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The Art of the Sell – Jaimee Newberry

Jul 25, 2016 | An Event Apart 2016

She came up with 2 rules of design when she was a professor:


Rule 1: Kill Your Darlings 

– You have to kill a lot of things you put a lot of soul and time and care and research into. We grow attached to our work and when someone wants us to change something we get offended


Rule 2: Sell Your Shit

– This is really just about being better  talking about your stuff so you didn’t have to kill it!





They key to selling your shit is communication. If you get Rule #2 down, you hopefully won’t need Rule #1!

When you communicate well you create understanding between parties. When you have understanding there’s confidence. When you have confidence you have trust. When you have trust, selling is easy. But you have to work really hard to get to the trust point.


She had a lot of frustrating experiences as a designer. Stupid client doesn’t understand, stupid VP doesn’t understand the feature, stupid stupid stupid. Even in the best case scenarios, frustrating situations come up, but if communication and trust is there it goes better definitely.


The common denominator in the frustrating situations was HER – she was the common denominator. Ok, I can’t always control the environment around me but I can control ME. Sales is interaction. Sales is part of everything we do. Selling your ideas, your concepts, your thoughts, it’s all a part of what we do.




12 Check-Yourself Checkpoints


  1. Communication Design – often we’re so focused on the thing we’re making we forget about a touchpoint like an email. Think about how the layout of an email is reflects on you and how you communicate and how you receive your communication. Is it easy to digest, or do you amble on in a giant block of text that’s hard to read? Better communication leads to happier teams! Just clean up your email, the world would be better! But there’s more than email – there’s scope of work contracts, stuff you write on a wall that outlines the project…
  2. Be Specific Immediately – still, email. An example is when you’re trying to schedule something, and you shoot an email that says “I’m flexible all week, what time works for you, and I’ll make it work” but then 8 emails later you’ve landed on when to meet. When someone says they want to meet with you, your response should ALWAYS include a specific date, time window, and time zone! Take 5 minutes, look at your calendar, find dates and times! The person receiving your email isn’t going to say ‘wow, that was very proactive of you!’ but the experience will be good and you are respecting their time and productivity. Any time you can be specific, do it!
  3. Word Choices – The word choice we use is very important in everything we do. The word ‘just’ is a great example. Remove it from anything you write or speak unless referring to justICE. In your day to day communication remove it and see if it’s necessary, because it carries a slightly negative connotation with it, and anything you can do to move from negativity to positivity is worth doing! Word choices underscore intention. It’s hugely important. “There is no try. There is only do” – Yoda. Commit or don’t commit. Get out. “Let’s find time to do that” – there is no intention behind that! Make time or don’t make time, but don’t FIND time. Another one – “let’s have a conversation to make them feel like they’re a part of this.” NO, either they are or aren’t a part of it, you don’t need to make them FEEL anything. “We need to educate the client” – that sounds to cocky! Maybe we are better way what we do than the client, that’s why they hired us! A little bit of humble goes a long way. Positivity goes a long way when interacting with someone.
  4. Speak With Confidence – Don’t say “I think this might help”. Say “THIS WILL HELP!”
  5. Don’t Be a Jerk – There is a way to talk with confidence but not be a jerk. Separate the person and the situation – don’t be accusatory. Don’t say “You said you’d schedule the meeting but you never did”. Say “The meeting didn’t get scheduled.”
  6. Don’t be “Judgey” – She had a client that one time said “I can sling some Photoshop” and she dismissed / judged him as not being adequate to touch Photoshop. But, when she got back to her desk, he had spent 5-10 minutes and send her a visual of what he meant and was super efficient in communicating his thoughts. Try to find a common ground and have a conversation about things. Let them speak.
  7. Accepting Responsibility – Sort through things and claim what you can accept responsibility for. Positive and Negative, although this is usually more applicable to negative situations. She has a staff member right now who is on a project with a client that they love, and she got a complaint from the client. The client thinks that he’s not working when they don’t see him on his office hours times, so they think he’s not paying attention. So, by him not communicating enough, he’s created a gap of communication, and anytime there’s a gap, the client is left to wonder. “Don’t let gaps of wonder happen!” We needed to dissect all the conversations over the past week and determine what the staff member and client and responsible for, and discuss what can be fixed. If the things we are responsible for can be improved, the relationship can improve and continue
  8. Silence Will Hurt You – This is the thing we are most guilty of as designers and developers! We need silence and sometimes to be ‘heads down’. Let’s say your boss asks you for a feature and asks you how long it will take. You say 1 developer, 8 days. However, 3 days in you know you’re not going to meet your deadline, so communicate it immediately! “Look, I didn’t expect A, B, and C when I gave you the estimate, and I am still going to do what I can to meet this timeline, but I need you to be aware, because I am pretty sure I’m going to go over.” Don’t go silent! “I am running late, I will update you later” is even better than nothing! If you don’t communicate their mind starts to create a story to fill in the wonder gap.  This simple thing saves a lot of time and anguish! Their mind goes to the WORST POSSIBLE PLACE – it MUST be a disaster otherwise I would have heard from them. You don’t even have to give them an excuse! In fact, DON’T, it’s unnecessary. Be succinct.
  9. Follow Up – Slightly different than the last one. A prospective client emailing you saying “I’d like to work with you” should result in an immediate response. Yes, a scope of work takes time, but SEND IT. Not sending a scope of work is leaving work on the table! With a past client, follow up with them. See how they are doing, either as a person, company, or how the thing you built for them is doing.
  10. Meet Them Where They’re At – A client in 2009 had literally sent all of the content for the website BY FAX. She realized this was her responsibility to have been better understanding where the client was at. This was her fault, not the client’s. This made her reflect ‘how can I understand where they’re at and meet them there.’ Often we get frustrated at how a client does things. But it is us that didn’t take the time to understand where they’re at. This goes a long way when we get frustrated with things
  11. Love What You Do – A lot of people go through the motions, and we reach a point where we’re stale, or burnt out, and we’re not loving what we do. When you’re selling stuff, whether it’s your idea, your work, it’s infused with what you’re feeling. You’re baking your feelings into whatever you’re making. So, if you’re in a funky spot, look into it. This sounds simple but it’s a huge thing and a big part of selling. When you love what you do it comes out and it’s infectious and people want to work with you because they FEEL it!
  12. Be You – With all her rumblings and mistakes, the BE YOU aspect is important. We compete with a lot of people in this industry that have similar skills (or better) – so YOU are the difference. All of these tips (#1-11) can make you a better you. Word of mouth is the best tool you have for sales, and people find you wherever you are to bring you work if they liked working with YOU.


This past point is huge, and it really is how I get all of my business. That is my selling point, and how I pitch my company – that I’m easy to work with, that we make this process painless, and that I make poop jokes.




Communication is the foundation.






When you have trust, selling is easy. And when we’re good at selling our shit, we don’t have to kill our darlings so much. So now, Rule #1 from the beginning is a footnote!



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