The rules of engagement.

I work with a lot of freelancers. Whenever I engage a new freelancer, I usually lay down three ground rules.

At a glance, the rules are self-contradicting:

  1. Be open for feedback, but take ownership.
  2. No surprises, but surprise me
  3. Don’t be calculative, but be very calculative

Let me elaborate.

1. Be open for feedback, but take ownership

Be open for feedback… I expect a freelancer to leave aside the ego, and always reach out when facing doubts or making decisions before moving on to the next phase. Some bad experiences include sending across fully-developed design routes, whether it is an identity project or a UI design, or a video. It becomes a take-it-or-leave-it scenario, where feedback becomes an intensive reworking scenario. This is also applicable to situations where a vision is shared, but along the way the freelancer discovered that he/she has overestimated his/her capabilities and simply would not be able to complete the job. This admission would have been nice: “I thought I could do it, but this brand architecture job is complex, way beyond anything I have done in the past. I need help.”

… but take ownership. I avoid freelancers who are high maintenance. These are the type who will ping you every 30 minutes, asking you to make a decision on everything, from should the colour be C100Y80 or C100Y90, selecting between Helvetica Medium 12 points or Helvetica Bold 11 points, to whether an image should be centrally cropped or 10 pixels to the right. Basically – micro-decisions. I understand that some freelancers had been burned by control freaks in the past and this is the only way to protect themselves. I, on the other hand, while being an OCD, had learned to let go of smaller decisions.

2. No surprises, but surprise me.

No surprises… I can’t stress enough that a freelancer relationship is about us, together, working to deliver a solution to a paying client, on an agreed deadline. The worst-case scenario would be a freelancer ghosting me, hanging me out to dry – suddenly not responding to messages or calls, when the deadline is near the corner. Other nasty surprises include receiving an inferior output because the freelancer discovered that a licensed plug-in is required to complete the job, and what he has is a pirated outdated version.

We are humans, and life is full of surprises (shocks). It is totally alright if one has to drop out from a project midway when life takes an unexpected turn – the key here is to be truthful, transparent and be responsible. A freelancer once did a nice thing by introducing a friend to take over a project, because she had a family emergency.

… but surprise me. Don’t just be a box-ticker. Surprise me with solutions that could make things better. In every job, there’s always an approach that the client or I might have missed, and the freelancer can bring in a different perspective. A recent example is an identity job in which amongst the deliverables is an invoice design. Instead of delivering a design, the freelancer suggested checking with the client on what kind of accounting systems (Quickbooks, Zoho, Tally, etc) they use, and delivering assets that can be used within the invoice templates. “Every invoice is generated from the accounting software’s template, there’s no point designing an invoice. We should focus on customising the built-in invoicing template.”

3. Don’t be calculative, but be very calculative

Don’t be calculative… The process of engagement starts with an agreed price, but along the way, scope changes. 1 revision becomes 3 revisions. 1 option becomes 2 more alternate versions. Or when the project is supposed to be over, suddenly the client receives an instruction from the legal team to add an extra disclaimer module. The worse part? Everything is on fire and it has to be quickly done.

Note the “everything is on fire” part? The client is under extreme stress because of an unexpected situation. We are trying to help the client solve his/her problem. This is the worst time possible for a freelancer to start negotiating additional fees. No one has the mental space for that – not the client and not us. I would want the freelancer to work along with us and resolve the crisis – leave the money talk for later.

… but be very calculative. At the end of a project, before issuing an invoice, be very calculative. While there’s an agreed price before a project is started, I would assure the freelancer that he/she could increase the amount if the scope has been increased – just be fair, because I would pay and won’t be negotiating anymore. There’s a catch here – the word “fair”. If the final amount is unreasonably high, I will still pay, but that is probably the end of our working relationship.

There will also be situations where extra support/resources were provided to help the freelancer complete his/her job – sort of a bail-out situation to meet deadlines. Be fair, and bill a lesser amount.

A very nice experience I had was a freelancer who billed me less than agreed. “I didn’t have to do that much – I thought the job was much more complex hence the initial quote. This is a more reasonable amount for me to invoice you.”


Engaging a freelancer is like hiring a caterer for a party. The same three rules apply. I want the caterer to discuss with me the menu and the costs. But I don’t need to know where he gets his ingredients or his cutlery for that evening. I want to be informed early on if due to some emergency, the roast chicken will not be served, but equally important, he will be replacing it (surprise!) with stuffed turkey. I don’t want him to start a new round of negotiations when the day before the event, I had to add an unforeseen 15pax to the 100pax event. But, I expect him to bill me fairly for the extra last-minute efforts to prepare for 15pax, but don’t send me an invoice for 200pax because of the extra 15pax. If I had to hire extra waiters on my own expense because his part-time waiters quit on him, compensate me for that.


One last point. I am engaging a freelancer for a specific skill set to accomplish a specific task. It is similar to seeing a skin specialist, calling for a plumber, or hiring a caterer for a party. Freelancing is not employment. The difference? I am obligated to invest in the growth and well-being of an employee, but realistically, engaging a freelancer is a business transaction. Freelancing is not the beginning of a mentor-mentee relationship. When a freelancer says “…I’m excited to start because I can learn from you”, that worries me.


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