Selling to CIOs is a difficult process and getting tougher

He reached out to the CIO with resolute frequency almost like clockwork; his connects were based on the timeline given by the CIO on when to reconnect for the decision on the solution. The CIO on his part never closed the loop, kept him lingering in the background with a hope that he will someday be successful in getting the order. This continued for almost a year with distractions in the form of small activity that he had to engage in with the IT team to validate a use case or elaborate on technology integration, scalability, etc.

His organization was running out of patience with the prolonged engagement which for most of the year continued to remain in the active pipeline but failing to convert. The management wondered on the investments made over the year with the lure of a referenceable customer with high value business. The story was beginning to look like a stretch of belief with a growing feeling that the CIO will not be able to convince internally. It was a tricky situation where reaching out to the CEO could potentially make or break the deal, the relationship with the CIO would have anyway broken.

On his part the CIO – a veteran of years – would keep finding new clarifications or actions in every meeting, each sounding logical and never really answering the question on what will result in closure. The vendor systematically addressing each and every query, his team finally signed off the pilot and put the ball back in the CIOs court. The CIO sought help to present the solution to the Management which was promptly provided as time continued to slide. The vendor CEO cracked the whip and demanded closure either way in a defined timeline.

Agreeing with the direction set forth, the salesperson confronted the CIO and pleaded for closure citing helplessness in offering the enviable deal beyond the timeline. He hoped against hope that the fish will bite and was seemingly rewarded with an opening that promised closure with a foot in the door and conditional commitment to scale up should the initial engagement deliver to promise. This was taken in the spirit of partnership but he was cautious in his pronouncements internally. The wait appeared to have been worth the efforts invested.

The ordained time came and went; the order continued to elude him, the message from the CIO was that the powers that be wanted further evaluation of options. It was quite evident that the business was not really coming to fruition in the near foreseeable future. The inability of the CIO to push internally was quite apparent, in hindsight his demeanor was always defensive, lacking assertiveness required to push through a decision. With lost credibility the salesperson had nowhere to go except to grin and bear it and keep the CIO humored.

Why do CIOs not come clean on the need, process, decision making hierarchy and metrics, timeline, urgency, and finally the budget upfront before engaging the partner ecosystem ? What keeps them opaque to the external world, at times even to their teams ? Is it power that they enjoy or they try to hide their insecurities behind the bravado and resultant activity with occasional outcomes ? Are their successes random occurrences of chance or the teams’ hard work that happens because or despite the CIOs interventions ? The broad brush that I paint applies to a large cross-section !

Why don’t vendors ask tough questions on the need, the timeline in which the decision will get taken and allocation of budgets ? I know some who do and some CIOs who give straight answers; in many cases the sales teams hear but don’t listen in their desperation to close a sale driven by period end pressures and targets indulging in wishful thinking, running towards a mirage. Then there are CIOs who are uncomfortable elucidating a clear and crisp no thereby resulting in long periods of courtship and eventual breakup.

For the vicious circle to break it requires change on both sides; the change begins from sales leadership who need to be ruthless in their pipeline management moving off when they don’t see traction. They push sales teams hard resulting in wasted efforts. Internal and external expert facilitated sales training and mentoring are required to imbibe and sustain the sales process using experiential training rather than templated workshops. Changing your customer is going to take a long time and then again it may not happen.

My sales pitch: Workshops on “Don’t sell – help your customers buy” available to the interested !