How Assistants Become Leaders

Speaker 1 · 0:00

Welcome to episode three of The Leader Assistant Podcast. Today's leadership quote comes from John Maxwell. A leader is one that knows the way, goes the way, and shows the way.

Speaker 2 · 0:15

The Leader Assistant Podcast exists to encourage and challenge assistants to become irreplaceable, game-changing leader assistants.

Speaker 1 · 0:24

And here's your host, my dad.

Jeremy · 0:28

Hey everyone, welcome to episode three. Today's episode is special in that I taught a webinar for my friend Nikki Christmas at practicallyperfectpa.com a while back, and I'm going to play back a part of that talk. And then you can check out the show notes at leaderassistant.com forward slash three. To get a copy of the outline in case you missed something. But I talk about how assistants become leaders. I share a little bit about life at my startup in St. Louis, and it's hopefully helpful to you all as I wore different hats and learned how to manage three different tensions that I'll talk about. So without further ado, here's a clip from one of my webinar teaching sessions. And I hope you enjoy it. Also, I'd really appreciate it if you take a few minutes to leave a review on iTunes. It would really help get the word out, help the show rank better in iTunes and show up in search results better. So just go to iTunes on your computer, or you can review via the podcasts app on your iPhone. Okay, let's jump right in to how assistants become leaders. Today I'm going to talk about a challenging scenario that taught me how to manage three tensions and how each of those tensions forced me to become a leader. But before I get started, I thought I'd share a bit about myself. I'm an extroverted introvert who loves Jesus, my wife Megan, my sons Weston and Silas, spending time with family and friends in the Kansas City Royals baseball team. Professionally, I have almost 10 years of experience as an executive assistant supporting fast-paced, high-capacity executives. I'm also the founder and executive coach at GoBurrows, where I help executives and assistants accomplish their goals without burning out. I do this via my blog, group training, one-on-one coaching with executives and assistants. Today, I'm going to share some insights from my last year and a half as an EA at a fast-growing startup. So let's jump right in. In January of 2017, my boss, a very successful serial entrepreneur, by the way, he sold his last company for $900 million, came to me and said, I need you to oversee accounting, human resources, and operations for the company. Not forever, but probably for the next 12 to 18 months. At least until we can hire an experienced accountant, director of HR, and operations manager. As you can imagine, I was a bit overwhelmed at the thought, but with my prior experience at a fast growing organization, I was confident I could figure it out at least. So I said something along the lines of, to be honest, I don't enjoy accounting or paperwork, but I'm happy to handle all this so you can focus on building our AI product and selling it. Just know that for your sake and the company's, you probably don't want me handling all of this long term. He appreciated my honesty and committed to hiring a team to take those items off my plate when the time was right. While I was honest with him, I have to admit my internal reaction was something more humorous like, I'm an introvert, I hate math, and now I get to spend my time working with numbers and people. Well, what could possibly go wrong? But fast forward 17 months, we now have a CFO, an accounting manager, an HR recruiter, and even an office manager. So thankfully, I no longer have to balance our budget or gather onboarding paperwork, which is amazing. All right, now that you know the story has a happy ending, what did I learn about becoming a leader throughout that time? And how can you tackle a scenario like this? Over the past 17 months, I learned to become a leader by managing the following three tensions. The first was proactive versus reactive. Second is flexible versus focused. And the third is confident versus humble. So I'm going to talk about these three tensions and how Leader Assistants, as I like to call them, can manage each one. The first one is proactive versus reactive. I believe that a Leader Assistant anticipates problems before they arise. Here's an example. I was very proactive in that I kept every receipt and had a detailed spreadsheet with all reimbursement information. I was anticipating being asked for information about certain expenses via our eventual CFO or accounting manager. When our accounting manager was hired and started going through our expenses, guess what? She asked me about several specific expenses. So thankfully, I had receipts and detailed spreadsheets to hand over so she was equipped to find the information needed. I also learned that being proactive isn't everything. I can't anticipate everything. So I must learn to be reactive as well. I believe that a leader assistant quickly tackles problems as they pop up. For example, as a software startup, 95% of our team members in the first year were software developers. Many were international students who either just graduated or were about to and who were in America on an H1B visa. Come to find out, this is a very complicated HR onboarding process. Of course, I had little to no experience in human resources in general, so I certainly had no idea how the onboarding process worked with international employees. So I had to react, and I had to react quickly. Thankfully, early on, I hired an HR expert to help us get set up with payroll and employment verifications, etc. So when the time came to tackle the H1B visa complexity, I called her and she was able to walk me through the process or handle some of it on her own. So that brings me to a bonus lesson that I learned. A leader assistant outsources to experts. There was no use pretending I knew everything or that I could do it on my own. Sure, I could have spent a week researching H1B visa onboarding to teach myself, but remember, I was also the full-time EA to the CEO, so I couldn't just drop everything to become an H1B visa expert. Sometimes there are items we need to become experts