Executive assistants have veto power over multi-million dollar software sales.

Complex selling involves a lot of complexity, none more complex than having to deal with many different stakeholders with very different motivations. Once two or more people collaborate on a purchase decision, they raise questions, voice objections, derail progress and drag-out your sales cycle until the Second Coming.

Sometimes the lowest caste can kill a sales single handedly. IT techies are the worst in many respects – having been one in a former career, I can attest to their ultimate veto power. Tell an avid Windows admin that you want to install a Linux infrastructure and you’ll meet a wall that howitzers couldn’t knock over. Techies know nothing happens without their expert participation, and they gladly use their veto power to guard their empires.

Marketing and sales need to manage the sales cycle, engaging stakeholders at points in time when they need to be involved … and not a moment sooner. This is never completely in your control – if a COO wants his IT department to do a technical evaluation now instead of after the entire C-Suite has fallen in love with your product, then you must oblige. But managing the engagement and advising when the right time to bring in each stakeholder allows you to proactively handle their motivations and objections, which shortens the sales cycle and improves your win/loss ratio.

Marketing folks, your jobs is to understand what prospect stakeholders are thinking at the moment of each encounter, in each phase of the sales cycle, and produce materials to answers questions or nullify objections. Ninety percent of sales materials may go under-used, but a lack of the right material at the right time hinders your sales team and keeps you from getting timely paychecks. For example, in enterprise software sales, there comes a point when techies need to become involved. You should map when in the sales cycle they should be summoned (in the second half, and maybe even the last quarter), bias them by noting their top motivations, and answer their chief objections before they are even voiced.

If you are really good, you address underling misgivings with their superiors first so the boss makes clear what junior objections are prima facie invalid.

If in doubt, push the next phase of the statement/argument/response earlier rather than later. When you present a solution to a prospect, they instantly start asking themselves questions which they don’t ask you. Better to answer those questions/objections early in order to manage their expectations now.