Entrepreneurs love to set lofty, ambitious goals…after all, it’s in our nature. But what separates those of us who reach our goals from those who don’t are the skills we obtain and use to get there. Leah Carr’s approach to entrepreneurship is a highly grounded one. She’s the CEO of a learning and development company called TILR (that’s T.I.L.R.). They help HR teams and people leaders to hone in on the proficiencies their employees need. Her work philosophy is simple: she chases opportunities, no matter where they crop up, over hyper-defined goals. Leah shares her best learning and development advice. If you’re looking to future-proof your career or your company through a skills-first approach, then this episode is essential listening.
Entrepreneurs love to set lofty, ambitious goals for ourselves…after all, it’s in our nature. But what separates those of us who reach our goals from those who don’t are the skills we obtain and use to get there.
Leah Carr’s approach to entrepreneurship is a highly grounded one. She’s the CEO of a learning and development company called TILR (that’s T.I.L.R.). They help HR teams and people leaders to hone in on the proficiencies their employees need. Her work philosophy is simple: she chases opportunities, no matter where they crop up, over hyper-defined goals.
Leah shares her best learning and development advice. If you’re looking to future-proof your career or your company through a skills-first approach, then this episode is essential listening.
Leah talks about:
We'd love to hear your feedback!
Here's a quick 5-question survey. Your answers will help us to make the show even better: https://forms.gle/5JnfCUWbgLRw1NTa8
Hosted by Katherin Vasilopoulos. Made by Cansulta and Ethan Lee.
Music by © Chris Zabriskie, published by You've Been a Wonderful Laugh Track (ASCAP).
Songs used in this episode include: "Air Hockey Saloon," "Everyone Will Notice, No One Will Say Anything," "Hitchcock Would Have F___ed Up Charades," "What True Self? Feels Bogus, Let's Watch Jason X," " Short Song 022123."
Used under the Creative Commons 4.0 International License
Ethan Lee [00:00:00]:
Hi, everyone. Ethan here. Before we get started today, I just wanted to jump in on behalf of the entire team and say thank you so much for listening to the show this year. It's been a really crazy 1st year for And So She left. We won a couple of awards. We were nominated for a few others. And, of course, we got to speak to dozens of Wonderful entrepreneurs listen to their stories, their practical advice, and it's just been an absolute blast. We're gonna be taking the rest of December off as we wind down the year, But we're going to be back in January with new episodes, so look forward to that very soon.
Ethan Lee [00:00:32]:
So thank you so much again for listening. Have a wonderful holiday break, and enjoy the episode.
Katherin Vasilopoulos [00:00:37]:
Picture the goals you have for your company. If you're like most entrepreneurs, your north star hangs pretty high. We love to set lofty ambitious goals for ourselves. After all, it's in our nature. But what separates those of us who reach our goals from those who don't are the skills we obtain and the skills we use to get there.
Katherin Vasilopoulos [00:01:00]:
Leah Carr's approach to entrepreneurship is a highly grounded one. She's the CEO of a learning and development company called tilr, that's TILR. They help HR teams and people leaders to hone in on the proficiencies their employees need, shedding light on upskilling opportunities while aligning employee and company goals. Leah herself has held a wide range of jobs. Unlike most of our guests, she jumped from early stage startups to enter the banking world Then leaped back into startup life once again. Her reasoning is simple: she chases opportunities no matter where they crop up over hyper defined goals.
Katherin Vasilopoulos [00:01:37]:
With a masterful grasp of learning and development, Leah joins us for a practical discussion about absorbing new skills as a nimble operator. This episode hands you the answers to burning questions like, what skills are most valuable right now, how do you adapt to a job market in constant flux, And how can I take a skills based approach to picking a realistic long term career? You're about to hear Leah's best learning and development advice. If you're looking to future proof your career or your company through a skills first approach, then this episode is essential learning. I'm Katherin Vasilopoulos, and this is And So, She Left, the podcast about incredible women entrepreneurs and the wisdom they uncovered beyond the corporate world. There's really no end to the list of skills you can acquire, but each of us has a different destination. Not every skill will help you land the next opportunity that you're excited about. So to start out, I ask Leah to narrow that list a little. What skill are most companies looking for?
