Help needed: Hiring an executive assistant

Audiogram - BCBO ep. 111 - Help needed: Hiring an executive assistant

Many of you have succeeded in your practice by wearing multiple hats. But playing the part of CEO, CMO, COO and advisor all at the same time can be exhausting. That’s where an executive assistant, or EA for short, can come in to provide you with better leverage for your time and results for your business.

Blake Stratton joins the podcast to share behind-the-scenes insights into how to hire, work with and delegate to a world-class executive assistant. You may think you can’t afford to hire, but you might learn you can’t afford not to hire an EA for you and your practice.


Blake Stratton – Don’t confuse being busy with being effective, right?  Being effective doesn’t mean that you’ve got to work all hours.  That you’ve got to push — or that you should do it by yourself.  There is such a glorification of busy.

Ben Jones – Welcome to Better Conversations. Better Outcomes. presented by BMO Global Asset Management. I’m Ben Jones.

Emily Larsen – And I’m Emily Larsen.  On this show we explore the world of wealth advising from every angle, providing actionable ideas designed to improve outcomes for advisors and their clients.

Disclosure – The views expressed here are those of the participants and not those of BMO Global Asset Management, its affiliates, or subsidiaries.  

Emily Larsen – Many of you have likely succeeded in your practice by wearing multiple hats at the same time.  Playing the part of CEO, CMO, COO and advisor all at the same time can be exhausting.  If you’re participating in or even are responsible for creating this type of hustle culture, then today’s episode is going to give you a lot to think about.  Today, we dive into how to hire, work with, and delegate to a world-class executive assistant, or EA.

Ben Jones – One of the areas I wanted to learn more about this year was how to hire and work more effectively with an executive assistant.  Now, when I started researching the subject, it turns out there wasn’t a ton of pragmatic information out there.  There was a lot of this is what I do or this is how we work, but not really a system for working well with an executive assistant.  That’s when I found this gem of actionable advice, Michael Hyatt’s book called Your World-Class Assistant.  Today, I’m very excited to welcome Blake Stratton, a business consultant with Michael Hyatt and Company to the podcast.  Blake has behind the scenes insight into what it looks like when working in a corporate culture where great executive assistants make the business run so much smoother.  So, who are the kind of people that need executive assistants anyways?

Blake Stratton – Sometimes people think — I’ll even reference myself.  I can remember when I was consulting, really wishing that I had an assistant, or that I had someone that could help.  But I always thought, you know, I can’t afford that.  Being vulnerable with a bunch of advisors here, they would just be sweating if they saw how I was trying to manage my books and all that type of stuff.  Like, I was just not good with that side of the business.  I was really good at consulting, really good at marketing.  Not so much good at running the business and — I wish I had some help.  But my thought, you know, I can’t afford it.  Or maybe when I get more successful, then I’ll afford it.  Not realizing that an assistant can actually function in a much broader sense than I think a lot of us think they can, right?  Sometimes we think, oh, an admin is really just a secretary, someone to, like, help take care of some paperwork, some meetings, and maybe my e-mail, that sort of thing.  But the truth is, an EA is valuable for anyone who is overwhelmed.  Either they feel like, I thought this was just a season, but actually this is just my life.  There’s always way too much to do and not enough time to do it.  Or people who are really distracted by administrative anything.  They wish that they could be spending more time doing the things they really enjoy doing, they’re really good at doing, but man, there’s so much admin to sort through, paperwork to fill out, that sort of thing.  Then I think, kind of on that same token, anyone who finds themselves not focusing on their strengths, you know?  So it does take a little self-knowledge.  What are my strengths?  What do I bring to the table?  And, I would say, if you’re doing less than 80% to 90% of your time not focused on your strengths, then that’s a red flag.  You deserve to look into getting an EA.

Ben Jones – Well, that makes a lot of sense.  And one of the things that I think keeps a lot of advisors from going down this path is that math equation of I can’t afford it.  So how do you justify — or what’s the business case to help people understand what the EA does and how they might cover their own costs?

