Do You Really Need HR Support, or Are You Fine Without It?

Jason Randall (00:00)

The decision to seek HR support is usually not formal or even particularly clear. It happens when payroll gets handled by someone reliable, benefits are figured out as they come up, policies are written up and live in a folder somewhere. In other words, the business gets by. It's small, it's nimble, it's growing. Managers solve their people problems case by case, and for a while, that can seem fine.

And then the business grows and hires more people — and gets more complex. With more employees come more questions, more compliance requirements, more pressure on leaders and managers to handle situations they were not necessarily trained for.

So this episode is about that tipping point. What happens when HR support becomes something the business really needs? What starts to happen when it doesn't get that support? And how can leaders tell the difference between normal growing pains and a system that is starting to crack?

So with that, I wanted to introduce an expert in this space — someone who has guided a large number of organizations through a transition toward greater support and toward greater success. Jason Millman, welcome to the conversation.

Jason Millman (01:19)

Thank you, Jason. I appreciate it.

Jason Randall (01:21)

Well, it's our pleasure to host you. I hope you could start by telling us a little about yourself and how you came to this line of work.

Jason Millman (01:28)

I've always had a lot of respect for people who run businesses. I grew up in a small town and my parents managed a local grocery store. They didn't own the business, but it was owned by a wonderful family, and what stood out to me was how much the family cared about their employees and their customers. You could see it in how they treated their people. So that was really my first exposure to business — not from a strategy standpoint, but from a service standpoint. I got to see what it meant to take care of people, what it meant to really know your customers, and how important a single business can be to a community.

That shaped how I view business owners. I've always had a lot of respect for people who start and run businesses, because they're not just building something for themselves. They're creating jobs for other people, supporting families, and contributing to their communities.

As I got into my career, I had the opportunity to work for a phenomenal business owner who really lived that out. He cared deeply about his employees, he cared about his customers, and he understood that the way you lead people matters. What stood out to me is that he didn't expect his leaders to figure things out on their own. He made sure they had the tools, the training, and the support they needed to manage people well. And I got to see firsthand what that looked like — more confident managers, more consistent decisions, and just a better experience for employees overall.

As I got further into my career and worked with other business owners, I noticed that many of them are incredibly strong in what they do, but the people side of the business can get complicated quickly. Not because they don't care, but because that's not why they started their business. For well over a decade, a lot of what I focused on is helping bring structure, clarity, and support to that side of the business, so that they can keep growing without getting pulled into areas they were never really prepared for.

Jason Randall (03:47)

That's a great insight — that the desire is a prerequisite, but not sufficient to really have the results show up. In other words, execution depends on taking some tangible steps. So I wanted to get more specific with you. When leaders say, "we don't really have HR support, but we're fine" — what does that really mean to you?

Jason Millman (04:08)

Well, it normally means that nothing has gone seriously wrong yet. So they're hiring, they're paying people, they're handling issues as they come up. And from their perspective, everything's working just fine.

To be fair, most business owners don't start a business because they're excited about HR. Whether it's a medical office, a manufacturing company, or anything in between, they start it because they're passionate about what they do and they feel like they can create an experience for their customers that's one of a kind. So HR just happens to show up along the way, and a lot of times they're not prepared for it when it does.

At the beginning, running fine without HR usually looks like this: the owner is involved in most decisions being made, hiring is based on instinct and relationships, issues are handled informally and quickly, and there's kind of an unspoken understanding of how things operate in that business. Because everything is so centralized, it actually feels very efficient.

Jason Randall (05:27)

So the answer to my next question is sort of implied by your insight — that everything runs through the owner initially. But at what stage does that approach start to break down?

Jason Millman (05:43)

Well, it starts to break down when the business grows to the point where the owner can't be involved in every single decision. Now you've got managers stepping in, and most of those managers are there because they've earned the trust of the business owner — not because they've been formally trained to manage people. It's kind of a talent-over-training situation.

What I've seen is that for someone to be successful in any role, they need three things: tools, training, and follow-up. That applies to every employee — and it applies to managers too. When managers don't have those things, especially around people decisions, that's where inconsistency starts to show up.

Jason Randall (06:29)

Is it like the frog being boiled? Does the business owner start to notice this happening, or does something bad happen that forces a look in the mirror?

