A Better Way to Hire & Scale Your Team

Growing your business beyond yourself can feel scary, but it doesn't have to be. This guide teaches you how to hire responsibly and get it right the first time.
A Better Way to Hire & Scale Your Team
Photo by Austin Distel / Unsplash

There was a moment in my time as a freelancer where I felt this strange mix of fear, uncertainty, ambition, and a twinge of excitement.

The fear was that I’d be doing what I’m doing—trading my hours at my keyboard for dollars—forever. I thought back then, “freelancing is fine, for now. But for the next 3 or 4 decades? Boy, I hope that’s not what my future holds!”

The uncertainty was that I didn’t have a clue how to go from there to growing a “real business”. I knew that I would need to start hiring employees, at some point, somehow. But the perceived risk seemed insurmountable: Paying other people’s salaries (I had my own salary to worry about it!)? Me, being a “boss” of other people?  Yeah, right.

Still, I felt a sense of ambition here too.  I had a picture in my mind of what I wanted my future to look like and it included me owning a business that didn’t depend entirely on me sitting at my computer logging billable hours.  I was determined to crack this code, somehow.

That now-familiar twinge of excitement came from visualizing the payoff that awaited on “the other side” of this hurdle. The challenge ahead of me was to figure out how to make that jump without falling on my ass.

· · ·

Fast forward to today: I’m running a business with around 30 teammates. We have a steadily growing customer-base. An operation that frees me up to do what I want with my own hours. I can (and do) take time “off” with my family at will. And I can (and do) put time “on”, creating new products and ideas.

It took many trials, errors, and course corrections. But eventually, I figured out my “people” strategy.

I’m sharing that strategy with you today.

The business of people

No matter what type of business you’re hoping to grow—whether you’re in services, software, physical goods, or consulting—the quality and scalability of your business will depend on your people.

Specifically, your ability to identify and recruit talented people, manage and collaborate with them, and create strong, sustainable working relationships with and among your team.

It turns out, this is insanely hard to get right.

In fact, hiring and management is where most businesses make and re-make the most mistakes. And you better believe I made plenty (and still do).

As always, the advice I’ll share below are my lessons learned the hard way: Through stumbling, trial, error and course correction. That’s basically my entire approach to teaching and coaching—sharing what has actually worked (and not worked) in my real-world businesses.

Speaking of—Have you taken my free video crash course on how to Productize Your Service? It covers how to shift to a more scalable version of your service (even if everything you do today is “custom”).

How to “de-risk” hiring

Here’s a dirty little secret: That sense of risk that you feel when taking the leap to your first hire? Yeah, that doesn’t really go away when you’re up to your 20th hire or beyond. Sorry

The good news is that there are ways to manage this risk, reduce it, and leverage it so it can make you and your business better.

Like everything I do in business, I approach it with a bootstrapper’s mentality. I self-funded the growth of my business up to this point, without taking on debt or investors. I took a slow, methodical, learn-as-I-go approach. That meant learning how to grow my team without unmanageable risk.

The result: I’ve built (multiple) productized service businesses, largely team-driven, which can run and grow without me in the day-to-day.

Here’s the metric I’m most proud of:  More than half of my teammates have been on my team for more than 2 years, some more than 3 years. I’m honored to work with amazing people who value the system and process we’ve put together. In my advice below, I’ll show you how I created a win-win-win for my team, our clients, and myself as the business owner (i.e. how you can too).

Question Conventional Hiring Advice

A lot of conventional hiring advice out there says that if you want the best talent and if you want them to “give you their all”, then you have to offer competitive, full-time salaries, benefits, and a job that demands full-time hours.

But for most tiny businesses who are trying to bootstrap their way to a small team, this advice doesn’t hold up. Following it blindly too often leads to over-committing resources (i.e. cash) for too long of a period, while adding unnecessary overhead and administrative headaches.  This can lead to cash crunches, under-utilizing your people, and ongoing stress and pressure for you as the business owner.  That leads to more poor decision making. It’s not pretty.

Actually, it gets worse.

I think this “full-time or bust” mentality misses a huge opportunity.

I found that you can hire truly world-class talent, without taking on unnecessary risk or falling into debt. Plus, managing your people doesn’t need to be a scary or frustrating exercise.

Here are a few key insights I picked up by ignoring conventional hiring advice these past few years:

Full-Time Freelancers, Part-Time

Putting the practical savings of costs and headaches aside, I believe most tiny businesses (especially productized services businesses), can attract better talent and better fits this way.

You have to recognize there is a pool of amazingly talented people who want to do excellent, meaningful work, but don’t want to work full-time for a single company, and especially don’t want to commute to an office.

They’re freelancers.  They’re stay-at-home parents.  They’re travelers.  They’re side-hustle entrepreneurs.  They’re talented, creative, strategic, driven, focused, and yes—committed—if given the right type of work to sink their teeth into (more on this in a minute).

The key is to find people who’ve already committed themselves to freelancing full-time.  Meaning, they’re not “nights and weekends” people with a day job.  They’ve got a handful of client projects going at any given time.