Blake Stratton – Sure.  So, you know, a simple way to think about it is to look at how much you earn, right?  Just look at your salary or however you pay yourself and go, okay, this is my take-home.  Then come up with your hourly rate.  Or maybe, if you bill by the hour for instance, you kind of know here’s sort of the hourly rate that I have for my clients or whatever.  I would encourage you to do a time audit.  Go through a week and kind of track where you’re spending your time, and then think about, on those things where you’re not particularly good at it — or maybe you are good at it, but it’s like sending an e-mail or running errands or checking your voicemails or scheduling meetings or following up the meetings or translating notes.  Whatever it is, calculate, okay, how many hours did I spend on that?  Then you can literally come up with a dollar value that you spent on e-mail this week.  Let’s say you’re a $100 an hour advisor, right?  So now you are essentially saying that I’m going to pay someone $100 an hour to go through e-mail, right?  And the truth is that you can find a great EA for far less than $100 an hour, and it doesn’t need to be — you know, I think there’s another illusion that I had was I thought I can’t hire someone because I can’t support a full-time person right now.  I’m not even close, right?  But the truth is you can actually hire someone in a very limited capacity.  Even five, ten hours a week, right?  So that is sort of a starting point, because that’s kind of one side of the cost.  The other side, Ben, is to ask yourself this question.  And this is a little bit more nuanced.  I mean, you can find some hard numbers, but some of this is a little nuanced.  Ask what’s my lack of focus, or my lack of energy, or my lack of productivity — feeling overwhelmed, feeling distracted by these other tasks that aren’t driving revenue in my business — what is that actually costing my business?  If I weren’t buried in those things, what would be possible, right?  What would be possible if 80%, 90% of your time was directed on the things that really move the needle in your business, that you’re excellent at doing?  That’ll take a little bit of imagination, but for most of your listeners, the answer is like, whoa, that would be worth quite a bit.  And what you find when you take baby steps into getting an EA is that it is well, well worth it.  So it’s definitely worth the exercise of doing the math.  

Emily Larsen – Just to put a finer point on this, or as Ben might say, do the industrial math, let’s use a simple example from the book.  Imagine you make $150,000 per year and you can hire an excellent executive assistant for $50,000.  By hiring an assistant, you can be 30% more productive.  Actually, the EA will have generated enough additional business to cover his or her salary.  If you do the math, you may well find that an executive assistant will pay for themselves.  One of the other changes in mindset that I took away from the conversation is that you don’t need to commit to full-time right away.  You’ll hear more about this, and about the benefits of starting small with an EA later.  But first, Michael Hyatt and Company have created a helpful tool for you to identify the areas of your work that could benefit from delegation to an EA, which in turn will help you leverage your talents and time more productively.

Blake Stratton – The Freedom Compass is a tool that any leader can use — really even an employee could use this as well — but to determine where do I really need to place my focus, or what are the activities.  This is a conversation about executive assistants, what are the activities that I should be looking to delegate to an executive assistant.  So, think of The Freedom Compass as kind of a two by two matrix.  When we illustrate it, we typically will make that two by two kind of a compass looking graphic.  But really it’s just comprised of four zones.  The first zone is what we call the drudgery zone.  The drudgery zone is those tasks that you aren’t particularly proficient in, and also they don’t really drive results.  You know, the results that you’re being paid to produce?  They’re things like — it’ll be different for every person, but for me, maybe it’s things like checking e-mail or booking meetings.  Now it’s something like travel.  Fortunately I get to share in some of the assistant help booking travel.  You know, it’s a lot of back and forth timing of — all that type of stuff.  I hate doing that.  I’ll just be honest, I hate doing that stuff.  Also, I’m not paid — that doesn’t really drive results for me, so that’s in the drudgery zone.  The second zone is something called the disinterest zone.  So these are tasks that you’re good at doing, you’re capable, you’re proficient at them, but you aren’t really interested in it, right?  You don’t really enjoy doing those things.  So they’re valuable, they often really need to get done.  But man, you don’t really like doing those things.  It’s a drain on you from a mental capacity.  The other zone — the third zone would be the distraction zone.  This is kind of the polar opposite of the disinterest zone, where you are really interested in it.  You love doing this, but it doesn’t actually move the needle in your business, you know?  So maybe some of your listeners, maybe they love making updates to the website, or designing cool graphics or images for their social media, right?  That could be interesting, that’s kind of a fun release almost.  But, does it really drive results for the business?  Is that the highest use of their time?  Definitely not.  Finally, the key zone, and this is really where you want to pour as much of your focus in as you can, is what we call the desire zone.  The desire zone, your listeners will probably put it together, this is where passion and proficiency meet, right?  This is the things that I really enjoy doing.  They bring me life, they bring me energy.  But also, they really move the needle in my business.  These are the things that oftentimes you’re the best at doing it.  Really moves the needle.  Maybe for your advisors it’s having those sit-down meetings with potential clients, and they’re showing what’s possible for that client, the prospect’s eyes are lighting up with possibility.  And then they come to an agreement.  Maybe they love doing that.  Maybe that’s why they got into the business.  And guess what?  That’s what moves revenue in the business.  So those are the four zones.  How you use The Freedom Compass is to simply list out all of the tasks that you do.  Everything from making appointments, responding to e-mail, booking calls, to managing finances to having meetings, to executing to teaching.  You write out all those tasks.  Start by looking back at your last couple of weeks calendar and just write down all those things that you did.  Then you place them in those zones.  You go, okay, do I like this?  Am I great at this?  Does this move the needle in my business?  Then you place them accordingly.  So that’s how The Freedom Compass works.  