Jason Millman (06:47)

Yeah, it's kind of one of two things. If you're really in tune with your business, then when everything starts to feel just a little bit harder than it should, that's usually the business telling you that you've outgrown the "we'll handle it as we go" approach to HR. But most of the time, it's after something happens — a termination that gets challenged, an employee saying "that's not how it was handled for someone else," or leadership realizing they don't have the documentation to support a decision they want to make. That's usually when it starts to click for them that it's not just about handling this one situation — it's about how consistently they've been handling every situation.

Jason Randall (07:35)

I think something else I've heard a lot is that just because an owner can do something doesn't mean they should. It's not sufficient to say, "I could do this." The better question is: is this the best use of my time?

Jason Millman (07:55)

Absolutely. They moved into that role because they have a focus and a passion for what they want to do — but that's not necessarily managing people and making those types of people decisions.

Jason Randall (08:10)

So is there one place you've seen where the strains start to show up first? Is it payroll, benefits, employee issues? What are some stories from the field?

Jason Millman (08:24)

Well, most companies don't go from fine to broken overnight. There's a period of time where things are still working, but they're getting harder than what they should be. You start to see friction in areas that used to feel simple.

For example, a hire that doesn't work out because there wasn't a clear onboarding or expectation-setting process. Managers who hesitate to address performance issues because they're not sure how to have those conversations. Or you as a leader getting pulled back into employee issues more than you expected. It's usually not one big moment — it's a buildup of smaller moments.

Jason Randall (09:12)

And then eventually there's the straw that breaks the camel's back — and it's undeniable that help might be worth considering.

Jason Millman (09:21)

Absolutely.

Jason Randall (09:24)

A lot of small businesses have someone handling HR by default — an office manager, a finance person, even a spouse. Someone gets voluntold. What works about that for a while, and when is it no longer the right answer?

Jason Millman (09:51)

Most businesses promote for performance but don't always prepare for leadership. Those managers put in HR roles do their absolute best, but they rely on their own instincts. One manager might avoid conflict and another might address things immediately. One may document everything and another may document nothing at all.

When managers don't have the tools, training, and follow-up to be successful, employees notice very quickly. They start asking, "why was this handled differently?" And "why does one manager do this and another one doesn't?" That's where things like policies, handbooks, and clear guidelines really matter — not just as paperwork, but as a way to make sure that everyone's operating from the same playbook. Without that, you're relying on individual judgment. That's where inconsistency — and eventually risk — starts to show up.

Jason Randall (11:00)

You're onto something super important. In a business's infancy, when everything runs through the owner, policy can be made up on the fly and get you through. But as you scale and start adding employees, the absence of policy is asking for trouble — legal trouble at a minimum, but also just not operating as efficiently as you should.

Jason Millman (11:33)

Absolutely. And those gaps create friction. And where you have friction, you have risk.

Jason Randall (11:42)

At the risk of being slightly repetitive — how can a leader tell the difference between "I'm running a lean organization" and "we're underresourced and we're suffering"?

Jason Millman (12:01)

That's a good question, because a lot of businesses pride themselves on being lean. And that's a good thing. But there's a difference between being lean by design and being underbuilt.

Lean means you've made intentional decisions to keep things simple, but there's still clarity and consistency behind how the business operates. Underbuilt means you're relying on individual judgment and memory instead of any type of structure.

A simple way to think about it: if I asked three of your managers how they would handle the same situation, do I get roughly the same answer? If yes, you have a lean business. If I get three different approaches, you're underbuilt. You can see it in practical areas too. In hiring, lean means clear role expectations and a consistent interview approach. Underbuilt means every manager has their own strategy based on instinct. In performance management, lean means managers know when and how to address issues. Underbuilt means issues get ignored or delayed. In answering employee questions, lean means people know where to go and what to expect. Underbuilt means the answer depends on who you ask.

Structure comes in because clear expectations, basic policies, and a handbook aren't about adding layers — they're about making sure the business operates consistently without reinventing decisions every time. What I've seen personally is that lean will scale, but underbuilt eventually creates friction. And when that friction shows up, it usually pulls leadership back into areas they thought they had already delegated.

Jason Randall (14:19)

I love the language of lean versus underbuilt. I think that's a really clean and useful way to help a business owner assess where they actually are. So let's take a specific example that could be a flashpoint. Walk me through a termination from the underbuilt perspective — what it looks like when it breaks down.

