Episode 134: During The Learning Process: Stay Low Before Reaching High With Lindsay Wheeler
Success isn't about how high you climb; it's about how well you balance the ascent with the life you love. Join us for an inspiring conversation with Lindsay Wheeler, Strategic Sales Director at BILL and a passionate advocate for work-life balance. Lindsay shares her pivotal experiences, from her early days learning to navigate the complexities of the sales industry to her current role in a cutting-edge technology company. Throughout her remarkable journey, Lindsay learns the most valuable lesson of achieving success without compromising your personal life. She emphasizes the importance of effective time management, maintaining a strong work ethic, and fostering open communication, both at home and in the workplace. Tune in to learn how to stay low during the learning process and reach great heights in your career, all while maintaining a balanced and fulfilling life.
To learn more about BILL and their Accountant Partner Program, please visit bill.com/for-accountants.
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During The Learning Process: Stay Low Before Reaching High With Lindsay Wheeler
In this episode, I interviewed Lindsay Wheeler. She leads the Strategic Sales Team at BILL. She works with the industry's top 100 accounting firms to help them grow their CAS offerings. She has fifteen years of experience helping firms automate their client's back office and then becoming their trusted advisor. During this interview with Lindsay, we talk about her journey during childhood and how that journey gave her the skills as an adult to learn from the people around her and lead people effectively by listening before speaking. This episode is sponsored by BILL.
BILL is a leader in financial automation software for small and mid-size businesses dedicated to automating the future of finance so businesses can thrive. Hundreds of thousands of businesses trust BILL solutions to manage financial workflows, including payables, receivables, and spend and expense management. Lindsay is a great friend of mine. We've known each other for years. I'm so excited for you to hear about her journey during this episode.
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I'm so excited to be here with my good friend Lindsay Wheeler from BILL. Lindsay, do you want to give a little background on yourself, who you are, and what you do for BILL before we get started?
I run the Strategic Sales Team over here at BILL. That means I work with the top 100 accounting firms building out their CAS department and also, some other nimble firms that are BPO firms that are making space in the industry. We're trying to automate their whole back office financials.
I’m so glad to have you on. This show is all about our belief systems and the foundation of who we are. I want to start right in the beginning so our audience can get to know you. Tell me where you began, what your parents did, where you lived when you grew up, and how many siblings you have, and we'll get started there.
I grew up half of my childhood in Cincinnati, Ohio, and then in middle school, I moved in 8th grade to Atlanta, Georgia. I have a younger sister named Courtney. My dad worked for a company in Ohio called Lazarus. They got bought by Rich's, and Rich's was based out of Atlanta so we moved. They got bought by Macy's and my dad was like, “I'm not going to move them to New York. There's a little small town for that.”
We stayed in Atlanta, but he ran the men's merchandising department for the Southeast. Now, he's retired and he spent his time playing pickleball and running the neighborhood HOA. I can't fault him. My mom was a teacher but she has MS so she was in and out of the hospital the whole time I was younger so she didn't have a job per se.
Did your mom get MS in Cincinnati, or diagnosed with it?
She was diagnosed when she was 21. She had it even before she had my sister and me. My sister's almost five years younger than me. After she would have one of one of us, then she would be in hospital for 1 year or 2 off and on.
She was determined to have children.
She was.
What drove that in her? What did she tell you about that because that's a huge risk?
She wanted to have a family and have kids. She probably wanted a bigger family but she wanted to have a child and then have that child have a sibling. I feel the same way. I have two kids. I’m like, “No one's going to understand how crazy I am like my children so they need to be able to talk to each other about it.” I think she felt the same way but she was determined to have kids. They have her on acids by now and it's manageable as it is. They call them a TAC when you have MS. She hasn't been in the hospital for many years, knock on wood.
She functions every day fine?
She does. She's in a wheelchair. If my dad wasn't there, she wouldn't be able to live independently.
What do you think you learned from her watching her growing up?
She has a lot of grit which I probably got. She has a, “For better or worse, I can do it. Don't help me. I've got it,” type of attitude, which I probably also have a little bit of. She’s steadfast and determined in her goals and whatever she wants to do. If it's in her capacity, she'll do it.
