Freelancer Project Management

Project Management Advice for Productive Freelancing

Category Archives: Project management

Don’t just Duck and Cover: Risk Management for Freelancers

Sometimes, things go wrong with projects. That’s life. If you are taking on a new project you can take one of two approaches when dealing with the risks that might cause your project to veer off track:

1/ Stick your head in the sand, your fingers in your ears, hum loudly and wish for the magic pixies to make them all go away, or

2/ Put together a plan for factors that could derail your project and decide what steps you can take to protect from them.

If you pick the first strategy stop reading now and Google ‘magic pixies will fix my project’ instead. If you think the second would be more appropriate for your project, read on.

Your risk management plan does not have to be fancy. The most important thing is that you are going through the process of identifying risks early on in your project planning and considering contingencies. If you get used to thinking in this way before problems arise, the battle is already half won.

Going through the following simple 4-step process with each new project should help to identify threats, decide how likely they are to occur and create a contingency plan.

Step 1: Brainstorming

Sit down, either alone or with others who will be working on this project (your project team) and take some time to think of all the reasons why your project might run into difficulties. These could be anything from

  • team members who are inexperienced in this kind of project
  • using technology that some of your team might be unfamiliar with
  • bad weather in a project that relies on outdoor work
  • a new client you haven’t worked with before
  • funding difficulties

to other, more unlikely ones such as

  • tornadoes, snowstorms or volcanic ash clouds
  • several of your team all getting sick at once
  • your client going bust

The main thing is to get them all down at this point.

Try to be specific. For example, rather than saying that the task of producing invitations to a launch party might overrun, say that producing invitations to the launch party might overrun because the outside company you are relying on to produce them might not be used to such a large order. It is much easier to come up with contingencies if you are specific.

Step 2: Ranking your risks

If you are feeling overwhelmed with disasters at this point, don’t worry!  The next step is to rank the likelihood of these risks actually happening, putting the most likely at the top.

For example, it might be very likely for a wedding photographer to experience bad weather on the day. The threat of the wedding being cancelled might be much further down on his list, with the risk of a snowstorm in July in Florida would be right down at the bottom.

Step 3: Contingency planning

This is the stage when you can start thinking of what you might do in the event that one of these risk factors starts to affect your project. Now you have ranked your risks you can decide

  • how far down the list you will look to make contingency plans
  • whether you will start that planning now or wait until the event of it actually happening.

You may decide that only the top risk factors are ever likely to happen, so you will only develop a plan for those eventualities.


Your project is to organise an event to launch a new brand of perfume. You have five people in your project team, one of whom has never worked on a launch event before. The event is in January in Boston.

You risk management strategy might look something like this:

Risk Contingency
The inexperienced staff member might underestimate how long each of their tasks will take, resulting in project delays Set up a thorough reporting schedule so that the team can track their progress against the project plan and report back frequently
Bad weather might cause transport problems on the night of the event Send out transport options with the invitations so that guests are aware of the alternatives
The client has had some funding issues so cash flow could become a problem Agree with client to be paid in stages, at each significant milestone
The catering company might be unable to meet the order Choose a second catering company to supply the drinks
Sickness may affect more than one member of the team resulting in delays to tasks Have other freelancers on standby in case of serious illness

In this instance, the team decide that the first three risks are very likely, so work on actually implementing the contingencies, but that the fourth and fifth are less likely as they have worked with the caterer before with no problems and they consider it unlikely that more than one team member will get seriously ill. They will only deal with those eventualities if they arise, rather than spending time on it now.

Step 4: Communication

It is no good in having a risk management plan if nobody knows about it. Make sure you communicate your plan with the rest of your team, and with other parties such as your client if you think it is necessary. After all, it could be you that is unable to work and your team needs to know what to do!

Photo by Flickr user Zolierdos


Keeping your eye on the ball: how to stay focused on your project goals

It’s all too easy to get sidetracked by the things that need to be done day-to-day: emails to send, invoices to pay, phone calls, thinking up new ways to market your business… Twitter…

Freelancers have to organise so many aspects of their businesses that it’s easy to lose sight of the bigger picture.  All these things are important, but so is the reason we set up our businesses in the first place: our freelance projects.  There’s not much point in being a freelance writer, event planner or designer if you don’t ever get time to do the writing, planning or designing!

There are four simple strategies you can adopt in order to keep your goals clear and your mind on the result.

