In Episode 3 I share an excerpt from a webinar I taught for my friend Nicky Christmas’ Virtual Summit on in June of 2018.
I talk about 3 tensions assistants must learn to manage well if they want to become Leader Assistants.

leader assistant episode 3

For this episode, I have a transcript of that session I thought I’d share so check it out below.


“A leader is one who knows the way, goes the way, and shows the way.”

– John C. Maxwell


Subscribe to The Leader Assistant Podcast so you don’t miss a new episode!

You can find the show on iTunes, Spotify, Google Podcasts, and Stitcher.

Join my email list here if you want to get an email when a new episode goes live.


The first 10 people who leave an honest review on iTunes – AND email a screenshot of your review to – will get FREE access to my 30-Day Assistant Challenge email course. Or if you’ve already taken the course, you will get a FREE 30min coaching call with yours truly.


Do you have questions you’d like me to answer, guests you think I should interview, or suggested topics you’d like me to address on the show? Or maybe you have some constructive feedback? Either way, I’d love to hear from you! You can email me at


Today I’m going to talk about a challenging scenario that taught me how to manage 3 tensions and how each of those tensions forced me to become a leader.

Ok, before I get started, I thought I’d share a bit about myself.

I’m an extroverted introvert who loves Jesus, my wife Meghan, my sons Weston and Silas, spending time with family and friends, coming up with business ideas, playing music, and the Kansas City Royals baseball team.

Professionally, I have 12+ years of experience as an Executive Assistant supporting fast-paced, high-capacity executives.

Currently I’m EA to the CEO of Capacity here in St. Louis, MO.

We are building an artificial intelligence platform – kind of like Siri or Alexa but for enterprise companies. It has been fun to be part of the AI revolution!

I am also Founder of Go Burrows, LLC where I help executives and assistants accomplish their goals without burning out.

I do this via my blog, group training, one-on-one coaching, and online courses on my website at

Now for the reason we’re all here!

Today I’m going to share some insights from my last year and a half as an EA at a fast-growing startup.

How Assistants Become Leaders

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 $900mil) – 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 12-18 months… 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.

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 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… what could possibly go wrong…?” 🙂

But fast forward to today…

We now have a CFO, Accounting Manager, HR Recruiter, and an Office Manager. So – thankfully – I no longer have to balance our budget or gather onboarding paperwork which is awesome.

Alright, now that you know this story has a happy ending, what did I learn about becoming a leader throughout that time?

How can you tackle a scenario like this?

Over the past couple of years, I’ve learned to become a leader by managing the following 3 tensions:

  • Proactive VS Reactive
  • Flexible VS Focused
  • Confident VS Humble

I’m going to talk about these tensions and how “Leader Assistants” as I like to call them, can manage each of one.

Proactive VS Reactive

A Leader Assistant anticipates problems before they arise.

I was 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 by our eventual CFO/Accounting Manager. When our accounting manager was hired and started going through our expenses, guess what? She asked me about several particular expenses, so thankfully I had receipts and detailed spreadsheets to hand over so she was equipped to find the information needed.

When it came to HR, I did the same. I kept our HR files organized and have been able to hand over that workflow more easily because of it.

But I learned I can’t anticipate everything, so I must be reactive as well…

A Leader Assistant quickly tackles problems as they pop up.

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 a H-1B Visa. Come to find out, this complicated the HR / Onboarding process.

Or 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 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 H1-B Visa complexity, I called her and she was able to walk me through the process.

This brings up a bonus lesson learned I want to share.


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 H1-B 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 H1-B Visa expert.

Sometimes there are items we need to become experts in, but I made the game-time decision that this was not a topic I needed to spend my time mastering.

So I outsourced. I hired an HR expert I used to work with (so I trusted her) to handle this difficult aspects of human resources for the first year.

If you find yourself stuck on a problem, don’t be afraid to ask for help, and sometimes even hire help.

Ok, back to the tensions…

Flexible VS Focused

A Leader 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 needed to get done on a given day.


A Leader Assistant has 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.

A Leader Assistant knows when to say “NO” in order to stay on task.

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 co-workers pinging me every 20 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, off-loaded 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 one more bonus Lesson learned…


A Leader Assistant asks clarifying questions.

Especially if you haven’t been working with your boss for long, but even if you have for 5+ years, 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, 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 it from the get go.

Ok, the final tension can have the most impact on your attitude and performance as a Leader Assistant.

Confident VS Humble

A Leader Assistant knows they have what it takes to get the job done.

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 and 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. Another thing I learned is that…

A Leader Assistant is grateful for the opportunity to serve others.

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.

Good leaders must first become good servants.

– Robert Greenleaf

Having humility is so crucial to becoming a Leader. You cannot help others if you’re not willing to set aside your pride.

Jim Yong 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.

-Jim Yong Kim

Being humble means asking for and applying feedback from others, and also 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.

The question is:

Will you let your screw ups 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 3 tensions…


  • Proactive VS Reactive
  • Flexible VS Focused
  • Confident VS Humble

I hope this episode helps you work within these tensions as well!

Download FREE Chapters