September 29, 2014

What I Learned About Project Management from a Gangster

Published: 29 September 2014 



Let me preface this story by saying before racing to the comments or the project management tips and throwing in your two cents about my gratuitous use of the word gangster in the title please read this.

Please understand I was afraid and it made me a better project manager.

Table of contents

  1. The question
  2. The reasons
  3. The business of Web Design is broken
    1. Where it went wrong for me: the 'gangster'
    2. Job done
    3. A professional transformation
    4. In charge
    5. Failure
    6. Worried?
    7. The real world has the same problems
    8. Not putting up with it
  4. Top tips
  5. But...I'm different
  6. The impact
  7. What happened with Scott?
  8. Why tell this story now?

The question


I've been running my business for over 14 years and I've learned a few things along the way. Something I learned early on was that projects could drag on.

I founded the Brisbane Web Design Meetup Group in November 2006 when I first moved to Australia. When I meet web designers, even today, I’m interested in their pain and difficulties we (web designers) go through. Since then I must have asked hundreds of people the same questions...

How old is the oldest project you have on your books right now?

They usually answer 6 months, 12 months, 2 years - sometimes more.

At the WordCamp in Sydney 2014 I shared this story with the audience in a lightning talk. It was meant to be quick but the audience got really into the problem with suggestions, questions and stories of their challenges. In the end it went on for over 20 minutes. Even one of the conference organisers afterward told me of a 2 year outstanding project that had only just finished.

I usually follow up this question by asking why?

Why on earth do you put up with this situation?

... and then I can’t help it, I want to know...

How does it feel to have this hanging over you?

The reasons


Everyone has reasons but usually the answers are (roughly) in order of frequency...

  1. The client doesn't give me the text
  2. The client doesn't provide the logos or pictures
  3. The client doesn't give me the input I need
  4. We’re waiting on the boss’ son/daughter/cousin/mate to do something

They're not whining, they’re not crying or even complaining - but maybe they should be.

They have a problem that (a) stops them from finishing, (b) 99% of the time stops them being paid and (c) is completely out of their control.

This last point (c) is really interesting to me.

I wonder why people operate as freelancers and one-man-businesses. Freedom, creative freedom, financial freedom - running their own show etc... but then this client behaviour is totally contrary to the idea of freedom. You’ve done work, you can’t bill and you’re trapped with an obligation on a price you gave months or years ago.

The business of Web Design is broken


Any business coach can identify the issue and address this issue. It isn’t unique to digital companies, but what is disturbing is that it seems to be the norm.

I regularly meet business people, often prospective clients, who complain about their website designers. They complain about the service they got, and when I tell them project management is part of the reason we charge more they object.

They don’t want to pay for a project manager, but they really need one. It isn’t optional, someone needs to be in charge.

I’ve seen regular business coaches help address this issue.

The digital world isn’t that different from the real world - would a plumber or builder put up with this behaviour? No. They wouldn’t.

To be specific would a builder agree to build an extension, take a deposit and then wait around forever for you to choose the curtains? No. They would build what you’re ordered and deliver it. If you told them “stop, I want to change my mind”, you’d get a variation quote and you’d be charged for the privilege of putting guys on and off site.

Why do web designers the world over put up with this?

Web designers, you're avoiding taking responsibility. I’m totally familiar with the mindset, I was there. The client has clearly abdicated responsibility too. In the client’s mind they're paying the money so why should they be bothered to do work too.

Where it went wrong for me: the 'gangster'

Okay well I lived and worked in the East End of London. Well known as a rough place to live and work but I’d always dealt with professional, hard working, solid people. I enjoyed what I did and loved building websites. I started my business in April 2000 and in 2006 I took on a project for a company. The business was a modest size and was linked to two other successful businesses. They had an alliance with another huge business and it looked like a great opportunity for me to impress.

I offered a price to build an HTML/CSS website. Remember websites before Content Management Systems (CMS)? They were happy and clearly understood what they were getting and they paid a deposit, 30% (I think).

