Assertiveness Training Guide

Your chances of success in any undertaking can always be measured by your belief in yourself. – Robert Collier

Life can be unfair.

Plum assignments go to the most confident people, not the most able.

People who have learned to be assertive have fewer client issues.

It’s obvious that they won’t allow themselves to be pushed around and so people don’t even try.

For better or worse, this is the way the world works.

Why is life like this? It turns out that life isn’t as unfair as we might like to think.

Research shows that confidence matters as much as ability for many tasks.

Confidence can be a battle at the best of times, but when you are working on your own, it’s even tougher.

And even more important as you don’t have the support of a large organisation.

Learning to be more assertive when dealing with these inevitable challenges will pay huge dividends.

Aside from this article, we run assertiveness training courses regularly.

Let’s break down our 6 steps to becoming assertive!

Step 1 – Why Is Confidence So Important?

Nothing in this life is given to us on a plate.

Any significant goal will require you to go out and pursue it, usually in competition with others, who have the same goal.

External competition is tough enough, but if you are unsure of your ability or worth, then you also have to defeat your self-doubts.

This makes achieving your goals even more difficult.

When the going gets tough and the pressure is on, who is more likely to crack?

Someone who is relaxed and confident in their abilities or someone who is nervous and unsure?

Worse still, if you don’t defeat your internal doubts, you might not even pursue your goal in the first place. You will never get out of the blocks.

“If you don’t ask the answer is always no”

But don’t give up. Confidence and assertiveness are learned behaviours.

Yes some people are naturally more assertive than others but that doesn’t mean that you can’t improve yours significantly.

It’s no different to any other skill.

Stock image of team working on project

Step 2 – What Is Assertiveness?

We need to deal with a widely held misconception here. Many people think that assertiveness is pushing people around.

They have confused it with being aggressive.

Put simply assertiveness is standing up for yourself.

It is not pushing other people around but equally it is having the self-confidence to not let other people push you around.

A more specific definition of assertiveness would be that it is “the ability to express your opinions and feelings clearly without undue anxiety”.

Want a quick guide on how to become assertive? Check out our top 6 assertiveness tips here.

Step 3 – Before The Meeting & First Impressions

Confidence is a self-fulfilling prophecy.

As we said earlier, high confidence actually increases performance so perhaps it isn’t as illogical as we first think that confident people get hired.

So how do you build your confidence so that you can go to a new job meeting feeling relaxed and focused on doing the best job you can?

Stock image of team working on project 2

Before The Meeting

“One important key to success is self-confidence. An important key to self-confidence is preparation.” Arthur Ashe·

    1. Research

Know who you are selling to. Find out about the company and the people who will be in the meeting. This sets the scene for the meeting and for you.

Use LinkedIn, the company’s website, industry websites, and Twitter.

Speak to friends who might have dealt with them. The critical question you are trying to answer with all of your research is ‘Why?’.

Try to put yourself in their shoes and think about questions like:

Why do they want to meet me? Why is the project we are going to talk about important to them? Why would they hire me over someone else, what exactly are they looking for?

Buying is an emotional decision. The better you can understand their ‘Why’ the more likely you are to build rapport and emphasise the things that are most important to them.

As a web designer if you were to discover that a company’s competitor had just very successfully launched a new website then that gives you a big advantage as you can compare the two websites before the meeting.

Similarly, if you find that you share an interest in the same football team, or went to the same school as someone you are meeting that can be a very useful way to break the ice.

Also, try to prepare some questions for them. They won’t expect you to know everything. Just as with a job interview having some prepared questions is a great way to show that you’ve done your research and also to get them talking.

Having done your research you then walk into the meeting feeling confident and in control. Knowing who you’re speaking to, what you have to offer them and why that is of interest to them is a good start.

You will also need to prepare some great ideas for their project! But don’t worry, we will cover this in detail in section 3.

    1. Practice Answers To Obvious Questions

It is inevitable that certain generic questions will come up.
Practice your answers to these. Don’t do this in your head. Do this out loud, ideally to a friend or colleague.