I always think those kinds of stories, getting diagnosed with something like that at 21, you're either going to fall to it or say, “I'm going to still live life.” I can't imagine getting diagnosed at such an early age with it. What was her support system like or why do you think she was so positive that she could overcome it?
My grandparents were great. They were very supportive. She has a sister, my aunt who was really supportive, and then my dad. He knew she had MS when they got married. He was like, “She was very stunning, that lady,” and he was in. It's been many years and they're still together. They met right when my mom was ending college.
It was right when she was diagnosed. He knew coming in. That says a lot about your dad, too.
It does. He's a great guy. We could have a whole show on him.
I would like to get into it a little bit. Why do you think he took that on in his mind?
I think that he loved my mom and was probably like, “I don't know what I'm getting into,” like a lot of people with anything in life. I don't think that he knew the severity of the MS she would have or that she would be in a wheelchair and so on but he loved her and was determined to make it work. They had me and my sister. You have children. Once you have kids, you're like, “I'll do anything for my kids.” He's like, “We'll make it work.”
Watching your dad do all of this, I'm sure he had to take on more as well. What did you learn from him with all this?
I learned that you have to do what you have to do to get it done, whatever you're trying to do. Whether it's like running a household or doing your job. Whatever your objective is, there's no error for failing. We're going to succeed. Also, looking back as an adult, he was still focused on raising us and getting food for me to make dinner for my sister and visiting my mom that he didn't have as much time to be more thoughtful about other things that I do have time to be more thoughtful on. I think about that and balancing work in life to make sure I have time for each section.
Learning Process: Whatever your objective is, you have to find it. There's no error for failing. We're going to succeed.
From your and your sister's perspective, do you have to take on more in the household from a responsibility perspective or was your dad taking the brunt of it?
No. When we were younger, I took on more, which is helpful. I know how to cook. It’s life skills. Also, do the laundry. I can go grocery shopping. I could walk to the grocery store and get groceries or walk to the mall from a young age. I would let my children do that but we also lived in Cincinnati versus Los Angeles so there are a lot of factors.
I took on a lot more when I was younger. My sister not so much because she didn't need to because I could do it but now, I live in Los Angeles. They live in Atlanta still. My sister's in North Carolina, which is so much closer. Now, she takes on. If she had to go out of town for work, she would come stay with my mom and stuff like that.
When you were that age, what did you imagine you were going to be when you grew up?
I always thought I would be a lawyer just because I like to argue. I picked a point and went after it, whether it made sense or not just to see if I’d win the argument. I always thought I'd be a lawyer. When I was younger, there were specific jobs that you would have like lawyer, doctor, teacher, or dentist. There wasn't a Director of Sales. It wasn't something that they talked about in high school.;
Also, blockchain consultant.
These things didn't exist or weren't widely discussed. I thought I would do that and I went to college. When I was young, I was like, “I'll probably be a lawyer. I'll make a lot of money. I'll argue. It'll be great then.” As I got older, when I was in high school, I did get into the yearbook and I did the news for our school like, “Good morning. It's Lindsay.” I thought that was great. I’m like, “For sure. I'll be on the Today Show. That'll be great for me.”
I went to college and I was like, “I'm going to be a journalist,” and they were like, “You're going to have to take 50 hours of writing classes.” I was like, “I don't think I'm going to do that. That seems like a lot.” I switched quickly to marketing at a liberal arts school, which I realized is like a choose-your-own-adventure type of path. I then ended up in sales because ever since I sold Girl Scout cookies, I was good at it. I have been doing sales so I kept going with it.
Moving into eighth grade, how was that experience? I'm sure you had a lot of middle school crazy times with understanding who you are or trying to fit in. What was that like to leave your friends and start a new place in eighth grade?
It was not awesome but it was a foundational point for the rest of my life because then when I was 22, I left and moved across the country by myself. I realized that you can always start over which is a fun thing to do when you're going into high school. I've been in Cincinnati my whole life so I had friends since kindergarten.
Learning Process: You can always start over.
We all went to Ayer Elementary and then went to Anderson High School. We all went together and then I had to move to Georgia, where they listened to country music and some people had a little bit of an accent. My grandfather said, “I talk too fast and no one would understand me,” but they did and it was fine. It was a little rough. I didn't know anybody.
