Early-Stage Hiring Foundations That Prevent Mishires with Cassie Chao Leemans, Craft Ventures

Early hiring gets expensive fast when founders skip alignment.

Cassie Chao Leemans, VP of Talent at Craft Ventures, joins Shannon to share how early-stage teams can make stronger hiring decisions before scale adds complexity. She explains why pedigree can distract founders from what the business actually needs, how unclear expectations create mis-hires, and why every new role should connect back to company goals.

Cassie also shares how to define competencies, build trust in the interview process, and help recruiters move from order-takers to strategic partners.

Key takeaways:

1. Start with business needs: Define what the role must accomplish before writing the job description.
2. Context beats pedigree: A great background does not always match the company’s current stage.
3. Alignment prevents drift: Shared definitions help interviewers evaluate candidates against the same bar.
4. Process builds confidence: Strong hiring systems reduce overreliance on back channels and outside validation.

Timestamps: 

(00:00) Introduction

(00:43) Meet Cassie Chao Leemans

(02:06) Why founder alignment matters early

(06:09) Connecting hiring plans to business goals

(11:09) Preparing recruiting teams before scale hits

(13:29) Why great hiring takes longer than founders expect

(16:41) How hiring needs change as companies grow

(20:38) Defining what success looks like in a role

(25:10) Aligning interviewers on values and competencies

(27:58) What happens when hiring alignment breaks

(33:20) Where to connect with Cassie

Transcript

Cassie Leemans (00:00):
We do see that a lot of times of, funny enough, high pedigree person, that's what they were going after, but no performance was actually set up and they're like, "Well, the person isn't actually doing what we wanted them to. " It's like, "What did you tell them they were going to do? What did you interview them for? " Only because they had a great looking background, but what were they actually going to do at your company and did everybody on the interview panel understand that that's what they were going to do as well?

Shannon Ogborn (00:26):
Welcome to Offer Accepted, the podcast that elevates your recruiting game. I'm your host, Shannon Ogborn. Join us for conversations with talent leaders, executives and more to uncover the secrets to building and leading successful talent acquisition teams. Gain valuable insights and actionable advice from analyzing cutting edge metrics to confidently claiming your seat at the table. Let's get started. Hello and welcome to Offer Accepted. I'm Shannon Ogborn, your host, and this episode is brought to you by Ashby, the all-in-one recruiting platform, empowering ambitious teams from seed to IPO and beyond. I am super excited to be at Transform, but even more excited to be here with Cassie Leemans, who is the VP of talent at Kraft Ventures, where she partners with portfolios, a portfolio of over 250 companies from Series A through Growth Stage. She spent her career inside high growth environments, including scaling through Uber's rocket ship phase from 500 to 15,000 employees and joining companies as early as 15 people with experience across four startups and four exits.

(01:29):
She is deeply passionate about recruiting fundamentals and believes getting hiring right early on is one of the most important drivers of the company's success. So that's kind of what we're going to talk about today. And she works closely now with founders to define what great looks like, build thoughtful compensation strategies, and really make high impact leadership hires and is known for her practical perspective on scaling recruiting. Cassie, thank you so much for joining us

Cassie Leemans (01:50):
Today. Thank you for having me. Excited to chat.

Shannon Ogborn (01:52):
Well, like I said, we are going to be talking today about alignment and really setting up founders for scale. So just kind of taking a big step back on the alignment piece, when we think about that, especially at series A and B, why is it so important to get that alignment and start building that muscle early on?

Cassie Leemans (02:13):
It's so critical and this is all I work with. Series A and B, it's a lot of the times founders, they're building their vision, they're building their dream and they do end up getting stretched very, very thin early on. So they need to hire their third, fourth, fifth, through 10th person at the company and many of them think, "Well, I just need to go get the best and the brightest and they have to come from X, Y, Z background and have X pedigree." And I talk about this a lot because while that does sound nice and fancy and you have another company that's already vetted this person before, that might not actually be the right hire for where the company is right now. And a context from another company might not translate to the context of your company. So what I find very fascinating is that's always where founder's mindset goes versus what do we need right here right now for what we're doing, what we're building, and we need very context specific people to come in.

