Hot Girl Summer episode revisits one of our earliest interviews with Heidi Craun on what makes a great manager. Whether you’re managing a team or building a team, Heidi’s insight comes from years experience managing teams at Expedia and now as Head of Customer Experience at Clearcover. 

In this episode you’ll learn:

  • ⁠The power of vulnerability in managing teams⁠
  • How to have difficult conversations⁠
  • How to set up your employees for success

Brave by Design helps creative consultants get booked solid with clients they love.Your most profitable year begins today. Take the quiz to discover the hidden revenue in your business. bravebydesign.net/quiz




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Laura Khalil:

You're listening to brave by design the show dedicated to helping creative women thrive as entrepreneurs. My name is Laura Khalil, and I'm a business coach. Helping creatives get booked solid with clients they just love. Since 2013. My marketing agency has consulted with some of the world's biggest brands. You'll hear interviews, strategies and tools that can help you do work you love with people who energize you while building your bank account. And did I mentioned more kind of fun? Stay tuned. Hey, you bad beautiful bitches. Welcome to this episode of brave by design. It is part of our hot girls summer series. And I am your host, Laura Khalil. And my goal with the hot girl summer series is to share some of our best episodes of brave by design to help you embody a hot girl summer, what is a hot girl summer, it has nothing to do with your appearance, your age, how much how much work you've had done on your face? how thin how fat you are? None of that is what we're talking about. What we're talking about with a hot girl summer is your mindset is building that confidence. And that is the sexiest thing ever. I think most of you will agree. So today's episode is one of my favorites. It is with Heidi cron, who is a really great friend of mine. And it's about how to be a great manager. And you're going to hear a lot in this episode. But I want to start off before we even dive in. And I want to ask you this. Are you a solopreneur? Are you a leader? Are you a founder of a company? Are you a creative consultant? Because if you are, what you're going to learn today is going to help you do business better. And one of the things I want you to really think about especially if you run your own business, is are you the little bitch of your clients? Or are you the peer of your clients. And here's why I bring this up. I've been running a creative agency since 2013. And I've been working with very, very big companies, Twitter, GE, Intel, Intuit QuickBooks, you know, people like that. And one of the things that I've learned, and one of the ways that I've been able to command the fee that I command for my work is by treating the people I work with, as my peers, and not as my master. Okay, and I think this is where I see a lot of freelancers, and a lot of consultants and a lot of creatives go really astray as I say, Well, I just have to do whatever they say, you know, I mean, they said to do this, they emailed me, you know, 9pm the night before, and they want it done. So I guess I have to do it. Wait a minute, wait a minute, wait backup, a great leader, and you are a leader, if you're running your own business, even if you're a solopreneur, a great leader treats others equally. So it's your job, as a great leader, as the founder and owner of your own business, no matter how big or small to treat your clients, as your peers to step into the role of a trusted expert that you are in whatever it is that you do whatever your specialty is, and to be able to set healthy boundaries with clients so that you can reconnect to the joy of the work. Okay, so that, you know, a lot of people start like creative agencies, and they get so burned out. And they get burned out because they have absolutely no boundaries. Right? They do everything that the client says they're, you know, they're just whatever they want. They do, they don't ever think about themselves. They're constantly concerned about a race to the bottom pricing. And so they get overworked, underpaid, stressed out wonder why they ever did this, don't feel creative at all. And you know, eventually will try to go back into a full time role. So the way to break out of that is to break through that type of limited thinking and say, No, no, I'm an expert in what I do. I know what I do helps people and I'm going to act as a trusted expert. And I will command that level of respect. And people who do not respect me when I you know, assume that role. Those are people I want to work with, right? Those aren't my people. So I just want to leave that with you. Up on brave by design dotnet. We have a quiz if you want to make this your most profitable year. This is designed for consultants and creatives who, let's say you're you could be a content writer. You could be running your own agency. You could be in UX or UI. You could be a graphic designer, a web designer, print designer, if you're running your Your own agency and you're really struggling to get ahead, I want you to head to brave by design dotnet and take the quiz. It's about five minutes long, about how to make this your most profitable year yet. It's 29 questions. I see all the results that come through. And if you want help, that's what we do. So, want to shout out to that? brave by design dotnet forward slash quiz. It is a wonderful resource and it's very eye opening, I think you'd really enjoy it. If you are a freelancer, consultants, or creative agency that wants to make this a really freakin profitable year, guess what you can, I can show you how. So without further ado, let's dive into this week's hot girl summer episode with Heidi Crum. So on today's episode, we are going to talk all about the traits of a great manager and I am thrilled to bring on Heidi Kron. She is the head of customer advocacy at clear cover. She's also the co founder and president of intermittent the conference for change makers. I've had the pleasure of being involved in that conference for the last three years. And most recently, I gave a talk on how to respond to microaggression unconscious bias and minimization in the workplace. If you want to see that and all of the other wonderful talks, you can head on over to my website force of badass read calm. I will also put a link to the YouTube videos in the show notes for this episode. Heidi is a powerhouse. She truly walks her talk around diversity, equity and inclusion. And I am so thrilled Heidi to call you a friend of mine. And I'm so inspired by you because I know that you really want to help women and minorities, bright bravely rise and thrive in their careers and lives. I have seen you do it. You are amazing. Heidi, welcome to the show.