Questions like, “Run me through your experience?”, “What makes you better / stand out from your competition?” and “What was your last project?” are almost guaranteed to come up.

More importantly, they’re likely to come up early in the meeting

The ability to answer these in an easy and relaxed fashion means that you can get the meeting off to a good start, building your confidence.

    1. Before The Meeting

The odds are that you’ll be meeting at your client’s offices. Make sure that you plan for delays.

Aim to arrive at least 20 minutes early that way a small delay won’t matter. Rushing into a meeting 5 minutes late, after a journey spent worrying about being late, is guaranteed to put you off your game.

If you arrive 20 minutes early, don’t go in. Aim to arrive 5 minutes early.

Being too early can be inconvenient. It may also look as if you have time on your hands which diminishes your value. Talk a walk around the block or grab a drink for 15 minutes and then go in.

Take care once you arrive at your client’s offices. Sitting hunched over your phone checking email is a bad idea. Sitting at all isn’t ideal.

Recent research shows that your posture has a significant impact on your mood and confidence. Managing this to your advantage is incredibly simple so make sure you do.

Stock image of team working on project 3

First Impressions

“How you present yourself is how people first see you. What are you showcasing?” Anon

    1. How Do I Dress?

How you dress is important.

First impressions count. Everyone knows you should take some time to think about what you are going to wear.

Research also shows that how people dress actually impacts their performance, and it also impacts their attitude.

So if you get this right not only will you make a better first impression but you’ll also be more confident during the meeting.

If you’re unsure about what to wear great advice is:

    • Err on the side of overdressed
    • Wear one thing that is eye catching.

This ensures that you are memorable but for the right reason!

People will take things at face value unless they have a reason not to.

If you dress like a web designer, people will naturally be inclined to accept what you say about web design. If you dress like a banker people will find it harder to accept what you say about web design as they will be confused.

So dress well. Dress as people expect you to. Don’t make things harder for yourself.

If you’ve ever wondered why the Army is so obsessed with uniform this is your answer. Dressing well gives people more confidence and makes them perform better.

Also being honest, who wants to ordered into battle by someone who can’t be bothered to dress well!

This probably speaks to the old adage about dressing one level above where you are currently which is something that most new line managers should think about.

    1. Smile & Prepare Some Small Talk

Especially when meeting someone for the first time your aim for the first half of the meeting should be to put them at ease and establish rapport.

When you first meet someone smile, look them in the eye and introduce yourself clearly.

Then try to take the initiative and start making some small talk.
Remember ‘There is nothing small about small talk’. People often dislike it and so try to dismiss it, but it is important!

It is an opportunity to start building a relationship and to try to put the other person at ease.

Because many people dislike it and find it awkward it is also a great way to differentiate yourself from rivals.

Don’t over think small talk. What you say will be forgotten but your ability to get the conversation going and put someone at ease will definitely not.

Often it just needs a simple statement or question to get the conversation going. A genuine compliment can also work very well.

Before your interview prepare 3 or 4 potential openers, which you can then use depending on the situation.

    1. Breathe & Move Slowly

Pitching is stressful. So is being pitched to!

Remember, the people that you are meeting are probably a little nervous as well. They’ve not met you before and they’re human too. They will also be hoping that the meeting is both fun and useful!

These are people that you’re going to be working with if you win the pitch and people do business with people they like.

Technically you may be world-class but if they don’t like you you are very unlikely to get the work. So you need to slow down and try to relax. Self-confidence is magnetic and makes you more likeable.

So how do you calm your nerves and slow down a little?

Try to breathe and focus externally. The more you focus on your nerves and how nervous you are, the more nervous you will get.

Also the more you focus on yourself the less you are focusing on your clients, which is vital if you want to build rapport. So if you can, try to forget your nerves and focus on the client.

Another great tip is to try to deliberately move and speak slowly. In short to act confidently. It will actually make you more confident.

