When Should You Stop ‘Winging It’ and Get HR Support?
5 Signs You’ve Outgrown DIY People Management
HR’s not just for big companies. It’s for smart ones. Here’s how to know when it’s time to call in backup.
In the early days of running a business, “winging it” is almost a badge of honour.
You move fast. Make decisions on the fly. Deal with people issues as they come up.
And honestly, that works for a while.
But as your business grows, your team gets bigger. Expectations change. Problems get messier.
And suddenly, what used to be simple now feels risky—or worse, legally shaky.
So how do you know when it's time to stop DIY-ing your HR?
Here are 5 red flags that suggest you’ve outgrown the wing-it phase:
1. You’re Googling Employment Law at 11pm
If you’re trawling forums, government sites, or ChatGPT for “Can I fire someone during probation?”—it’s a clear sign you need professional support.
Reactive HR leads to mistakes. And mistakes lead to tribunals, stress, and expensive lessons.
2. You Avoid Difficult Conversations Because You’re Not Sure What You’re Allowed to Say
Performance issues. Attendance problems. Culture clashes.
If you’re hesitating because you don’t want to say the wrong thing, you’re not alone.
But avoidance doesn’t protect your business—it exposes it. You need a process and someone to walk you through it.
3. You’ve Got People… But No Policies
Contracts? Maybe.
Handbook? Probably not.
Disciplinary process? Err…
No one loves paperwork. But having clear, compliant policies in place protects everyone—especially you.
If you’ve got more than 5 employees and no written policies, it’s time to plug the gaps.
4. You’re Wasting Time on Repeating the Same Conversations
“Can I take holiday next Friday?”
“What’s the sick pay policy?”
“Do we get paid for bank holidays?”
Without clear systems, every question turns into an ad hoc debate.
Multiply that by a growing team, and suddenly you’re running an HR department without even realising it.
5. You’re Losing Sleep Over People Problems
Not every business challenge keeps you up at night. But when it’s people-related—stress spikes.
You worry about legal risks, morale dips, how to support your managers… and whether your decisions are even fair.
If people problems are robbing you of headspace, it’s time to get structured support.
This Isn’t About Red Tape—It’s About Readiness
You don’t need a corporate-style HR team.
But you do need someone who understands your business, your risks, and your goals—and can give you the right tools at the right time.
Think of it like bringing in an accountant. You could do it yourself.
But at some point, you realise that expertise pays for itself.
So… Have You Outgrown Winging It?
If any of those signs sound familiar, it might be time to get some proper support in place.
That’s where I come in.
No big contracts. No fluff. Just a smarter way to protect your time, money, and team.