How did you go about it? What kind of approach did you take to meeting people?
I played well back then, to be honest, and probably tried to fly under the radar because I wasn't super confident as a teenager. I didn't have anything. I'm going to say by myself and then I would meet people in my class or meet people that at lunch or whatever. We would gradually start hanging out and I floated around friend groups until I found one that I liked the people. It took a while.
Were your hobbies in the news or getting involved with that as far as that in school?
Yeah, I did choir in school. I've met some people in there too and whatever but I wasn't exceptionally sporty. I played soccer. I played tennis, but I wasn't great at any of them.
Did you go to school in Atlanta for college?
I went to college at Georgia College & State University in Milledgeville.
Did you end up graduating in Marketing?
Yeah.
What was the transition between there and going to LA?
I got a job after college because I'm always determined to make my own way. I was leasing apartments for a giant apartment place in Atlanta called Post Properties. I went on a trip with some of my sorority sisters to Las Vegas and I met my now husband. We started dating long-distance and then he was like, “I'm going to move to LA.” I was like, “Sure, I'll move to LA. It sounds great.” I did, much to my dad's dismay. I was going to get a U-Haul and I'm going to move.
After all the moves I've had, U-Haul is amazing.
I got a Jeep. I hooked up the U-Haul. I could not back it up so I could only get gas when you could pull through but it worked out.
What did you find the difference was when you got to LA?
It was very different. I was in Atlanta, but I was in the suburbs. I was in Lawrenceville. It was 45 minutes Northeast. I went to a liberal arts college in Georgia with 5,000 kids. You could walk past and you pretty much knew almost everyone at school or had seen their face. I moved to LA where everything's expensive and there's a ton of people.
At first, they cared about things and I didn't. I don't know that I fit in right away, but what was lucky is my then-boyfriend and now-husband had a friend whose girlfriend was moving out here so we got an apartment together. She was from Michigan and she went to Michigan State with Kevin, my husband. We were both on the same page where we were like fish out of water trying to stay under the radar but figure out where we were going.
Have you seen yourself do that in other situations at work where you stayed under the radar to get the lay of the land?
Yeah, for sure. Every time you start a new sales position, you’re like, “Let me see how I’m going to do here.” I've worked at every back-office accounting automation company you can work like Paychex and all of them. I went to Xero because it was new and a little sexier and sass. In there, I was trying to figure out what they were doing because I went from a giant Thompson where everything's very corporate to like, “Here’s the CEO.” He's going to eat lunch with us and it's going to be great.
In every job, for the first little bit, I’m trying to figure it out. It's a little different now at BILL and with this role because I've been here for over five years. I've been in sales here. I've also worked cross-functionally with a lot of departments and a lot of teams. I'm a little more experienced and confident. I have a different approach to it than I did when I was 22.
What would be the difference now? What have you learned to do differently?
One, surrounding myself with a good group of people like you that I can bounce ideas off of not only inside the corporation but my network of people has gotten so wide. The nice thing about the time at Xero was that was the time when I realized we're not all working against each other because often in sales, you are.
You're all quota-driven and it's who is the best. It still was that. You still want to be the best but we can all support each other. We're working towards a common goal. That changed my outlook or my perspective. It's not a doggy dog. It's more like, “Let's all work together to achieve the goal that we're trying to achieve.”
Learning Process: Often in sales, you're all quota-driven and it's who's the best. But you can want to be the best while also supporting each other. We're working towards a common goal.
I came from a large company when we were starting up Xero at the time in the US. When you talk about that teamwork and so forth that you hadn't experienced before, it was like going after something together that no one's ever done before. It was almost like a movement. Everyone had a belief in why we were doing it. It was exciting. There was something to go after that we thought would be different. When you have like-minded people and all those functions, it's a very different experience and then how that affects you later of what things you try to pick out in your roles later to make sure that you can still have that.
That whole experience and that shift of, “We’re all going after this together,” has stayed with me because now at BILL, we're going after helping SMBs in general. I work with accounting firms to help their clients but I help them run their back office a little cleaner and smoother but it's still the same kind of movement. It’s because you have these firms. Some are nimble and they're looking for new technology and some are niche and they're only working with a non-profit. Also, everyone can still work together and bounce ideas off each other. It seems like a very collaborative and almost community that I have fallen into. I feel lucky in that sense.