Ben Jones – When I went through The Freedom Compass exercise, I was really surprised to see how much time I spend in the drudgery and disinterest zone.  Now, it’s definitely a good use of your time to use the tool and reflect upon how you’re spending your days.  You can find a link our show notes, as well as other resources mentioned during today’s conversation.  Now, I want to talk about the hiring process, because I think this is a struggle for everyone who’s ever hired anyone, is sitting down and thinking about what are the qualities that you want to hire for.  And you guys have spent quite a bit of time thinking about this, so what are the qualities that you recommend that people hire an EA for.

Blake Stratton – Sure.  So, when it comes to hiring, again, I think it starts sort of with just being honest about, okay, do we really need this?  What should be there?  I think we look for a handful of things when you’re talking about qualities in an executive assistant.  One, as I alluded to, they need to have the skills to do the things that you need to be taken off your plate, right?  Don’t think of your EA as kind of your protégé that’s just going to take your job and do the same things that you do.  But specifically have the skill set to do the things that you ought not to be doing, so that you can focus on what you do the best and what moves the needle in your business.  The second quality would be aptitude.  I think this one is huge.  Things shift a lot.  In 2020, I don’t know if there’s been a year where people’s business model or way of doing business has had to change so rapidly.  So, being able to have the aptitude to pick up on things, to learn things quickly, and to negotiate change with some skill, with some grace, I think is huge.  And then the other two qualities are much more personal.  Attitude would be one and character would be the other.  I mean, this is pretty important, because when we think of an executive assistant and sort of where they could go, you know, this is someone you ultimately want to give access to pretty much everything.  I mean, not everything everything, but bank accounts, all kinds of different accounts that are highly, highly valuable and sensitive.  Of course you want to make sure that you’re hiring someone with sterling character, so background checks and references, those things are important.

Ben Jones – I like that a lot.  And I’m curious, you know, character is a hard thing to assess.  Could you share some tips on how you go about thinking through or assessing character with people?

Blake Stratton – Sure.  Outside of the obvious, a background check, that’s a big one of course.  But, you know, I think something that we do in the hiring process that can be illuminating is to actually have other people interview the potential hire.  So other people on your team, for instance.  They’ll naturally see things a little differently.  They may bring some interesting questions to the table.  That can be really helpful to sort of assess that character piece.  Depending on where you sourced the potential hire from, that could be, as well — obviously a personal reference, like if you crowd source for instance.  Hey, I’m looking to hire someone that does X, Y, and Z.  You can check back with the person that referenced.  But then, also get creative with some of your interview questions.  I think Michael mentions one in the book that I thought was great, which is just asking a question like, when is it okay to break the rules, right?  For instance, if they say, if someone was at physical risk and I could prevent that physical danger to them, then I would consider breaking the rules.  That’s a solid answer, character-wise, right?  And, ultimately, you know, be it character, skill, aptitude, any of those qualities, you want to be really cognizant of that because the right hire is key in this role.  So what we oftentimes do is do test assignments.  So it’s not like, hey, we hired this person, so now here’s absolutely everything and you’re just going to go full-on.  It can be that way at times, but I think if you are new to this, starting small helps as well, right?  Some test assignments where you’re testing the waters in general for how this person will act and behave.  Typically, within 90 days, you should have a really good grasp of whether or not it’s a fit.  