Leah Carr [00:03:06]:
The, you know, number one set of skills that a lot of customers are looking for to invest in first are leadership skills. That seems to be where companies at least perceive the biggest gap is. And, you know, it it's not surprising because as we look at how skills are changing, The soft skills are really what's in demand. I think according to LinkedIn, the biggest skill in demand in their report last year was communication And empathy. So it makes sense to me that leadership would be one of the most in demand, skill sets.
Katherin Vasilopoulos [00:03:40]:
Oh, that's very interesting. So because when I think of skill set, I'm thinking about, you know, hard labor, manual labor, and, those Software skills, yes, are very important. And I think it's interesting that those are the ones that future employers are looking for also in in candidates, like leadership and communication, as you said. Those are really important. And how do you develop that?
Leah Carr [00:04:00]:
I'm gonna answer your question, but I I just wanna add 1 more thing to what you said. You know, Brene Brown Came out with this and I thought it was so great. She talked about how we moved from the era of physical strength, and you talked about this, that manual labor, you know, in the 19 twenties, that was really What was required, and then we moved into, I think she calls it the era of brain strength, you know, developers, data scientists. Yes. And I I don't wanna imply in any way that that's not important. But now she talks about how we're moving into the era of heart, you know, those people skills, the empathy, the Being able to communicate that those are really what's important and and the pandemic has has really had that shift. But to answer your question, you know, how do you train those skills? Again, I think there's various options. You know, we tend to integrate with e learning providers.
Leah Carr [00:04:47]:
So, you know, we offer a lot of courses through our platform. We also have custom content. But at the end of the day, it's one thing to learn a skill, it's another thing to develop a skill. And so what we really recommend for our customers is make sure that when someone's taking a course, there's opportunities To use those skills. So let's talk about, you know, one of the communication skills would be presentations. If you have someone and they're gonna take a course in presentations, Have this person teach a lunch and learn afterwards. Gives them an opportunity to not only share their knowledge with other people, but also to really test out and and use those skills.
Katherin Vasilopoulos [00:05:25]:
So it's, tell me what I've just taught you kind of thing.
Leah Carr [00:05:28]:
Yeah. Yeah. Exactly.
Katherin Vasilopoulos [00:05:29]:
And so with all this work that you're doing in this current job, are you seeing some challenges in implementing all this?
Leah Carr [00:05:38]:
Yeah. You know, I I think one of the bigger challenges That we've been facing, for a while is HR budgets are almost always the first to be cut, especially in technology. We've moved From, you know, this growth at all cost mindset to a leaner mindset, which overall I think is great, but often That means that the learning and development budget is being cut. It's been a challenge not just for, you know, companies like ours, but also a real challenge for learning and development and HR professionals who get into it because one of the things they love the most is helping other people build and grow their Careers. And, you know, it's also a challenge because skills have changed so much. Companies Often don't have the skills they need to compete, and so they're missing out on business opportunities. They're missing out on sales, and it's just this vicious Cycle. And so the challenge is really helping companies and our customers understand, like, you can't afford not to invest in learning and development, But you've probably been doing it wrong and seeing no return and let us help you do it right.
Katherin Vasilopoulos [00:06:50]:
Yes. And the investment in the Skill set for each individual also then has to translate into employability or upscaling or being able To have better opportunities down the road, it it can't just be I'm gonna learn something and then there's no opportunity. So tell me if there's, a mismatch currently happening.
Leah Carr [00:07:08]:
Yeah. I think that we often don't realize that learning and development is in fact learning and then development, I see a lot of learning going on. There's a lot of people taking a lot of courses, especially since it's so accessible right now, but the most important piece is the development. And so you need to make sure those opportunities are available when someone completes a course and, you know, you don't always have to do the learning for the development, sometimes you can do it together. One of the other things we do in our product is we have this amazing boolean search, when you put in, you know, your and or logic, we have a little learning icon that you can click on. So we'll show you people who meet the, you know, requirements of your skill search, but we'll also show you individuals who want to learn a skill. And so we encourage companies, hey, you're building a project team, like, why don't you put 2 people who have the skills and 1 person who just learned the skill or who wants to acquire the skill and make sure that you're thinking about that as you're signing work and building teams.