Jason Millman (14:43)

Yeah, so usually what happens in that situation is a business has an employee that they know isn't meeting expectations, but there was never a formal expectation set. And there's no clear record of prior conversations about performance. The only thing that's documented might be the final event that led to the decision.

And so what happens is, when you sit down with that employee to let them go, the employee is caught off guard because no one ever clearly addressed the performance issues with them before. And now you're at the most critical moment — the end of the employment relationship — and there's no documentation to support how you got there. What should have been a very straightforward situation becomes something much more complicated.

So it's not the decision that creates the problem. It's the lack of consistency that led up to it. That's one of the things we coach on regularly.

Jason Randall (17:33)

And these are consequential things. What can happen when a termination isn't executed well?

Jason Millman (17:44)

It can lead to big issues. The termination can get challenged. In certain situations, you could find yourself in court — if the employee felt they weren't being held to the same standard as others, for example. It also creates a difficult situation for the other employees who witnessed it. They don't know why the person was let go, and they may start to wonder if their job is at risk too. That's why clear expectations are so important — so every employee understands what's expected of them, and no one is working in fear.

Jason Randall (18:41)

I suspect some of the audience is saying, "I resemble that remark." So when an operator reaches that inflection point, what should they do first?

Jason Millman (19:06)

One of the things you can do is start by creating consistency in a few key areas. One is how you hire. Two is how you onboard new employees. And three is how you handle employee issues. Part of that is having some basic structure in place — clear expectations, simple policies, a handbook that reflects how you actually operate. Not to overcomplicate things, but to make sure that managers and employees are aligned so they're not making decisions in a vacuum.

I would probably start with those three things: how you hire, how you onboard, and how you handle employee issues.

Jason Randall (19:53)

The means to do that can look different. A company might hire internally, use a technology-only solution, or partner with an organization like Questco. How do you contextualize that decision?

Jason Millman (20:17)

I would look at three things when deciding whether to handle it internally or go with an outside model.

First, complexity. How many employees do you have? Are you in multiple locations? Are you dealing with different types of roles or compliance requirements? A 15-person team in one location is very different from a 75-person team across multiple states with managers making independent decisions.

Second, growth. If the business is growing quickly, the people side changes fast — hiring, onboarding, new managers, new issues. Growth exposes your gaps. What worked for 10 employees doesn't work for 35 to 50.

Third, capacity. Do you actually have the time and internal expertise to build this out? Because building HR internally isn't just hiring one person — it's creating systems, training managers, maintaining consistency, keeping up with compliance, and supporting the business as it continues to evolve.

What I've seen is that companies hire their first HR person, but that person spends most of their time reacting to issues instead of building the structure the business actually needs. That's where a partner model like a PEO can make sense — it allows businesses to access structure, expertise, and support without having to build it all internally right away. It's not really a question of which model is better. It's a question of what the business needs right now, and how they want to scale that capability over time.

Jason Randall (22:46)

You mentioned something incredibly vital and often overlooked — that the decision to make an internal hire can be wonderful, but it requires forethought, structure, and investment. It's not enough to bring someone in if they're unarmed to the needs of the business. They end up very tactical at a very expensive price point.

Jason Millman (23:32)

Absolutely. I get the question all the time: "Does my business need a full HR team?" And the answer is: not necessarily. What you need is capability. Some businesses build that internally. Others choose to partner with a company like Questco to get that expertise, structure, and support without having to build it all themselves. It really comes down to how they want to scale that part of their business.

Jason Randall (23:59)

You mentioned there are some compelling technologies out there. But in your view, what are the hallmarks of when technology might not get the business where it's looking to go?

Jason Millman (24:16)

I just don't think we're quite there yet. I've worked with business owners on a regular basis, and while many situations look similar, every situation is different. Technology, from an HR standpoint, doesn't always have the ability to understand all of those fine points, take everything into consideration, or factor in feedback from other members of the team to arrive at the best answer.