Ben Jones – I think that makes a lot of sense.  I’m curious, one of the things that’s always stuck out to me is you have to kind of have 40 hours of work for the person, or what if you make a bad hire.  Obviously it takes a lot longer to unwind a hire than it does to make the hire.  So, what are some of the pros and cons of hiring full-time versus part-time, or temp to perm?

Ben Jones – Yeah, obviously there is different financial advantages or disadvantages for contracting versus full-time.  But, in my experience, I think what’s great about starting small is it allows the trust building process to take place in a way where the expectations can be set really clearly.  Especially if you’re someone that thinks they can’t afford an EA.  I think just the freedom to go, hey, you know what?  What if you could get 10 hours back?  What if we just started there?  And the potential to build that relationship and that trust slowly, I think especially with the EA role, is really, really helpful.  And, also, if you’re a small business, sometimes you’re paying a little bit more initially or out-of-pocket for a contract.  But I think it also is a provision that can protect you from feeling like, oh, I’m in over my head, or, you know, you don’t want to get in a situation where you’re not sure if you could even fill a full-time workload.  You can solve that problem by starting small.

Emily Larsen – Skill, aptitude, attitude, and character.  Taking steps to make sure you have a grasp on all of the EA’s traits is key to the hiring process.  Whether it be creative interview questions, test assignments, or asking multiple team members to speak to potential new hires, we really encourage you to have a good gut feeling before you bring someone on board full or part-time.  Once you’ve made the new hire, you need to figure out how to work together and how to delegate tasks appropriately.

Ben Jones – Where is the first place to start working with an EA?

Blake Stratton – Yeah, good question.  So, I actually want to mention a resource that we have, because I think it’s really helpful as a mirror.  There is an assessment we have called The Leader’s Score Assessment.  What that will do — it’s a short assessment — but it will illuminate some strengths and weaknesses that you have.  So, I would encourage, not just to take that, but to even show that to your EA, and go, okay, here’s where there’s maybe some opportunity.

Ben Jones – We will make sure and include that in the notes.

Blake Stratton – I think once that’s there, a good starting place with an EA is to simply have them shadow you a little bit.  So, for instance, let’s say you want some help with e-mail, right?  You can create — and we give examples of this by different templates and things like that, but it can be a little daunting, I think, to go hand off your e-mail.  But what could be helpful is to actually start by just giving your EA access to your e-mail with no real responsibility, other than to monitor what kind of e-mails are coming in, what’s the volume like, what are your responses like, what’s your response time like, what are you saying yes and no to.  A good EA, Ben, will be able to pick up on trends, sometimes even better than you are able to, right?  So, the shadowing, whatever are the tasks that you wanted your EA to do, starting just by some shadowing I think can really, really be helpful.

Ben Jones – That’s awesome.  I want to talk about delegation and abdication, because I think this is a super important point for people who are working with an EA.  There a big difference between delegation and abdication.

Blake Stratton – Yeah, so, what delegating is not is to just simply give a task.  Say, alright, go do this, and then don’t check in, right?  Like, I think when we talk about the difference between delegation and abdication, there’s really a few things that are problems with good delegation that lead to abdication, or kind of just letting something go.  The first thing is, with abdication, you have a fuzzy goal, right?  You haven’t created the clarity on what is the outcome, what does success look like for this task or for this project, right?  The second thing is poor communication.  You haven’t really communicated with your EA about, okay, well, what are the expectations?  How do I want this done?  And then finally, low engagement.  So there’s really no touch points built in to the project or to the task.  When you’re abdicating, you’re just saying, alright, go do it.  And then it’s — they return it back to you, and you’re like, what?  This is terrible.  And then — you know, I’ve talked to clients like this.  They’re like, well, you know, I tried to hire an assistant before and they just couldn’t get anything right.  Like, well, actually, maybe there was something about your leadership that wasn’t right.  Maybe you’ve been abdicating.  So often I think we start hesitating when it comes to hiring an EA or giving them tasks because all our experience is abdication disguised as delegation.  When you are giving a task, what you want to do is make sure that you have crystal clear goals, define what success is, and that there is communication.  Even the communication expectations are there that they have — you know, something I think is helpful is understanding the rationale.  Like, why am I being assigned this task?  Well, I want you to do this project, or this project is important because X, Y, and Z.  Having that information alone is so helpful.  And then you want to have a level of engagement that is appropriate.  Especially if it’s a newer EA.  You’re going to need some higher engagement, you know?  Some check points.  You know, we have, and again, this is one of the tools we offer at, but is just some frameworks for engagement.  I would recommend a standing weekly one-on-one meeting, if not a daily check-in as well, we recommend.  So those types of engagement points when they are built in are huge to keep you away from these mistakes of abdication and provide a way for you to delegate with effectiveness.

