If you choose wisely and make good decisions about your first few hires, your team will work well together and everything will run smoothly. But if you choose poorly, it could lead to confusion and chaos. Hiring your first five team members can feel a little scary, kind of like walking on a tightrope. You’re excited because your business is growing, and now you can work with a team instead of doing everything alone! But at the same time, you might be worried about what if you pick the wrong people? Especially when it really matters.
Every founder I’ve ever seen in a Reddit thread, or in an Aussie startup forum, or in a messy Slack community or in a late-night chat says something like, “Your early hires will impact your business in ways that far exceed their actual and literal work.”
They set the tone, they set the pace, they set the jokes, they set the overall standard of effort… they set the entire emotional stamp of the company. If their influence is so strong, if making the first few decisions is done correctly, it can either lead to coherence or chaos for the rest of the work.
Here’s a full guide on bringing in your early team without losing your footing, with real advice from the founders who’ve lived through the chaos.
1. Don’t Chase Perfection, Look for the Right Energy
Your new team won’t sit next to neat roles or positions. Some days they’re in customer support up to their necks; the next day, they’re prototyping product flow or fiddling around on a half-built landing page that is crying out for help.
A founder on r/startups said something that genuinely stuck with me:
“Mindset is more important than raw skill. People who’ve shipped side projects adapt faster. The first month might slow you down, but it pays off later.”
The right person isn’t the one who ticks every box on paper; it’s the one who says, “Yeah, I’ll figure it out,” and actually means it. That attitude is priceless in the early chapters.
2. Values Before Skills Matter Most
Plenty of founders say their worst early hire wasn’t someone unskilled. It was someone who didn’t fit. Someone who didn’t care about the same things the team cared about, pace, ownership, curiosity, kindness, whatever your culture naturally leans toward.
Another Redditor framed it perfectly:
“Early hires shouldn’t just be executors. Hire people who can see the business point of view.”
Ask questions that reveal how a person thinks, not just what they’ve done:
- “Tell me about a moment you were thrown into something unfamiliar. What was your first instinct?”
- “What sort of work rhythms make you feel alive, not drained?”
- “What bothers you more: chaos or boredom?”
Those answers tell you far more than a polished portfolio ever will.
3. Start With a Small Engagement: It’s Smart
A short trial, a month part-time, or a temp-to-perm setup helps you see how someone truly works. Not how they talk about working, but how they actually show up.
This comes up constantly on Reddit:
“If 1099 is an option, start with that. Far less complex. Always start small.”
You will observe their communication methods, their behaviours, their pace, and their unique solutions to problems. And if it doesn’t work out, it serves as a kind of exit strategy for both. People generally prefer to be honest rather than work through lengthy contracts.
4. Be Honest About the Real Day-to-Day
Early-stage work isn’t always glamorous. Some days feel electric, others a bit wobbly. There’s uncertainty, scrappy systems, quick pivots, and those “Wait, didn’t we fix this yesterday?” moments.
A founder on Reddit described it like this:
“The grind is real. Average pay, long hours sometimes, because you believe in the vision.”
You don’t have to scare people off, but give them the honest version:
- Some things change fast.
- Some decisions aren’t final the first time.
- Some days will feel chaotic.
- And no one is too senior to do hands-on work.
People stick around when they feel emotionally prepared, not blindsided.
5. Use Your Network, Don’t Stay Inside It
Founders often find their first hires through warm intros, former colleagues, or friends-of-friends. That early familiarity helps with trust.
One r/startups commenter put it simply:
“Mostly referrals and friends-of-friends. Early hires usually come from your network.”
Your network is a great starting point, but it isn’t your only solution. Sometimes, the best hire you can make is someone you run across in a niche Discord community or while replying at 1 am on a forum you check once a month.
Cast your net wider when you can, because the right person isn’t always the person right next to you.
6. Clear Expectations = Fewer Headaches Later
Put it out there early that you want the employees to come to the office for a couple of days a week. If your team works from home, explain that you organise virtual coffee breaks so people can have a chat and feel connected.
That piece of advice from Reddit is invaluable:
“If you’ll need them in person eventually, mention that early. No surprises.”
r/startups
Expectations are what keep people grounded. Unforeseen events are what make people leave.
7. Don’t Underpay, But Think Beyond Salary
It isn’t necessary to have salaries as in large companies, but the offer shouldn’t be disrespectful or unrealistic.
Australian founders on forums often talk about providing “fair above average” when it is possible, because those who join the company at the very beginning literally determine the business flow.
Think in layers:
- Fair pay
- Flexible hours
- Small but meaningful equity
- Autonomy
- Clear directions for personal development
People don’t leave because of money but for a combination of fairness, trust, and engagement.
8. Check Real References
Don’t believe everything written on a CV. Get honest opinions from people who have collaborated in the past, and also from mutual contacts and coworkers.
A very short message like:
“Hey, what’s your opinion about working with them day-to-day? This can rescue you from heavy burdens later on.”
The early team is heavy on trust. Be thorough.
9. Give Enough Structure Without the Weight
There is definitely no need for a 40-page handbook in onboarding.
But a new employee certainly needs:
- A clear first project
- Weekly meetings
- Someone they can approach with questions and not feel that their question is stupid
- Business direction
Most of the early resignations in remote work are due to people feeling lost rather than a lack of skills. Stories of this kind are what most Reddit threads are made of.
Just a little structure can achieve a lot.
10. Reflect After Every Hire to Sharpen Instincts
Each new employee uncovers something for you:
- Your leadership blind spot
- A new department you didn’t realise you needed
- A communication habit that you need to change
- A skill shortage that you hadn’t spotted
- An organisational value that you hadn’t considered
The founder I saw online once said:
“Hiring is a skill you only learn by doing it wrong a few times.”
After each hire, reflect on the moment to ask:
- What astonished us?
- Where did we get things right?
- What would be different if we did it again?
Such small reflections of yours create your hiring playbook quicker than any book or course.
The Harsh Reality: Everyone Fails Early
Sometimes, everyone makes mistakes when they start something new, and that’s okay. The important part is noticing those mistakes early on so you can fix them and help your team stay strong. Being clear about what to do is kind and helpful, especially when you’re working with a small group. Having this kind of clear guidance helps the new person do well and feel confident. Without it, they might feel unsure and quietly stop trying.
And when a new member steps into your little band of people? A heartfelt “Welcome to the team” should not only feel genuinely warm, but it should also set the tone. It is warm, but grounded. It is encouraging, but let them know what the expectations are. Almost, like to say, “We are delighted to have you along, and here is how we do things so you do not feel lost on day two.”
It is that type of clarity and framework that often becomes the difference. The difference between a team member who thrives… and one who quietly fades away.