Katherin Vasilopoulos: Describe what that term means, the Boolean search.
Leah Carr [00:08:19]:
Oh, so Boolean search is is and or logic. So you can say, you know, I need someone who has sales skills, or they have customer service and leadership skills.
Katherin Vasilopoulos [00:08:30]:
Oh, oh, I see. I see. So it's a way to maximize the the database, search results.
Leah Carr [00:08:36]:
That's exactly right.
Katherin Vasilopoulos [00:08:37]:
Oh, okay. Okay. I gotcha. Okay. We were talking about issues that come up, over the the last few decades. You know, like automation has taken over, and We thought we would lose jobs on the on the basis of that or the pandemic came along and just disrupted everything. Can you tell me more about how that has influenced your your career?
Leah Carr [00:08:55]:
Yeah. So in 2007, it was predicted that 45% of jobs would be eliminated because of automation, and we just sort of accepted that as reality and, you know, went on with our day. And then, you know, that didn't happen. And, you know, you combine that with the advances in AI, the digital acceleration because of COVID, and the skills for jobs have just changed so much, you know, in terms of how that's personally affected me. Well, the biggest way is that I happened to have been working at the bank leading digital banking when the pandemic hits, which is when a massive digital acceleration happened especially in banking. It was just such an amazing opportunity to scale my team quickly, work with the government delivering projects. So I I personally really got to upskill during that time. I happened to be in in the right place at the right time.
Leah Carr [00:09:47]:
And then coming out of the bank and the pandemic, actually similar timing for me. I joined a company that was originally in the hiring space, and, you know, I had had all this experience in the bank with needing to invest in skills really quickly because of that digital acceleration and really struggling to work within the bank's framework of how they did learning and development. It really just gave me the idea for what we're doing now.
Katherin Vasilopoulos [00:10:16]:
I think that's very interesting what you said. Like, when people are faced with a a big tragedy or something that shifts everything, you need to pivot. The banking system is an excellent example. I remember standing outside in the lineup with 2 meters apart between myself and someone else and the masks and everything. And the banks had to completely change. How many people were in your team at that point? Do you remember?
Leah Carr [00:10:40]:
I had about 250. When the pandemic hit and we had 400, within the in the 1st 6 months.
Katherin Vasilopoulos [00:10:48]:
And does that fuel you to have so many people working, with you? Or do you prefer to have smaller teams, like, in a start up kind of situation?
Leah Carr [00:10:56]:
You know, it it's interesting because when we were in office, Yeah. It was great. I mean, I could walk the floor. I could talk to everyone and build those relationships, help them build their career. But when the Pandemic hit. The team was growing, but I didn't get so much exposure beyond my leadership team. Because, I mean, it's a bank. Like, I was in back to back meetings all day.
Leah Carr [00:11:17]:
I don't know. I really just love being a people leader, so I'm really grateful to have that opportunity whether it's a small team or a big team, but for me, the most success and joy comes from seeing others achieve and build their careers.
Katherin Vasilopoulos [00:11:39]:
We're thinking about future generations and their skills and development and what's coming up for them? What opportunities are open to them? And are they being realistic in terms of the jobs that are available to them? Are we looking at a whole generation coming up saying, I just wanna be an influencer.
Leah Carr [00:11:56]:
It's such an interesting question. I mean, I have maybe a little bit of fact and a lot of opinion on it. In terms of the influencers, I mean, I think it looks way easier than it is. You know, you hear these stories, oh, 12 year old is opening toys and Yeah. Make $1,000,000 a year, and you're like, oh, I wanna do that. And, again, this is not a fact. I just I don't think this is going to continue forever. I think the era of influencers will be short lived, and maybe I'm biased because I I don't really like it that much.