Also, in the moment you’re unlikely to actually move or speak that slowly, you’ll probably just slow down enough that you will no longer appear nervous.

Step 4 – During The Meeting

“Successful people have fear, successful people have doubts, and successful people have worries. They just don’t let these feelings stop them.” –T. Harv Eker

Confident, successful freelancers pick their projects carefully.

They are also asked to work on the vast majority of the projects that are a good fit for them.

Initial meetings are a chance to find out more about the client and their project and whether it is a good fit for them.

They will always prepare carefully so that they present themselves in the best possible light, but they are also looking for signs that the client or project isn’t a good fit for them.

Perhaps the client’s timescale or budget is unreasonable?

Perhaps the project depends on other freelancers or companies that haven’t yet been chosen and so it is currently impossible to commit to the completion date as they are asking?

There are lots of reasons why a project may be a problem waiting to happen. It is far better to know about it upfront and discuss it with the client.

It may well be something that they haven’t thought of and they’ll thank you for bringing it to their attention.

If you don’t qualify your clients you are setting yourself up for failure. You can also look desperate. Be assertive as it’s important to really understand the project. Ask the tough questions respectfully and set yourself up for success.

Now that you are clear on what you need to get from the meeting how do we make sure that the client asks you to work on the projects that are a good fit for you?

Again much of it is down to your confidence. As a professional it is unlikely that there are others who could clearly do a better job than you.

Your challenge is communicating to your client your confidence that you could do an exceptional job for them.

That confidence will come across from the way in which you discuss the project and how you act in the meeting.

Let’s take a look at how you demonstrate that confidence to a client, and then have a look at the keys to selling.

Confidence Techniques

1. Try To Enjoy Yourself

As a freelancer you need to learn to sell your work. Your work maybe great but nothing sells itself. You will have to learn to go out and sell.

Many people struggle selling their business. They feel that it is manipulative or somehow underhand. This comes from viewing sales negatively. Or from dealing with someone selling something with little or now value.

You are selling something of real value – your time and experience – and if you don’t believe that no-one else will. You are there to help someone solve a problem of theirs and should approach it that way.

If you struggle with changing your mindset try these two tricks. They’re very similar but interesting different people find different ones work best for them.

    • You’re going to be discussing a client’s project. So say to yourself that you’re giving someone free advice. If they hire you as a result of that advice great, however for the meeting you’re there to do nothing more than provide free advice.
    • Selling is problem-solving. Your work will help the other person grow their business and move forward and that is valuable to them. They want to speak to you for a reason. So selling is nothing more than problem-solving on some else’s behalf.

2. Body Language

Over half of communcation is non-verbal, so pay close attention to your body language.

Good posture and confident body language both communicate and will actually increase your confidence further. Studies show that sitting straight actually increases your confidence!

The keys to good confident body language are being still, unhurried and direct. Sit up straight, look people in the eye when you speak to them and try not to speak too quickly.

If you’re not confident it comes across as if you don’t trust yourself. If you don’t trust yourself why would anyone else trust you, let alone buy from you?

If you feel your body language is coming across as weak or unconfident during a meeting, then a quick fix is to smile, take a deep breath and then adjust your position to take up a little more space.

This will show that you are confident and relaxed. Make sure you avoid crossing your arms or fidgeting!

Remember to use appropriate hand gestures. They give you something to do with your hands. Also, they have been shown to help you both feel more confident and make you come across as more passionate and engaged.

Another useful body language tip is to try mirroring the other person’s behaviour. People who mirror each other’s posture and actions generally trust and are comfortable with each other.

Used sparingly mirroring can help to build rapport and still remain natural. Don’t mirror everything someone does, that feels strange.

3. Voice – Tone, Speed and Emphasis

Some studies show that 38% of communication is from how something is said rather than what is said. This has been disputed but what isn’t disputed is that how you say something is very important.

Try to avoid being monotone. Changing your tone, emphasising certain words and pausing all show that you are someone who is at ease. You’re not embarrassed and trying to fade into the background.

