You get burned when you outsource a crucial business function before you know how to judge it.
I’ve seen it and I’ve done it myself when I was stretched and trying to keep too many things moving at once.
Marketing feels vague and product feels too technical, so you bring in outside help to “handle it”. It feels sensible because you’re finally out of the weeds.
The trouble starts when outside help becomes a way to avoid learning a function you still need to understand. You hand part of the business away before you know enough to judge the work or spot when it’s going wrong. 👇🏻
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You skipped the hard bit
Melissa Kwan ran into this twice. She kept hiring agencies to do work she didn’t want to learn herself, then struggled to judge the results because she didn’t know the basics of marketing.
She told herself marketing wasn’t for her. In the end, she put what she called “the most important revenue role” in someone else’s hands.
If the function is still a black box to you, you don’t know what you’re buying.
You don’t know how to write the brief or interview for the role, and you can’t tell whether the person in front of you is excellent or just saying the right words.
Melissa eventually realised that “you cannot hire someone to do a good job if you don’t even know how to interview for them… It’s not that they’re not good. It’s that I don’t know how to direct them.”
You hire because you can’t do the work yourself, then lose the ability to see whether it’s being done well.
A product doesn’t stay finished
Melissa hit the same problem when she outsourced product development.
She hired a dev shop to cover the whole build, including the PM, developers and technical lead. The deal was milestone-based. The product didn’t work properly, the shop kept burning time, and real users exposed gaps everywhere.
Once a product is live, things break and change quickly, so somebody has to make fast decisions. A dev shop doesn’t work at that pace.
“A dev shop will never be able to fix that. They’ll be like, yeah, maybe next week.”
Treating a live product like a finite outsourced project leaves the business waiting on decisions it needs now. If the work needs constant judgement and fast iteration, you can’t leave all that understanding outside the business.
Agencies optimise for what you pay them for
Gary Das was paying marketing companies to generate leads for his mortgage business. They were paid for leads, so that’s what they focused on.
Their job stopped at the lead. Whether anyone answered the phone, booked an appointment or eventually became a client sat outside the metric they were being paid for. The metric stopped one step before what Gary actually needed.
Outside help focuses on what you pay for. If you don’t understand the function well enough to see the gap, you can burn time and money while everyone involved still says the work is working. Outsource the work and you still own what comes back.
You still need a clear view
Damon Flowers suggests bringing in someone independent when you’re hiring for technical work you can’t judge yourself.
Get somebody who understands the work to shadow it, review what’s being built or tell you when something is going wrong. You need enough understanding to know what good looks like, or someone close to the business who does.
The damage starts when you lose sight of what’s happening and what it’s costing you.
Melissa found her way out of that problem when the outsourced dev team kept burning through time and money without getting the product working. David, who had been her boyfriend for seven years, stepped in pro bono to help.
Once she saw what he could do, paying an external agency for poor results stopped making sense. She brought him in as CTO and co-founder, sorted the equity, and he now runs the remote engineering team in Vietnam.
That gave Melissa room to take marketing back in-house, rework the messaging and stop outsourcing a part of the business she’d spent years avoiding.
Some knowledge needs to stay inside
“Do you want to have your own army, or do you want to pay mercenaries?”
Yannik Schrade keeps technical knowledge inside when it’s part of what makes the business valuable.
If every gap becomes something to outsource, you miss whether the knowledge itself needs to stay with the company.
If a function shapes revenue or product quality, handing it away too early can stop the business building its own judgement.
Where outsourcing actually works
Liam White deliberately kept manufacturing outside his sauces business. Learning to manufacture it themselves would have taken years, so he found a manufacturer and kept his own team focused on selling and developing the product.
Outsourcing let the business grow faster without building a manufacturing operation it didn’t need to own.
Harvey Armstrong and Sam Holmes built Prime Time around the brand and worked with professional brewers on the product. They keep the knowledge that matters to their business close while buying specialist production expertise elsewhere.
Joe Averill used a fractional CFO because his startup couldn’t justify hiring one full-time. It gave him access to experienced financial help without carrying the full-time cost.
Outsourcing works when you’re buying specialist help you don’t need to build inside the business. It breaks down when you use it to avoid understanding a core function.
Know enough to judge the work
If the work shapes revenue or product quality, you need enough understanding to judge it.
You can outsource it once you understand enough to see whether it’s being done well.
The expensive mistake is handing it away before you know how to judge it.
Great piece!
You don't need to *do* the function. You need enough understanding to write the brief, read the output, and spot the leak.
That's a week of learning, not a career.
The expensive mistake isn't outsourcing.
It's outsourcing before you've done that week.
This is one of those patterns that’s so easy to fall into when you’re stretched: outsourcing looks like progress but it’s really just deferring the learning you still need. Deloitte’s outsourcing research consistently flags oversight failure, rather than supplier failure, as the primary reason these relationships break down. As I see it, you need just enough working knowledge of a function to know whether you’re being well-served or simply well-managed. What’s the function you’d most warn founders against handing over too soon?