I am often asked, “So, what are your sales conversations like?” My response is that I ask questions and share successes around two related themes: 1) How are you doing with getting new hires, new partners, new investors, etc. on-board with your sales process and how do you want folks to behave, communicate within that process; and 2) How are you doing with getting your existing team understanding your desired sales processes, patterns, or some might say, sales rhythms?
Below is the content of an actual email conversation I am currently having with a prospect.
I hope you will notice that I ask specific diagnostic type questions that map to my offerings.  My prospect’s answers, if I am listening, will guide me on where to take the conversation. I know, for example, that it’s a recipe for disaster if a manager or executive is not asking tough questions about individual opportunities during sales forecasting meetings. I also know from my experience that forecasting disaster is something I can help my clients avoid.
Do you know what answers to your questions indicate a need for your product or service?  Have you socialized these questions and highly probable answers internally?  Do they map to real world example which you or your teammates can effortlessly and confidently describe?
Although this was an email conversation, we could have had the same conversation over the phone, in person, or even over twitter.  The key is that I have been thoughtful ahead of time with the questions I want to ask.
I have been talking you up big-time around here, Adam. “Get our sales act together” has made it into the top 3 priorities for 2012. Pipeline, account planning, you name it….
So, how do we make this happen – me helping [company] out?
The timing is perfect. It’s now recognized and internalized that we need to get a number of areas of our act in order. (Pipeline mgt, real forecasting, account planning in particular.) Everyone on the exec team (about seven-ten folks) recognizes this. What kinds of things could you do? The urgency is that we know/want to crush it in the first half of the year. We’ve got a handful of big accounts (~12) and a myriad of dogs-and-cats. We’re trying to consolidate to go deeper/broader (both in portfolio of our services purchased, as well as number of BUs across BigCo’s like XXX) rather than try to service a gazillion clients. Gimme an approach I can take in. [key player] is here today, and I’m having dinner with him this afternoon/evening. 
(I responded with a series of questions to understand my contact’s situation more specifically and to indicate the sort of capabilities I provide my clients.  He replied to my questions with in-line answers.  Check it out.)
Is there any concept of a pipeline?
Do you have the stomach for a pipeline and business review to see where you are with particular opportunities that you hope will contribute to “crushing” it in the first half.
To wit:
1) What deals are in the pipeline with new or existing customers that can get you to “crush it” status?
We have a list.
2) With the identified deals – a subset of these must close – why do you think they will close?
There is the big question…it’s “gut feel.”
3) Defend the realism of these ID’d deals by undergoing an opportunity review:

  • What has happened so far?
  • Who do you know will champion us with the selectors, funders, implementers?
  • Why should they? Have they agreed to the value, usage and implementation stories and what are they?
  • What are the steps to gaining a signed contract?

This would be a hugely valuable exercise.
4) If you do not have enough real deals to gain “crush it” status, what are you doing to get more into the pipeline?
Need a plan.
5) What is your business development process and within that process, how do you execute each step?
Not that structured.
6) Have you identified the conversations you want to have – with whom and what IN PARTICULAR you are going to say – to generate interest to the point of gaining trust and having your prospect kick off an evaluation of your skills and capabiiities?
Nope. Need this, too.
I can help with all of the above.