Like the Discwold Anke Morpork board game: you sometimes don't realise you've lost until you do.

Why I failed at a Sales Conversation that looked like it went well

Back when I was a technical sales person trying to help customers find the right hosting solutions for their products, I had a sales memorable interaction.

A customer “Alice” get in touch, looking for an onsite meeting to discuss what they needed. Me and a less technical colleague, “Brendan”, went to visit.

At the meeting, we picked up the basics of the situation: Alice was a solo senior developer within a nontechnical organisation, working on a business-critical piece of software that the organisation used every day. The organisation was hoping they might spin the software out and get other organisations in their niche to use it – SaaS-style.

Like the Discwold Anke Morpork board game: you sometimes don't realise you've lost until you do.
Like the Discwold Anke Morpork board game: you sometimes don’t realise you’ve lost until you do.

Alice had complete technical control over the development, and whilst I didn’t know the technical realm too well, I asked LOTS of questions. “How were they handling this?”, “What libraries were they using?”, “How were they deploying?”, “Would they be comfortable working like this?”, “Who was looking after these kind of things?”, “When was the system in use?”.

Alice loved it. She took me through the technical architecture in great detail, with me treading along the edge of my conversant line of that technology, with my colleague Brendan well out of his depth.

After we left, Alice tweeted about how great it had been to chat to sales people who understood and took such an interest. I was elated. What better feedback could you get from a prospect?

One thing that’s better is an order. We didn’t get the deal.

During the entire conversation, we’d done a great job of winning Alice over, but failed to discover the key decision maker was Alice’s boss. This cost us the deal.

Ultimately, Alice’s Boss, a nontechnical decision maker within their organisation, made a decision to go with a household-name brand because of a sense of familiarity and legitimacy. Failing to discover and anticipate this caused us to sell to the technical person, but miss the opportunities to address the Boss’s concerns.

We could have asked “When are you looking to make a decision about this? Who’s involved in making this decision? How do things like this get decided in your organisation?”. I could have been presumptuous and just asked “Does your boss give you the freedom to decide suppliers like this on your own?”. It’s possible I’d have got some reply along the lines of “I’m not sure” – and even that would have better than being blindsided by it later.

If we’d found out that their Boss was involved in the decision, we might have been able to provide some extra context or collateral to Alice to take to the Boss – maybe organisations in their sector using us. Maybe a very tailored case study written from a nontechnical perspective of an organisation also trying to make a side business selling their line of business software. Maybe things mentioning the very precious business critical things we kept running and supported everyday. Crucially – none of this would be aimed at the highly technical person – Alice.

Classically trained sales people have used mnemonics for years to help them check (amongst other things) that the person they’re talking has the authority to make the purchase they’re discussing with you. This was a timely impetus for me to revise up on those things to check for – we shouldn’t have stumbled on such a basic hurdle.

Being such a great fit for the on-the ground users really rubbed salt in the wound – we could have done better!

Live & Learn!


Names have been changed.

Do you have a story of a sales conversation that didn’t go to plan? I’d love to hear about it in the comments!

Founders at Work

Notes on a book: Founders at Work

Yesterday, I finally completed Founders at Work: Stories of Startups’ Early Days.

Founders at Work
Founders at Work

The book is a collection of interviews conducted by Jessica Livingston of YCombinator with cofounders and key people of a great deal of well known (and in some cases, less well known, but notable) companies.

Because each chapter is a different interview with a different person, about a different product, company or service, it’s very easy to read small amounts at a time.

There’s quite big variety of products and services that are discussed, but the chapters I particuarly enjoyed were:

