Sales Chronicles #1: Holy Fish I Suck at Sales


In trying to grow my business, I’ve realized I need to either A) hire a salesman or B) learn sales.  A isn’t working out, so I’m picking up the torch.  I wanted to write out today what I’m doing wrong in hopes to help other freelancers, contractors, consultants, and those wishing to grow their business.  These don’t have anything to do with software. Instead they have to do with engaging with clients.


When I was a freelancer/contractor, getting the gig was easy to put into motion.  A client would find me through networking (blog, twitter, people I know, event I spoke at), we’d talk over email or phone once or twice, and boom, I’d start working within usually 3 days.

The bigger clients, the ones I do consulting for through other firms/companies, are the ones I want to do business with on my own.  I want to grow my business to beyond just me.  I’ve done a few engagements where I’ve hired/sub-contracted others, but I want to do more to ensure I work on the work I want to work on, and it gets done to my standards.  Those kind of clients require more than just a phone call and email; they require engagement, basically a sales cycle.  This means getting them to sign a contract, a statement of work (SoW).  This is done by spending time with them to learn their needs and build rapport.  I think.

I suck at this.  Through listening to Guru Ganesha recommended to me by a startup I worked for, asking my father questions (pimp salesman), to asking others in the industry at 360Flex (thanks Michael, Lisa, and David!) how they do it, I’ve learned a lot of what I’ve been doing wrong.  I still don’t know what I don’t know, and am working to find various mentors to help.

Type of Client

I’ve looked around at successful (success defined as making/charging high rates) companies in our industry, and they all have the following traits:

  • above average at development
  • have Java in their skill set/marketing
  • are a team of developers vs. an individual

What I missed, however, was ability to close bigger clients.  The type of clients I would work on at IBM, Universal Mind, ESRIA, and Roundarch were completely different than those I’d get on my own.  If I did, it was through a 3rd party recruiting firm that provided no value and took tons of money off the top of my rate, or through networking.

I no longer work with recruiting firms because the amount of money they take off the top is insane, and they provide no value to my client (beyond preferred vendor for tax purposes which I’ll get to in another post).  Thus, the onus is on me to engage, be found, and/or network with them.  I’ve started to get exposed to these types of clients, but my negotiations with them have suffered because I don’t have the experience, nor training, in doing so.

With UM it was easy; Todd, the then CEO now President, had usually qualified the lead.  Tom, CTO, would get a deeper sense of the high level requirements and start identifying appropriate resources, and then engage with them over the phone/email to guage their interest, and help him flesh out the details.  Roundarch worked about the same way from what I cold tell.  I’d then go on-site and do my thing, by myself or with a team.

With WASI, we’re basically doing the same thing.  I’m still learning their process, how they approach clients, how they qualify them, the contracts, yadda yadda yadda… but it’s still a team effort in terms of getting clients.  Either I’ll get a lead from networking (email, blog, twitter, conferences), a client will find me online/through referrals, or my partners will have done the same thing and we’ll collaborate.

Some of these leads, however, are wayyy different than my previous standard fare.  They require long sales cycles, a significant amount of time to negotiate & adjust contracts, and ways to find an in as a preferred vendor.  However, you need to play the game (sometimes) because these are the types of clients who want a company, not an individual, to solve a problem for them.  This means longer & larger engagements, more money, and my target client to grow my business (assuming we mesh obviously).

What I’ve Done Wrong

The following is a quick list of things I’ve done wrong.

  • followed up with past clients I’ve done work with
  • followed up with clients who I failed to get a contract signed with
  • stood my ground on price vs. discovered why the lack of conviction
  • use email vs. phone
  • not used verbal contracts with agreed upon timetables
  • done free consulting without knowing it
  • didn’t use reward and reverse; talked too much about what I could do
  • never strip lined

…yeah, that’s enough for now.

Following Up with Past Clients

The best salesman is yourself. — My Granddad

That’s never more true than on clients you’ve done work with in the past and you did a good job.  Thus, they are the easiest to sell.  Ed Grasing asked me that couple weeks ago, and was shocked that I never did.  In thinking about it, I’m shocked I never contacted them either. n00b.