(03:14):
And early stage it matters so much more because every incremental hire you have has that exponential output that's going to get you to your next funding stage or product market fit or whatever it may be, these big milestones. And if you miss hire, that is extremely detrimental when you're a five person company. Someone coming in is one fifth of the company, 20% of the company. And if you've mishired that person, it could crush morale. It could really set you off the rails of what you're actually trying to accomplish. So being early stage, you really have to think of every net new hire that you have and what their purpose is, what the context is of the role at your company.

Shannon Ogborn (03:59):
I've noticed that a lot of companies at these stages tend to do a lot of opportunistic hiring. And I'm not saying that the person can't come along and you'd be like, "We actually do need that. " And I hadn't really thought about it until this moment, but I think that can create some chaos of like, we're trying to fit around Peg into a square hole. We don't quite know. And on morale, like you said, it's not just about how well someone can do a job. It's about what they add to the culture. It's about the company that you're trying to build in the way people work. And if you're not thoughtful about it and you don't have that alignment, I feel like things can go sideways very quickly and you could have been on track to build an amazing company and now you're stalled because you've hired the wrong person.

Cassie Leemans (04:48):
Exactly. It's interesting though, there have been a lot of opportunistic hires that have worked out well and I think those conversations have- I've

Shannon Ogborn (04:54):
Been one of them.

Cassie Leemans (04:55):
Yeah. Really? That's amazing. I think it comes from when we make these introductions to founders of executives inside of our network, founders are also learning from these conversations, right? Let me talk to ... I don't need a sales leader now. I have a great AE, they're hitting their goals, they're helping our business metrics on the revenue side, but I'd like to talk to a head of sales. I'd like to see who you have in your network that I could learn from. I make these conversations happen all the time within our portfolio. And then as founders are talking to more and more of them, they're just like, "Oh, actually I could probably use one in five months and let's continue to have these conversations. I really enjoyed the conversation with so- and-so. Let's hire them," but have them go through the interview process, meeting everyone at the company as well, not just hire on the spot.

Shannon Ogborn (05:45):
Yes, hiring on the spot. That's probably more of the issue. And today we're going to get into what people need to hire for, what they need to be thinking about, and then also how they build a process that helps them get there. So speaking to what do people actually need to hire for to achieve that alignment? I know that we've talked about before that it's a lot about business and business choices and you mentioned some in the why, but curious to dig more into that.

Cassie Leemans (06:16):
So I've been at many companies where they said, "We need to hire 50 more people on the engineering team." And it wasn't until I joined an earlier stage company that I realized, wow, just saying a number out there, number one, it changes the entire dynamic of my team on the hiring side. Do we have capacity to even build this out? And we can talk through how to even capacity plan on the recruiting side to fit this. But one company that I had joined was extremely thoughtful of how they labeled every net new hire on that engineering team. This is what we want to build on the product roadmap. This is what this engineer will do. Every category of engineer underneath it as well. The front end person needs to build this specific UI for this customer use case and would sequentially go down all of these business metrics of what they're trying to accomplish on their product roadmap and how it tied into the company's overall OKRs.

(07:09):
And that was probably the most detailed way I had seen it built versus, I mean, we've talked about my hyperscaling experience is just like, there's a thousand more that you need to hire and it's just never ending. And you don't actually know what these people are going to be building at your company. I'm sure the company will find something for them to do, but when you're very early stage, you can't just hire someone and be like, build something and have no actual goals set to it. So I try and have those earlier stage companies think through, why do you need this person here? They are going to have to take on a lot. And we're having massive conversations about that with early, early stage founders now that can't compete on compensation with the large research labs and AI, a whole nother topic. But what do you want to see from this next individual that's joining the company?

(08:00):
And does the rest of your team know that is what the expectation is of this person? And then you work it backwards and building out what that interview process looks like.

Shannon Ogborn (08:09):
Yeah. I think before you had stated it sort of in one sentence as start with the business not the job description. And I think that fits it perfectly because it even impacts interviews. If you don't know what the person is going to be working on, it is hard to evaluate the skills that the person is going to need to be successful in the role because you're like, "No, no, we'll find something, but then the onboarding's not great." And all of these things actually set you back long term, but I don't think founders are necessarily thinking that way. They're like, "I just want to hire amazing people. " And you're like, yes, we should hire amazing people, but we also need to think about what the business needs and then we need to describe who that person is before we can just hire the amazing person because I think people have it in their mind like, "I know this amazing person, but that amazing person might not be what the business needs right now." And then you have someone that's there taking up capital and not actually needed for the business where it is at that moment.