Heidi Craun:

Oh my gosh, thank you so much for having me here. And that was just the kindest introduction I have ever received. I'm going to have you just walk a few steps ahead of me everywhere I

Unknown:

go in life.

Laura Khalil:

Everyone hiding it, ladies and gentlemen, I'm rolling out the red carpet.

Heidi Craun:

Please set the tone. No, because the pleasure is all mine. Laura, you've been an enormous mentor to me over the last few years. So I'm so grateful.

Unknown:

And honored.

Laura Khalil:

Well, thank you. Um, as I was telling our audience on the last episode, I was in Chicago last week, but I was actually speaking at your company, about developing 2020 vision. And you know, one of the things that really struck me, I know, you're amazing, because I know you, but to see you in action with your team. Wow. I mean, I was so impressed by you know what I saw of your management skills. I knew we had to have you on this episode. And as I know you and I were kind of like going back and forth and talking about what we wanted to discuss. And as this all came up, I saw this quote from Diane Von Furstenberg, who was speaking in New York, about the CEO of her company. Her name is Sandra Campos and DBF set of her, I will do anything to help her succeed. And I read that and I said, you know else will do anything to help people succeed. It is you because you have helped me enormously and we don't even work together. And just to experience that I know that you go the extra mile for people. And the fact is, many managers and many people don't so many people, experience managers who completely undermine their success. So I know you've experienced that I've experienced that. But that really got us talking about this episode. So I wanted to kick it off by sharing some really depressing research, which looks let's, let's I want to let's bring everyone down, and then we'll lift them up. How about that. So the research shows that the global workforce has over 70% of employees disengaged at work. That is absolutely terrifying. If you are a manager if you're in HR if you are in leadership, 70% of employees globally are disengaged at work and of those Only 4% have anything nice to say about their boss. I have more research on this on my website. So if you want to see the sources for that, Heidi, why do you think that is like, let's just start big like, can you? Can you solve that problem for me, please? Oh,

Heidi Craun:

yeah. Let's talk about slave labor. No.