Following Up with Clients Who Said No

Some clients who don’t get software development and skimp on price often get what they are paying for: death, pain, and misery.  This often leads to projects in trouble, and then people like me are called in to help save it.  Michael Labriola suggested this one, citing a lot of clients who end up learning the hard way are happy to hear those who know what they are doing calling back to check up on ’em.  And then they sign the SoW they originally said no on.  I’ve actually tried this and got a bite, so clearly something there.

Selling on Price vs. Empowering with Conviction

Price doesn’t matter to a client.  David, and others have said you should sell on value, not price.  In listening to Ganesha, the only reason clients say no to your price is that they lack the conviction you can get it done.  If a client has the will, they’ll find the money.  I used to think it was a negotiation.  In fact, it wasn’t me standing my ground but rather me disappointing a potential client in my inability to give them the conviction I could get their project done.

This is EXTREMELY frustrating to me. I’ve spent 10 years building a personal brand to ensure people in the industry have an iron clad perception I know what I’m doing and I love doing it.  Just about every single client, I’m introducing them to this brand that they’ve heard nothing about it.  If they were a long time blog reader or twitter follower, they’d have conviction.  They aren’t.  This is an area where I’m currently struggling on.  How do I give my client conviction I can git-r-done without doing free consulting during a sales cycle to convince them?

Using Email vs. Phone

I have 40 leads whereas 2 years ago it’d be 4.  It’s easier to manage & communicate using email than phone for that many leads.  Still, voice mail & voice itself are more powerful than email… sometimes.  I just need to make an effort to reach out more to engage potential clients.

No Agreed Upon Verbal Timetable Contracts / Free Consulting

Ganesha talks about how to prevent getting clients where you don’t know if they’ll sign or not.  Where they basically say, “we’ll get back to you” and you never hear from them again.  They string you along for months, all the while costing you time, money, and stress.  His attitude is the client needs to sell YOU on if they are worth working with.  Once you find that out, you find out their pains, and identify if you can solve them.  Once you get that understanding, sometimes it leads to another meeting or more exploratory meetings with other people from the company.  With larger meetings, these take time and money.  Your time.  Your money.

From 7 Habits of Highly Effective People:

“Begin with the end in mind.”

Jesse Freeman & Elad Elrom were obsessed with charging for this time.  Lisa was too.  It doesn’t jive at all with what I’ve witnessed in how my dad, and other sales people do business.  They work on a commission from the sale, not a Time & Materials.

Anyway, bottom line, each meeting you work towards a verbal contract with your client to determine if you’re going to proceed with a black and white & yes or no.  That way, you get a lot more “no’s”, but NO “maybe’s”, nor “I hope they’ll call me back”.

Since I suck at this, I’ve spent a lot of unpaid hours working with clients to get them to sign an SoW.

Reward Reverse vs. Running My Mouth

In consulting, your first job is to listen.  You need to understand what the client’s true problems are so you can make accurate recommendations that the client can actually implement.  Reward Reverse is a communication technique to ensure the client does the talking, and feels like they are controlling the meeting.  Like Tennis where you volley the ball back in the center, or when you put your kid in the car shopping cart to make them feel like they are driving.  Most salesman have diarrhea of the mouth, and the client doesn’t feel in control.  This is done before the salesman has a true understanding of what the client actually needs.

From 7 Habits of Highly Effective People:

“First seek to understand, then seek to be understood.”

I love to meet new people and talk to them.  I love talking in general.  When I see a client with a software need, I’ll often think to myself, “Dude, I KNOW my team and I can knock that shit out of the park!”  Clients have often liked me because of my passion.  I love this stuff.  This is the cornerstone of what I built my brand on.  I just assumed that passion would help me sell.  It has often done the opposite to larger clients.

When a client asks a question, and I go off on a rant for 5 minutes, they’ll be polite and ask another question.  Repeat.  Instead, using Reward Reverse, you answer their question (the reward), and ask one in return to get a better/more understanding from the client (the reverse).  Get them to do the talking.  Get them to think they’re leading the dance.

This is hard.  “I WANNA WRITE PIMP CODE FOR YOU, ZOMG FXG SKINS MVC ROBOTLEGS BLAAAHHHH!!!!” instead becomes me asking short questions and taking notes. alskjdfkljasdklfjlkj


A Sandler word, a sales strategy.  It’s a metaphor based on a fishing technique where you let out more line to tire the fish out and reduce pressure on less strong fishing line.  It’s basically reverse psychology used on clients who you feel are pulling away.  If you get a fish on, you’re first inclination is to yank and reel in like mad.  Striplining you go the other way.

