None of these are the obvious ones. Every one of them has landed in a real business this year, and in almost every case the owner had no idea it was sitting there.
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I sit in a lot of businesses. Different industries, different sizes, different countries, all at different stages of growth.
Over the last year the same set of problems has kept surfacing. Not the ones you read about. These are the quiet ones, the ones that sit in a business for years without making a sound, and then cost somebody a great deal of money in a very short space of time.
None of them are exotic. Every one is ordinary, common, and entirely preventable. And in almost every case the owner was capable, diligent and doing a good job, and had simply never been told.
This is not an exhaustive list. It is not meant to be. These are simply the things that have crossed my desk in the last twelve months, in real businesses, often more than once. There will be plenty I have not seen, and plenty that do not apply to you. Take what is relevant and leave the rest.
We work with women across Australia, New Zealand, the United Kingdom, the United States and the Philippines. The detail under each of these changes enormously depending on where you sit. The question does not. So I have given you the question, why it matters, and who to take it to.
Do not assume the rules travel. They do not. That is the most expensive assumption I see people make.
1. Every personal guarantee you have ever signed
You have probably signed guarantees on a lease, equipment finance, a supplier account or a bank facility, and then forgotten all of them. The company structure you think protects you does not, because you personally promised to cover the debt.
Selling the business or handing over a lease does not automatically release you either.
Check: every guarantee you have signed, and whether you were ever released.
Talk to: your commercial lawyer.
2. What can be pushed onto you personally when tax goes unpaid
Almost every country lets the tax authority chase directors personally for money the business withheld from employees or collected on its behalf. The mechanisms differ. The exposure is the same.
The pattern is consistent everywhere: filing on time protects your options even when you cannot pay, and missing the filing deadline is what removes them.
Check: that every return and filing is current, regardless of whether you can pay the bill.
Talk to: your accountant. Ask directly what exposes you personally and what deadlines protect you.
3. Who actually owns your domain and digital accounts
Domains registered in a developer’s name. Ad accounts owned by an agency. Admin access held by somebody who left three years ago. It is far more common than you would think, and businesses lose their entire online presence over it.
Check: the registrant and admin access on your domain, ad accounts, business profiles, email hosting, client database and payment gateway.
Talk to: nobody. Go and look yourself today. It takes five minutes.
4. Who owns the work you paid for
In most countries, work created by an employee belongs to the business, and work created by a contractor belongs to the contractor unless the contract says otherwise. Your logo, your website, your course content, your photography.
Paying for something is not the same as owning it.
Check: whether your contractor agreements contain an intellectual property assignment.
Talk to: your commercial lawyer. One review of your standard agreement covers you from then on.
5. A registered business name is not a trade mark
Registering a business or company name gives you very little protection. It will not stop somebody else registering your name as a trade mark and asking you to stop using it. And protection is territorial, so it does not follow you into new markets.
Check: whether your brand is actually protected, in every market that matters to you.
Talk to: a trade mark attorney, before you invest further in the brand.
6. Terms and conditions you can actually enforce
Most service businesses have nothing enforceable. No scope, no payment terms, no cancellation policy, no dispute process. It only becomes obvious when a client goes wrong and there is nothing to point at.
If you sell across borders, your terms also need to say whose law applies and where disputes get resolved.
Check: whether your terms exist, sit on your site, and are agreed before work starts.
Talk to: your commercial lawyer. A one-off cost that pays for itself the first time you need it.
7. Your privacy obligations and your data
Privacy law generally follows the person whose data you hold, not the country you operate from. So the rules that apply to you are driven by where your customers are, and they are stricter almost everywhere than they are in Australia.
You hold names, emails, phone numbers and payment details. That makes this your problem.
Check: whether you have a proper privacy policy, whether you know where your data is stored and who can access it, and whether you have a plan for a breach.
Talk to: a privacy or commercial lawyer. Tell them every country your customers and subscribers sit in.
8. Whether your email marketing complies
Every developed market regulates commercial email, and the requirements rhyme: consent, clear identification of the sender, and an unsubscribe that works and is honoured promptly. In some places breaches are strict liability, so intent counts for nothing.
The two traps I see constantly are purchased lists, and the belief that business to business email is exempt. Usually it is not.
Check: how you obtained every name on your list, and that your unsubscribe actually works.
Talk to: your email platform provider first, as they often have compliance settings you are not using. Then your lawyer if you send into the UK or Europe.
9. Contractors who are not really contractors
The label on the arrangement does not decide the obligation. Regulators look at substance: who controls the work, whether the person can send somebody else, who carries the risk. Get it wrong and the consequences are almost always retrospective, covering back taxes and entitlements for the whole engagement.
This exists in every market, under a different name and a different test.
Check: every contractor arrangement you have, against the current test in their country. Tests change, and agreements written years ago may no longer hold.
Talk to: your accountant and an employment specialist, in each country where you engage people.
10. Injury, health and social obligations for your people
What you must provide or contribute varies enormously by country, and in some places extends to contractors you would never think to cover.
There is no transferable answer here. Only a transferable question.
Check: who should be covered under your policies, and what you are obliged to contribute.
Talk to: your insurance broker and your accountant, specifically and directly.
11. Offshore engagement
If your VA is in one country, your developer in another and you sit in a third, you are operating across three legal systems at once. Contract enforceability, IP assignment, local employment rules, data obligations and payment treatment all need checking at both ends.