Jason Randall (24:52)

It's something I've observed too. On the HR advice-giving side of what we do, we're trying to help people move from confusion into confidence. An AI-generated response to a situation always looks great and sounds very good. But we have to appreciate that while AI tools and technology generally can be very helpful, AI is only about 70 percent accurate. And I wouldn't be comfortable with a 70 percent accuracy rate on things that are consequential to my business — handling a sensitive HR issue, understanding the legal requirements to operate in a particular state. I think that's something that gets overlooked as we rush to embrace new technologies. It can be transformative. And the human element, the expertise that can be provided, remains an essential part of what we do.

Jason Millman (25:56)

Yeah, I want to talk to someone who is going to be able to walk me through this conversation — to know what to say, what to avoid, and also talk about what some of the possible reactions might be. And not just "here's the conversation you need to have" — but also, is this employee ready to receive the information I'm going to give them? These are things we talk about with business leaders and owners regularly: when do you plan on having this conversation, and what does that look like? Here are some possible ways it can go, and here's how you might respond in each scenario. I love that personal, human touch that our people are able to provide.

Jason Randall (26:48)

Sure. And what do you see out there in terms of what happens when a business or owner waits too long to move from owner-centered decision-making to investing in an outside resource, a technology, or a team? What are some of the consequences of waiting too long?

Jason Millman (27:12)

Well, it can create really expensive messes. Usually around hiring and terminations — that's where it really costs people. Hiring quickly without structure leads to a lot of turnover. Letting issues go on too long creates even bigger problems. And terminating without documentation or consistency creates a ton of risk. Those are the areas where waiting too long really starts to show up.

Jason Randall (27:52)

I don't think we want to leave the audience on gloom and doom, because there's so much room for optimism — and so much power in what good HR advice can do for a business. So I was hoping you could share some of the stories you're proudest of when it comes to helping a business succeed through your expertise.

Jason Millman (28:21)

I've got a lot of them. One I'm probably most proud of is working with a company that was growing quickly. They had great people, strong leadership, and they were starting to feel the strain of the people side of the business. Managers were handling things differently, leaders were getting pulled back into employee issues, and what used to feel simple was suddenly taking more time and more energy.

We didn't have to overhaul everything. We just focused on a few key areas — helping managers understand how to handle employee situations consistently, providing them with the tools to be successful, and teaching them how to turn tough discussions into productive conversations. The idea is that the best companies are the ones having productive conversations with their employees. Anyone who's a parent knows this: the people you care about most are your kids, and you have productive conversations with them all the time — not because you want to fire them, but because you know they have potential and you want what's best for them. Managers can approach their employees the same way.

After one of those training sessions, one of the gentlemen came up to me afterward. He said, "I'm 46 years old, and no company has ever gotten this information to me before. I've been managing people for 20 years, and this is the first time someone took the time to explain this to me." There was a bit of a tear in his eyes. Those are great days.

When you know that walking a business owner or manager through those conversations — so they're comfortable and confident — is only going to make them want to go out and have more of those conversations, and get better at it. And you know it's going to make that business better and the experience better, not just for that manager, but for every single employee and ultimately every customer they come in contact with.

Jason Randall (31:02)

You have a ton of respect for the way you approach your own advice-giving, because we work with very smart, accomplished, successful people who simply need help and support to become even more so. Your demeanor and acumen are to the benefit of the clients we serve. So I thank you not only for your participation here today, but for the great work you do on behalf of our clients and their people every day.

Jason, when our audience wants to get in touch or learn more, how can they connect with you?

Jason Millman (31:38)

They can find me on LinkedIn — Jason Millman — and reach out to me through there. I'm happy to work with other businesses and share information on how they can help grow and scale their business.

At the end of the day, most business owners didn't start their business because they wanted to manage HR. They started because they believed they could build something meaningful. I've always had deep respect for that. The people side of the business is a big part of that responsibility, and I hope people understand that every business is making people decisions whether they have HR or not. The difference is whether those decisions are supported with the right structure. Because when you get that part right, you're not just reducing risk — you're creating an environment where people can really succeed, where managers can lead with confidence, and where businesses continue to grow the way they were intended to. I appreciate the opportunity to talk today.

Jason Randall (33:05)

Jason, thank you so much for sharing your perspective today.

And to our audience — thank you for tuning into this episode of Up In Your Business. If this conversation helped you think more clearly about whether your business has outgrown DIY HR and is ready for more support, please share this conversation with a founder, operator, or manager who is feeling that pressure right now. You can find more resources and more episodes in the show notes, and we'll see you next time.