Three freelancing conversation tips for getting what you want

Posted on Dec 8th, 2009 | Marketing

The problem with being a freelancer is that when push comes to shove, there’s no one to pass things on to. So whatever problem you have there’s only one person who’s going to sort it out: you.

Courageous conversations

How to say what you mean and get what you want

If, like most of us, you’ve spent time as an employee, you’ll know the advantages of having other people to deal with some of the sticky stuff. For example, you can task the Accounts Department with finding out why your client hasn’t paid; or tell your secretary to say that you’re out of the office in order to avoid a tricky phone call.

But as a freelancer, you’re on your own when it comes to dealing with issues and problems. If and when they need sorting out, you’re the one who has to do it and (you know what I’m going to say here, don’t you?) the longer you avoid dealing with things, the worse they get. Not that I’m suggesting you leap on every issue as soon as things run less than smoothly, but sometime or other you’ll have to do something about those situations that lurk like a worsening toothache.

Don’t just sit there – do something!

There are a number of reasons why most of us procrastinate: first, we predict that raising the issue will seem antagonistic and critical and will, therefore, worsen the situation rather than improve matters.second, we believe that it will probably involve emotion on both sides – from anger, to resentment, to hurt – all of which can be difficult to deal with and may show us up in a poor light (shouting and/or crying are never good).

Second, we believe that it will probably involve emotion on both sides – from anger, to resentment, to hurt – all of which can be difficult to deal with and may show us up in a poor light (shouting and/or crying are never good).and third, we suspect we might sidestep the issue when faced with saying what we mean, so we end up letting the other party off the hook.

And third, we suspect we might sidestep the issue when faced with saying what we mean, so we end up letting the other party off the hook.

The way around all these concerns lies in improving your ability to undertake courageous conversations – those in which open and positive communication is used to create constructive solutions to difficult issues within the context of a strong and trusting relationship.

Sounds great, doesn’t it? And so easy! So why don’t we do it?

Mainly because as well as those fears mentioned above, we are held back simply by the terror of jumping off the diving board and getting on with it. Hence the name “courageous conversations” – we need to be brave and fearless if we want results.

Conversations for any situation

So what sort of situations might call for courageous conversations in your work as a freelancer? There could be any number of challenges with all sorts of people – from clients who blame you for mistakes they make themselves, to customers who are always late paying invoices; or perhaps problems closer to home such as your neighbour’s loud parties which make it impossible for you to work or sleep.

In essence, they all share a common basis: they’re causing you tension, that tension is leading to you to feel resentment and possible irrationality, and you want them to change their behaviour.

Rules of engagement

Holding successful courageous conversations takes practice, but a good way to start is with a few simple objectives:

Positive intent

This means that you have to embark upon the conversation intending to achieve a mutually beneficial, positive outcome i.e. a win/win situation where you may get the other party to agree to making some changes, but you co-create the outcome and they don’t lose face or feel diminished or bullied.


You must be clear about exactly how you want their behaviour to change. It’s no good saying “I’d like you to pay your invoices more promptly”. If they never pay anyone within six months, “more promptly” for them might mean four months whereas what you want is payment within 30 days. So be specific.


This is perhaps the most important area of all and reflects the fact that whatever you believe the issue is you are only seeing it from your perspective – the other person may not see it as an issue of any significance whatsoever – and, of course, you may not be seeing the bigger picture.

Candid, challenging and courageous

Forewarn the person that you want to talk to them about the issue. (e.g. I’d like to come and see you on Thursday to discuss how to improve the timing problem we keep having around your invoice payments”).

  • Start the conversation by stating what you believe the issue is and the impact you feel it is having on you and your relationship with them. Be assertive and clear – if not, you risk losing momentum from the start.
  • Tell them why the situation matters to you and what you feel are the implications if it is not sorted out.
  • Ask them to acknowledge that they’ve understood what you’ve said and for their perspective on the situation. Listen carefully, asking for elaboration or clarification if necessary.
  • Tell them what outcome you would like to see, then ask them to suggest a solution that would address your concerns.
  • Discuss their proposals using lots of questions and reflecting back what they agree to so you are both clear about what is involved.
  • Ask them for their commitment to making the change and stipulate a timescale. Agree with them how you will both know when the change has been made.

Once the conversation has finished, take a few moments to reflect internally how it went. No doubt it won’t have been painless if you’re new to it, but vow to keep practicing – it gets much easier every time.

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Written by Dianne Bown-Wilson

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