Engaging somebody offshore full time, exclusively, under your direction, for years, starts to look a great deal like employment.
Check: whether your offshore arrangements would survive scrutiny in the other country.
Talk to: an international employment specialist, or use an employer of record service that carries the compliance obligation for you.
12. Staffing decisions made without advice
Owners will engage an accountant without hesitating, then make hiring, classification, performance and termination decisions entirely on instinct. Employment law is one of the least transferable areas there is, and what is standard practice in one country is unlawful in another.
Most owners spend more fixing one badly handled termination than a full year of sensible HR support would have cost.
Check: that you have advice lined up before you need to make a decision, not after.
Talk to: an HR consultant or employment lawyer in the country where the person works, not the country where you sit.
13. Insurance that has not scaled with the business
The cover you took out at the start was priced for the business you had then. Revenue, team, data held, contractual obligations and delivery value have all moved since.
Territorial limits are also real. Plenty of policies quietly stop at the border.
Check: every policy against the business as it is now, including any new markets you have entered.
Talk to: your insurance broker, annually, and walk them through everything that has changed.
14. Subscriptions running away from you
This gets out of control faster than any other cost line in a small business. Trials that converted, tools nobody uses, duplicate platforms, renewals nobody remembers agreeing to.
Check: twelve months of transactions, sorted by merchant, line by line. Then put one person in charge of approving anything new.
Talk to: your bookkeeper to pull the report. Do the review yourself, because only you know what is actually being used.
15. One person able to move money unchecked
Small business fraud is almost never a stranger. It is the trusted long term bookkeeper, and it is almost always found by accident. One person should not be able to raise an invoice, approve a payment and release the funds.
Even in a small team, split it. Especially if it feels awkward.
Check: who can authorise and release payments, and whether anybody reviews it.
Talk to: your accountant, to review your payment authorities and controls.
16. A structure you have outgrown
Structures get set up once, at the beginning, and then quietly outgrown. Meanwhile thresholds keep approaching: tax registration, employee numbers, reporting obligations, new market obligations. Crossing one without noticing is expensive, and it is always discovered in arrears.
Check: whether your structure still fits, and what thresholds you are close to triggering.
Talk to: your accountant, annually, with that exact question.
17. A partnership with nothing in writing
A partnership agreement covering contributions, decisions, drawings, disputes and exit. And a funded buy sell agreement covering what happens if a partner dies, becomes disabled, wants out, or has a marriage breakdown.
Without one you can end up in business with a former partner’s spouse, or with a right to buy somebody out and no money to do it. Of everything here, this is the one I would action first.
Check: whether both agreements exist, and whether the buy sell is actually funded.
Talk to: your commercial lawyer for the agreements, and your financial adviser or broker to fund it. The agreement without the funding is half a job.
18. A business that only runs because you are in it
Your procedures are what separate a business from a very busy person. If how things get done lives only in your head, everything routes back through you and nothing can be properly delegated.
A business with no process is a business built on sand.
Writing them once is not the job either. They go stale the moment you change a system, a supplier or a price, and out of date instructions are worse than none, because people follow them.
Check: whether your core processes are documented, current, and somewhere the team can find them.
Talk to: nobody. This one is yours, and it is the highest value work on the list.
19. Where your value actually sits if you ever sell
A buyer is paying for a system that produces a predictable result without you in it. Your talent leaves on settlement day. Your processes stay, and they are what earns a multiple.
Documented procedures, clean financials, contracts in place, IP you actually own and a team that can run the work are what turn an income stream into a saleable asset.
Check: get a valuation even if you have no intention of selling. It benchmarks everything else.
Talk to: a business valuer or a broker who sells businesses in your sector. They will tell you plainly what a buyer would and would not pay for.
Where to start
Do not try to fix all nineteen at once. Pick three.
If you have partners and no agreement, start there. If you are a director, check your filings are current. If you have never checked who owns your domain, do that today.
And if you operate across borders, treat each market as a genuinely separate jurisdiction. Privacy, employment, insurance and trade marks are the four areas where assuming your home rules apply will cost you the most.
To say it again, because it matters: this is a list of what I have observed over the past year, not a compliance checklist. Your business will have its own version of these, and it may have three things on it that never appear here. The habit worth building is the one underneath all nineteen. Ask the question before you need the answer.
None of this is glamorous work. It does not win clients, it does not show up on your revenue line, and nobody will congratulate you for doing it. It simply means that when something goes wrong, and eventually something will, the business survives it.
There is a cost to staying where you are, and in business that cost is almost always sitting in something nobody has looked at.
Go and look.
Ready to work on this properly?
The FEMPIRE Academy is where women who are serious about their business do this work, with the structure and accountability to actually get through it. Join the FEMPIRE Academy.
This article is general information only and does not take your personal circumstances into account. Laws differ significantly between countries and change regularly. For advice specific to your situation, speak with a qualified professional in your own jurisdiction.
As the owner of Fempire and Trudy Heins Business Coaching, Trudy’s mission is to help women create strong, strategic, and financially resilient businesses, the kind that support the life you really want.
With over 35 years in business and finance including 30 years as a Certified Financial Planner. Trudy has built and sold multiple businesses, led high-performing national sales teams, and coached hundreds of women to achieve lasting success.
She knows what it takes to go from idea to income and from coach to company owner.
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