4. What You Say

As much as you can, speak directly and without hedging your opinions too much. Direct communication gives the impression of confidence.

Stating things clearly shows that you value the truth and clarity and are not spending too much time worrying about the other person’s feelings.

An example would be:

Approach 1: “The best way to proceed with the project is to do X, Y and Z”

Approach 2: “It’s difficult to say without more information. However, we could think about doing X and then perhaps Y, although it depends on your budget. If you have time you have you could also do Z”

In the second case, the person speaking has shown repeatedly that they are unsure and also worried about the other person’s feelings, budget and time.

They’ve made their communication significantly more complicated in order to communicate this.

Obviously taking into account the other person’s feelings is not a bad thing but it can make you significantly less persuasive and come across as much less confident.

If you try to always speak directly you will probably find a happy balance. You will occasionally lapse and so communicate a level of empathy but generally communicate directly and so communicate confidence.

5. Don’t Rush To Sell

Generally you should take the potential client’s lead about when to transition from small talk to business.

If they are happy to chat for 10 minutes about the weather, football or anything else then you should let them. It’s a good sign and shows that you are building a relationship. It also shows that you’re not in a hurry to sell.

However, if after 10 minutes the client is still showing no inclination to talk about business it is worth trying to move the conversation to business.

If they show no interest in doing so, chat some more and try to bring the conversation back to business again in 5 minutes.

You need to show that you are relaxed, friendly and personable but also that you are here to discuss business.

For more on confidence, check out our 4 top tips for new managers here.

Stock image of team working on project 5


Sales Techniques

Selling is a psychological business. We like to think that we live in a rational world where choices are made on the basis of pros and cons.

This simply isn’t the case.

Selling is a highly emotional business. Understand the basics and you will find selling a far easier. Who knows you might even come to enjoy it!

1. The Benefits That You Offer The Client

The key to any sale is to make sure that your potential client is crystal clear about the clear benefits that you offer them.

Where possible try to quantify what you offer them, rather than offering vague promises.

Who would you be more likely to buy from:

“I’ve previously built 8 fully responsive websites. Given my experience, I’m confident that I can deliver one for you in 3 working days. This element of the project could be finished for you by XXXX.”


“I think I could do that quickly for you for you as I’ve done some before. You wouldn’t need to worry as that wouldn’t take me long to complete.”

Taking this technique one step further is Ramit Sethi’s ‘Briefcase technique’.

This involves presenting some ideas for the project during that initial meeting.

The fact that you have done this work upfront clearly demonstrates your enthusiasm to them, and there is no better way to get them excited about working with you than showing them some ideas of what you could do for them.

2. Testimonials & Examples Of Previous Work

During the meeting, you need to be sure to explain to your potential client other work that you’ve done.

Also, prepare some client testimonials! The key is to ‘Show don’t tell’.

Telling someone you are a great web designer will have very little impact. That is a claim anyone could make!

Showing someone a great website that you’ve designed will get them excited about what you could do for their business.  The closer the examples that you can show them are to the type of work that they are asking you to do the better.

Also prepare some client testimonials from prior customers. Again the closer these customers are to your potential client in terms of industry and project type the better.

Collecting a small number of short clear testimonials helps put people at ease about your capability and acts as social proof that you can do what you say you can.

3. Scarcity

Scarcity gives a feeling of value, just as abundance devalues something. Therefore, you need to create a feeling of scarcity both around your skillset and also your time.

So, when presenting what you do and your experience, emphasise how rare your skillset is. This could be emphasising your experience in their sector, with this particular type of project or some other vital aspect of the project.

Ideally, you can show expertise in more than one of these areas.

Don’t hide your light under a bushel. You need to be sure that they clearly understand how well your skill set fits with their requirements.

If they suggest that your skills are not that rare, you need to come back on that assertively, otherwise your day will drop rapidly.

Secondly, make sure that they understand that there is an existing demand for your skills and time.