Unknown:

That's,

Heidi Craun:

that is, as you said, incredibly depressing. And way worse than I would have guessed. And, and I think most of us have experienced that. at work. I personally have primarily worked in tech startups, where

Unknown:

kind of everyone is rising and grinding, and people who are that disengaged, don't usually last too long, right. But

Heidi Craun:

I totally get, you know, where this is coming from, especially as it relates to management. And I guess, when I think about it, I, in my experience, people leave their jobs for like, a couple of reasons. One is they're no longer growing. Or they're miserable at work, because they're no longer growing. Previously, I worked at a startup that was acquired by Expedia and the Chief Product officer at Expedia, john Kim taught me something really, really powerful. He's the one who taught me this. When I would fly out to headquarters in Seattle, he would make time for me and have you know, skip level one on ones with me, he wasn't my manager, he was my manager of manager. And he flat out said to me, people leave when when they stop growing, and you got potential in me and went out of his way to invest in me. So he looked for opportunities within Expedia that would benefit the business and helped me really expand my knowledge, my skill set in, in that situation, he invested in my ability to learn how to conduct usability studies, and even went so far as sending me to Seoul, South Korea, so that I could study how other authors were using our app that we were creating. And that was not necessary for me or my team. But it certainly benefited everybody. And my work doing that ultimately led to a dramatic increase in our Expedia app, hotel booking conversions. And that was a problem that we hadn't diagnosed up until that point, like we knew that the problem existed, but we didn't understand why. And

Laura Khalil:

that's fascinating.

Heidi Craun:

It is fascinating, because it was, it has helped me so much in my career, even though that wasn't necessarily something that I was looking to learn. It was more tangential. And, you know, he spent 1000s and 1000s and 1000s of dollars,

Unknown:

helping me

Heidi Craun:

learn knowing that it would pay back,

Laura Khalil:

let me ask you this, because you said he was not your direct manager. So it's something Yeah, so he met you. And you must have left quite an impression on him for or had he heard of you, like, have your reputation brought him to learn about you.

Heidi Craun:

This is kind of funny talking about setting the bar low, and then building back up. So my manager inherited me from the previous leader of our organization, and that leader, told my manager as he was leaving that Heidi is my most challenging employee. And so he went, yeah, you really set the bar low. And, and I don't, I don't know how I was this person's most challenging employee, because literally we like never had one on ones. So I don't know where that but it's kind of it kind of became like the running joke, but so that got back to you. So yeah, my manager came in, told me that one time on a visit, he said, You know, I was told that you were the most challenging of the leaders, this organization, and that, like you have impressed me the most. So then he went up to his manager and said that, like, I have a high potential leader on my team, and he was especially interested because I was ama one Amen and Expedia, especially I don't I can't speak for where it is now. But at Expedia, which is an old company, there weren't a lot of women in leadership positions. And I think everyone was looking, they were trying to make a concerted effort to look for high potential people, especially women and minorities to invest in. And so I was really fortunate. I don't know if if I hadn't hadn't been given such a low perception if I would have made such

Unknown:

a high impression. And the

Heidi Craun:

either way, I'm, I'm grateful.

Laura Khalil:

Yeah, I mean, that's sort of an interesting gift. If he had walked in and said, you know, what, Heidi is such a rock star, and then the bar is set so high for you. What do you have with? I mean, I know you're a rock star, I think everyone else knows that. But it does change perceptions. And I imagine that your new manager was quite pleasantly surprised.

Heidi Craun:

Yeah, I, when he told me that, I was like, Wow, that's a slap in the face, followed by like, a nice, soothing ball.

Laura Khalil:

Great. And it's it, I mean, I don't want to go down a rabbit hole about it. But it does make me wonder immediately, when we talk about a manager, saying that you're like his most challenging employee, I'm like, What was so challenging? Was it? Because clearly, we know that's not true. So I wonder, what personality traits could he not stand to see in you? And I wonder if that is that you are a bold, confident, highly intelligent woman. And and I'm totally I don't know this person. So I'm just kind of going off sort of the biases that we're all really familiar with, but it does make me wonder that yeah.