Leah Carr [00:12:28]:
But I still think you have a really good question about, you know, are, you know, those being educated now realistic about the job opportunities, and I I think it's hard for them to even know what they should plan for because jobs are changing so much right now. So I think I don't remember the exact stat, but it's the kids in elementary school today are, for the majority, going to be in jobs that don't even exist. I read Adam Grant's Think Again, and he says something that's just always really stuck with me. And I kind of alluded to it, at the beginning, which is that I've chased opportunities instead of goals, and maybe that's why this sticks with me so much, but he said, you know, we start asking kids when they're, like, 2 or 3, what do you wanna be when you grow up? And, you know, a lot of kids are gonna pick their parents do. I wanna be a teacher. I wanna be an engineer.
Katherin Vasilopoulos [00:13:20]:
Yes. Yes.
Leah Carr [00:13:20]:
Because that's what they're exposed to. I know, you know, just cute little fun story. I was with my 5 year old niece the other day. We were playing Barbies, and she was saying, you know, Barbie is going to a meeting. And I was like, but what's the meeting about? And she's like, it's a meeting. What do you, what do you need? I know she knows enough that she sees her dad in meetings, but, like, that's the extent. She wouldn't know that he's an accountant and what he's dealing with, So she probably wouldn't answer accountant. She's answering, you know, meetings.
Leah Carr [00:13:44]:
When a lot of us were growing up, we sort of knew the jobs that were gonna be available to us. And, you know, for some people, you you pick that career early on and you just work towards it. And I think for the older generations, they picked it and stuck to it. You know, I wanna be a doctor, and then you study to be a doctor. And then sometimes you get there, and you're like, wait a minute. Did I really wanna do this? Or did I just say I wanted to do this for so long that I thought I was going to want it. And I think what these, you know, kids today will have is that they're not gonna have the ability to do that for the most part, you're not gonna be able to say I wanna be x, and then x might not exist when they get there. And so I think that's an exciting opportunity for them.
Leah Carr [00:14:25]:
But what I think is challenging for them, especially those that are in the, you know, high school university phase is the High schools and universities haven't necessarily been able to adapt, as fast as we need them to to offer the skills for those who are entering the workforce today and in the near future. And so I think you're seeing that education is changing. E learning is becoming huge. E learning and more specifically microlearning, you know, I need to know this one thing. I'm gonna watch a 20 minute course, and I'm gonna learn how to do it. And when I need to do the next part of it, I'm gonna watch another 20 minute course.
Katherin Vasilopoulos [00:15:03]:
Right. Right. Interesting. And I'm I'm looking at this whole picture and thinking, we have to just keep allowing people to learn as they go because we need to adapt to what's quickly changing in our markets, especially in technology, especially in AI, any anything that has to do with rapidly growing sectors that we know universities or even the legal system can't keep up with. It's just too it moves too quickly.
Leah Carr [00:15:28]:
I think where we need to really adapt is on the job. I think we need to be more open to it. You know, where where I think hiring is gonna go is, You know, I need 12 skills for this role, and these are the 3 I need you to have when I hire you, but I'm willing to train you on these other 9 and, you know, you'll get hired with a training plan in place because I think that's going to be what the company needs to do.
Katherin Vasilopoulos [00:15:54]:
Let's talk a bit about the optics that companies wanna project when they put together these skills and development and learning and development programs. What's your take on this? Do companies do it because they want to or because they have to?
Leah Carr [00:16:07]:
You know, there's still a lot of companies out there that are doing it to look good. It's a perk that a lot of people expect. So, you know, you get offered your salary, you get offered your PTO, you get offered your benefits. And, you know, one of the benefits is often like, hey. Here's 500 or 1,000 a year that you can use for learning and development, but that's where it starts and ends. There's no one telling you these are the skills that we believe you should learn to get better at your job or hit your next goal and even worse, you know, sometimes someone goes off and I'll accuse an extreme example, you know, they learn to play guitar and they come back and they're like, well, I wanna play guitar for the company, and you're like. And they come back, and they're like, well, I wanna play guitar for the company. And you're like, well, we don't need anyone to play guitar.
Leah Carr [00:16:50]:
But if you had talked in advance, maybe you would learn that your company does need someone to play the ukulele, and you would have suggested that instead. And that person would have been really happy learning how to play ukulele, and then they could have come back and done that for the company. And now this individual has their growth and development. You have someone who's making a bigger impact and getting better outcomes for the company. And we don't have that alignment. Like, we're way too surface level, and we need to get in way deeper.