Ben Jones – On the subject of delegation versus abdication, I want to take a minute and share a concept that I found incredibly useful from Michael’s book.  It’s known as the five levels of delegation.  Think of these as different levels of trust and authority that you’re delegating.  Level one is when you ask your EA to simply do as I say, whereas level five is when you trust your EA to act independently on your behalf.  Now, using these levels, you can quickly ensure that you’re on the same page and set clear expectations about what you’re asking and authorizing them to do.  For example, are they researching a topic and reporting back?  Level two.  Or, are they taking action and reporting back to you on what they did, level four.  This is a really elegant way to improve clarity and outcomes for everyone involved.  

Emily Larsen – We hope you found today’s episode informative.  Hiring an executive assistant might seem scary or expensive, but the truth is that the right EA can pay for themselves and give you the freedom to focus on your best work.  And remember, you can always start small.  We want to thank Blake for sharing his insights with us.  And before we go, here’s a final thought from Blake.

Ben Jones – What does it feel like when an advisor gets the EA relationship right?

Blake Stratton – I think it feels like that time, if you’ve ever woken up after an amazing night’s sleep and you got to sleep like a full eight hours.  And you’re like, whoa, I have energy, I feel rested, I feel hopeful.  I think that’s what it’s like once you’re a few months into a good EA relationship.  I think it’s the freedom that you feel, the energy that you feel to engage in what matters most.  When you look at your calendar and go, oh, I actually don’t have to do those things.  I think it takes a while to sort of get used to that.  But when you actually are realizing I can just work on what’s really going to affect the business, what’s really going to move the needle.  And you should see that.  You’ll begin to see that, you know, in the monthly balance sheet of your business.

Ben Jones – Thank you for listening to Better Conversations. Better Outcomes.  This podcast is presented by BMO Global Asset Management.  To access the resources discussed in today’s show, please visit us at   

Emily Larsen – We love feedback and would love to hear what you thought about today’s episode.  You can send an e-mail to [email protected]  

Ben Jones – And we really respond.  

Emily Larsen – We do.  

Ben Jones – If you thought of someone during today’s episode, we would be flattered if you would take a moment and share this podcast with them.  You can listen and subscribe to our show on Apple Podcasts, or whatever your favorite podcast platform is, and of course, we would greatly appreciate it if you would take a moment to review us on that app.  Our podcasts and resources are supported by a very talented team of dedicated professionals at BMO including Pat Bordak, Derek Devereaux.  The show is edited and produced by Jonah Geil-Neufeld and Sam Peers Nitzberg of Puddle Creative.  These are the real people that make the show happen, so thank you, and until next time, I’m Ben Jones.  

Emily Larsen – And I’m Emily Larsen.  From all of us at BMO Global Asset Management, hoping you have a productive and wonderful week.  

Disclosures – The views expressed here are those of the participants and not those of BMO Global Asset Management, its affiliates, or subsidiaries. This is not intended to serve as a complete analysis of every material fact regarding any company, industry, strategy, or security. This presentation may contain forward looking statements. Investors are cautioned not to place undue reliance on such statements as actual results could vary. This presentation is for general information purposes only, and does not constitute investment, legal or tax advice and is not intended as an endorsement of any specific investment product or service. Individual investors are to consult with an investment, legal, and/or tax professional about their personal situation. Past performance is not indicative of future results.  BMO Global Asset Management is the brand name for various affiliated entities of BMO Financial Group that provide investment management, trust, and custody services. BMO Financial Group is a service mark of Bank of Montreal.  Further information can be found at

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