Heidi Craun:

I, I would go out and limb go out on a limb and say that you are, your guest is probably pretty accurate. The original leader was pretty inexperienced in in new managing, and also someone who I think was like, generally uncomfortable around women is like I perceived, and so they have a leader who is not, who is both a woman and not timid or shy, I think, was probably a lot for him to handle. Yeah, but I don't know. I'm not I, you know, he'll maybe settle that with this. therapist someday. Yeah, exactly. have our things that we take. We don't

Laura Khalil:

need to do more emotional labor for this dude. Okay, so But you said, the first thing is that as people leave when they stop growing, I could not agree with that. more strongly. What else do you say?

Heidi Craun:

So I know, people say, employees quit their manager, they don't quit their jobs, they quit their managers. And I think that's true. But I think we can get more specific than that. Which is to say, it's not necessarily like their managers personality, or, or whatever, because I think most of us can get along with most people, right. But what that really boils down to, in my mind is people leave when their managers stop advocating for them. And you said something earlier about managers like undermining their employees work and things like that. And I think a lot of managers really struggle with letting go of the day to day tactics and focusing more on strategy. Because when strategy is done, well, it's invisible in those strategies, invisible managers feel invisible. But one of my favorite human beings and

Laura Khalil:

that's really Wait, hang on a second. Sorry. I think that's a really interesting statement. Can you expand on that a little bit?

Heidi Craun:

I think when work gets done, when good work gets done, people tend to perceive that those who actually executed the work are the ones who did it all end to end. Right. And that's usually not the case. Usually, there's a manager or leadership that has decided that this work was the work that needed to be done. And set up an environment so that it could be executed successfully. And there's a lot behind the scenes that happens to lead to the point of the execution. But people don't see what happens behind the scenes, right. And so, for a manager, I think it's really hard because they're like, Oh, my team did this work. And, you know, I don't really get credit for it. And oftentimes you don't, but that's okay. And I was, excuse me, what I was gonna say is one of my former colleagues, kyrsten, muchnick. He was at a previous startup with me, and just incredible specific people. To once phrase, this in the best way, a manager's job is to make their team look good. So that's how I think about it, if if a team is doing a great job, that means that their manager has advocated for them, and help them accomplish big things. And it's from a management when you transition from an individual contributor to a management role. You think there's a hard adjustment sometimes to not necessarily be able to see, like a tangible product of what you did. So adjusting to a different kind of gratification is a hard adjustment for a lot of people.

Laura Khalil:

It also seems like a sort of learning how to pacify the ego a little bit, you know, when you're not the one who's necessarily doing the work, but you're actually helping enable the smooth running of the machine or people who want to speak a little more mainly about it, right, who are doing this incredible work? And, yeah, you're you're an integral part of that process. But you're not it.

Heidi Craun:

No, you're not. And then your job, when the team does, like knock it out of the park, your job is to go back and advocate for that team to keep growing and keep doing more big things. And I think that's another place where a lot of managers fail, especially as an employee, at least this is for me. I typically, I've been very lucky, I've been able to work at companies where I have been either, like really aligned with the mission of the company, or really excited about my role within that company. And I think when that happens, and you're really loving what you do, or who you're working for, it's easy to just be like, Oh, I'm so grateful for this job. And I'm so lucky, and forget that. The employer employee relationship is bad. transactional, right? It's a value exchange, to when an employee continually does great work, it is the manager's job to notice, highlight, and then advocate to give value back from the company to the employee. And I think, again, when this doesn't happen is when people leave their managers, they're not getting enough pay. They're not getting promoted, even though they continually prove themselves, or they're not being given new opportunities. Or maybe there's just inequity across the team. Right?