Remember people buy from successful people. Successful people are busy. Successful freelancers have other clients. Don’t be afraid to talking about other clients past and present.

Confidently walking a client through some of your other projects and how they have benefited those clients is the most concrete example of your abilities.

Already know these tips? Maybe you are already on your way to becoming a highly assertive freelancer! Check out this guide on how to assess your assertiveness level to find out.

Stock image of team working on project 6

Step 5 – Negotiating Your Rate

“Always go into meetings or negotiations with a positive attitude. Tell yourself you’re going to make this the best deal for all parties.” Natalie Massenet

At some point you have to have the “So how much do you charge?” conversation.

If the thought of it brings you out in a cold sweat you’re not alone.

The key to this, as ever, is to be prepared and to stay positive and professional. This gets much easier with experience.

You need to clearly understand what you charge, and why before you get into this conversation. This allows you to discuss it calmly and confidently when it comes up.

Remember your terms and conditions are part of your rate as well.

When asked about your rate you should also state any key parts of your terms and conditions.

We talk about terms and conditions and contracts in more detail at the end of this article. They’re important don’t forget them. They ensure that you actually get paid for your work!

So what should you charge? What are your terms and conditions?

Before we get into that let’s take away some of your concerns.

How well informed do you think your buyer will be? Interestingly it turns out not really at all.

“People tend to be clueless about prices. Contrary to economic theory, we don’t really decide between A and B by consulting our invisible price tags and purchasing the one that yields the higher utility, he says. We make do with guesstimates and a vague recollection of what things are “supposed to cost.” ” William Poundstone.

There are a huge number of experiments that show that humans perceive value, and so look at price, in very unscientific ways.

Key elements to remember are:

1. Context is (almost) everything

As people don’t know what things are worth the context becomes very important. It guides their decision.

Consulting is perceived as more valuable than freelancing, in the same way that studies show that people are very happy to pay more for exactly the same beer if it purchased from an expensive hotel bar rather than a corner shop even when it’s not drunk there.

Think about how you can frame your offering as higher quality, and also more specific to your client’s requirements.

Are you a freelance SEO, a web consultant or an inbound strategist?

Since client testimonials and having a quality website and business cards are all part of the context, this shows why they help with pricing.

Similarly, a price that is quoted confidently is more likely to be viewed as fair than one that is quoted timidly.

2. Pricing impacts perceived value

The price that you quote for your services actually impacts the value that a client will put on your services.

Price very cheaply and the client will assume that your service is low value. Price highly and the client will believe that your service is high value. This is as true from $5 wine as it is for houses.

If you price your services cheaply they will be perceived as cheap.Which explains why people buy branded painkillers despite knowing that it contains the same ingredients as generic brands.

Be proud of the rate that you quote rather than embarrassed by it. Give your price confidently knowing that it is a fair price for the work that you do and the value that you offer.

3. Everyone loves a deal
This effect is why there are laws that control how shops present their sales. They know that we are hard-wired to love a bargain and use this to their advantage, marking products down to ‘sale prices’ as often as they can.

This means that when you quote a price you should expect the other side to negotiate. Be sure to allow for some negotiation within the price that you come up with so that you can give a little.

However, you shouldn’t allow for too much negotiation.

Dropping your price substantially looks desperate and will only encourage further negotiation.

Ideally, you should offer one relatively modest discount only. If they attempt to involve you in a protracted negotiation then you need to be assertive and hold your price.

Stock image of team working on project 7

Step 6 – Setting A Price

Now we’ve looked at how buyers perceive your prices let’s look at how you come up with a price.

For those who want to understand pricing in great detail this article on pricing by Nick Kolenda is great and well worth the time to read it.
The key data points you need to think about this are:

    1. What is your service worth to the client?
    2. What is the realistic market rate for your services?
    3. How much do you need to earn as a freelancer?

The answer to 1 should be bigger than the answer to 2, and the answer to 2 bigger than the answer to 3. If not, you are probably in the wrong business.