Cassie Leemans (09:10):
You just also don't know how to evaluate performance at that point, right? If you haven't set those goals up of how you're going to hire that person and what that person's going to do, how do you evaluate that they're actually helping the business- Doing the thing, right? Yeah, doing the thing that you're asking them to do. And we do see that a lot of times of, funny enough, high pedigree person, that's what they were going after, but no performance was actually set up and they're like, "Well, the person isn't actually doing what we wanted them to. " It's like, "What did you tell them they were going to do? What did you interview them for? " Only because they had a great looking background, but what were they actually going to do at your company and did everybody on the interview panel understand that that's what they were going to do as well?

Shannon Ogborn (09:51):
Right. There's exceptional people who just don't match a stage and role in a company and we have to be okay with that. I think when people are excited to hire the person but the person doesn't fit, I think that's when the mishires happen.

Cassie Leemans (10:07):
Exactly.

Shannon Ogborn (10:07):
And these are real humans we're talking about, right? A mishire doesn't just affect the company, also affects the human on the other side of it. Exactly. And it's not their fault that the business wasn't aligned on what they needed to be doing. That's

Cassie Leemans (10:24):
When you see a lot of negative glass door reviews, right? And it's because you now have what you'd consider a disgruntled employee, but they're disgruntled because things were not laid out clearly for them of what you wanted from them. And that's going to now reflect back on your business that you weren't setting them up for success.

Shannon Ogborn (10:43):
Not all the

Cassie Leemans (10:43):
Time, but

Shannon Ogborn (10:43):
Many

Cassie Leemans (10:44):
A

Shannon Ogborn (10:44):
Time.

Cassie Leemans (10:44):
But sometimes.

Shannon Ogborn (10:44):
And I think because sometimes it does work out, people start to feel like, well, it just always works out. Sometimes it works out by chance and sometimes just the stars align, but it wasn't intentional. And one of the things that we had talked about before is just kind of advice you got from this engineering leader who said that you should always be thinking in the back of your mind about how we would hire these people. How would we scale? Would love you to speak more to that mindset. I

Cassie Leemans (11:15):
Will never forget when he told this to me. I had followed an engineering leader from Uber to my next company, Sonder, and he gave me just these words of wisdom and it was the first time that I was becoming a people manager as well from an IC, something I always wanted to try and he said, "Cassie, you're really good at executing and doing the work and I tell you what our headcount goals are and then you almost yourself go and execute it. " Yeah, you

Shannon Ogborn (11:40):
Make it happen.

Cassie Leemans (11:41):
You make it happen, but now you need to scale your team.

(11:44):
Any moment of the day when you have any free time, including when you're sitting on the toilet, scrolling your phone, you should be thinking about if I asked you to hire a hundred people tomorrow, do you know how you're going to set your team up? What is each one of their roles? What are they going to be doing? How are you going to evaluate them and what their output looks like? How are you going to support them and ensure that they know what good looks like, what great looks like and as your team skills, how are they going to mentor the next group of people that are going to join your team? And that has always sat with me. Can't say that I've always put it into effect, but it is something that's always in the back of my mind of, if this happened tomorrow, am I prepared for it and can I quickly think through that and be resourceful?

Shannon Ogborn (12:27):
Yeah. It's not about creating anxiety of what if situations, it's- It's

Cassie Leemans (12:32):
Being prepared.

Shannon Ogborn (12:32):
Yeah. It's an exercise of problem solving and being prepared and not ... I feel like it's the reps of not even that specific situation, but just the problem solving process and continuing to build that muscle before you need it so that when it's there, you can fully exercise it. It's like, maybe this isn't the exact situation I thought of when I was on the toilet, but I did have a good problem solving process of like- Exactly. What are the assumptions? What do I need to think about? Who would I need? And then you actually have sort of a mental framework and model built so that when the situation does arise, you're ready to quickly start actioning on it.

