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!