If I’m just not convincing the client I can work magic with Flex & people to help them on their already troubled project, one thing I’ve done is striplining without knowing it.  It’s like the Observer design pattern in that you can use it without actually knowing what the Observer pattern is.

“So, your existing consultants are going to meet their next Friday deadline so you don’t need me, right?”

“Well, no no no… they’ve never hit a deadline and ruined all rapport with us.”

“Yeah, but they’ve been doing that for months; what’s another missed deadline?”

“It’ll cost us the project!”

Oh.  If they don’t hit their deadline, you lose the project.  LEVERAGE!

The point is, I’m not trying to convince the client how great I am; I’m getting them to convince me, and thus themselves, that I’m the one to solve the problems… by telling them they don’t need me.  It’s not something you do all the time; only when you get resistance.  This is hard for me to because I WANT to help people.  It’s what makes me feel good.  Hard to keep this in check and stripline on those leads that may be swinging the other way.


In the past 7 years, I’ve gotten a lot of leads and a lot of work.  As I’ve tried to get the bigger clients which I know my team and I are more than capable of handling… I’ve failed on a few occasions where I should of had it.  It makes me feel really good to know as much as I suck at sales, I must have SOMETHING clients see that more than compensates for this, else they wouldn’t hire me.  If I can fix the sales part, then I’m clearly on the right track.

The frustrating part is that in reading the above, I feel like I’m with sales where I was at with coding back in 2001.  I have a loooong way to go.

25 Replies to “Sales Chronicles #1: Holy Fish I Suck at Sales”

  1. Jesse,

    you have SOMETHING? hehe. Nice post and good explanation of some key points to selling.

    One thing to add – repetition. In Advertising it takes some 6+ times to become remembered/recognized. So keep up the verbal contacts, don’t even discuss business (talk family, cool stuff, geek stuff , whatever).

    Also T&M billing only really works after you have convinced client they need it. This consulting approach can be good in landing the bigger business but has its challenges.

  2. Jesse why are you trying to find some clients????? It should be the other way around.
    EVERY day I have a recruiter phone call, a company calling me for some consulting.
    Flash/Flex are highly in demand now & you know that very well. I mean last year I made over 170K (This year it is a little less 145 K)that’s close to 13K per month after taxes. Is 13K every damn month not enough for you? I feel that you are searching the big clients and not getting anywhere while EVERYBODY is accumulating money around. You might regret that greedy move and say in a few years : I missed the train and I should have listen to that crazy Lisa:)

  3. We have a new sales strategy: doing rather than just talking.

    When we meet with clients, right from the first meeting, we’re making, showing, coding, doing, playing with graphics etc, to put something on the screen with them that they can react to.

    Ideally @badgerthat and I do this in a relay – she does visuals, I do functional. She talks with them while I work for a few minutes, then I show them something while she works. We don’t worry that most things can’t be achieved in 10 minutes – we’re looking to find the things that can become ‘real’ – that we can collaborate with the client on, right there in real time. It doesn’t matter that it’s not polished – we’re just sketching and the clients are cool with that (and actually as a spin off benefit they then have a better understanding of what ‘rough’ means when we start sending them early work for feedback).

    They have (so far) never walked away. Before the end of the first meeting they are already emotionally committed – and they have absolute confidence that we can do what we do, and that we’ll work collaboratively with them and not shrug our shoulders or pout when they have trouble expressing (or knowing) their requirements at the first asking.

    It takes some balls. It also takes the right set up – I use TDD through ASUnit to compile small parts of functionality. I grab a menu I’ve done before, copy it, mock up some data that describes their requirements, and we start playing. We usually do this with them for around an hour – sometimes a little more.

    We also put our clients on the project code base – they don’t have commit rights, but they see every git upload we do. They know that we’re making progress, they feel reassured and they don’t pester me for updates by email.

    They tell us that:
    1) We are actually interest in solving their problem rather than just spouting sales crap like the Oracle guys.
    2) We are fun to work with.
    3) They like seeing how much we enjoy doing what we do – how excited we get about making their dream come to life.