We had planned...

  • A site map. This consisted of a Word document with boxes and lines. Simple to understand for me and the client.
  • A copy deck. A simple Word document that listed all the pages in the website.
  • I’d been briefed on colours and ideas for the design.

I was upfront about asking for...

  • The text: even just a draft and ideally a date of when I could expect the final.
  • The logo: I had a terrible version from the old website but I’d asked for a better one, ideally a vector based one - this was back in the day when a watermark in the background was considered a good idea.
  • Photos: we needed pictures of projects, staff and equipment.

I was organised. We agreed on a nominated point of contact, Scott (not his real name). He’d been specifically delegated the project by the CEO... the attitude seemed to be 'get this done and give me what I need'.

We went around in circles for months.

Scott would email me asking for a design concept. I’d email and say that I needed some content, something to give me something to present.... like we’d agreed. I needed at least an idea of what he wanted to say, some headlines so I could write.

I put this responsibility on the client and THAT was a mistake.

In the meantime I was hosting their email and the old website - both of which they hadn’t paid for. Since they’d not seen the design (the design I was waiting on content and images for and therefore couldn’t provide) they refused to pay.

After going back and forth about non-payment for the hosting I said I’d have to turn it off.

The CEO emailed to say they wanted a design, they weren’t going to put up with my process and if I did anything to their hosting I’d be in trouble. There was a threat of violence too - along the lines of "I will break your legs".

I was shocked. Stunned in fact.

I had no idea running a web design business could be so hardcore.

My fianceé, now my wife, was shocked too.

At the time I worked from home so they knew where I lived.

We were worried.

I called my friend who is a Barrister. We talked about the horrible feeling you get in your guts when you know, you just know that you’re in danger and there is nothing you can really do. He asked me to forward him the email. He also said to tell the Police, so I did. The Police put it on record and said they’d use the record if anything happened, oh great. My friend advised me about closing things down quickly and effectively… barrister advice for project management. It was great… and I listened.

I spoke with Scott, who had been cc’d on the email. He was shocked too and said the CEO did it when he was drunk but was still completely unapologetic. I felt for Scott working side by side with a guy like that but I had more important things to do.

Scott agreed to settle the unpaid hosting immediately and we agreed they should get off our servers, the CEO wanted that too.

I needed to produce a design from nothing and fast.

Instead of rushing headlong like a frightened mouse I listened to my friend’s advice (the barrister). I agreed on an action plan with Scott over the phone. It was much like the one we’d agreed on before (in my mind) but this time I followed up the call with an email.

It had a list like this, actions and a time line for important things...

  • Me: Use Lorum Ipsum text and guess work to mock up a design and send to Scott
  • Scott: Show design mockup to CEO and get it signed off for feedback for revision
  • Me: Do a revision if necessary and return to Scott
  • Scott: Sign off or revise (2 rounds of amendments allowed)
  • Me: When signed off I would build the website
  • Scott: Send the text within 2 weeks (can’t remember)
  • Me: Add the text
  • Scott: Pay the final balance
  • Me: Make the site live

Most importantly it had two things...

  1. Clarity about what steps were contingent on previous steps, i.e. what could block things up, and
  2. It also had a contingency. If they still didn’t supply the text I would be invoicing for the final balance after 2 weeks of the sign off. “What if….” had been considered.

Job done

You might not be surprised to learn that I got that design done pretty fast. It happened within days.

Copy done. Even back then I knew it was very bad practice to design without content but I just grabbed lorum ipsum text and mixed it in with text from their existing website.

Design done. I pasted the text into the design idea I’d been thinking of and literally guessed what services they wanted to promote.

Within a day or so I’d sent this to Scott to accept.

A professional transformation

Amazingly this horrible experience taught me to be more professional.

You can see that I blamed the client for failing to deliver. I hear this in the answers I get when I talk to web designers.

When they prompted me for a design, I prompted them in reply for the content.

It was funny... until it got serious.

Wake up, like I did.