There's always going to be the people that are in sales just for the number. There are people made for that, but it's important to realize the purpose behind selling, even for accountants who are selling to clients. Also, other professions are selling to clients so that it doesn't feel like a hardcore sale. There's still the excitement of closing a sale from a personal perspective. However, when everyone understands the purpose behind why you're doing it and what you're trying to solve, that is the difference between when someone looks at it as car sales versus purpose-driven.
At the end of the day, you're like, “What's your problem? What are we trying to solve?” and let's work backwards from there. In a perfect world, what would it look like? Hopefully, it's what I'm pitching but it might not be, and that could be true. It's just if we can find that out sooner than later, it's more advantageous for everybody.
It also would be important to talk about this from a sales perspective the noes. How did you learn to deal with rejection getting into sales as well and how did you overcome that?
At first, as a younger salesperson, you take it personally, “Why wouldn't you buy what I'm selling? Was it me? Why would you buy from that person and not from me,” but now, it's hard because selling to accountants, it's so hard to get to no. I would love a no. It's like, “Not yet. Maybe later. Soon.” It’s working with the firm that we're talking to, saying, “When are you going to do this?” It’s because there are different points people are at in solving the problem. Do we want a solution to the problem? Are we at the point where we want to tell everybody about our problems and be in the problem? We have to figure out which point we're at.
This is something that people spin on the maybes. A lot of times in sales, people talk about the noes to get the yes but what about all the time you're wasting on maybes? What do you do to scoop a maybe bucket? This is for anyone who is dealing with a relationship sale perspective so that you can drive someone to get the yes or quickly get out because they're spinning.
For me, what's worked is studying clear objectives like, “This is my goal for this meeting, this relationship, this call, or whatever. This is what I would like to do. What do you want to do? Let's figure out if we can make that work together.” If we can't, that's fine, and it doesn't have to be that we’ll never talk again, but maybe we won't talk again for a year because you're not ready to do that.
Letting people know and also having the confidence to say, “It's not the right fit. You're not ready. I would love to help you and I will help you when you're ready, but you're not ready yet.” A lot of firms appreciate that. It’s because no one ever wants to tell you no, but as the salesperson, you want to yes or no. Anything else is not helpful.
It's a waste of time. There are plenty of times you and I were spending on stuff when we were working together and it's an important part of the learning process. A lot of times in sales, people do not feel like they can say what you said. It’s like, “As a salesperson, this is our objective for being here and what we want to have out of it and by when. If you can't do it by when, let's now schedule. I will come check-up in 6 months, in 1 year, or whenever. Does this align?” and that's important.
What do you think now? You've grown from an individual contributor to managing people. When you're moving from that thought process of, “I want to do well. I want to meet my numbers and the team meeting their numbers.” How have you had to change or break some patterns that you've had individually in order to do that?
It's funny because I feel like I haven't wanted to manage people or hadn't wanted to manage people for so long because if you're an individual contributor, you have autonomy. You can do whatever you want as long as you do it well. Now that I have kids, I'm like, “I’m managing a bunch of people anyway. I should do that more often.” The shift for me and what I had to change was I can only get so far as an individual contributor and I can only move the needle at BILL so much and talk to so many firms.
There are only 40 maybe max that I can have like a real relationship with. It’s on some level and that you know the scope of sales. Now, I can get a little more information on a larger breadth of firms in the industry as a whole. I can help the reps on my team look at their job differently. It’s because the way I've always sold is a little more direct and less salesy. I want to make it work for everybody but very pointed with, as we said before, time and when we're all looking to do this stuff. It was an opportunity to hopefully learn good habits from some of the other reps who have been on the team for a long time and share my perspective that's worked well.
Going back to you growing up and laying low, in sales, that's an underrated quality. A lot of salespeople just want to tell you what they sell and force themselves on you. They keep talking. One of the biggest things that you can do is listen and watch to know if someone's the right fit and that you can deliver the right product or service. That skill in itself is a superpower in sales that I don't think people realize because they expect a salesperson to be extroverted over the top and so forth.
