If It's Not 8 Figures, It's Not a Big Deal: Tips for Resetting Sales Expectations from Microsoft VP Hayden Stafford

“What do you think a big deal is?” That’s the first question Hayden Stafford, vice president of Global Enterprise Sales at Microsoft, asks a new sales team. Stafford operates on the principle that all salespeople can close big deals, and closing the “biggest deal ever” requires a major change in thinking: going big or going home.

1. Start with the numbers—then go bigger

Stafford firmly believes “when a sales manager sets a target, people aspire to that target.” He says, “if you look at a new company, a company that’s just getting going, expectations are set at a certain number, and salespeople become accustomed to that number.” It’s basic psychology, he says, which makes it important to ask: what do you think a big deal is?

2. Big deals need big rewards

The answer depends on the organization, but typical responses include “$1 million, or $500,000. This involves some reeducation: a big deal is eight figures minimum.” Stafford knows that not every company can close eight-figure deals, so this is about closing the biggest deals they can. “Expect more from them. Incent them on the big deal. Push them beyond complacency.” If the typical deal is $1 million, then incentivize them to lose a $5 million deal.

Stafford created a new sales award at Microsoft: the Titanium Award, which at press time is about to be handed out for the first time, serving as an incentive for sales reps to close enormous deals. “You must focus on that big deal and drive them to it. You have to push sales teams beyond complacency,” Stafford explains. “The Titanium Award is for deals above a certain level. You want them thinking big to sell big. And you want to reward them in a big way.”

Recognition goes beyond awards, Stafford notes. “Recognize hard work. Recognize the hours put in. Recognize spouses for being supportive when your partner is on the road.” The more gratitude you show, the more your reps will strive to earn your respect.

3. Listen as well as you speak

And how do sales reps live up to such high expectations? Stafford asks his teams to cultivate a different set of skills, based in part on his background as a management consultant. “Salespeople speak a lot. Consultants listen. They’re trained to deconstruct a business problem. They look at strategy, at how a company is oriented, then think about the products and services that solve that company’s problems.”

Sales reps, Stafford says, need to do the same. “It’s not good enough to just sell someone on features. You have to develop that long-term relationship, to think about process innovation, and understand your customer’s strategy and long-term focus.” That, Stafford says, requires listening and being a good partner.

4. The post-sale is the thing

Sales, Stafford believes, is a partnership. “This is something I stress with all of my sales teams. The post-sale is the most important piece. The cheapest customer for new products is the existing customer.” Supporting buyers after they buy is key, Stafford says. “Listening to concerns, listening to outcomes of implementation, it opens opportunities to cross-sell and upsell. Plus, you have a wonderful professional reference.”

It’s crushing time

Stafford’s philosophies are a great North Star; point yourself in this direction and get your teams to start crushing their quotas. Remember: think bigger or go home. Raise expectations and don’t get complacent. And above all, develop those partnerships that pay off with the biggest deals.

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