Entrepreneur School with Lindsay White: How to Successfully recruit your first employee

This week on Entrepreneur School, we speak with Lindsay White, founder of High Voltage Leadership. In this workshop, Lindsay will walk participants through everything they need to think about as they approach their very first hire. Who they need, why they need them, how to find that perfect person, when to hire, what questions to ask, and how to do that all successfully. 

Lindsay is a sought-after leadership coach and people operations consultant who believes that every business, no matter how small, deserves three things – great leadership, an impactful people strategy, and a culture that inspires.


First, and foremost, Lindsay is passionate about guiding female entrepreneurs in creating the work & life blend they long for, and a leadership brand that is authentic and grounded in their own values and purpose. Her powerful coaching style leverages her extensive background coaching senior leaders and executives, empowering small business CEOs as they develop and embrace their personal leadership practice.

Lindsay also utilizes her 15 years in strategic talent management to guide these incredible leaders in creating culture and developing the people strategy that is often missing from their business plans. Knowing when amazing teams are connected by purpose, programs and processes that add value, they create amazing results.

As an entrepreneur, working Mom, and first-time Grandmother, Lindsay knows that the blend between work and life can be difficult to create. That’s why she loves to coach and guide female business owners as they navigate their personal leadership journey. Her focus on people strategy, team engagement, and leadership development all help clients drive their business goals while creating an inspiring culture.

Today we are going to talk a little bit about hiring your first team member, and how there’s so much more than just the job description. 

This is your brand, and you want to find someone who is just as enthusiastic about your work as you are. Someone who can take on the values and customer service that you do. So it’s really more than just the job description when you’re looking to recruit a rockstar.

So we’re going to jump into some hiring strategies to help us solo-entrepreneurs to find the perfect fit.

I believe that every business, no matter how small, deserves the three things which are great leadership, an impactful people strategy, and a culture that inspires people. 

With these three things we can create a place where our teams can contribute their best, serve clients most efficiently, and grow our business.

You know, recruitment does not have to be hard. But what it does need to be is well planned and very intentionally executed. When you have a recruitment plan that connects back to our business strategy, we are bringing talent in that can ultimately help us execute that business strategy.

When is the right time to hire?

This is a question that comes up with a lot of entrepreneurs I work with, and for good reason; it’s not easy to answer. But here’s three of the most important indicators that it is time to add someone to your business.

Important relationships are starting to suffer.

Now, usually this is because you’re becoming a bit of a workaholic. Right now we’re all passionate about our businesses and we all like to work in and with our clients. But if your important relationships are suffering, you know this is your kids, your partner; the important people in your life, that’s a pretty good indication that It might be time to bring someone into your business.

 Business shifts

Another great indicator is when you see some pivots, or shifts in your business. I’m thinking, specifically, growth. When your business is blooming, and expanding, that is a great sign that you should be welcoming some new team members into your business.


One of the most important indicators; exhaustion, burnout, etc. If you are really creeping up to some burnout, that is a great time to really start thinking about: ‘Is it time for me to add some talent here?’ or ‘Is it time for me to bring on a team member?’

How do I bring on a new team member?

If it is time, and you see those indicators, there are three really simple steps in order to do this really effectively.


Have a clear vision

What I mean by having a clear vision, is to reflect on your business, your needs, and define your why. Take into account your business plan, perhaps you recognize a talent gap, clarify some big goals, do a SWOT analysis. When you take the time to reflect and analyze your issues, you understand the changes and challenges that are happening in your business.

This is why it’s so important to have a developed business plan; so you can go back to that why. Why are you doing this? What is your purpose? when we talk about those things like your vision, your mission and also your values, this is where it comes in handy, because ultimately what we want to do. So essentially, ‘What are the skills and experience that we would need in order to accomplish those things?’

Beyond someone fitting your business strategy, It’s not just about finding someone who has this long list of skills that you are looking for, it’s about finding the kind of person who doesn’t just do the tasks you line up for them, but takes initiative, creates, and thinks for you.

 Have a simple strategy

When it comes to finding this rockstar, it is important to have a simple strategy.  Finding your perfect match comes down to two things; skill, and values. You can’t hire for one without the other.

One thing I see all the time is that business owners will hire someone based on skills and experience alone, but they dont end up sharing some of the important values with the business. What ends up happening is that their behavior and work doesn’t align.

A healthy balance of values and skills is essential, and once we think of what that looks like, we can start building our job posting.

Now, this is not exactly critical, but a job description is likely going to be longer and more detailed. Whereas a job posting is marketing your job, so it’s going to be shorter, punchier, more energetic. This is where We want to have a brief discussion about our brand and culture. because it’s really important that we start to bring that into the discussion right from the start, about the values, and main accountabilities.