Cassie Leemans (13:09):
Exactly.

Shannon Ogborn (13:10):
When it comes to hiring, the other thing I think founders can often lose track of because hiring is just one of their jobs. It's an important job. It's probably one of their most important jobs as an early stag founder, but they have a million other important jobs too. I think what can get lost is how long it actually takes to hire somebody and hire the person you want and hire well. Have you seen this across your

Cassie Leemans (13:35):
Company? You're going on the inside. This is one where it's funny a lot of my talent leaders, they don't struggle with this per se, but it's something where they have to be up against all the time, whether it's a hiring manager, a founder just saying, "We need this person yesterday." I'm like, "How did you think that was going to happen if we never heard that this role even existed?" And, "Okay, maybe fine you thought about it yesterday and now you want me to get this person by tomorrow." That's not how it works. And you do want to be extremely thorough with again, what are the business goals, why are we hiring this person? How are we going to evaluate them and ensure that we don't miss hire or we hire the right person with the right context for this role?

Shannon Ogborn (14:21):
Especially if it's so important and it's like we need to hire this AI engineer to accelerate our business. And then it's like, we really should have thought about that three months ago. And we'll get into deeper into the how, but I do think there's that misguided perception that hiring is just easy. You just get

Cassie Leemans (14:42):
Them. Just do it. Yeah. Where do you think they come from? Well, from this guy I think many founders do know how difficult it is. That's why they reach out to us on the talent side. They reach out to the resources that we have to support them, but I don't think they understand what goes into the process as well of why it does take time. You are courting this person to leave their full-time job from another place where they could be very highly compensated. And if you are not involved as the founder or the hiring manager and you're just expecting recruiting to do it, it's going to take even longer. Not trying to shame the recruiting team. We're doing great jobs, but

(15:24):
A big part of why someone leaves another company and joins a startup, maybe taking a pay cut, most likely taking a pay cut is because the founder's involvement, the founder's vision, the founder's roadmap for this person and ultimately selling and pitching and closing this person. I told my founders, "No one's joining because Cassie smiled at them." Every day that I talk to them through the interview process, it's because everybody on the team was involved, but especially the founder and the hiring manager and they showed that the candidate that they cared. So that's a really big portion and then also the clarity. So through the interview process, the candidate is learning, wow, they know exactly why they need to hire me, what I'm going to be doing at the business. Everybody I talk to is aligned and saying the same thing. That's a really big one and they all treat me with respect.

(16:19):
That's part of that candidate journey of building that structured interview process that is going to close the candidate as well.

Shannon Ogborn (16:27):
One of my follow-ups here is we're talking about, I guess your first 10 hires. Does your mindset change as you scale? Does it change at 15 and 30 and 60 and 90, 100? What changes at that point, if anything?

Cassie Leemans (16:47):
A lot changes. I think when you're hiring your first 10, you are already thinking through what do we need to execute to get to that next fundraise. If you're at seed stage, how do we get to series A? Or how do we get to product market fit? Every net new person you're adding is just raw output. It's that execution. Yes, they're taking a lot on their plate. You're going to be wearing many hats, but it's very operational. Then you start adding in management the next level. Sometimes these are first line managers that were first time managers. Do they know how to do that? So there's a little bit of friction there too. Do they understand how to create performance metrics for the people underneath them? Yeah.

Shannon Ogborn (17:27):
There's a lot of internal mobility at that stage, especially at startups because you want people to grow, you want people to learn. And if someone got in early, you want to reward them for their work and put them in a position for success.

Cassie Leemans (17:39):
Exactly.

Shannon Ogborn (17:40):
That means then you're basically backfilling them with someone new and that's another complexity.

Cassie Leemans (17:46):
Exactly. And I mean, even just through my own experience too, being a first time manager, it was so hard for me to relinquish my execution mindset and being an operator and to going to managerial mode and how do I hold my team accountable, make sure they're set up for success. So there's a transition period when that happens at a company. And I would say even scaling beyond that and doubling again, there's a lot more. It's an org structure and design complexity that really makes the founder have to think through how many people are going to report. And to me as a leader, do I have enough time? Should I have 15 direct reports that are all VP and DC? That happens all the

Shannon Ogborn (18:23):
Time.

