Why sales should never lose alone

- - Sales

Sales can be a very lonely role. You’re out on the front lines with everything exposed. You put out a forecast, pipeline or end of quarter report, and everybody in the organization feels like they can take pops at you. You can quickly go from being the hero–which every salesperson lives for–to being a zero because you didn’t post anything.

With half your income riding on your ability to sell, the only thing worse than posting a zero is having your colleagues throughout the company second guess you. The best way to combat this is for sales leadership to create a culture in which no one loses alone. It’s not easy to do, but it’s a win for the entire company.

Never lose alone

I was first introduced to this concept by Bill McDermott, who is now the CEO of SAP. At the time, he was running North America, and every Friday he would lead a deal call for the top 20 deals in the region.

Bill always asked the standard questions such as, “Are you leveraging the value engineering team? Have you asked marketing for a customer case study? Have you brought in the product team?”

What caught my attention was the degree to which he would press the logic of his case, in very simple language. It went something like this: “We are a company full of resources. If you leveraged all of them and we lost the deal, then we know we did the best we could. But if you try to do it alone and you lose the deal, we don’t really know if we put our best deal forward. We just know you were unsuccessful.”

His mantra, which he would repeat at the end of every call, was “Never lose alone.” I was sold, and have tried to bring this philosophy to every company I’ve worked at since.

Radical transparency

Putting this into practice this requires radical transparency. It means making the details of every deal, the overall sales process, and everyone’s role in it, visible to the entire company. That places ownership of the pipeline, and of sales outcomes, where it belongs: on the whole company. When everyone is included in the process, they have a vested interest in the success of each deal.

This also gives the leadership a real pulse into what’s happening in the business, which allows them to make the right decisions. And, it gets people across functions thinking strategically about how to win deals.

A counterintuitive approach

Unfortunately, this is counterintuitive for a lot of sales leaders who see part of their role as insulating the sales team from the rest of the organization.

That’s their best response to business leaders who have never been sales people and don’t understand how they work. Too often, these leaders tend to think, “We have the best product and once we get a conversation going, people will see that and magically buy.”

There isn’t an appreciation for the fact that there is not only a selling process, but a buying process that the customer has, and sometimes those don’t overlap. Sometimes the person that you’re talking to doesn’t value what you think your value proposition is.

For example, some people buy Ferraris not because they’re the fastest cars in the world, but because they’re a status symbol. So, if you have an engineer come in to talk about horsepower and gear ratios to a person who wants to buy a status symbol, you miss your mark.

A good sales person is going to ferret out the buyer’s goals and map the value prop to what the buyer really wants to buy. It’s a highly specialized and disciplined skill that’s poorly understood outside the field. So, sales leaders’ natural reaction is to protect their team from uninformed criticism, and from people who know nothing about sales trying to insert themselves into the process.

A more inclusive process

The better answer is to make the sales process more inclusive. But there’s a certain amount of faith and mutual respect that needs to occur, along with an investment in education. I did say this was not going to be easy!

It starts with making everything transparent, and I don’t mean just the end-of-quarter report. I mean everyday transparency. In my current organization, we review our pipe once a week at our operations meetings, but it’s fully exposed and available all the time on flat screen displays in the office. Related business intelligence reports are available to all employees.

That’s the first step, but if you only do that, you’re still open to people taking pops at you. You also have to educate people and provide context. Every sales organization has deal stages, so we teach people what those are. We make sure we communicate the hurdles each deal faces, such as price, or product capabilities.

We also share our goals and provide perspective. If we’re working 58 deals, we help people understand if that’s a good number or a bad number. Are we tracking to goal? How does it relate to last quarter, or the same time last year? If you don’t provide that background and framing you’ll get pulled into rat hole discussions.

A role for everyone

By making all of this visible, everyone can see how they can support the deals. If there’s a product capabilities issue, we create a JIRA ticket and we tie those tickets back to the opportunities. At any point in time we can run a report that says, “Here’s this opportunity and here are all of the enhancement requests that we need to close the deal.”

Or vice versa, somebody can run a report that shows the JIRA tickets that have the most deals, or the highest dollar volume associated with them, so we can prioritize.

If the same objections keep coming up over and over, marketing can see that and create a marketing asset or improve the wording on the website.

The goal is to create ownership across the company. A big part of never losing alone is helping everyone understand how what they do is valued and required to close deals and retain customers.


We also do something called 15-5s. This is something that came out of GE, and I implemented it when I was running Pilot Software. Now there’s a software company called 15Five that has automated it.

The basic concept is to spend 15 minutes writing and publishing a deal update that takes about five minutes for anyone to consume. It’s a way to cascade information up and down the organization to build greater alignment. It takes discipline on the part of the salesperson, but it saves them time having one-off hallway conversations about deals. And, it de-mystifies the sales process.

Winning together

When you combine these initiatives, it starts to transform conversations within the company. The cross-functional organizations start to see obstacles in the aggregate. Instead of focusing on a sales rep and what they might be doing or not doing, they focus on removing whatever is blocking their success. You move out of deal-by-deal tactical firefighting and into strategic thinking about what you can do that will help win ten deals. The mindset changes to going hard on the issues and easy on the people.

It takes a leap of faith because you’re exposing yourself, but the reality is if you’re not successful, you’re exposed anyhow, and the outcome is probably even worse. You lose your job. A no-one-loses-alone culture means a lost deal is no longer an exercise in pointing fingers at the sales rep. People understand it’s because you didn’t have a key feature, or we didn’t want to lower our price, or the prospect decided to build the capability themselves. And when we win, we win together.

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