1/ Define your project’s scope

It is much easier to keep your goals in mind if you know what they are!  Write down the goals of your project at the outset, and make sure you have agreed them with your client: you could both have very different ideas about what constitutes a successful project.  For more information, have a look at this previous post about the project scope.

2/ Track tasks

I have written previously about breaking your work down into tasks; once your project has been divided into bite-sized chunks it is much easier to keep track of your progress.  You can use a low-tech approach such as Post-it notes and a wall planner to keep track of your tasks, or use one of the multitude of software packages specifically designed for project management.

3/ Set milestones

If you have a larger project you can divide it into phases before breaking it down into tasks.  The end of each phase is denoted by a milestone, which might be something like submitting a piece of work, a website going live, your design being approved or moving from a planning to an implementation stage.

Reaching a milestone can give you a good sense of achievement and a reason to celebrate.  It helps to have smaller goals to focus on within your project when the end is too far away to see right now.

4/ Schedule in time-outs

It can be helpful at various points in your project to have a time-out to review your progress so far and look ahead at what is to come.  Reaching a milestone is an obvious point to do this, although you can do it at any time, especially if you feel that you have hit a wall.

Your time-out can be used to evaluate:

  • What is going well
  • What could be going better
  • What problems you have faced and how you overcame them
  • What you could change as you enter the next stage

By taking the time out to assess your progress you can avoid repeating mistakes and get yourself out of any ruts you might find yourself in.  You can monitor your work and consider whether you are still on track to meeting your goals or whether you are getting diverted or sidetracked.

Photo by Flickr user chispita_666

What to do if your project falls behind schedule: A 5-Point Plan

Sometimes no matter how well you plan, estimate and schedule, a project can fall behind schedule.  It may be because of something out of your control, lack of experience in that particular field or just plain old life getting in the way.

So once you have found yourself in this situation, what should you do?

1/ Don’t Panic!

The first thing to remember is not to panic.  You are behind schedule, but this is why you have a project plan: so that you recognise situations before they become problems and do something about them.

2/ Assess the situation

Take a look at your project plan and ask yourself:

  • What is the new finish date of your project if everything continues on this track?
  • What resources would be needed to bring your project back on schedule?

3/ Communication, communication, communication

It might be tempting to stick your head in the sand and hope that everything works out okay, but you will probably need to communicate with your client at this point to make some decisions.

This is why you have already assessed the situation: you can go to your client with solutions, not problems.  You may have already agreed project priorities with your client, which should help you make decisions about how to proceed, but if not the questions you need to be asking at this point are how to prioritise.

4/ Prioritise

There are three variables to a project:

  • Time
  • Quality
  • Cost

At this point, the time frame has slipped.  You need to decide which is the most important variable at this point, if you haven’t already done so.


How important is the time frame?

If the project isn’t time critical, your client may appreciate an update about the new deadline but decide not to act.

If the deadline is key and cannot be moved, you and your client may choose to prioritise this over quality or cost.


The client may choose to let the quality slip in order to get the project completed on time.

An example of this might be a project to create decorations for a launch party.  Clearly the date of the party cannot be moved, but the client may choose to have fewer banners or to use pre-printed posters rather than custom-made ones in order to complete on schedule.  (Of course, you may have to take a reduced fee to compensate for the loss in quality).


Your client may decide to allocate a higher budget in order to complete the project by the deadline.  This is why you went through the assessment stage: you are now able to go to your client with an idea of what resources you will need to complete on time.  This may be anything from extra hours to hiring extra staff, more equipment or other resources.

5/ Consequences

If you are working on multiple projects, you now need to assess what the knock-on effects are for your other projects.  Are you allocating more hours to get this project completed on time, and what does that mean for your other project plans?

Remember: Don’t Panic!

Photo by Flickr user Patrick Hoesly

The Importance of Celebrating Success

In the previous post I talked about setting objectives that you can measure.  But why do you need to measure your progress?  There are four main reasons for this:

1/ To keep you on track

2/ To communicate your progress

3/ To celebrate your success!

4/ Evaluation

Keeping you on track

Too many projects fail because of inadequate planning and unrealistic expectations.  As a freelancer, missed deadlines can mean that a) you don’t get paid and b) your reputation can be damaged.

But by breaking your project down into smaller chunks and setting deadlines for each individual stage, you can keep an eye on your overall progress.  It doesn’t have to be complicated, just block out the length of time each task in your project should take and set deadlines for each one.  By keeping track of each individual task you can monitor the progress of the overall project and take care of any slippage before it becomes an issue.