I don’t expect to be dealing with a “gangster” ever again, and I doubt you will be either, but I organise my projects tightly enough to know that steps are agreed and written down.hen there is a variation that’s written down too.

You be organised like this too.

I’ve been running projects 5-10 at a time for years. Clients get a website once every few years, sometimes this is their first time. I believe firmly that the onus is on the website designer to communicate well and be in charge of the project.

In Charge

What does “in charge” mean? You might automatically assume that means you’re the boss. Not exactly.

I was in the Royal Navy Reserve in the UK but I know that I was never the boss. That is the Captain’s job - even when he’s asleep he is responsible. He is the one going in front of a court-marshall if something happens, but he can delegate the operation of a task, the project in this case. The point is, someone is in charge of that. They are responsible to everyone, in our case the client, the web design firm and the staff for the allocation and gathering of resources to complete the project successfully on time and on budget.


I failed. I failed this guy and I jokingly remember this as 'the gangster'. I didn’t communicate well enough. I should have detected the issue long before his frustration boiled over. These days I do.

He paid me to provide a professional service. Now I take that project management responsibility very seriously.


Am I worried about this ever happening again? No.

Am I worried that this blog post will invite clients, new and existing, to threaten me? No. My current clients are awesome and I take care about the kind of client we take on. We have a zero tolerance policy to hostility and I ask anyone reading this to understand that despite the short-term stress, this whole drama affected me in a very positive way.

Better communications mean that clients know what they need to do. They know when they are failing to do what was agreed and I deal with those failures, if and when they occur, in a proactive way.

The real world has the same problems

Imagine you hire a builder. You get them in to build an extension. They give you a plan and they allow you to buy some floorboards yourself. They schedule the job in 4 weeks on the condition that you get the floorboards within 3 weeks.

Three weeks later you can bet that a good builder is checking that you have the floorboards so they can start. If you don’t, they’re on you and reassigning their guys. They might give you a day to get the floorboards, but a good builder is likely to present you with a variation form. This form would say they’re not putting people on site, they’re not going to do the job in the agreed time frame and until you have the floorboards, they are not scheduling anything. There may even be a fee to pay.

As the client you failed. They didn’t. You don’t get the building work to start when you wanted and you’re the blocker. You are in the way of your own project. Suddenly you see the need to prioritise and you’re on it if you really want it to start.

Not putting up with it

Why do digital people put up with this rubbish? You, the website designer, are the professional. You are the project manager. Be in-charge, get on with managing the project.

Top tips


I’d like to see even our competitors do this properly, so here are our top tips.

1. Get some money

Don’t start without a deposit. Obvious I know. When I asked at WordCamp Sydney most people asked for 50% but heaps of people waited right until the end to get the rest.

Be fair but learn from other industries. At Matter Solutions we usually charge 40% as a deposit, 40% when the design is signed off and 20% when the website is complete from our perspective - and that “complete” is defined as no more work for us apart from deploying to the hosting.

If the client still hasn’t added their text or images that’s okay, they still need to pay. Withholding payment at that stage would be like telling a builder you’re not paying for an extension because you haven’t bought your furniture - most builders would think you were crazy. Why do digital people put up with it?

2. Talk to a copywriter

Ask them to give you a package you can offer. Put it in your proposals, add it to the order form (I assume you have a contract of some kind) if clients don’t want to pay extra for it then put a line through it. Use strikethrough!

Why? If you put it in your proposal and specifically give them an option to pay for it and they choose not to then you’re not responsible and you can point at it later.

3. Need a logo? Ask the client for the name of their printer

In my experience most clients have had something printed in the past. If the client can’t seem to get hold of their logo then contact the printer they used most recently for business cards, logo design, brochures or even vehicle artwork. These printers will almost certainly have a vector based logo and when you ask them for an RGB vs CMYK version they will know what you’re talking about.

Another bonus tip is to ask the printer who is good at getting things done at the client’s company.

