Chasing payments, especially at this time of year, is stressful, difficult and fraught with social sensitivities. What’s more, failure to swiftly secure money owed can have pretty dire effects on your cash flow, leading to more significant issues down the line. Eoin O'Hara gives his advice on what you can do to ensure timely payments.


Chasing payments, especially at this time of year, is stressful, difficult and fraught with social sensitivities. What’s more, failure to swiftly secure money owed can have pretty dire effects on your cash flow, leading to more significant issues down the line.    

The problem of chasing payments becomes even more acute for the likes of startups, sole traders and freelancers, who can find themselves ill-equipped to meet the challenge with the same vigour and dexterity as their larger counterparts. Couple this with the fact that the very future of many small operations may rely on prompt payment of invoices, and the importance of having an effective strategy comes into sharp focus.  

So what can you do to ensure timely payments and how can you encourage those dragging their heels to pick up the pace?

Prevention is the best cure

Whilst you’ll never be 100% confident that a particular payment will be made on time, there are a few steps you can take to maximise your chances.  

1. Terms and Conditions

Clarity is key here and having comprehensive, unambiguous, succinct, terms and conditions of business, pre-agreed before the delivery of any goods or services, is a really basic way to help minimise any confusion or ‘crossed wires’.  

Within your Ts & Cs be sure to memorialise the following relevant details, alongside your other stipulations and agreements:

  • When you usually invoice
  • How you usually invoice
  • When payment will be due
  • Specific timelines detailing the delivery of goods and performance of services
  • What notice period is required to void the agreement
  • Details of late payment fees / incentives for early or prompt payments 
Make sure that you get written confirmation of the other party’s agreement to abide by these terms and conditions, before you deliver any goods or perform any services.  

Many people find it challenging to be this formal in their communications, especially if they have built a friendly relationship with the client / customer. But remember ‘business is business’ and there can be no room for sentimentality, wishy-washy terms and conditions or ambiguous agreements. 

2. Make payment as straightforward as possible

Easier said than done right? But as a small enterprise you do have a few straightforward options that might not be available to larger businesses.  

These options (such as PayPal) can be very convenient for you and some of your clients, but remember that most larger companies will have best practice guidelines in place, which may not include less orthodox methods such as this. Make sure that you have a number of payment methods available and pre-agree which will be used before work is carried out.  

3. Set your standards and abide by them 

You are under no obligation to work with every client that comes along.

You may on occasion have cause for suspicion, that providing goods or performing services for a certain party will be more 
trouble than it’s worth.  You are perfectly entitled to hold this opinion and act on it accordingly.  

Whilst it can be especially difficult for a freelancer, small business or startup to turn down an offer of work, you need to think about what the negative implications could be for you and your business, should problems with payments become an issue.

Requesting a partial payment in your business terms and conditions can be a way of increasing your confidence when larger sums of money are involved; although this solution is certainly not appropriate in all circumstances. 

Should prevention fail

Be confident and self-assured in your approach to pursuing payments; you have every right to receive money promptly for work that you have carried out

Begin with a polite reminder email, explaining the missed payment situation and cordially requesting that payment be made as soon as possible. It is quite possible that the other party has simply forgotten to make the payment and therefore you must give them the benefit of the doubt. Above all, approach the situation as professionally and amiably as possible, you would not wish to damage your reputation and risk missing out on further business.

Pick up the phone. Where an email can be easily ignored or set aside to be dealt with at a later time, a more direct approach, like a phone call, demonstrates your determination to resolve the problem.  Speaking directly to the person which whom you have made the agreement should give you a chance to appeal to their better nature and broker a solution.  Should you consistently fail to receive the payment you are owed...

Consider taking legal action. In most cases of non-payments, freelancers and small businesses don’t follow this route, mainly because it can be very expensive and time consuming.  If however, the amount of money you are owed is too large for you to simply right-off, speak to a solicitor with specialist knowledge in this field and they will be able to support and guide you. 

Most importantly...

For every £ lost, learn a £’s worth of lessons. Sometimes the only thing that you can do is admit defeat, identify the ways that you could’ve prevented the situation from developing and move on.  

You might not be any richer, but you’ll certainly be a little wiser. 
eoin-startacus-(1).pngEoin O'Hara is a business developer and lead content writer at He has a background combining arts and culture with strategic business development, and now plays a central role in the growth of the Startacus brand., The Self Start Society, is the place for enterprising people to learn, share, connect and bring ideas to life. Follow them at @Iamstartacus