Communicating your progress

You may have agreed a reporting schedule with your client but if not, achieving your milestones or objectives can be an excellent prompt for updating your progress.  (For more about communications plans take a look at my recent posts)

Celebrating your success!

The freelancing lifestyle can be tough: we frequently work alone and have to be constantly self-motivated.  It’s easy to get overwhelmed by work and feel that we are swimming against the tide.

This is where celebrating success can be very important for our own self-motivation.  If you wait until you have finished a project to celebrate your success you can become de-motivated in the meantime, especially if your projects are long-term.  This can mean you fall behind and struggle to meet deadlines.  Finishing a project can become an exhausting battle: you may be onto the next one before you have a chance to congratulate yourself on a job well done.

By giving yourself a pat on the back or small reward after each stage of your project you can really improve your motivation and therefore your productivity.

Evaluation: What went well?

Pausing at each milestone or objective can be a great chance to reflect on your work and evaluate what went well in that stage of the project and what could be improved upon.  You don’t need to spend too much time on this, but by getting in the habit of taking the opportunity to reflect on your working practices and problems you may have faced you can improve your work for future projects.

Photo by Flickr user seelensturm

Staying on Track: Setting Project Objectives that Work

What will your project produce?  What are its outcomes or deliverables?

If you are clear from the beginning what your project is going to achieve, you are not only more likely to achieve it but also save time in the long run.  Many projects become bogged down in unnecessary detail or go off at time-consuming tangents.  Having clear objectives from the outset will help you stay on track as the project progresses.

You will also see how setting measurable, defined objectives also benefits your business as a freelancer.

Woolly objectives achieve nothing

Your objectives should be agreed with your client, but ensure that you are both clear about what they are from the outset.  Remember:

  • When you are setting your project objectives you must be specific.
  • Set values, if appropriate.
  • Make sure your objectives are measurable (see below).
  • Set time parameters so that you have clear deadlines to work towards for each stage.
  • Each objective should be able to be described concisely.  If you can’t define it in a brief statement then it is probably too vague and open to interpretation.

Setting objectives you can measure

For each objective you set, state how you will measure its success.  For example, if you are designing a new website for a company you can measure how many hits it gets.  If the objective is to increase traffic to the company’s site, agree a target with them, say an increase of 20%.  Be specific, don’t say ‘about 10-30%’ as everyone will have a different interpretation about what this means.

If you have multiple objectives, set targets for each one.  For example, as well as increasing traffic generally by 20%, you may also wish to increase traffic from outside the US by 15% and repeat visits by 30%.

Setting targets is good for your business

As a freelancer, having easily measurable objectives is good for your business too.  When you are trying to attract new clients you can use these targets to demonstrate your own track record.  For example, if you can show that your websites consistently deliver a 20% increase in web traffic it is far more useful to a new client than merely having experience in web design.  They want to know what your web design will do for them.

Photo by Flickr user CJ Schmit

Do Freelancers need to set Project Milestones?

Freelancers are usually split into two camps when it comes to using project management.

  • Those who use their clients’ framework as part of their work
  • Those who create their own framework as a helpful tool to manage their projects.

In this post I will be dealing with the second group as they must make their own decisions which elements of project management they want to adopt.


What is a Project Milestone?

A milestone is an event during the life of a project that signifies a new stage.  Often a milestone is reached when a key task or deliverable has been achieved.

Milestones are set along the critical path of your project plan.

Why might I want to set them?


Setting milestones can help keep your project on schedule.  When you reach a milestone it is a chance to re-visit your project plan and identify any problems in your project schedule.

Celebrating success

Like any milestones in life, completing a stage of your project is a cause for celebration.  Especially if you are working on a long-term project, reaching a milestone can be a chance for you to congratulate yourself on a job well done.

Project evaluation

Re-visiting your project plan from time to time is essential and reaching a milestone is a good time to step back from the project and take a critical look.

  • What is going well?
  • What problems are you encountering?
  • Are your tasks realistic?
  • How about your time estimations?

Re-evaluating your project when you reach milestones is a good way to keep it on track and to identify potential problems before they become serious.


What are the downsides of setting milestones?

Over-complication of smaller projects

Not all projects need milestones.  Smaller projects can become unnecessarily complicated if you break them down into too many tasks and milestones.  You don’t want your project planning to take over from doing the actual work!