It’s like shoving things down your throat. I remember one time when I started at Paychex, I was selling 401(k) TPA services and I didn't know anything about 401(k). I went out on a call with the manager and I remember we were sitting in a meeting with an auto body shop and he probably said five words. He slid the tablet towards the guy, and he signed. I was like, “What just happened here? You didn't even talk.” He's like, “No, I listened. The things that I said were thoughtful. I chose the words I needed to say.” That stuck with me.
It’s choosing your words carefully. When someone is talking to you, they want to know you heard them. If you're going to speak, it should be in reference to what they say. How do you practice that with your team if that's not a natural trait?
Now, it's great because we have so much technology that can automate this. For any calls, we have a recorder truly for coaching and training and stuff like that so we can listen. We are constantly having discussions and trainings on speed to answer because that's important to your point. If you email me and have a question, even if I don't know just reply, “I got this. I don't know. I'll get back to you by Friday,” I feel like it makes people feel like, at least, you've read it and seen it. Also, being thoughtful and responsive and stopping to listen to what the customer is saying.
More of the conversations I have with my team are about why. I'm always asking why and quantifying the things I tell them to bring to me. Don't tell me a problem without telling me how much time it’s taking this person, how much money it's costing them, or how many projects they can't do because they're trying to figure this out. I need to be able to quantify the pain or the problem to be able to tell if we have a solution.
Learning Process: Quantify the pain or the problem to be able to tell if we have a solution.
I trained accountants on this all the time, but the biggest thing is this is an advisory and consulting skill. People don't see it that way. Sales training is the best way to become a good advisor because you've got to prepare. You've got to listen and take all that information together in order to propose a solution. You can't just come in and say, “This is what we got.”
You have to have a solution. We can't say, “You got a problem. You should find someone to fix that.” You have to be able to help fix it or else, why are you talking?
As you said, if you don't have the solution, you could be valuable and memorable when you provide the right person for them to go to. When they need you again, they're going to come back to you.
A lot of the conversations are about automating everything in a lot of that is outside. The payment piece is easy. It's one portion of it. Once we can get that automated, then we can go into GL and everything we used to do. It's like, “That's not what I sell, but I can point you in the right direction of someone to talk to.”
As you've grown and evolved in your roles that work, how have the changes you've made in yourself affected the people around you, whether it be at home or at work? What have you seen?
I'm very cognizant of the times now. I have two kids and a husband, all those people that I'm running their lives to, but I'm very cognizant. On my calendar, there's pickup and drop-off probably because my mom and dad couldn't be there when I was younger to pick me up at school or bring me to afterschool activities or any of that. I want to give that to my kids.
I try to make sure that I'm utilizing the time in my day very efficiently so that I can still do all those other things that I want to do. Be a mom and be at flag football practice and whatnot. That's probably the biggest thing that's changed. I used to work all the time. It didn't matter. I don’t have anything else I need to do. Now, I can work in the early morning and 9:00 to 4:00 and then I can email you back at 8:30 if you need something but other than that, I'm pretty much offline.
Do you let people know that?
Yes, I do. In the first meeting, I'm like, “Let me tell you a little bit about my life at home, and what my schedule is.” They appreciate it because everyone has that. We've moved to this work-from-home environment and everyone's multitasking. Everyone has a ton of stuff to do. It's good to know, “If you need something urgently from me at 6:00 on a weekday, you're going to have to text me or call me but probably text is faster. That's how I'll answer you,” and then they know.
That upfront communication is so important. It’s like saying when you're going to respond but also, being proactive of what to expect so that when you don't respond, they don't take personal offense. There are so many great lessons here and also, seeing the changes you've made in your life based on how you grew up as well and what it taught you was also inspiring. Thank you for sharing that. I like to close with some rapid-fire questions. You pick a category. It can either be family, friends, money, spiritual, or health.
Let's go health.
Things or actions I don't have that I want to have with my health.
I would like to get more sleep. I already get a lot, but I'm really tired when I wake up. I'm pretty good at exercising, but as I'm getting older, I do like to get better at nutrition like supplements. I’m in LA so I'm reading Goop but I don't know what I should take. I'd like somebody to give me a cliff notes guide of the vitamins and nutrients you should take. I would love it.