Laura Khalil:

Absolutely. I mean, boy, I this is really hitting home. For me, I'm just listening to this. I remember one of my early jobs in the tech world I was so grateful to have because it was also right around the Great Recession. And, you know, I mean, when a lot of us were coming up, right? And so I was thrilled to have this job. And I remember talking to my boss, and he said, Laura, you're doing great work, great work, great work for about a year. And I was like, Okay, I'm ready. I'm ready. You know, after a year for my raise, like I'm, I want a title raise I want, you know, let's talk about compensation. Whatever it may be maybe more responsibilities. And he said, Oh, no, everything's on hold or not doing anything. And part of that was because the company had decided to completely stop all forms of raise, but at least that's what I was told because of the recession. But it had this terrible effect of really disengaging me as an employee. I felt like Wow, I've done all this work and I there's absolutely zero recognition for what I've done. Nothing. You know, you can't even change my title. I thought okay, well And then it was probably Yeah, I don't know, seven or eight months after that when I decided to leave. Because I just, you know, you just feel like what am I doing here?

Heidi Craun:

Right? Right, because you were not seeing that value exchange,

Laura Khalil:

I was not seeing it. Yeah. And I liked, it is a transaction, I was not seeing the value exchange for the amount of work I was putting in, over the course of a year and a half, two years to stick around. So totally feel this. Anyway, I don't mean to interrupt you, I'll let you continue. This is amazing. Oh, you are preaching to the choir on that one,

Heidi Craun:

I had a very similar experience. Early in my career, my first job outside of academia was in a tech startup, I finished graduate school kind of fell into the role. And it was just a few months later that the great recession hit. And in that year, I was, I think, one of Devin, people in my industry that got a job in the state of Michigan, Oh, my God. And so I felt super, super lucky. And I survived layoff after layoff, which again, I will always be grateful for because, for me, I didn't, I wasn't married, I didn't have anybody else to rely on to pay my rent and health insurance. And you know, I just had to start paying back on my student loans. So if I, you know, lost my job, I was going to be in a world of hurt, or have to move back in with my parents. Like, yeah, that was what that would have looked like. So very grateful for that experience. But I also worked my ass off, I kept taking on the work of those who were laid off. And that meant that I was growing and taking on new challenges. And it honestly, like, it was very good for me. And then it forced me to think creatively about how I could work

Unknown:

smarter, not harder, because,

Heidi Craun:

you know, there were still only 24 hours in a day. But it made me more innovative. Those parts were all very good. And learning about new products, because I was taking on the responsibility of working on different teams and things like that. But I also felt so trapped, because I wasn't being compensated for taking on the work of the employees who were laid off. And yeah, well at it, you know, and I was continually told, like you, I think there were some freezes on raises. But then I was told that I wasn't receiving big promotions or raises because I didn't have the necessary years of experience for the title. Oh, my gosh, I really resented my lack of years of experience didn't stop the company from giving me the responsibilities of those roles that were above my

Unknown:

favorite.

Heidi Craun:

And so I think in the four years I was at that company, I only received about$4,000. And raise it when you're starting out those early years is when you make the biggest strides and

Unknown:

raises. And

Heidi Craun:

that was really frustrating stuff. As the you know, I have the opportunity to leave as quickly as you did. Somewhat envious of that

Laura Khalil:

I was living in the Bay Area. So you have to remember, I was just gonna say the Bay Area was a different place. Yeah, the recession never really fully it did hit but it did not hit in the way that the rest of the country was devastated. Yeah.

Heidi Craun:

So that is nice that you had opportunities. I mean, as the economy improved across the board, I did start interviewing and was offered jobs at other companies, which, because of everything that I had done in the last four years, meant that I was receiving job offers that were $20,000 higher in salary than what you know, I was earning at the time.

Laura Khalil:

However, did you try to negotiate with them? No,

Heidi Craun:

I just knew that my time I needed to leave.

Laura Khalil:

Yeah, it was time.

Heidi Craun:

Yeah. But because those companies were compensating employees more fairly based on how they perform. My responsibilities and ability to learn at those companies would have actually decreased from where I was currently. So I felt like well, I could go there and you know, make $20,000 more a year, but I'm not going to learn anything. This is all stuff I've done before. So I guess that's why I say I felt trapped. I could leave and take more money but I'd stop growing or I guess stay where I was go to work everyday presenting how underpaid I was which made me not A great employee.