Non-critical task slippage

There is a danger in concentrating too much on the milestones along your critical path: you might miss the non-critical tasks that can slip as a result.  If you do set milestones be sure to use them as an opportunity to review the whole project, not just the tasks along the critical path.


To recap…

As with everything related to project management as a freelancer, only set milestones if you think they are useful and relevant to your projects.  Don’t over-complicate your project plan unnecessarily… but remember to celebrate your successes as you achieve them!


Photo by Flickr user Tim Green

Managing Multiple Projects: Problems and Solutions

Freelancers often work on several projects at once, and working as a freelancer can bring some unique challenges.  But just how do you keep all the balls in the air?

Problem #1: Project updates are taking over your life

Problem: You have three clients who all phone you constantly to get project updates.  They all want assurance that their project is getting top priority but you are spending so much time giving updates you are falling behind.

Solution: You need to put a Communications Plan in place so that they know when to expect progress reports.  Good communication doesn’t necessarily mean frequent communication, it is about making the client feel reassured that the project is on track.

Problem #2: Unbalanced workload

Problem: One of your projects is taking over.  You never seem to have any time to deal with the others and the work is piling up whilst deadlines are looming.

Solution: Time management is key here.  Breaking projects down into tasks and scheduling them in a calendar can help you see what time you have for each project.  If it looks like you really aren’t going to meet your deadlines you need to talk to your clients to decide how to prioritise you time, quality and costs. Discussing problems early on means that you can start creating solutions – don’t wait until after the deadline when it is too late.

Problem #3: Work overload

Problem: You’ve bitten off more than you can chew: you have more work than hours in the day, but you just don’t feel you can turn projects down.

Solution: You need to introduce some project planning to estimate your capacity before you take on more work.  Create project plans for each of your projects and put them together to make a master-plan.  You can use a low-tech approach with a simple wall planner or else try one of the many free or low-cost project planning software packages available.

Now when a client comes to you with a project you can look at your master-plan and see if you have any spare capacity.

N/B Clients are generally much happier to be told that you can’t take on a project outright rather than dealing with missed deadlines or sloppy work later.

Photo by Flickr user Helico

Projects vs Tasks: How to Break Down Your Work and Get Back In Control

It’s easy to get bogged down in To Do Lists and feel like you’re drowning under Post-it Notes.

Especially if you have multiple projects on the go, it can be difficult to know where to start with your workload and swimming can very soon turn into drowning.  Even though it feels like you are working hard, your productivity can drop as your stress levels rise.

But by breaking Projects down into Tasks you can very quickly regain control of your work and once again feel like you’re back in your element.  With this simple method you don’t have to learn to use project management software either.

1/ Know the Difference between a Project and a Task

I have covered What We Mean By A Project on a previous post but put simply, a project:

  • Is a piece of work with a defined beginning and end
  • Has a specific goal or objective
  • Takes place within a pre-arranged timeframe

A task on the other hand:

  • Is a defined piece of work within a project
  • Can be seen as a ‘unit’ of a project: the smallest parts that a project can be broken down into.

2/ Write a List

This is the brainstorming part.

Write down everything that has to happen in your project for it to be completed.  These are your tasks.

You might like to group them into tasks and sub-tasks: for example, if you are organising a conference the task ‘ordering technology’ might be broken down into ‘ordering laptops’, ‘ordering video conferencing technology’ and so on.

This will become your Task List.

3/ Organise Your List

Re-organise your list into chronological order, noting what tasks are dependent on the previous tasks being completed.

4/ Assign Timeframes to your Tasks

Note down how long you expect each task to take.  Try to be accurate – it is worth getting this stage right.

5/ Work Backwards

Working back from your deadline, write each task down in your calendar or work organiser.

You may have to re-assess the length of some of the tasks if they look like over-running.  If they really can’t be done more quickly this is an indication you may need to use extra resources, such as paying for extra staff or equipment, to get the task completed on time.

It is best you know this now so you can plan ahead.

Remember that if a task is dependent on another one being completed, it must be scheduled after it.  If not, you can have several tasks running concurrently.

Once you have done this you can see if there is any slack time or time when you can schedule extra, non-dependent tasks to save time later.

6/ Multiple Projects

Go through the same process for each of your projects.

Once you start plotting the tasks on your work organiser you’ll build up a comprehensive work schedule that you can work to.