Katherin Vasilopoulos [00:17:17]:
How do we do that?
Leah Carr [00:17:19]:
Number 1, you need to understand the skills for your roles, the proficiency that's needed in those skills. You need to then look at the skills of an individual, and I always say, like, let's start with skills gaps and upskilling opportunities. Because I think another thing we have on, I don't wanna put it all in employers, some of it is also entitled employees. You know, you're 6 months into your job and you're like, I want this promotion. I want this lateral move. Well, I think people need to think about growth not only as moving roles or being promoted, but also as developing their skills. And so, you know, we always say, let's start with the upskilling opportunities and skills gaps that you wanna close within your existing role. Once you've done that, now we wanna look at growth.
Leah Carr [00:18:01]:
And when it comes to growth, let's align the goals of that employee with the needs of the company so that there is that win win situation going on, and I think you need to take a skills first approach to that because how else can you possibly and what you need. And, you know, a really good company, we haven't quite figured out how to crack this, not yet, but I think we'll get there is being able to say, well, this is how this role is gonna change in the next, you know, 6 to 18 months, and you start pre giving people the skills that they're going to need.
Katherin Vasilopoulos [00:18:31]:
As you're talking, I'm thinking about, you know, you have you've had a journey in multiple sectors and multiple size companies. And what has been very difficult for you in this whole journey.
Leah Carr [00:18:43]:
I think people expect me to say adapting to the bank, but it was really the bank adapting to me. In banks, you have a lot of people who have only ever worked in banks, often only ever in that one bank. And, you know, you have someone like me who's fairly far into their career. And, you know, I'm just working, and people are, like, pulling me aside, and they're like, you're pretty rogue. And I'm like, I I'm like, I can be rogue, but I'm not being rogue. I'm like, this is just how I work and how everyone I know works. And so, you know, little things that they want you to adapt to that I refuse to adapt to is, like, I was on the tech team, and we'd have tech and business leadership meetings. And if I didn't, like, pre meet with the senior tech people before presenting something at that meeting, like, the tech guy would never be on my side.
Leah Carr [00:19:28]:
And I'm like, why would I waste my time pre meeting with the tech side, when the business side controls the money, doesn't even make any sense. And so, you know, I think there was a lot of, like, love hate relationships with someone like me because I'm really good at delivering, but I'm not following their rules, mostly because to me, they're not rational and they're not efficient. And, you know, I'd say, like, one of my most interesting things was how people didn't understand how strategically things worked. You know, I worked for someone at one point who would be, like, texting me, like, don't talk to my boss like that in front of this and I was like, yeah. But this other guy is gonna get me what I want. He's like, it's not how it works. And I eventually was really teaching him strategy, and he'd never believed me. I'd say, like, this is how things work, And he'd be like, no.
Leah Carr [00:20:11]:
No. It's not how things work. I'd say go away for a week and and observe, and he'd always come back and say like, oh, that is how things work. And It was one of the the my most favorite parts was, like, seeing this individual who had been in the bank for, you know, two and a half decades change because an outsider came in. And, yeah, of course, you know, sort of starting something from from scratch is the biggest challenge of all and also doing it in such a challenging time. VCs are changing the way they invest. The economy is going down. The way sales are done is changing, and that's been the biggest challenge to date.
Leah Carr [00:20:50]:
You know, feeling like an absolute failure on some days and, like, a total success on others.
Katherin Vasilopoulos [00:20:57]:
But I think I like what you said before when you said you you went rogue. It's a cool characteristic to have as a human to say I can go rogue anytime I want, and maybe that helps you manage that roller coaster, the the some days that are great and the other days that are not. You have that ability to I'm gonna step outside the box. I'm gonna do something that breaks all the rules, or this doesn't make sense to me, then I'm gonna do the opposite.