4. Agree deadlines

Set specific timeframes for specific deliverables and break those down too. Instead of just asking a client for a final copy on a far future date, ask for a first draft in a week and then agree a final on a few pages one or two weeks later.

5. Don’t be an introvert

Use the phone. I know web designers that hide behind email. Call the client, tell them they are causing problems and explain their project needs to move onwards.

6. Get commitment

Don’t tell, ask what can they commit to? Work with them to make a plan that works for them.

7. Put it in writing

I make notes when I’m on the phone planning and agreeing on things with the client. I actually make those notes in email and then send that email, i.e. a summary to confirm.

8. Use a calendar

Put appointments in your calendar before agreed deadlines pass. Remind clients when a deadline is approaching and make sure they have time to deliver. Don’t call them the afternoon before the content delivery, they’ll give up and will want to agree a new deadline. That’s the way to shuffle even the most reluctant client forwards.

9. Use file notes or a CRM

Every time you deal with the client on the project make a note. A Word document or a Google Doc of the clients file in your archive is sufficient. We BCC our CRM so the writing plan is recorded each time. If you don’t have a CRM, make a file in the client’s project folder and add the latest notes to the top (with the date).

It doesn’t need to be much but a project note on one file is a very simple and effective way to get a picture of progress if things do get sticky later.

10. Sell, sell, sell

Okay don’t over do it but be prepared to offer help. You should still have the option to take problems off the client’s shoulders. Perhaps the client under-estimated what writing their website would take (most do).

Maybe now they’re faced with the challenge, they’re open to the idea of having a professional write it. Sell the benefits. A professional copywriter will make life much easier for the client and they will thank you for the advice.

11. Be aware of going off track

When deadlines are missed over and over and the client is reluctant to commit to future deadlines, you’ll know you have a real problem on your hands.... deal with it. Being aware is half the problem the other half is finding a solution that works.

Be careful. If you let things just drag on and on you will waste time, time you should be using later to code or QA or both! Do this at appropriate time, not too early and not too late.

Having a frank conversation with a client is very easy when you have a proven history of their failures.

Explain this to the client so they know they have a bad habit and need to stop it or you’ll need to charge extra for the back and forth.

12. Scope creep

In the WordCamp Sydney talk I said something like “Get the copy or get your legs broken” @thenbrent got in quick and tweeted it.

You can be authentic and generous, you can accommodate some levels of scope creep but know your numbers. If a client asks for 2 hours extra and you know you have 5 hours of contingency in the project… tell the client. 'Okay but we’re using my contingency time for that…'. If they want to scope creep again, quote it (and also explain the term to them).

If you genuinely don’t have any room in the budget politely say no. You can either quote it and the client can decide whether pay for the extra (and know the impact on timeframe – if any), or let you deliver as planned originally. Give the client options, be helpful but know your numbers.

If you don’t plan your projects with estimated time and hours…. get on it!

13. Close the project

If you’re left with a dead duck project tell your client that you can’t keep it on your books indefinitely. Call them, and then email (see #5 and #7). Tell them in 6 weeks time, yes be specific, and use your calendar (#6) if you don’t have everything you need then you have to suspend your commitment to the project. If they want to restart the project, they can contact you for a new quote. Total up for them all the work you’ve done so far and then send them a bill (if appropriate) for the work done to date.

14. Lastly but most importantly: Talk to your peers

Do not be afraid to talk to other web developers or designers. These problems are universal and even people who have solved the problems can clearly remember what it was like.

Get some advice, get some help and be professional.

You can even talk to other business people. Tradies who do project work will understand your pain. Ask their advice.

I had a job in Scaffolding when I was 18. I learned a few things about builders and collecting money.

But.... I'm different


I’ve said this stuff to web designers before. Their immediate reaction is to tell me why this client, this project, their business is different.

No it isn’t.

I probably lost like half the readers there... but you’re still here.

No, it isn’t different and you know it.

You’re in this bad situation and you need to change how you do business if you’re suffering. Just stop it.