Things or actions I do have that I want to keep.
Ever since I got married, I've been pretty active. Ever since the pandemic though, I get up every day at 6:00 and I go work out in our back house with my husband. I want to keep doing that because it's cheesy but we do this together first thing in the morning and we can hold each other accountable. For me, if I don't work out first thing in the morning, I can tell throughout the day. I'm less patient. My brain doesn't run as quickly. I do want to keep doing that and then I also was running a lot. I would like to get back into that but that takes a lot of time. It's a hard one to do.
Things or actions that you don't have that you don't want to have.
I'm pretty healthy during the week so I want to keep doing that. I don't do anything bad for me Monday to Thursday so that I can run as fast as I as I run. I try to eat healthy and not have a margarita or anything until Friday. I would like to keep doing that. Also, this is about work and health, but I've been a lot more thoughtful about my travel and making sure that if I am going to travel, it's for a good reason. I'd like to keep that going. To not travel when it's not necessary.
The last one is things or actions that I do have that I want to stop.
I feel like I want to I want to stop being in the sun as much but I'm so cold always that I always want to be warm. Coming back from Florida, everyone on my team was giving me a little crap about being so tan. It's always a dichotomy there of, “How much sun is too much sun in Southern California?”
It feels so good though.
It's so relaxing and is nice vitamin D.
I'm wearing 70 now.
I am too. We just got back from our beach vacation and head had fifteen. We’re like, “What is this? This isn’t even worth it. You need an 80 at minimum for you to apply.”
It doesn't repair all the years of laying out with oil.
I was a lifeguard in high school. If I could get those years back, I would do anything and put some sunscreen on.
Is there anything that we didn't talk about that you want to make sure people leave with and understand before we close out this episode?
I want to make sure that if people have questions, need help, or are in this phase of growing what we're growing over here, which is a CAS department, we're very happy to help you. I'm happy to help you. You can reach out to me however you'd like. What we're trying to do is make small businesses run faster at a mass scale through the accounting channel.
Thank you so much for being on and sharing your story. I look forward to sharing this with our audience.
Thanks for having me.
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Now, for my mindful moments on this interview with Lindsay. We have known each other for a long time. I always enjoy talking to her. She is not only super smart but also, a lot of fun to be around. It was great to get to know this other side of Lindsay and learn about her story. I did not know about her parents and what they did to thrive during her upbringing. She talked about how her mom had MS as she was growing up. Her mom was diagnosed at 21.
What she learned from her mom was seeing just the self-starter, staying confident, and knowing that she can accomplish what she needs to accomplish. She didn't know. She didn't ask for help. She wanted to try to do things on her own and got a lot of support from her dad. The stories that Lindsay shared of staying focused on how much he loved her and raising their daughters. He was able to do that by balancing his work and life in order to make sure everyone was able to thrive. The example that that was for her and now, in her adulthood that she refers back to make sure she's doing the same thing.
These are always great reminders that everybody has a story and that story is so important to truly understand maybe why we do the things that we do or why we're so driven. Also, the examples that people gave us so we can have gratitude for that as well. She also talked about how when her dad had a job change, they moved from Cincinnati to Atlanta. That was a big learning experience for her at the time. She learned that she was able to start over. It was a very hard time being in middle school, moving from Cincinnati to Atlanta.
One of the things that she learned during that move is an important skill that we might not realize we create in ourselves, but in every new situation that she's used it over and over again is laying low and flying under the radar to learn the environment that you're in and learn about the people around you to see where you fit and to see where you can enhance other people's lives, become friends, network, and whatever that is.
A lot of times, there are many people who will walk into the situation and try to force who they are and get offended if that doesn't fit. In every new situation, whether it's a job, whether it's going to another state or country, or whatever it is, people have their way of life. We even find that in families even when you bring two people together as a couple, everyone comes from a different background and expectations. It's important to take that time to try to understand the environment you're in and how people interact so that you can thrive in that situation and also, make the best out of that situation as well.
She found herself in that situation again when she met her husband in college, and they decided to move to LA. Again, in that situation, it was so different coming from the Midwest going to LA that she didn't fit in right away and had to use that same skill of trying to understand the environment and where she could find her path and the people that she related with as well. We got into when we met. Lindsay and I met very early on at Xero, but her path getting there and learning sales and how she became good at sales.