Leah Carr [00:21:20]:
You know, others would call it rogue. I would say, like, I am just a hyper rational and logical person to the point that, like, I am in a constant debate with a couple of my friends, including this morning, where they say rational and logical is subjective. And my argument is you may think you're being rational and logical based on your values and goals, but, you know, it's still black and white. But my my point in all that is I'm so hyper rational and logical that I am operating by what I think is the most rational, the most logical, the most efficient. And so I think it looks rogue to a lot of people because they're like, well, this is how we do things here. And I'm like, well, I don't care because I was brought here to have impact, and I'm gonna do what it takes. Always people first for me. I'm always gonna support my people and and, you know, that's my main focus, but then I want I wanna deliver.
Leah Carr [00:22:13]:
And so when the way things are done is inefficient, I'm not going to do that, and I'm ok if people call me rogue for that.
Katherin Vasilopoulos [00:22:26]:
Tell me about, any kind of advice that you would have to people who are thinking of either starting their own venture or leaving something that they're currently in and wanna start something new or do what you did, which is just to jump around from small to big to small and just explore and investigate what comes next for them.
Leah Carr [00:22:47]:
I think I would definitely advise people to try to do something at a bigger company earlier in their career because I think what you really learn in those bigger companies is process. I think the other thing that's really important is you learn how these bigger organizations work because when you're working in a smaller organization, they often wanna work with bigger organizations. And if you understand how things work internally and how to navigate, that will really help you. So that's 1 piece. You know, if you're looking to start your own thing, I would just say, like, make sure the pieces are in place. Do some validation on your product before you're hopping out of your job and making that leap. Make sure that you've set yourself a timeline, like, here's how long I can afford to do this too. Build a list of your contacts.
Leah Carr [00:23:33]:
Make sure you're chatting with people. You're building relationships with the right people. I mean, raising money is a community effort. Like, you will need intros. You will need advice. You will need help. And just be prepared. Like, people tell you, it's an emotional roller coaster.
Leah Carr [00:23:46]:
I I have someone from BMO who joined me at tilr, and I told them, like, it's a roller and I said, not like 1 week is up, 1 week is down. It's like one day may have a bunch of ups and downs. So I think before you do it, you just need to talk to a bunch of people who have done it so you can really mentally and and even physically to an extent prepare for it. And I think that's my other piece of advice is you have to learn what's really important to you. For me, it's health and fitness. I know if I'm not making time to eat the right things and get in a workout, I am miserable, and I am not productive. And so really figuring out before you start, like, what are the things I cannot compromise in my life in order for me to be successful and making sure that you stick to those?
Katherin Vasilopoulos [00:24:33]:
And what kind of advice would you have given your former self when you were much younger, knowing what you know now.
Leah Carr [00:24:39]:
Oh, that is a good question. I'll give you a piece of advice that I like to give to others, Which is that if it doesn't equally excite you and scare you, it's probably not the right opportunity. You'll probably be bored really quickly. I think a lot of us, especially women, turn down opportunities because we feel like we can't do it. It's scary. We've never done it before and we don't take those chances, but it's good when something scares you a little. You know? Scary and exciting, that's where growth takes place. And so I I think you need to sometimes take that step back and say, like, okay.
Leah Carr [00:25:14]:
Wait. Why am I scared? And then say, okay. I'm scared because I don't think I can do this. But then starting to say to yourself, well, I've done that. And then you get pumped up and you're like, okay. I'm ready. So really, like, don't be too hard on yourself and and take some risks.
Katherin Vasilopoulos [00:25:33]:
Thank you so much to Leah Carr. You can learn more about tilr through the link in the episode description. If you like the show, please rate, review, and subscribe to And So, She Left wherever you listen. Your feedback helps us to better serve current and reach new ones. You can also fill out our quick feedback form. It's just 5 questions long, and your response helps us to make the show that you want to hear. And So, She Left is made by Cansulta and Ethan Lee. Cansulta connects entrepreneurs and leaders with a global roster of over 150 pre vetted consultants and experts like Ethan and I, who can help organizations in any business area from strategy to finance, to sales and marketing, and even training, learning, and development. Our music is by Chris Zabriskie edited for your enjoyment.
Katherin Vasilopoulos [00:26:19]:
You can find a list of all the songs you heard here in the episode notes. I'm Katharine Vasilopoulos, and thanks for listening.