    1. What Is Your Service Worth To The Client?

“Labourers price by the hour, leaders price by value.”

Pricing on perceived value is the most difficult way to price yourself. It is also likely to get you paid the most so it is worth looking at.

Discussions around hours of work will commoditise your work and end up as a race to the bottom which will never work out well for you.

It is far better to price using the value that you are bringing to your client.

So how do you work out what the value of your work might be?

The simplest way to do this is to do some market research. The price for your product may well be relatively well established. Make sure you find out what that price is.

If it isn’t then is there anything else similar in complexity and value to the client that you could use as a proxy.

    • Ask client’s what their budget it. As you discuss projects with a number of clients it will become clear what people tend to budget for your types of project.
    • Ask a mentor or other senior industry figure that isn’t a competitor.
    1. What Is A Realistic Market Rate For My Services?

As someone in the market, you should hopefully have a good feel for the market rate for your services. If not, ask around. Also, look online for companies that publish surveys of hourly rates.

Good examples would be this one for web freelancers from Mud in the UK and international surveys from Payoneer.

If you’re still unsure then another way is to look at what your full-time employed salary would be. Divide the year into working hours, after allowing for holidays, sickness and the like.

Again, if you’re unsure about what salary to use, look for benchmark figures in online salary surveys.

Once you have this figure you should multiply the figure by 3 to get your hourly rate. The multiplier of 3 is a rule of thumb. In in-demand areas it may be a little more, and in some less in-demand areas a little less.

The multiplier allows for the fact that you won’t be working 100% of the time and that you have to pay all of your own costs. You’ve got insurance, tax, accounting and numerous other costs to cover within your rate.

    1. How Much Do I Need To Earn?

That last way to look at your hourly rate is to work out what you need to earn. This is really only useful as a way of working out what your absolute minimum rate should be.

Now that you have gathered all of that information you should have a pretty good idea of what your price will be and where you will start the negotiation.

However, there is one final step.

If the figures are round figures change them to something that’s looks like it hasn’t been rounded. Round numbers look as if they’ve been plucked from the air or rounded up.

Exact numbers look as if they have been calculated and so clients tend to quibble over then less.

What to do after you mention your price?

After you give the buyer your price. Stop. Don’t say anything.

You’ll have heard this mentioned a number of times in this article but the ability to just sit in silence, albeit briefly, at key moments during your meeting will transform the discussion.

If you appear nervous talking about your price and fill the silence they are far more likely to push you on it.

The effect is to devalue your whole pitch.

Wait for the client to speak first.

Check this article out for more on dealing with difficult conversations.

Stock image of team working on project 8

Dealing With Objections

The first thing to remember about dealing with price objections is that you shouldn’t aim to win every piece of business you pitch.

If you are winning every piece of business that you are pitching for you are underpricing your services.

All that said here is how to confidently deal with some common objections.

Firstly when a prospect raises any type of concern, again, you should pause before answering.

Often they will then continue to talk and explain more about their objection.

This gives you time to think about your answer and also more detail on what their issue is. Also not rushing to answer their objection will make you appear relaxed about their objection.

Pricing Objections:

In this event, you need to re-emphasise what you offer. You also need to re-emphasise your credentials and why buying from you would be both a safe and stress-free choice.

By way of example, here is a great response to this type of objection from corporate sales by Butch Bellah:

“I know you are looking at others and I’m sure they’re all good companies. But, we do offer one thing they can’t: ME. My commitment to you to make sure your business is handled in a professional manner and that you’re more than satisfied. The one thing you get when you do business with my company is me—and I can assure you, I’ll work each day to earn your trust and confidence.”

This is a confident response reiterating what is special about you and your service. Who wouldn’t want to buy from someone with that level of confidence in their service?

If they continue to push for a price reduction, then, as discussed above, you hopefully set your price high enough that you can offer a relatively modest reduction.

If you do so, you should always ask for something in return. Offering a ‘free’ price reduction will only encourage them to ask for more and make you look weak.