A lot of times, when we talk about sales, many people feel that it's a forced thing or that someone doesn't want to salesperson around. That's one thing to understand is that in sales, the biggest skill that you can have is the one that Lindsay is talking about. It’s laying low and learning your environment, the customers, and how people interact. Also, what's important to the business and to your clients, as well, so that you can solve their pain points and you can get to the right solutions.
We talked about how when you start out in sales, there is so much rejection or even maybes that you can take it personally and how to take that out of the equation that it's not about you. It's about how you're solving someone's pain. What she's learned over time, especially in the maybes where you can keep wasting a lot of time and hoping somebody is going to come to the end is truly having that business discussion with any prospect. Setting clear objectives and making sure you’re asking them what they want out of this and you're very clear about what you want out of the relationship and have the confidence to say, “When it's not a good fit or when someone isn't ready.”
Also, even having that discussion of when is it a good time to contact someone again. Not every person you talk to is the right fit and a lot of times, when I'm working with clients on sales, we get upset if people are saying no or we're not getting the success rate that we want. However, if we are getting too many yeses, that means that we haven't thought about our solution in the way that we should think about and price it in the way that we should as well. Also, we learn from the process to make sure that we have a balance of noes and yeses so that we keep striving for better solutions for our prospects and our clients.
The other thing is that we also talked about how important it is during your career when you start pushing yourself out of your comfort zone. One of the areas that she pushed herself out of was going from an individual contributor to a manager role in sales and how for so long, she didn't want to manage people. However, she came to this shift in her life and realized that she can only get so far as an individual contributor.
She wanted to get more out of the organization as a whole so she started learning and approaching sales and her work differently. By doing that, she had to lay low, listen again, and learn from the people around her to make sure that she was doing things in the right way because managing people and being an individual contributor is very different.
When you're managing people, one of the things that she talked about that was so important was how important it is to choose your words carefully. When you're training salespeople, it is looking at them and assessing and observing where their needs are. Also, make sure that when you're training them, they're thinking about how to be thoughtful, how to listen, and how to make sure they're not answering right away.
Any mindfulness discussion or training that I have is learning how to be slow to respond. A lot of times, when we respond too quickly, we respond in ways that later were like, “I wish I would have said this. I wish I hadn't said this. I wish I wouldn't have erupted.” It's a skill that we have to practice. Part of practicing in business is going back and reviewing recordings, having meetings with your co-workers, or even if you don't have co-workers, your family and friends, and practicing with them to make sure that you are getting it down so that you feel comfortable approaching a conversation in a different way.
The other thing that was a key thing here that she learned from her father who had so much on his plate with taking care of her mom and both of his daughters was being cognizant of time. Also, having clear communication on your work-life boundaries, letting your team and clients know when you're available and when you're not available, and not breaking that. Make sure that you are communicating that up front and that you're consistent with your communication on it.
If people forget, they might take it personally if you're not responding right away. It's important to make sure that people are aware of it. When to expect responses and that you uphold what you say that you're going to do as well. I want to thank Lindsay for giving us these lessons during her interview. It was a very interesting life journey and I am always excited to talk to Lindsay.
Again, I want to thank BILL for sponsoring this episode. If you want to learn more about their accountant partner program, you can visit BILL.com/for-accountants. I want to thank you, again, for being a reader. If this episode was important to you, make sure that you share it with the people that you care about so that it could help as well. Also, my audiobook is now out Disconnect to Connect: Tap Into The Power Within You to Create the Life You Desire. You can find it on Audible and be able to listen to it anywhere. Until next time.
Important Links
Disconnect to Connect: Tap Into The Power Within You to Create the Life You Desire
Lindsay Wheeler - LinkedIn
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About Lindsay Wheeler
Lindsay leads the strategic sales team at BILL, working with the industry's top 100 accounting firms to help them grow their CAS offerings. She has 15 years of experience helping firms automate their clients' back office and in becoming their trusted advisor. BILL is a leader in financial software for small and midsize business—dedicated to automating the future of finance so businesses can thrive.