Cassie Leemans (18:23):
All the time. And so then you start to see a lot of complexity there that founders also have to think about. And sometimes it's happening earlier than some may think. It could be even 50 people at the company already. So this is a shout out to people leaders out there. Not many founders think to hire a people leader early. I do think there is a huge recommendation for it because if you do want a high performance company that is executing these business metrics, you do need alignment across all the leaders that are reporting to you. You need to set up performance metrics. You need to talk about the career progression, right? People are staying at your company because they feel that they're being respected, involved, growing, scaling. Valued. Valued. Exactly. And without that, and if you don't have time as a founder to be working on that, you need to be thinking about it because yes, your revenue might look beautiful and we've seen that a lot right now.

(19:22):
A lot of revenue outgrowing company headcount, but then you have folks within your company that could be just hanging on because they see their equity growing, but they're really unhappy at their role. You don't want those people hanging on to your company and not contributing to what you ultimately want performance-wise for your business.

Shannon Ogborn (19:41):
I feel like there's a lot of situations right now to that point where the market has been really interesting in tech. Some roles are booming, some are being cut significantly and there's a lot of shuffling going around and some people are just really waiting for an employee market to come back around. And the last thing you want is that all those people flood out as soon as that happens or as soon as your company IPOs and they've reached the point where they can exercise and leave and then they all flood out. That would be a detrimental moment. So I agree. The shout out to the people leaders, they are truly doing incredible work. And in terms of the how, which we got into a little bit of if you were sitting down with a founder and you're trying to work with them to understand how they build a process to evaluate for what they need.

(20:34):
So it's like, now we're aligned, right? We have some alignment. We know what we need. How do I do that? How do you coach them there?

Cassie Leemans (20:45):
I want them thinking through what would this person have accomplished 12, 18 months after you've hired them, right? If they can't even define that, how are they going to notice if someone is doing the right thing for their business? Of course, things change, right? Like market shifts or you decide to pivot something inside of your business, but how adaptable is that person? You got to interview for that type of value as well, but they need to be able to break it down into what we're going to get built, what needs to be sold and where the current team is strong versus weak, where are those gaps currently and how are we going to be able to fill it with the right person? I want them thinking again, what are those cares of the business and then walking it back that way.

Shannon Ogborn (21:31):
The gap thing is so real because I think one of the earlier hiring mistakes is that you want to replicate what's already going well, but you miss the opportunity to be additive. So there's these circumstances where it's like, yes, there are attributes that you need to evaluate of what this role needs if we're going to bring on someone else in this role, but there's also something to be said about filling the gaps in your team. How does that resonate for you with your founders?

Cassie Leemans (21:59):
Yeah. So I've given many in interviewer training and in my interview training deck, I have one slide that has pictures of Voltron. I don't know if you know what Voltron is, but it's this Japanese anime and it is this megabot, which is a sum of, I think it's like five different characters that become into one and they're a weapon ultimately can destroy evil. And it's four of these Voltron characters and I'm like, I know you want to hire for Voltron. Everybody wants everyone who can do everything, but my next slide is different Pokemon and some Pokemon are strong in something and some are weak on the others and that's going to be what interviewing's actually like. Some people are really strong on one area of their expertise and they have gaps on the others. The way that we look at it is even I bring engineering up as an example.

(22:53):
Many of my teams have always wanted full stack engineers, which means they know front end, they know backend, they can do everything in between, but someone may be stronger, way much more on the backend and they can't do as much fine tuning on the UI side. But if they were hiring for Voltrons, they'd be like, no, this person is so weak on the front end side. Well, why wouldn't you just hire a more front end focused person and you can build more cohesively and compatibly together versus everyone is good at everything. Now they're all arguing what they want to be working on and mine is better, yours is better. It's really wanting to fill in the gaps of where the business is and then also filling in the gaps of where individuals are weaker and that's how you should build your Pokemon collection in a sense, but how you should build your team.