Trading a price reduction for something is a much more assertive position to take.

There is usually something that they could offer you at very little cost that you would value a great deal. How about participating in a client testimonial or acting as a future reference? How about a larger contract, payment terms or negotiating the scope of the work instead?

Timing Objections:

Timing objections are difficult. They can be because of genuine timing issues, but often they are raised because the prospect is not convinced or even as a way of saying no while avoiding confrontation.

If someone raises a timing issue, be sure to fully understand it. Ask them to explain what the root of their issue is.

Genuine timing issues are relatively rare. If a prospect has a genuine timing issue they will usually explain clearly what the issue is. They are then likely to talk about a time to pick up the conversation.

If their issue is being unconvinced or they are actually saying a polite “No” you need to address the issue now. This is more often the case. They are very unlikely to buy from you in future when you call back. Their concerns won’t have magically gone away in the meantime.

In this event you need to reiterate the value that your offer to be sure that they fully understand your offering and how it meets their needs.

Contracts: Terms & Conditions

“A verbal contract isn’t worth the paper it’s written on.” Samuel Goldwyn

As we mentioned earlier, this is the bit that will ensure that you get paid so it’s worth paying attention. It’s not interesting but it is VERY important.

The first rule is to make sure that you have a signed contract including your terms and conditions.

This may seem obvious but nervous freelancers are often concerned that requiring a signed contract will get in the way of their sale.

Be assertive. You’re a professional running a business now and deserve to be treated as such. You need to agree on a contract before beginning work and get it signed.

Contracts don’t need to be long or complicated, but they do need to ensure that both sides are clear about exactly what has been agreed and the terms and conditions that relate to that work.

In particular, pay attention to the scope. This will ensure that everyone is clear about what work you are expected to carry out, and by when.

Yes this is boring but it’s part of running your own business.

Get clear on the small number of contract items that are really important and focus on them.

The web has some great resources including some example contracts from BoDo.

Stock image of team working on project 9

Step 6 – Working With A Client

“ When we fail to set boundaries and hold people accountable we feel used and mistreated” Brene Brown

You’ve negotiated your rate. You’ve agreed a contract and terms and conditions. Finally, it’s time to get on with some real work. How do you make sure that it goes smoothly?

The web abounds with freelancer horror stories. The client who asks for endless out-of-scope changes. The client who micro-manages. The client who takes ages to pay.

Some problems are inevitable so don’t kid yourself. This is all part of running your own business. It is how you deal with the issues that will define how successful you are.

Firstly don’t panic. Don’t make a small problem into a big one.

If the client is being unreasonable you need to communicate this to them clearly. Often a clear, assertive conversation is all that is needed to deal with a problem.

Most issues will fall into one of the following categories.

  1. Deadlines
  2. Management
  3. Scope
  4. Payment


Take deadlines seriously. If you don’t meet your deadlines you can’t expect others to do so. If you miss a deadline at best you will look sloppy and unprofessional, at worst your client may not pay you for the work.

A deadline is a firm commitment. If you miss one you will plant a seed of doubt in your client’s mind about everything else you say.
Having said that sometimes missing a deadline is inevitable.

Deal with it early and professionally. It doesn’t have to be a disaster if you deal with it.

Firstly don’t dive in and tell your client as soon as you have a concern that you’ll miss your deadline.

Before you go to the client you need to get clear on the following things. This will allow you to explain it to them confidently and clearly and also give them confidence that you have the situation under control.

    • Run through the situation and why you can’t hit the deadline.
    • Explain what you have done to try to get the project back on track.
    • Acknowledge the impact that this will have.
    • Explain what you will do to complete it as fast as possible.
    • Give them a new deadline when the project will be completed. Be 100% sure that you will hit this new date.

Remember you’re a business supplier and need to act as such. You may need to hire a freelancer to help you complete the work or renegotiate your contract in this event.

Whatever you do, don’t shy away from the conversation. If you miss a deadline people will inevitably feel frustrated. If you don’t deal with the situation confidently and try to hide it people will be doubly frustrated.