Laura Khalil:

Right? Exactly.

Heidi Craun:

I was miserable. And, you know, I could keep learning, hoping that it would pay off in the end. And I ultimately decided on the ladder, and that was the right choice for me. And as a young professional, it was a privilege to be able to make that choice, because although I was just starting out and didn't have a spouse, or anybody to help me pay my bills, I also didn't have a mortgage, you know, I, I had more, I don't have a family that I had to provide.

Unknown:

So that was,

Heidi Craun:

that was a blessing. But when I did find a leave, I got a 60% raise. So guess what, I'm grateful for everything that I learned in that job, I vowed to never put an employee in that same situation, age experience, things like that should never color our perceptions of the actual value that is exchanged when someone does their work. So I decided then that if I couldn't advocate for one of my employees growth, then that would mean one of two things. I either wasn't doing a good enough job as a manager, like the employee wasn't performing, and I needed to address it. Or my values were misaligned with the companies. And I should question whether I could be a leader there and keep my integrity intact. And both of those things have happened. But I do truly believe that if you're not creating growth opportunities, and looking for ways to advocate for your employees, and make sure that they're working in an equitable environment, they will do their best work with and for you.

Laura Khalil:

You know, I want to really highlight, I mean, gosh, there were so many really juicy nuggets in there. But the one thing you said that I want to highlight, especially for me, because maybe this hits me, because when I was in my 20s, I felt that I was not old enough to be in certain roles, or make a certain amount of money. I had that sort of limiting belief, right. And so you said I vowed to never put an employee in that situation, where age or experience would color perceptions of their value. And what a powerful way to advocate for employees, and actually also help them understand their worth. Why so that you don't have to be a certain age to make a certain amount of money. I learned that by the time I started my own business. But it took a long time for me to figure that one out. You know, I always thought I can't make more money than my father. Isn't that interesting?

Heidi Craun:

That is interesting.

Laura Khalil:

Yeah, I said that. And this is actually I'm just like, we're basically in therapy right now, Heidi, I'm just having revelations as bringing all this up. I'm like, Oh, my gosh, where's this coming from?

Heidi Craun:

I'm gonna say that my i didn't i to this day don't even know how much my my parents make. But I certainly never dreamed bigger than that, you know, I've never dreamed of a lifestyle, bigger than the one that I grew up with. I just dreamed to have a good life. And we can be, and I will be speaking for myself, I think 90% of the limitations I have experienced in my life have been self imposed. And so having a manager or an advocate, someone, a mentor, a sponsor someone to

Unknown:

help pull

Heidi Craun:

all of these like little nuggets that people have about them, their strengths, highlight their strengths, show them opportunities, show them what could be done with those strengths is so important. Because not everybody has, you know, CEO parent, is set the bar really high.

Laura Khalil:

Exactly. And you know, I think I think a great manager is a great coach. They understand that while as you said, while this is a transaction while you are, you know, being employed to do certain amount of work, they're here to help you. They're not here to throw you under the bus or undermine you. And they're here to help you in ways that go beyond just the transaction of work. I mean, understanding and identifying the worth, that an individual has is is a beautiful thing that a manager can help us sort of dream bigger open our eyes is same thing a coach would do for example.

Heidi Craun:

Yes, absolutely. And I that's I've gotten so much out of coaching from you for that reason. I think with my team, I say like my, my job isn't to like hound you about, you know, setting the course like, this is the work that you're going to do. And I'm going to just like, make sure you're doing your job kind of thing. Because if I've hired you, I've expected that you're just going to do your job. If you're if you can't like them, we'll have a conversation. But my job as a manager is to figure out how to hold you accountable to your career growth goals, and figure out how to keep pulling you up. And in getting you to the next step in your, your growth goals. So I you know, that's why we brought you in the clear cover.

Laura Khalil:

I want to thank you for joining me and remember to subscribe to your favorite app so you can stay up to date.