  • Max Levchin/PayPal: I hadn’t realised PayPal had originally been a PDA based crypto-system.
  • Craigslist is always somewhat fascinating, and Craig Newark as always seems like a sensible and straightforward sort of person you’d like to work with.
    • Their “softly, softly, BAN, reconcile” approach with rogue apartment real estate agents in New York seems to work well for them.
    • In the long term, I’m concerned that Ebay’s influence on them, will mean they’re unable to compete in new markets because of Gumtree.
  • Charles Geschke/Adobe – I hadn’t realised Adobe developed PostScript for Apple to solve the problem of printer/computer communication.
    • Apple’s present day support for CUPS makes more sense.
  • James Hong/HOT or NOT and Joshua Schachter/del.icio.us – I found these chapters interesting as they were essentially developing “somewhat trivial” web services, that no-one would have said they would have needed.
    • HOT or NOT had the interesting ‘luck’ of being an instant, unexpected hit, with scaling problems associated with that, whilst del.icio.us was able to grow relatively smoothly and organically whilst its founder was still a programmer for an investment bank.
    • I found James Hong’s description of getting his uptight asian  parents to do the initial moderation for HOT or NOT (and when he decided it was time to get someone else to do it), exceptionally amusing.
  • In contrast, James Currier‘s Tickle.com (which I hated i 2007!) set out with a serious aim in mind (and arguably sold itself to Monster on its original ‘serious’ premise) but quickly realised it had to lighten up to make themselves appeal much more.
    • I’d say that HOT or NOT and del.icio.us probably had a much easier and less stressful growing experience, because they solved their growth problems and got their users first, and worried about everything else after that.
  • Most interestingly, none of them (and you can include Caterina Fake/Flickr in this), said “we going to set out to do a startup to dothis relatively trivial thing” – they all built things as a joke/side project/personal project – that only became the product of a startup, once they had lots of users.
  • Probably controversially, I didn’t actually find the Steve Wozniak/Apple Computers chapter very interesting, accessible or useful. I don’t doubt his mastery of his field (using as few chips as possible, to do as much as possible), but the detail just lost me.
  • Having said that, it was very interesting to contrast him with the Ron Gruner and what he had to say of his time at Alliant Computer Systems.
    • I think I’d definitely prefer to work with Wozniak than someone whose hiring process involves refusing to tell candidates what the process is, telling them they’re working every other Saturday and fostering what came across as an exceptionally competitive working environment (based on his background).
  • It was interesting read David Heinemeier Hansson‘s experiences at 37signals of writing the MVP of Basecamp – I’ve heard of agencies trying to build products on various occasions, but some of the reasons Basecamp succeeded.
    • (37signals already were well known, and widely looked up to by the people who [initially] were likely to find it most useful, and be most likely to consider adopting something new.)
  • In that regard, it’s somewhat similar to Joel Spolsky‘s Fog Creek Software – Joel was widely regarded via his blog, and then put out a product (FogBugz) that appealed directly to the people who were his blog’s audience.
    • On a sort of note, I’d be interested to know how much GitHub was slaughtering FogBugz’s market. I can see Fog Creek Software have git/hg products now, but when I was reading the interview – I sort of felt that the debates mentioned in the book about whether integrated wiki’s were what consumers wanted missed the point.
    • I suspect they’ll have legacy renewals, but I worry for the product’s future growth prospects – I’d suggest that perhaps that that product is now yesterday’s posterchild.
    • Today I learned he went on to create Stack Overflow… so I guess FogBugz worries may not be a personal concern so much.
  • I really liked the three interviews with Dan Bricklin/Software Arts, Michell Kapor/Lotus Development and Ray Ozzie/Iris Associates.
    • Being a child of the 00s, Lotus Notes wasn’t really a thing when I started playing with computers. I knew it existed from the Save As dialog that let you save in a format that it might accept, but I never understood anything about the background to the concept of spreadsheets (Visicalc) or the unusual development setup that Lotus Notes was produced under.
  • It’s quite hilarious to read (in 2014) about WebTV and how they managed to cause so much of a stir (to the point that Microsoft bought them) when that category of device was still (somewhat) trying to break through in 2014.
    • (Set top boxes are really the conceptual children, and whilst it’s easy to understand why Microsoft were probably being visionary in realising their significance, it’s most interesting that Microsoft didn’t succeed in the smartTV, setop box, PVR sector, even when the original XBOX was released)
  • Compared to the story of TiVo a few years later, it seems to me, that WebTV open people’s minds, but TiVO actually produced an MVP (and later real-life-actual-product) that people really wanted, once they realised it was possible – Mike Ramsay‘s description of demo’ing ‘pausing’ live TV – to people for the first time is a great example of how consumers should react when they’re presented with a feature that they didn’t know (until that moment) that they needed in their life.
  • Given the majority of people were at least somewhat technical, it was interesting to read about Lycos which was effectively founded by non-techies (the technology was sold to them by a university, and Bob Davis – previously a salesman – was positioned as CEO, which is somewhat unusual).
    • Financially, Lycos looks like a success in hindsight – it was sold to Telefonica -, but I struggle to associate it was much to sing about. I simply can’t help feeling that Telefonica was just getting a bad deal buying it (and indeed, they were!).
  • I particularly liked the chapter about ArsDigita from Philip Greenspun‘s perspective.
    • There’s a lot about how he ran ArsDigita that seemed to make sense from my point of view – for example, recruitment, working quality of life, technology stacks, small self-managed groups with responsibility for their own P/L and where everyone had some common responsibilities for key things.
    • His adventures with Venture Capital sound like a farcical nightmare, almost worthy of a sitcom. However, it does re-enforce – “if it ain’t totally broke” – don’t take someone else’s money in exchange for arguing with their people about how to do things – the distraction is never going to work out for you.
  • Firefox’s non-profit ‘intrapreneur’ development within Mozilla is quite interesting.
    • We forget the days when Firefox was the edgy browser that was up and coming, but Blake Ross did a good job in his interview of explaining how he took the Mozilla browser project as it stood, focused on things that users would want, simplified things, then managed to develop the community of raving users who (for example) took out a full page advert in the New York Times to shout about how awesome Firefox was.
  • Similarly, we forget that less than 10 years ago, Google was just a search company, and their first branch out, was Gmail.
    • Created by Paul Buchheit, at the time, Gmail radically changed the way people looked at email, and radically changed the way people looked at Google. He encountered quite a lot of organisational hurdles and technical hurdles (fun fact: an early [internal prototype] version of Gmail was stored on a single harddisk with no backups, Paul transplanted the hard disk platter into another housing and was able to recover all the data)