    The other thing it does is manage their experience of risk. They know, deep down, that the big name companies charge a fortune and are just as likely to blow the deadline. But nobody gets fired for buying Dell, or Oracle, or hiring IBM or Accenture. So by *doing* in the meeting, they seem to feel that the risk is reduced – if anything it’s reversed. We’ve at least demonstrated that we can understand their problem, and handle back and forth in a positive way.

    In a way, we’re training them to join a diet-agile / scrum-lite team. They seem to enjoy it – small clients and big ones alike.

    Oh – and we also no longer do any agency work at all – they just take a fat cut and get in the way.

  4. @Stray, I love your approach! I echo everything you’ve said. I operate in a very similar fashion.

    @Jesse, for your next article I request you tell us a single story demonstrating what you’re good at.

  5. @Jesse, Interesting article. I feel you pain. I used to work in sales (many years ago) and I am rubbish at it. It was the main reason I got in to development. One question. Your blog is very frank and you talk a lot about various clients. Are you concerned that this may have a detrimental effect on your client base? I mean would it be better to hide behind a more corporate persona?

    @Lisa, a bit a viral marketing there hmmm? I think I came across your site and you would have a motive to suggest making 6 figures is just as easy as sitting on sofa and waiting fro a call. I am not sure the real world works like that. Certainly not for Developers.

    1. Absolutely Sir. I have recruiters and head hunters working for me. My salary range is between 80K to 200K per year. I am accepting no contract under 3 months and I require special type of conditions(working conditions, working with MAC etc..). Absolutely they are eating in my hands Sir. If you have to struggle to get gigs then you are actually doing something wrong. I know numerous Flex/Flash Developers and none of them have issues finding exceptional job opportunities. Next year I have decide that I will not accept any contract under 140K Period. Also I use to do some freelancing aside of my contracts but I cannot accept them anymore as I am too busy. Again it is a FANTASTIC time to be a Flash or Flex developer.

        1. What do you mean how good I am? I have over 20 years of programming experience! I have been using Flex and AS3 for about 4 years now. But I was fluent in Java and C# so it took me a few months to be professionally productive. The problem is that most Flex and especially AS3 developers are coming from a designer background and feel that all they need is to follow the videos and buying Essential AS3/Mook to be called Developers. It just won’t happen. These individuals know crap about OOP but are using the cairngorm3 framework etc.. These same individuals think that they can become fluent in Objective C or learn C# 4 (Freeman) just to realize several weeks later that it is not intuitive a good way to say I cannot comprehend the material. If you are a serious developers you can comprehend ANY programming languages period! To answer your question is yes: I have a “professional portfolio of my Flex work”. But do you think that I am going to post it in public? Are you that naive. My word of advice is that ALL Flex developers start to learn OOP as well as UML. I am tired to nurse and babysit all those so called experienced Flex Developers. How many on this board use UML?? I bet none. :).

  6. @Stuart Thanks. I don’t mention clients by name unless I get their permission. Most clients don’t read my blog, either. I wish they did… then I wouldn’t have to introduce them to who I am every time. A few gigs I have actually gotten by people who “know me” internally, and went through the proper channels to bring me in. My blog, and now Twitter, are the most important thing I’ve done to improve my career next to continued networking.

    1. Troubles finding gigs? Here’s a few suggestions.
      I don’t want to be rude Jesse but I would advise you in the future not to introduce a different beer at every of your video show. If you give the impression to you future employer/client/recruiter that you are having some drinking tendencies none of them would hire you, period. Also that red bull drinking does not give the impression of maturity. I NEVER drink that crap, it raise blood pressure and that kind of drink has been linked to numerous cases of hearth attacks. In your show try to appear calm and in control not like somebody who is over excited by an energetic drink .

      1. @Lisa Thanks for watching my show! I need to make another soon; have some rad hardware to show off.

        I don’t have trouble finding gigs that you and I normally do. I have trouble landing the Roundarch/Universal Mind sized gigs. Those are the ones which last months and have teams of 3 or more.

        Beer is proof that God loves us. — Ben Franklin

        Have to show the beer; I know which ones rock and which ones suck! Some people actually skip all my code stuff just to get a good recommendation.

        Red Bull is a must for some Agency engagements or where certain clients have conference deadlines. As long as you’re not so exhausted your producing bugs, it helps a lot to go that extra 10 miles. There are also alternatives; 5 hour is getting a lot of press amongst fellow devs, and so far doesn’t have any negative press.