Shannon Ogborn (23:40):
Yeah, it's so true because it is nice to have people who can flex two different areas, but even I've noticed it at Ashby when I joined in the 30s and now we're in the early 300s, what you need from people is very different. In the beginning, you might need more generalists because you need people to play multiple roles when you're scaling, even when you go from series A to series B, okay, well now we need to think about do we need someone to do this niche part of the job exceptionally, exceptionally well, and then where do our generals still fit in and where do they want to grow and move forward as we become more into our niche areas? I think it's good to hire for agility. You were talking about earlier, especially with AI and just that as an attribute, but there's a point where you do need subject matter experts because that's actually what's going to move the business

Cassie Leemans (24:34):
Forward. Exactly.

Shannon Ogborn (24:34):
And so that alignment we talked a little bit about sort of building that profile, it's important to have that alignment to build the right profile

Cassie Leemans (24:44):
Because

Shannon Ogborn (24:44):
It's not always going to be a generalist.

Cassie Leemans (24:46):
Exactly.

Shannon Ogborn (24:47):
One of the things that you had mentioned previously is this underlying question underneath everything, which is like, what are you actually solving for? And then some of the more typical breakdown around values. Tell me more about how you coach founders on hiring for those attributes in values because I do think that that is something that people can easily miss or they overshoot it and then they're narrowing their talent pool too much.

Cassie Leemans (25:16):
So this is a really interesting conversation that I've had with many of my founders, talent leaders as well when it comes to interviewer training. I still remember at my last company I gave interviewer training and I made everyone go around and just define the word collaboration. Everyone gave their definition, there is no wrong answer, right? This is what your perception of collaboration is, but I let them know, did any two of yours match? And they looked around and were like, no. And just for an example, one person said, "Oh, I love when candidates ask me a bunch of questions and they really want to understand my world and then we get to work together and collaborate on it. " And then another person had said, "Oh, I prefer if someone doesn't ask me questions but I can see their gears thinking, they know I'm also thinking about it.

(26:08):
Both of us write our ideas down separately and then we come together with a solution." I'm like, "Well, if you evaluated one person that asked a bunch of questions during the interview process, you would've ended up being like, the person doesn't know what they're doing, that's not collaboration." And then you would've said no as a false negative on that signal for that competency. So I think it's really important that not only is a hiring leader going to open this up to the rest of the people interviewing on the team, but how they all define it together and align on what these definitions of the competencies are for that specific role think is hypercritical. Collaboration could mean something different on a different team within your same company, but as long as everyone within that team aligns that's what we need for our role and who we want on our team is how you get that alignment and kind of fill that gap there.

Shannon Ogborn (27:03):
The very big reality of these situations, if you don't define it for people, they will define it for themselves and it almost never aligns because people have their own thoughts of, "Oh, well, at my previous company, collaboration meant X." And it's like, "Well, we're not your previous company. We're this company." And so you really have to go through all those exercises to keep from having, obviously it's bad to have false positive, but it's also bad to have false negatives. You don't want to be rejecting people who could be the next best thing for your company. It's like the one that got away. I wish I would've hired that person and if we just were aligned maybe it would've happened. But in terms of results and I guess how you've seen this play out across, especially your portfolio companies that you've been working with over the last several years, what does it look like when this is right, when companies get this right and what is at stake if they don't?

(27:59):
So I guess we could start with like, when it is working, what happens? What are the outcomes?

Cassie Leemans (28:04):
When it's working, you've got your pipeline going, people are coming through the process, you're actually able to interview swiftly. Everyone understands in the debrief what they were covering, what competencies mattered they were all aligned on their competencies. So it's pretty easy to come up with a decision during the debrief of which I say also do within 24 hours of doing the final interview set with the candidate. So you see hiring happen so swiftly. And then when it goes wrong is when I hear from founders, "It's the recruiting team's fault. They're not giving us enough candidates." It's probably the number one thing I hear. Sourcing is a problem. We don't have enough pipeline. We did 40 interviews, nobody is good enough. Our bar is just high. I hear that. So I mean, I don't know what talent person hasn't heard that the bar is high. Yes, but our

Shannon Ogborn (28:57):
Bar is just too high.

Cassie Leemans (28:58):
Too high,

Shannon Ogborn (28:59):
But

Cassie Leemans (28:59):
I- No

Shannon Ogborn (28:59):
One can match it.

