Hiring Help vs Doing It Yourself – A Smart Founder’s Decision Tree

When you’re building a small business, you wear all the hats. You’re the marketer, bookkeeper, salesperson, HR manager, customer service rep, and sometimes even the IT department. In the early days, this is almost unavoidable. Budgets are tight, trust is hard to extend, and your energy runs on adrenaline and ambition. But eventually, every founder hits a wall.

At some point, the question is no longer “Can I do this myself?” but rather “Should I still be doing this myself?”

That’s where the real founder’s discipline comes in. Do you hire help? Do you outsource? Do you automate? Or do you double down and keep going solo for now?

There’s no one-size-fits-all answer, but there is a smart way to think about the decision. I call it The Smart Founder’s Decision Tree — a framework to help you decide with clarity, confidence, and a lot less guilt.

Let’s walk through it step by step.

Step 1: The Capacity Question — Do I Actually Have Time for This?

The first and most obvious filter is capacity. Ask yourself:

👉 Do I have time to do this well, consistently, and without it burning me out?

Be honest here. Hustle culture glorifies multitasking, but the truth is that multitasking kills quality and momentum. You can’t write a marketing plan while answering customer complaints while preparing your tax return. Something will break — and usually, it’s you.

Let’s take an example: imagine you’re running a boutique café. You love experimenting with new menus and connecting with customers. But between supplier calls, staff scheduling, payroll, and social media, you’re stretched thin. You could keep doing your own Instagram posts, but if they’re rushed, inconsistent, or uninspired, they won’t bring in new customers. Worse, you’ll resent the time you’re not spending improving your product.

If your honest answer is no, I don’t have time, you have four choices:

Reduce the task’s importance (do less of it or not at all).
Delegate it to someone on your team.
Systematise it so it takes less effort.
Outsource it entirely.

Founders who refuse to face this truth end up becoming their own bottleneck.

Step 2: The Value Question — Does This Directly Drive Revenue, Reputation, or Retention?

Not every task is created equal. Some things directly affect how much money you make, how customers see you, or whether they stick around. Other things are nice-to-have but not critical.

Here’s the simple filter:

If the task impacts revenue, reputation, or retention, it deserves your close attention — at least until you can fully trust someone else with it.
If the task doesn’t touch those three pillars, it’s a candidate for automation, delegation, or outsourcing.

For example:

Writing proposals for clients? That ties directly to revenue. Probably something you should keep doing (or at least closely review).
Responding to routine email queries? Important, but repetitive. A great candidate for automation or delegation.
Designing your logo yourself in Canva at 2 AM? That’s ego, not strategy. Outsource it and free your time.

The goal is to preserve your focus for high-value work. Your time is most valuable when it drives growth, not when it keeps the wheels turning.

Step 3: The Skill Question — Am I the Best Person to Do This?

This is where ego gets in the way for many entrepreneurs. Just because you can do something doesn’t mean you should.

Yes, you could learn to run Facebook ads, build a website, or reconcile invoices. But should you? Are you genuinely the best person to handle it, or are you just the cheapest option right now?

Think about it this way: if you’re spending 10 hours trying to figure out SEO when a professional could do it in 2 hours with better results, what’s the real cost?

Let’s take two scenarios:

DIY trap: A founder spends weeks learning graphic design to save money. The outcome is mediocre graphics, lost time, and delayed launches.
Smart delegation: Another founder hires a freelance designer for a few hundred rand per project. They get professional results, free up time, and focus on growing the business.

Small businesses don’t win by doing everything themselves. They win by doing the right things exceptionally well and leaning on experts for the rest.

Step 4: The Cost-to-Replace Question — Would I Pay Myself to Do This?

This is one of the most eye-opening questions you can ask yourself. If you were paying yourself an hourly rate, would you still do this task?

For example, let’s say your business has the potential to generate R600/hour in client work or sales. But you’re spending two hours reconciling receipts — a task you could outsource for R100/hour. You’re not saving R200. You’re losing R1,000 in opportunity cost.

Founders who cling to every task end up paying themselves the lowest wage in the business. Delegation and outsourcing are not expenses — they’re multipliers. They allow you to focus on high-value activities while lower-value tasks still get done.

Step 5: Running the Numbers — A Simple Formula for Decision-Making

If you’re still unsure, use this simple formula:

If a task:

Takes more than 5 hours per month,
Is not tied to your core genius,
And can be trained, templated, or automated…

Then it’s time to move it off your plate.

That doesn’t always mean hiring a full-time employee. You have multiple options:

Delegate to a current team member if they have capacity.
Outsource to a freelancer or agency on a per-project or retainer basis.
Automate with affordable tools (think invoicing software, scheduling apps, email responders).

The point isn’t just saving money — it’s scaling your impact.

Choosing Between Hiring, Outsourcing, and Automating

Once you’ve identified tasks to move off your plate, the next step is deciding how.

Hiring in-house makes sense if the role is ongoing, strategic, and closely tied to your business’s core. Think operations managers, sales reps, or customer service staff. These are functions where continuity and loyalty matter.
Outsourcing is ideal for specialist tasks you don’t need full-time. Marketing campaigns, web design, accounting, or video production are perfect examples. You pay for expertise when you need it, without the overhead of full employment.
Automation is for repetitive, rules-based tasks. Invoicing, appointment booking, and social media scheduling can all be automated with inexpensive software.

Smart founders often use a mix of all three. For example, a fitness studio owner might hire a receptionist (in-house), outsource ad campaigns (agency), and automate class bookings (software).

Common Pitfalls When Deciding

Founders often fall into traps when weighing DIY vs outsourcing. Here are the big ones:

Holding on too long. By the time you admit you need help, you’re already burnt out and behind.
Delegating without process. Dumping tasks without instructions guarantees frustration. Document systems before you hand them over.
Outsourcing too cheaply. You get what you pay for. Underpaying often leads to rework and wasted time.
Automating too soon. Automating a broken process just makes the mess faster. Test manually first.

Real-World Examples

Let’s ground this in a few scenarios:

The solo consultant: A consultant spends 15 hours/month managing invoicing and proposals. By moving to an invoicing tool (automation) and hiring a virtual assistant for proposal formatting (outsourcing), they reclaim half a week each month for billable work.
The retail store owner: A store owner insists on running their own social media. Posts are inconsistent and engagement is low. By outsourcing content creation for R4,000/month, they triple engagement and see a measurable uptick in foot traffic.
The startup founder: A tech founder refuses to outsource bookkeeping because “I need to know every detail.” They spend 20 hours/month reconciling accounts. Eventually, they hire a bookkeeper for R2,500/month and free themselves to close two new contracts worth R100,000.

Each story proves the same point: DIY has limits. Smart founders know when to let go.

Final Thought: You Are Your Business’s Most Expensive Asset

At the end of the day, your role as a founder isn’t to do everything. It’s to do the right things — and build a system that handles the rest.

The smartest founders see themselves as the most expensive and strategic asset in their business. Your energy, creativity, and leadership are worth far more than your ability to reconcile bank statements or schedule social posts.

So the next time you’re torn between doing it yourself, hiring, outsourcing, or automating, run through this decision tree. Ask the capacity question, the value question, the skill question, and the cost-to-replace question. Then run the numbers.

Because here’s the truth: growth doesn’t come from doing more. It comes from doing less — and doing it better.