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For many contractors the challenge of working for a range of clients may well come as a bit of a shock. If you’ve only ever had permanent roles then you may well have only ever had to deliver work to one individual at any given time. Of course, that individual may well have been a tyrant who threw briefs at you unpredictably, constantly expecting you to prioritise each different task.

If they were, then you will have some idea of what it’s like managing clients as a contractor.

When I quit my role to go freelance (again) a few years ago, a colleague messaged me to say congratulations. ‘You’re going to be your own boss!’ he said. It was only in considering my reply that I realised the irony of this phrase. I was actually getting ready to embrace the whims and requirements of an unknown number.

For some people this can be one of the hardest parts of the job. If you’re not a natural people person, or don’t have a knack for multi-tasking, then you may not be cut out for the freelance life. At the very least you may need to manage your work and working relationships to keep things as simple as possible.

There is a natural paradox built in to contracting. You are constantly trying to drum up and schedule new work, as keenly and quickly as possible, whilst delivering on what you’ve already promised. When you’re making promises to lots of people on the fly, good judgement is essential.

Here are some tips on keeping everybody happy, including yourself.

1. Empathy is invaluable

A sole trader commissioning you will have very different pressures on them to someone in a highly political corporate setting. There may be unique sign-off procedures or budgeting factors to consider. Your friendly advice may be welcome, essential or extremely patronising, depending on that individual. So get good at reading your client and their specific working challenges if you want that relationship to thrive.

2. Embrace the unpredictable

Managing different work and different clients in parallel can get complicated, there’s no two ways about it. And strange unpredictable winds can blow you all over the place. Sometimes the phone won’t ring for days then I get a flurry of work come in within a few hours of each other. Why? I have no idea. But being able to compartmentalise tasks, work on projects simultaneously and work out on the fly who to prioritise and how to juggle the calendar is an extremely valuable skill that has evolved over time.

It’s just the way it works, so learn to love it. If you want a simpler life, stick to your day job.

3. The customer is (almost) always right

If you think your client is wrong about something, it can be tempting to tell them. I’ve actually seen it done very bluntly by a contractor once (I was sat cringing in the corner). Needless to say, that relationship did not last much longer than the rest of that meeting. But there’s a delicate balance to be struck. Sometimes it is really necessary to push back. You’re being paid to produce great work and safeguard their interests, so if you think there’s a better way of doing things then it’s only appropriate to stick up for what you believe. But you need to be able to read the mood and choose your words carefully. If you do this they will respect and trust you all the better for it.

4. Learn to anticipate what your client needs

What your client asks for isn’t always what they need – or indeed the full scope of what they need. Learning how to look for clues to the bigger picture can be extremely rewarding for both of you. This again is the value in good communication – the more you talk to your client and find out about their wider business needs, wider team and challenges of their project or role, the better you can advise them now and in the future.

5. Some clients know they’re difficult, some don’t

I’ve worked with some people who are extremely easy to please. I’ve also worked with others who never seem to be happy unless we’ve had thirteen rounds of amends. But the latter can come in two very different forms, in my experience. Some clients of mine are constantly apologising for being difficult, which sometimes they are. Others seem to relish being critical. It doesn’t really make a difference, you need to still service both with diligence and patience, but both will learn to trust you over time and that two-way communication should become increasingly fluid and straightforward. Should.

6. Don’t over-promise

It’s a good idea to promise work well within what you’re capable of, particularly in terms of timescales. If you can bring a job in sooner, then you score extra points and build the relationship. Miss a deadline through over-promising and you might never get the chance to make amends.

7. Conversations are worth taking time over

Today I’ve lost between 45 minutes and an hour talking to clients of mine about things that could have been dealt with in about 7-8 minutes by email. Superficially it’s frustrating, I’d rather have that time back to do the work, or something else, but the value of those conversations is priceless. They trust me to understand them and if they choose to convey what they want verbally, at length, then who am I to argue?

Don’t presume to understand your client. Go the extra mile to make sure you do. It builds the relationship, reduces the likelihood of amends and increases the chance of loyalty in the future. And don’t presume that because you do understand them that they feel understood. Making them feel confident in you and looked after is just as important as doing a good job.

8. Know when – and how – to say no.

Sometimes clients are just unreasonable and what they ask is palpably unachievable or unfair. If this is the case, stand your ground and feel good about it. But don’t allow frustration or curtness on their part to stop you from being the exemplary, co-operative contractor. Respectfully agree to disagree, and leave communication channels open. You never know when they, or someone else in their team, might come back with a different attitude.


And while you’re there trying to manage you clients, why not let us take care of your accounts. Check out how we can make your contracting life, that little bit easier…

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