Your Ex, Your Current SO, and Your Staff

A workspace with a laptop, an open pink notebook, various pink, red, and orange pens in a mug, rolls of decorative tape, and gold paper clips on a white surface.

Nobody wants to talk about this… 

But I’m all about making the hard stuff a little bit more palatable, so here it goes. 

Your business isn’t so dissimilar from a long-term relationship. In fact, its very success is contingent upon many long-term relationships succeeding at the same time. 

And just like in our personal lives, some of these relationships will grow stronger as the years go by, while others will simply drift apart. 

You have to approach the relationships you have with your staff the same exact way, especially if you’re a small to mid-sized business. 

Here’s why. 

Small Businesses Often Hire Employees to Perform a Specific Function

But over time, the laundry list of responsibilities this employee takes on inevitably outgrows the original function they were hired to do. 

It’s a very common phenomenon in the finance world…

Companies hire a controller, who then adopts the roles and responsibilities of a Human Resources director or head of Facilities & Operations. 

Of course, in the beginning, this kind of move makes sense. They’re whip-smart, they’ve got common sense, and there are at least two or three hours in the day where they could use some extra work on their plate.

Plus, in their infancy, most companies can’t afford a full-time head of any of these departments… Nor do they have a pressing need for one. 


Once a company starts to grow, the needs of the business expand along with it. And suddenly, a controller with outstanding financial savvy is drowning under a sea of human resource issues they were never trained to deal with in the first place. 

Listen. At some point, it will become clear that the staff of five that took you from point to A to point B doesn’t fully represent the skill sets you need to get from point B to point C. 

And that’s a good thing. It means your business is growing in the right direction! 

Now, in some cases, you’ll want to retain the original job, and simply hire that head of human resources but in other scenarios, you might need to reevaluate the positions altogether. 

Keep in mind… 

Your Staff Is Likely One Of Your Biggest Expenses 

And as tempting as it can be to avoid the evaluation process, I recommend my clients do so regularly. 

Here’s a good roadmap I share with my clients to make objective decisions:

#1: Project 18 Months Into the Future

For a minute, forget how much you love Larry in marketing (and his enthusiastic good morning emails). 

Imagine that you had a clean slate to start staffing for both where your company is right now, and where you want it to be in the next 12 to 18 minutes. 

What are the ideal positions or skills you’d seek out? Which positions are missing from your staff that you absolutely need to accelerate toward your goals, and which were helpful in the beginning but no longer relevant to where you’re taking the business?

#2: Assess Your Current Staff

Again, don’t make it personal here. Instead of naming names, just list the titles, responsibilities, and skills of each position. Then, start mapping out those jobs to the future org chart you’ve created. 

Of course, you’ll find some natural fits. You may already have a few of these ideal positions fulfilled, or you could have a great growth opportunity on your hands for one of your most valuable team members. 

But you’ll also have a couple of people “leftover,” ones who no longer fit in with the direction you’re going or don’t possess the right skill set to get there. 

I know It’s one of the biggest challenges a business owner faces, especially after building a deeply personal connection with someone who’s stayed loyal to the company since day one.

However, for the sake of your business’ success, you’ll have to spend some time considering whether they can grow into one of your ideal positions with a little bit of training, or whether it’s time to move on. 

#3: Consider Outsourcing Options 

When mapping out your ideal staff, you’re also presented with the perfect opportunity to consider outsourced or fractional solutions. 

Many companies often find that for certain skill sets, what they require is someone with deep subject matter expertise on a part-time basis, rather than incurring the additional cost of another full-time employee. 

The bottom line is this…

As an empathetic entrepreneur, there is nothing quite as gut-wrenching as evaluating the long term potential in some of your primary employee relationships.

But the fact is, it’s a necessary growing pain in the evolution of your business.

If it feels impossible to plan for proper staffing with an unbiased eye, don’t hesitate to contact an objective third-party for help!

Both you — AND your business — deserve it.

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