On the other side if your client doesn’t meet a deadline you need to have an assertive conversation with them promptly. The issue may be driven by issues beyond their control so don’t make a big thing of it.

But do make sure you have the conversation. The main point of this is to demonstrate that you take deadlines seriously and that you expect to be treated as a professional.

Obviously, if the delay has implications for the project overall you will need to also discuss those with your client.


Hopefully, you have a clear contract and understanding of the scope of your project.

Inevitably a client will ask you for work that is outside that scope of work. It’ll probably be a small piece of work.

You want to have a reputation for delighting clients and going the extra mile and so you think you’ll just do it this one time. The problem is that you’re on your way to getting a reputation as a push over.

As a freelancer you have to stick up for yourself.

You may let the first small request go to build a relationship, but at some point early in the relationship you will need to deal with this.

At this stage, you should see scope creep as an opportunity, not a problem. It may be an opportunity to sell the client some additional services.

You will need to have a relaxed but assertive conversation with your client. It may be as simple as they’ve forgotten that it wasn’t included in the scope. It may be that they are pushing their luck.

If it is the latter then now is the moment that you have to stand up for yourself, otherwise you’ll be dealing with endless requests.

Explain that you’d be very happy to carry out the work but would need to charge for the work for it.

Most clients will either accept that or apologise and say that they can find someone else to carry out the work. Problem solved. You’ve now less work to do and also a reputation for standing up for yourself.

You’re much less likely to get any more of these types of requests and if you do you know how to deal with it. If the client reacts aggressively or dismissively then you have an issue. This is a defining moment in the relationship.

As a professional you can’t accept this behaviour. You have to assert yourself and communicate this clearly to your client, otherwise there is no point in having a contract.

What’s the worst that can happen? This type of client is usually the type that always finds faults and has endless changes they’d like to make. In short not a client that you want.

So at worst they might fire you. If they do they’ve done you a favour. The sooner you get on with finding some respectful clients the better.

Getting Paid

There is nothing more demoralising and frustrating than struggling to get paid once you have delivered the work.

The first thing is to make sure that you invoice promptly and professionally. If you haven’t submitted your invoice you can’t expect to get paid. So make sure that you are invoice promptly.

This doesn’t have to be a problem.

Online accounting systems like QuickBooks make this really easy for freelancers. It lets you customise and send invoice at the click of a button.

In order to avoid exactly this problem many freelancers will withhold part of the final piece of work until they have received full payment.

For example, they won’t deliver all of the images for a project electronically, only physically, or will withhold the source code that they have written.

If you are able to incorporate this into your terms and conditions it is a good way to ensure that you don’t struggle with this.

However, many freelancers have to complete all of the work before they can invoice for it. In this case, you are trusting that you will be paid promptly.

There is no formula that can fix this but the best way to drastically reduce this is clear prompt communication.

Firstly you need to remember that you are in the right. It’s unfair that you have to push for the money that you are owed, but that’s not the issue. You have done the work requested and your client is now not completing their part of the bargain.

Although money is an emotive subject you should treat it the same as any other missed deadline or commitment. You need to be assertive. A client that isn’t paying you on time is going to be a problem.

Letting it slide will only encourage this behaviour. They might even infer that you’re not worried about being paid promptly! Usually a positive but no-nonsense conversation fixes the problem. It’s often down to an administrative error or similar rather than anything more intentional.

If a clear conversation doesn’t fix the problem you need to escalate the issue within the organisation.

Looking for more on assertiveness? Check out our assertiveness facts and research for some key figures on how important this skill is!



About Ben Richardson

Ben is a director of Acuity Training which he has been running for over 10 years.

He is a Natural Sciences graduate from the University of Cambridge and a qualified accountant with the ICAEW.

He previously worked as a venture capitalist and banker and so had extensive experience with Excel from building financial models before moving to learn SQL, Microsoft Power BI and other technologies more recently.