You can tick off tasks on your Task Lists as they are completed, giving you a feeling of satisfaction.

Hey presto!  You are in control and back in your element!

Photo by Flickr user WJ (Bill) Harrison

What Makes an Effective Communications Plan?

As a freelancer running a project, you should consider having a communications plan to share the progress of your project with your client and any other stakeholders.

Having a regular reporting schedule means that your client can be assured that they don’t have to waste their own time chasing you up – they know that the information they need will be delivered to them when they need it in the manner that suits them.  They can see when to expect updates.  If you establish a communications plan from the outset they know that you will raise any issues with them before they become problems.  That leaves you to get on with the job.

The key to a good communications plan is that it should deliver the right information at the right time to the right person in the right way.

The right people: people with a stake in the project are called stakeholders.  Freelancers need to identify who are the key stakeholders and how they should be informed of the progress of the project.

The right information: stakeholders closer to the project will need more detail than those not directly involved, who only need the headlines.  They need to know whether the project is on target and of any potential problems that they need to deal with personally.

The right time: Stakeholders closest to the project might need daily updates, whereas those not directly involved might want updates only once a week or once a month, depending on the length of the project and that person’s involvement.

The right way: Phone calls, emails, electronic newsletters and meetings are all ways you might choose to communicate with the project’s stakeholders.  You need to decide which method is appropriate for each level of involvement.


Lee, a freelance events organiser is hired by an national supermarket chain to plan their annual conference.  The Human Resources department are in charge of planning events and the specific contact there is Cindy.  Cindy, her manager Terry and Laura, the head of HR, all need to be kept updated on the project, as do several of the company’s senior managers.

They don’t all need the same level of detail or regularity of updates.

Cindy needs a brief conversation by telephone each morning to discuss the day-to-day progress and an email at the end of the day giving an update.  Lee shares the project plan with her whenever it is revised so that she can report on progress and budget to her department.  Cindy’s manager, Terry, needs to be copied in on the daily email and should have a quick email at the end of each week to show progress and flag up any concerns.  Laura, the Head of HR is also copied into this.

Lee produces a brief bulletin twice a month to give an overview of the project for Laura and the senior managers.

Lee develops his communication plan with Cindy, as she can identify the key stakeholders and how they should be updated.

Lee’s communication plan looks something like this:

Stakeholder Medium Frequency Information
Cindy Email/phone 

Project plan


When updated

Details of costs, schedule, problems, solutions
Terry Email 




Overview of costs, schedule, problems, solutions
Laura Bulletin (by email) Twice monthly Overview of costs, schedule, high-level problems and solutions
Senior manager Bulletin (by email) Twice monthly Overview of costs, schedule, high-level problems and solutions

As the project progresses other stakeholders become involved and the communications plan is reviewed as necessary.  As a freelancer, you will find that each organisation you work with has different reporting mechanisms and preferred methods of communication.

For more on project communication within your project team, see Project Communication: 10 Top Tips

Planning your Project: Using Internet Forums as a Resource

When I was young we had a fascinating book called ‘How To Do Just About Anything’.  This was the book you went to for step-by-step advice if you wanted to hem a curtain, change the oil in your car, treat insect bites, shuffle cards professionally or clean a hot tub.  You didn’t need to be an expert, you just needed to know where to look.

These days we have the Internet as a research tool, which is a vital resource when project planning.  A successful project depends upon accurate planning, especially in predicting the duration and cost of each task, but you don’t need to be an expert to plan accurately – you just need to know where to look.

A freelancer who is planning a project may very well need to research tasks of which they have very little experience.  Making guesses at this stage is going to lead to problems along the line which can be easily avoided with some research.

Internet forums for freelancers are a great place to get advice and ask questions if you need information in your project planning stage.  For instance:

  • They are invaluable if you are putting together a team of freelancers from other disciplines to your own.
  • You can use them to get an idea of costs if you are calculating estimates.
  • You can get advice if you are new to running your own project team.
  • Other freelancers may have very different ways of working to you – you may need to understand work practices before committing yourself.
  • You can ask questions about technical specifications or other considerations that you are not familiar with.

Listed beneath are five forums specifically for freelancers:

Talk Freelance
Freelance Switch
Freelance UK
Freelance Forum
Why Do Work

It is worth taking your time to get your project plan accurate now; what you skimp on in the planning phase may well cost you time and money later.