In my experience, bad salespeople talk too much and LISTEN too little. If you’re closing deals and you haven’t been listening aggressively, you just got lucky. That success won’t be repeated. Active listening sounds tired: I think of it as extreme listening, and here I describe how to make it part of your work. But using your two ears more and your one mouth (in that famous proper ratio) will probably help in your entire life!

image: Zina Deretsky, National Science Foundation

At my previous company (SuccessFactors, which was acquired by SAP), we were able to instrument extreme listening by salespeople as a company practice. This became maybe the most important flow of information for delivering the earliest and timeliest product improvements, and for bringing together a whole company of over 1000 employees with strong focus.

The whole company will listen if sales listens well

If you successfully institute a culture where each sales rep uses his or her ears — and genuinely strives to process and to learn from what they’re hearing — that data can be collected. More importantly, that data will be one of the most important data flows in the company: the difference between success or failure.

If collected on a daily, monthly, and yearly basis, this data has the potential to both dramatically improve your sales team and to deeply inform the company’s strategy and competitiveness. But, to do so, sales teams need a path to communicate that information back. In other words, to get your sales team to be better listeners, they need to be heard as well: by sales ops, by product management, engineering, customer success and customer support, and, of course, the CEO and other leadership.

If the sales team listens systematically and strongly and has a real process by which to be heard, it will inform the company’s competitiveness and strategy more than anyone or anything else.

“The Pitch Show”

I’ve seen Chief Revenue Officers (CROs), VPs of Sales, and the rank-and-file of area sales managers, sales reps, lead generators, and sales development reps (SDRs) alike sit in front of their #1 target customer, have 20 minutes to pitch their product … and then click play on their deck and spend 80% of the pitch without letting the target customer get a breath in edgewise.

The deck is clearly one-size fits all, full of recycled language, delivered on auto-pilot without attention to the audience and, worst of all, entirely done without asking a single question. No intent or interest in listening. A strong target customer who can write a check or influence the sale to be closed will be bored and even “unsold”. These salespeople have missed the chance to stop and ask the infamous question the Mayor of New York once used to ask everyone, everywhere, that I love: “How am I doing…?” So it’s stunning to watch hard-working, accomplished sales reps present their pitches — which may in fact be full of entirely appropriate and well-drafted information — by droning on relentlessly until the end. It’s as if getting through the deck is the goal itself, and will free them from the anxiety of getting through it.

Only at the end of the pitch do they then finally ask what the customer thinks — after all the missed opportunities to co-develop ideas with the customer and really learn in the moment. Until then, many sales reps haven’t observed, let alone deciphered, the body language of everyone in the room. Deciphering these at first seemingly odd cues and clues about what the target customer actually needs for their business makes all the difference in building a strong relationship, whether it’s a potential or existing customer. Business is ephemeral and changing, and you need to adapt to the current rhythm of their business — that they’re so obviously willing to share with you, if you listen. I have been in so many business situations where the entire foundation and basis for the 6 hour flight I took to see them had completely changed by the time my plane landed. If a sales rep were to go in and just run their playbook without paying attention to these changes, they would lose.

So: how to avoid that onward rush of delivery and actually engage in a pitch that picks up on the room, that re-calibrates for the most important points towards each particular audience and each potential sale? You listen and ask probing questions. 

Ask, with interest, to listen and learn

It’s reframing sales as listening: Starting from a place of listening to your target customer’s needs, and then carving out the space to continually listen and observe any signals throughout.

How do you do “extreme listening”? Instead of saying, “Look at these X data points, and these Y outputs from our product (They will make you very happy! And no one else can do it)”, start by asking the audience what their goals are, the way their organization works, and what they hope to understand from you or solve for. Even if you think you already know, you really don’t: those goals and priorities have changed significantly since you agreed on the agenda. I can’t remember a time when I didn’t learn a ton just by asking seemingly basic questions that really helped me understand the nuances of the issues the customer was facing. I remember asking such basic questions that they felt embarrassing when asked, but they changed everything and allowed us to ask much more complex questions later because we had set a tone of inquiry from the start. An example could be as basic as “who in this room has actually signed a check before for software?” to “How will you truly know this software will be successful?…I see what’s in the request for proposal, but what resonates with you as employees here that will really make a truly difference in the business, a tangible and measurable one?”