But for many freelancers—while they enjoy the freelance lifestyle and the flexibility it offers—they often have to make a few sub-optimal trade-offs. These include:

  • Steady, reliable freelance retainers are very hard to come by. Most projects come and go unpredictably, hence the term “feast and famine”.
  • They work alone, with no “coworkers” to bounce ideas off of, have water cooler banter, etc. Coworking spaces and online communities can help, but those don’t replace actual working relationships.
  • As a solo act, the juicy creative work often has to take a backseat to “everything else”: Sales, marketing, administrivia, client management, yadda yadda.
  • The quality of the creative work a freelancer gets to work on depends so much on the quality of each client, their needs, their personality, their budget, etc. These factors are very hard for a freelancer to predict at the time they start an engagement, and often don’t align perfectly.

These trade-offs are difficult for freelancers to avoid. But what if your business could help (the right) freelancers solve this dilemma? That’s a unique opportunity that most small businesses are missing, and it’s one that many freelancers seek, but rarely find.

Now, the question is, what’s the key criteria to look for when building your team with freelancers?

Hire Specialists, Not Do-it-Alls

Most clients hire a freelancer as a budget-friendly way to outsource a job that might otherwise be handled by a full-service agency or an in-house department. So when clients take this approach, they seek out those who can (hopefully) “do-it-all”.

For example, they look for a designer who can also code, or a developer who can make it look good enough.  Or a writer who can also copy edit and set up email automation workflows.  Or a marketer who can also do sales consultations.

Because of this, too many freelancers market themselves as “jacks of all trades” rather than “specialists”.

My tip to you:  Hire the “specialists”.

You can’t afford to hire a world-class designer on a full-time salary with benefits.  And you don’t have nearly enough work to keep such a person busy for 40 hours per week.  But you can hire a world-class freelance designer for a few hours per week to deliver top-shelf work that your business needs.

“Specialists” might be harder to find, but the great ones tend to avoid those “do-it-all” projects and they’ll jump at the opportunity to do what they do best, without all the extra requirements that just slow them down.

Break up “what your business makes” into distinct roles, then hire specialists to fill those roles.

This is how you can shift away from you providing that “do-it-all” service into a you running a business that delivers even higher quality work than a solo jack-of-all-trades could, while growing in a scalable, cost-effective way.

OK, but now you’re wondering—Is that really more cost effective?

Yes, if you have your systems and processes dialed.

Micro-Manage The Process, Not The Work

Nobody likes to be micro-managed, especially freelancers who are delivering creative work. This only diminishes the final product and strains the working relationship.

At the same time, it’s easy for team members to waste many hours and precious mental energy on non-creative “busy work”. This too reduces quality and only drives up costs.

Things like communicating and checking on deadlines, fielding client feedback and responding in a timely way, fumbling around with project management tools, file sharing permissions, invoicing, chasing down late payments, contract negotiations, and on and on.  Or how about miscommunications around expectations, what’s needed, in what form, and by when?  These things detract from the hours of flow and focus that a talented member of your team needs in order to deliver their best work.

Your goal should be to clear away the “bloat” from every person’s tasks, and enable them to focus on their specialized role. It’s their job to deliver awesome work. It’s your job to provide the process by which that work should be delivered.

By micro-managing the process, you can continuously optimize it to make everyone’s jobs easier, faster, more enjoyable, less stressful, and ultimately way more effective at delivering quality.

By not mirco-managing the work , you’re giving your team the freedom and autonomy to use their creative skills to their max potential. That means, trust their instincts on creative decisions.

And so… That brings us to the final question:  How can any of this work “in the real world” when every project you do is different from the next?

I’m glad you asked

Productize & Become “Hire-Ready”

If every project you do is completely different from the next, and every client you take on wants something different, that’ll surely keep you busy.

And when you’re super busy and scattered, you might feel like you’re ready to finally hire your first employee or two.

That might work out for this month, while you have a project or two for them to work on. But what if the pipeline dries up next month? You’re back to square one. No team (or worse, employees who don’t have work to do).

You can’t build any sort of process, or define specific roles to fill because the work isn’t repeatable and predictable enough.

This is why so many consultants and agencies turn to the Productized Service model. This is the path that I (and many others) have taken to transition what they do into a more scalable service that is ready to hire people and grow in a sustainable, profitable way.

To that end, I created a video crash course called Productize Your Service. This is where I’ll teach you:

  • How to apply the Productized Service model, even if everything you do is custom and unique.
  • How to sell your service at scale, without writing custom proposals for every project.
  • A deep dive into hiring and delegating so you can free yourself from the day-to-day.
  • How to own a more valuable asset than just your billable hours.

Productized Crash Course

This free video training will teach you everything you need to know to decide whether starting a productized service is right for you.


Great! You’ve successfully signed up.

Welcome back! You've successfully signed in.

You've successfully subscribed to Productize & Scale.

Success! Check your email for magic link to sign-in.

Success! Your billing info has been updated.

Your billing was not updated.