There’s many more interesting stories – the story of Hotmail, the story of all the blogging platforms – Moveable Type, Blogger, the story of WAIS, Alexa rankings, toolbars, the Internet Archive, etc but honestly, if you want to read about them, you may as well grab a copy of the book and read through them yourself.


I also feel it worth noting that there were a few moments in the book where I felt people were talking out of their arse/commenting on things they didn’t seem to know about. It’s fact of life when taking advice from anyone, and I’m happy they weren’t edited out – you need to consider things people say, and decide for yourself whether it’s actually what you should do, or whether it simply was what once worked well for the person suggesting it.

The book feels slightly dated – as a 7 year old book of startup stories is likely to feel. In 2007, the recent memories were of the dotcom crash, and the post dotcom successes – the boom in consumer social or mobile startups isn’t really addressed at all (the iPhone was barely released when the book came out).

Jessica has said that she’d like to write another volume, if/when she gets time, and I certainly think, there’s scope for it. There are many new stories from the past 7 years, and many existing stories with new chapters to be told, as well as many other stories from times gone by that deserve page space.


As a book, it comes across as well written, and is full of genuinely interesting interviews. If you’re interested in the history, or how some of these companies and startups came into existence, or you’re interested in learning what people feel they did right… and wrong, then have a read through it.

Can you inspire people to find their own inspiration?

One thing I’ve noticed recently is that there’s a power in story. People love telling stories and explaining what they learnt from their own experiences.

Lot’s of motivational speakers and bloggers draw heavily from their own experiences, and lots of successful people have stories of “this one time when something happened and I overcame the difficulties”.

The problem is that by drawing on one’s own experiences, you’re betting that the audience relates quite deeply to you.

Let me give an example.

There are deeply inspiring sysadmin stories – stories of where persistent sysadmins have solved a mystery problem to the point where most people would have just shrugged, given up or something. Wearing my sysadmin hat, I them really impressive, and inspire me to be a better problem solver.

To the average person, they’re not anecdotes that one could relate to. If you’re a sysadmin, or in an occupation that requires creative thinking to solve problems, they may ring much closer to home and remind you of your own experiences.

Here lies the crux:

  • Things that inspire you, are most likely to inspire people like you.
  • Not everyone is just like you, and you probably think people are more like you than they are. (The bubble effect)
  • What inspires people most, is their own experiences.

and the last point is the most important.

Climbing Ben MacDui: Would someone who didn't like hiking find this photo inspirational?
Climbing Ben MacDui: Would someone who didn't like hiking find this photo inspirational?

It’s worth remembering that what inspires people about your anecdotes, is not that you climbed a high mountain, but is that you, as an equal human being, who tried, did something that they also could do. The emphasis is not on the mountain, but on the trying, and the what they could do.

If you could instead of inspiring people by telling anecdotes, if you used clever story telling, to get them to think about a similar experience in their life, then tie in suggestions about how it could have been handled, then you’d have a very powerfully inspiring tool.

Lots of people have done inspiring things: have had near death experiences, lost a loved one, run a marathon, and yet many people look away from themselves for inspiration. What if you could persuade people to learn from their own stories and own experiences?