If you really want to be free of (or at least minimise) the impact of this problem then you need to act. If you justify it by saying your situation is different nothing will change... and I’m sure you know that is the definition of insanity... Doing the same thing and expecting a different result.

The impact


Next I hear the objection: What impact? Web designers then tell me yes these projects hanging over me upset or disturb me but not enough to do anything about it. They say: "I’ll get the money in the end. It’ll be okay".

Just imagine a perfect situation where you are in control. You set the rules, you tell the client that they need to pay up and participate in their own project. Imagine how that would (a) feel and (b) look in your bank account.

Yes, I agree it seems like the same money... but getting the money in this financial year, in this quarter and getting the job out of the way and into your project portfolio means you can confidently move on to the next project and show it to prospective clients.

That dream is possible. You just have to want it and realise that an efficient operation where you can rely on money coming in means you have options.

I can tell you from experience that getting the money when you want it feels way better than getting it years later. You know it. You can grow, rent an office, take on staff, buy that new iMac for your new designer etc.

Finally, what happened with Scott?


Within a day or two I’d sent the design to Scott to accept.

Scott and the CEO approved the design after a couple of changes. I invoiced them after 2 weeks as agreed. They took months to deliver the content and in the end they got a website. I stuck to my commitment, I pasted that final content into the approved build and delivered the final files to their new host within days and that was that.

Why tell this story now?

I started my business in 2000 and things went very well for years. In 2001 I was #2 in for “London Web Design” and we were flat out.

For 6 years I had plugged away building websites in HTML/CSS and using server side includes to make websites efficient with shtml cgi and php. Yes, cgi – remember that?

I’ve told this story to a handful of people and used it with some effect to help people think about what they are doing.

It hit me hard and I nearly gave up everything I’d worked hard for.

Now 8+ years on, I’m glad I didn’t give up. I love what I do.

I don’t accept the threats were warranted, but I do see why this type of person could justify his aggressive behaviour. He just didn’t understand and like an angry child he lashed out.

I learned heaps thanks to that guy. Was he gangster? I don’t know but it sure felt like it.

I was very glad to see the back of that project and it felt good to tell WordCamp Sydney all about it on Saturday.

What do you think?

Did you like this? Did it help? Please comment and let me know.

Ben Maden

Read more posts by Ben

8 comments on “What I Learned About Project Management from a Gangster”

  1. Interesting post Ben.
    You wrote about charging the client two weeks after a milestone, whether they had provided the content or not, then completing the job months later when they came through with it.

    How do you handle this when finishing the job is still a lot of work and it may come back when you're very busy?

  2. Picky clients that are never happy are always entertaining to deal with. A successful strategy (and one that I mentioned briefly during the WordCamp talk) is to invite your client to work 'with' you during the revision process.

    Clients who see their money being spent before their eyes are often particularly quick to compromise. Inviting a client to sit with you to go through their detailed list of changes has almost always resulted in a 'actually we can do without that for now' attitude - and it means your creative genius is respected in the final product. It has the added bonus of not coming across as narky or argumentative, but instead as engaging. It can demonstrate your "willingness and eagerness" to build the perfect design/product/whatever for the project.

    Developing a billing model that is flexible is really important. Including e.g. 3 revisions as an explicit limitation is good because you can state further iteration 'is of course entirely possible and can be completed on an hourly basis'.

  3. Hi Ben,
    I really enjoyed reading this post, especially since I got to hear your lightning talk at WordCamp Sydney . It is educational, especially since you have learned to get over the hurdles and are generous enough to take the time to share the experience.

    It seems that the biggest problem I have is getting the content. A few of the clients I have dealt with tell me that they do not have any talent for writing. Most expect me to do the copy for them, and they see this as part of the quoted price. We are starting to learn the tell tale signs and add some contingency for us to do some of the copy in house and edit the rest.
    Can you tell me though, When you ask your clients to supply the copy, do you still send them a copy deck ? or do you employ some other tool to make it easier for the client to organise themselves?

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