When you are trying to figure out exactly what you are looking for; ‘Do they have a certain level of education?’, ‘Do they have certain certifications right?’, ‘Do they have a certain number of years doing those things?’ I like to tell people to ask themselves: “what does success look like in this role?”

If we can describe that, we know who we are looking for. Now we’re marketing our business, but we’re doing it in a slightly different way, so we really want to talk about what it’s like to work here, what this role will deliver, and how that will impact and be successful inside of the organization.

It’s also important to keep in mind that these should be short, people have short attention spans. I’d say the sweet spot is around a page and a half.

 Have an effective process

The picking process, like everything else, should be efficient, and well thought out. 

So once we’ve got our recruitment plan set up, we know where we want to find our person. We’ve got our job description ready to go and We’ve got some resumes coming in, now we can talk about the process.

 there’s four parts to a recruitment process; screening, interviewing, reference checks, and offer.


So we have our job description, which we’ve been very clear about, and we’ve used that to post, now we’re matching that up with the resumes that we’ve got.

The easiest way to do this is just to go down a resume and put marks; Xs and stars, and find the people who have the most matching skills. When it comes to values and personality, though, one of the most common ways to do this is to ask a question. This could be in the form of a cover letter; where you describe why you want to work there, why you’d be a great fit, etc, or, an increasingly popular form; a video.


The difficult thing about resumes and cover letters, is that it only really tells you about 70% of the person. Because, a lot of the time people over-exaggerate, lie, or even don’t boast as much as they should. This is where interviewing comes in.

It’s actually really critical because ultimately it’s going to save you a lot of time. you’re going to know pretty quickly; Through this casual conversation, find out if you want to speak with them further or not right?

So you’re going to talk a little bit about the details of the role, maybe go over that job description, could ask again, you know, what really motivated you to apply for the job? See if they come up with a different response, or maybe it’s the same right? You’re also going to confirm their education and their experience, and you’re going to, again, be listening for attitude and fit. And that includes some of the values some of the way they behaved, how they talk about previous employment opportunities, etc.

Reference checks

Reference checks are an unskippable part of the hiring process. Not only does it allow you to double-check the qualifications and experience of this person, but it also can give the chance to get to know the behaviour of the person in their past jobs, and their reputation.

You want to talk to, preferably the last manager they worked for and you want to ask them about how they performed. ‘What did they do?’, ‘Where did they struggle?’, ‘Would you hire them again?’


When it comes to an offer, the first step is to reach out and re-iterate the details in a conditional offer; this includes pay, start date, agreeing on the job description, etc. and this conditional offer happens before you get the reference checks.

After you have talked with their references, and made sure that they are a good match for you, that’s when you make a formal offer. This would include a formal start date, and you might want to get them to sign on the bottom line to make sure that you have all of that written down and that everybody is in agreement.

Certainly this would be the point where you could, if you wanted, to do an employment contract.

The last step to completing your new hire is to get them started. You must do some thinking; ‘what do you need them to learn?’, ‘When do you need them to learn it?’, ‘Who do they need to learn it from?’ All these things will help us schedule success.

Make sure that your hire aligns with your business schedule so that you have time to teach and guide, before scheduling work for this person.

It’s important when we’re boarding new team members to over communicate. We want to make sure that this person feels connected  to us, to the vision,  to our values and that they feel they belong.

We also, as a leader have to get great at delivering feedback and this is something that is really hard sometimes is to be clear and concise in that feedback when we know it’s likely going to hurt someone’s feelings.

And I’ll tell you, nobody really enjoys doing this. But as a leader and as a CEO, we have to create the mindset for ourselves that being clear in our feedback is actually helping the individual grow and ultimately helping our business grow.

Finding the right moment to hire, and finding the right person to hire; who shares those skills, values, and enthusiasm, are all difficult things to tackle, however, with these strategies, and tips, I hope you can gain some guidance into hiring.

It’s important to remember that the strategic approach to hiring your first team member always comes right back to your business plan. ‘What am I doing?’, ‘Where am I going?’, ‘What are the goals?’, ‘What am I trying to create?’,

That is really going to help you sort through some of that right from the start. It’s going to give you confidence, it’s going to give you clarity and that again is what you need as you move into the CEO role in your business, you really embrace that leadership and strategic mindset.

We Thank Lindsay White for sharing her wonderful strategies with us today for this interview, and thank you to all the viewers who joined in real time to send in questions for Her.

If you’d like to learn more about Lindsay’s work you can visit her website at highvoltageleadership.ca.

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