in, sure, but I made the game time decision that this was not a topic I needed to spend my time mastering. So I outsourced it. I hired an HR expert I used to work with to handle this difficult aspect of human resources for the first year. In summary, if you find yourself stuck on a problem, don't be afraid to ask for help and sometimes even hire help. Okay, back to the tensions. The next one is flexible versus focused. Flexible Assistant is willing to do almost anything. As I mentioned, I was not only handling HR and accounting, but I was the office manager. I had to be extremely adaptable, especially in the first 12 months when the team was small. So I would take out the trash, assemble a desk, order lunch for meetings, clean the toilets, and whatever else was needed to get done on a given day. So I'm going to actually share another bonus lesson. A leader assistant has to have a positive attitude. This is pretty straightforward, but a leader assistant is someone who serves with a good attitude no matter the task being done. It isn't always easy, but I try to keep a positive attitude no matter what is thrown my way. So a leader assistant is willing to do almost anything. They're flexible. But a leader assistant also knows when to say no in order to stay on task, i.e. they need to be focused. Focus is crucial to being productive. In today's distraction-filled world, it's become more and more difficult to focus on anything for long periods of time. There were several times in the first 12 months at our startup where I would ask my boss if I could work from home so I could lock myself in my home office and get everything done on my to-do list without coworkers pinging me every 20 minutes or every 2 minutes at the office. But focus does not just apply to your work environment. It also applies to your to-do list. Are there items on your list that are not allowing you to focus on higher priorities? I would regularly ask my CEO if a certain task was necessary or if it could be pushed back, offloaded to another team member, or disregarded completely. When a CEO says they want something done, they usually mean it, but not 100% of the time. So another bonus lesson learned, a leader assistant asks clarifying questions, especially if you haven't worked with your boss for long. But even if you have worked for 5-10 years with your executive, clarify what it is your boss wants to save you both the headache. I had to do this several times when it came to accounting. I had never worked for a for-profit before, so I knew nothing about how he wanted the books run. I was annoying him with clarifying questions over and over and over. But in the long run, it has made things easier on our accounting manager and CFO, since I had things mostly set up the way our CEO wanted from the get-go. Okay, the final tension can have the most impact on your attitude and performance as a leader assistant. It's being confident versus being humble. Let's start with being confident. A leader assistant knows they have what it takes to get the job done. Let me say that again. A leader assistant knows they have what it takes to get the job done. Sure, everyone has doubts. That's just part of being human. But a leader assistant must be confident. As you all know, we assistants are in contact with some of the most confident and powerful people in the world. How can we expect to lead from our role as assistants without being confident in ourselves and our ability to get the job done? When my boss first told me I was essentially going to run the company for a while, I knew it was going to be a challenge, but I never once doubted I could do it. Part of the reason I was so confident is because I have been an EA for so long that nothing fazes me anymore. So yes, some of you will gain more confidence the further along in your career. But if you struggle with doubting you have what it takes, I would encourage you to find someone with more experience, more confidence, and ask them to help you grow your confidence as an EA. It can be as simple as grabbing lunch with a fellow EA and sharing tips and tricks, horror stories, and success stories. Or you can reach out to me or one of the many other amazing executive assistant coaches out there to seek more professional training and coaching to help you gain confidence. But some assistants don't struggle with being confident. They have the opposite issue. They are not humble. So another thing that I learned is that a leader assistant is grateful for the opportunity to serve others. I'm going to say that again. A leader assistant is grateful for the opportunity to serve others. This isn't in my notes, but if you're not grateful for the opportunity to serve others, you may be in the wrong profession. All right, back to my notes. I've always been a helper and seem to have been wired to serve others. Not that it's always easy, but in general I find joy in serving others. There's something about helping others accomplish their goals that gets me up in the morning. Robert Greenleaf says, Good leaders must first become good servants. So having humility is so crucial to becoming a leader. You cannot help others if you're not willing to set aside your pride. Jim Young Kim says it well. No matter how good you think you are as a leader, my goodness, the people around you will have all kinds of ideas for how you can get better. So for me, the most fundamental thing about leadership is to have the humility to continue to get feedback and to try to get better. Because your job is to try to help everybody else get better. Being humble means asking for and applying feedback from others. And it also means admitting when you screw up. It doesn't matter how confident you are or how capable you are at doing your job. You will screw up. You will make mistakes. The question is, will you let your mistakes humble you, or will your pride get in the way of you becoming a respected leader? To recap, this challenging scenario taught me how to manage these three tensions. Proactive versus reactive, flexible versus focused, and confident versus humble. I hope today's session helps you work within these tensions as well. Bye for now.

Speaker 2 · 14:16

Check out this episode's show notes at leaderassistant.com forward slash three.