        Thanks for your suggestions.

        1. “Red Bull is a must for some Agency engagements or where certain clients have conference deadlines”

          Jesse think about it. What is a must for you?? Stay healthy or pleasing the agency caffeine expectations?
          I have been there so I perfectly know the issue. However your first wealth is your health. Our body needs “REAL” food to operate at his best level. By real food I mean a raw vegan diet. I switched into that diet 5 years ago and it has changed my life and my programming. Millions years ago humanity was in the trees and guess what was our diet at that time? Fruits and leaves, yes Sir:). The raw vegan diet will give you all the energy to stay a TOP class developer without the health hazards of dangerous boosters like Red Bull and the rest of that crap. As a developer you need to make sure to stay in TOP shape all the time , that means plenty excercise and a natural diet like raw veganism. Combined together it allows a “PERFECT” blood flow in your brain which contribute to better performances at work. Logic is also an important factor as a Flex Developer. How to develop or maintain a good logic? The answer is simple: Play chess. Chess is the “BEST” game or tool to keep up your logic in good shape. As you will get better in shape , you will start thinking in a more rational way which is extremely beneficial for your daily programming tasks.
          PS: alcohol is a poison period , it damages your liver(even in low intake) and destroy your brain cells. It should be a big nono for any serious developers.

  7. On the not doing work for free front, we’ve recently started offering a lower commitment initial engagement. What this means is after an initial meet-n-greet (sales meeting) we arrange to do just a few days consulting/designing/development during which we’ll prep mockups, project plans, graphic designs and if necesscary code demos for proof of concept or examples of existing alike work.

    The client DOES pay for this time but it’s only a few days rather than weeks/months so once that is done they have no commitment to stick with us and are welcome to use that material as a brief to look elsewhere for cheaper/better/whatever alternative.

    Of course as with Stray’s approach, after this we’ve demonstrated we can do what we say we do, they’ve invested time/resources working with us and are now comfortable with the team. Only once has anyone pulled the plug and gone off shore for the cheaper alternative but we didn’t care, we got paid for our time and they were still happy with our output.

    When working with someone for the first time both sides tend to be a little stand off-ish so it’s a good approach to ease into a new relationship whilst keeping the stakes low without either side getting shafted.

  8. @Lisa Preston I agree with you that developers need to take care of their mind and body to maintain health, happiness and productivity. I have written more than once about the special needs that developers need, such as Vitamin D supplements. And it’s great that being a vegan works for you. But that doesn’t mean that it’s the *natural* diet of homosapiens. You’re right that our ancestors millions of years ago were vegetarians living in the trees. But they also didn’t have our brain capacity. It wasn’t until we got down out of the trees and eventually became meat eaters that our brains started to grow. Big brains and meat go hand-n-hand.

    That however is little justification for being a meat eater today. It’s true that in a civilization with ample resources we can eat a nutritious vegan diet. Each person decides on their own based on personal preference which diet to follow since there is objective moral reason for or against either choice.

    1. “It wasn’t until we got down out of the trees and eventually became meat eaters that our brains started to grow. Big brains and meat go hand-n-hand.”

      Humans have been raw vegan for millions years and we became meat-eaters when the ice-age came and humanity had to adapt. Meat intake leads to chronic diseases. We are not carnivore. And there is no valid theory proving that meat allowed us to evolve intellectually.Look the result of our technology? We are destroying planet earth & soon it won’t be habitable ! Do you call this evolution? I call this destruction and our intellect surely did not help to live in healthy and happy. I am going to appear stupid now by making this statement but I believe it is true:
      ” We are animals, and our only purpose is to come on earth to procreate.”
      We should be in the trees eating fruits & leaves. Technology leads to destruction.

  9. @Lisa Sorry, I really shouldn’t have commented. You just go on believing what you want to believe. Doesn’t look like any amount of data is going to change what you think so there’s no point trying.

    1. That’s the truth Sir. It is not a matter of changing my mind or not. Global warming has already started and planet earth won’t be habitable in less than 100 years fro now.

  10. I work for one of those big companies that does hire outside help from time to time. When I am called into evaluate a potential provider, I look for their passion in what they do. You can tell when someone is totally in love with their job, it oozzes from their pores, it is spilling over, it is an aura. Keep up the communication and let your passion show.

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