Cassie Leemans (29:00):
No one can match our bar. But again, you're taking people from different companies to join your company. Are they all aligned on what that bar is and do they all know how to

Shannon Ogborn (29:12):
Interview correctly? Do you even know what the bar is? What does that even mean? I've talked to other people about this where it's like top 1% A players, these sorts of terminology that you just hear in the market a

Cassie Leemans (29:26):
Lot- Bock stars. Rock

Shannon Ogborn (29:28):
Stars, ninjas, purple squirrels, unicorns. And you're trying to gather all these people who are amazing, but like we were saying earlier, amazing can mean different things and you have to have that defining. And one of the things that we were really harping on previously was when it's not working, you start to actually have an extreme overreliance on referrals and back channels and external validation because your process isn't actually holding up. So you're like, "Well, now I need external validation And instead of trusting what you've built internally.

Cassie Leemans (30:02):
Exactly. I just wrote an article on this because I have seen it happen inside of our portfolio companies where they will interview a bunch of people and they'll have their conviction internally enough, but not enough so that they don't go out and start reaching out to back channels or saying, "Does anybody object that knows this person?" I'm like, "You've just invalidated every single one of your interviewers on your team, pretty much telling them you don't trust them."

Shannon Ogborn (30:33):
You don't trust yourself.

Cassie Leemans (30:34):
You don't trust yourself. Exactly. You've trained your team to interview, your interviewers were trained on this and now you've told them, "It doesn't matter. This other person outside could tell me if this person's cool or not for our company." It's like you're just dissolving trust among your entire team, but also why does another company's signal of this individual matter for your company? And I think about this a lot because I still remember my first startup. They really valued people who spoke up, but I did not feel safe to speak up. I just thought, "My first startup, I just want to execute." And I was always known as the executor on the team. I performed in metrics, but anytime it came to meetings, I just wouldn't say anything. I'm just doing my job. But if anyone had asked from Uber to my previous company, do you think Cassie stands by conviction of the decisions that she makes?

(31:32):
They'd probably say no. And if that's something that Uber cared enough to go and look at and validate from somebody else, it would've been a no, right? Thank God they didn't or maybe they did and I still made it through. But I found my voice at Uber and I found very supported. I'm an opinionated person. You couldn't tell from this podcast already, but I grew into my voice and that mattered so much for me. So another company's envision or judgment of me should not have catapulted to the next part of my career of which completely different context, completely different environment. I stayed at Uber for four and a half years and made hundreds of hires there. So I always try and tell my founders, great, if you want to do references, back channels, these are signals for you to be able to dive in a little bit more on your institutional knowledge you're creating at your firm and if this matters to you.

(32:31):
Yes, if you've talked to five other companies this person's worked at and there is a common trend that they're just a toxic person. Okay, maybe that is a different story. Different story.

Shannon Ogborn (32:40):
Toxicity, completely different.

Cassie Leemans (32:42):
Different.

Shannon Ogborn (32:42):
But everyone, like you said, different parts in your career. I think people earlier in my career would actually know me as someone who came on too strong. And now I've really dialed that in and now I'm working at a company who sees value in questions. I've worked at a company where they've told me I ask too many questions. So it does depend on what-

Cassie Leemans (33:04):
It's context dependent. Yeah. It really matters where you're going, what your company stands for. And that's where we talk about those values as well. It's like, what do you want as a business? Does not matter what the other company wanted for the individuals at their company.

Shannon Ogborn (33:19):
Well, if you want to hear what hiring excellence means to Cassie, her recruiting hot take, which I'm very interested in. And then one thing she would tell her earlier career self, please feel free to head to YouTube. Well, we are coming up on our time. Where should people go to learn more about you and your work?

Cassie Leemans (33:35):
I've been posting a lot on my LinkedIn, so Cassie Chao Leemans on LinkedIn. Feel free to follow. I've also been posting a lot for our portfolio, but it is public through Kraft Ventures blog.

Shannon Ogborn (33:47):
Amazing. Well, I think this is going to be particularly helpful, especially for early stage founders or that solo first recruiter who's trying to get founders on board. So thank you so much for joining us. The Alignment Conversation is one of the most foundational pieces to successful hiring.

Cassie Leemans (34:03):
Yes. Thank you so much for having me, Shannon.

Shannon Ogborn (34:07):
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