Pursue verbal and non-verbal cues

Sales reps need to be able to read a room aggressively to pick up cues — including body language and room energy — from their audience, especially when a pitch begins to lose its touch. You need to trust any “somatic” instincts you have here. And if you feel the energy sucks, change it up. Such cues indicate moments where you could ask confirming questions like, “Do you think this could be helpful to your organization?” or opening questions like “We’ve looked at your earnings call/your stated mission/the business challenges you are in, and we thought this product could help you like this — are we right?” Or my personal favorite: “Is there something here that would be a game changer for you or not? Could you use this effectively in your organization?”

My hope is that, apart from those questions, I get the chance to move the conversation beyond two suits exchanging professionalisms to what animates that person in their job; what makes them feel like this is one of the most important moments in their life; where they will have the chance to step up and impact the company and the customers in a meaningful way. The sort of stuff that one day ends up being the most powerful part of their interview for a promotion or new job. Ha, just reminding myself of those moments makes me laugh out loud with joy, even now because those are the moments where you get a chance to be legendary with your customer.

I have never seen deals close without asking with interest, listening, and responding with sincerity. How many more deals could be closed if this were done right?!

Start a dialogue

Closed assumptions are bad for business, and they’re bad for the pitch. Yet asking more open-ended questions at the end of the presentation is more or less useless, emptying them of any real meaning or intent. The heat, the energy, the opportunity to truly connect and make magic together is gone.

So, if you are attentive and listening during the pitch, you’ll start a true, productive dialogue — one that will bring you and your customer together and help earn you the right to their business. Open questions — those questions where you clearly have not already made your mind up about the answer or your opinion on the customers’ plan — signal that you invite feedback during the presentation. It’s really signaling the desire to learn as well as to put their priorities first, to work towards their goals, to make all the information you give them relevant.

Finally, not only do these openings create moments to re-engage and to re-direct towards those actual priorities (stated or unstated) that your target customers have — they also provide invaluable nuggets of information. And those nuggets can help you develop (if you’re early to product-market fit) or hone (if you’re further along) your own overall business.

Build listening into a competitive learning culture

In fact, listening and learning during the sales pitch isn’t just a route to closing deals; it’s a way to find out what you can do better as a company.

Instrumenting and operationalizing sales as a way to gather valuable insights — in addition to pitching and building long relationships — is critical to a company’s success. If it’s part of your culture in every instance, I guarantee the data collected will differentiate you from the competition. This is why I always scheduled “real” calls with “real” customers in the field (I say “real” instead of the “safe” ones that were curated and cued up for me by a formal function inside the company: “CEO-proof customers”). I also always spent extra time asking, “How are we doing?” The feedback I got was fun and rewarding, but often accompanied with brutal commentary; still, even then, it was followed by “but your product is the best, and you always listen to us.” Building that type of relationship with customers, with this approach, makes it very hard for you to be displaced by any other competitor.

My last act before signing the papers to sell our company for $3.7B and 11.6X revenue was to speak to two customers: Even at that stage, they were still kicking my ass with their feedback… and I loved it. Extreme listening, even in the last few minutes, gave me outstandingly relevant and fresh insight.

Three ways to operationalize all this listening
Don’t let the gold slip through your fingers

First and foremost, make sure you systematically request and receive information, opinions and intelligence from your sales team. This can happen in any form — email, notes, Slack, even texting from the meeting — that can be absorbed and analyzed, maybe even implemented, immediately. All a sales rep needs is the communication path for doing so. Without this, you are literally losing gigantic amounts of real, highly relevant and valuable information.

I tell a story of one of my very first jobs, in-house in a 50,000 people global company; messages were left on a machine by the 3,000 sales reps calling in from the field, and when I finally listened to them, on my first day in the job, I found that no one had listened to them for years. We found new products and real business acceleration nuggets in those messages. I couldn’t take any credit for all the brilliant ideas produced by the field, but I was able to listen to them and put them to work for the whole organization to benefit. Though I wasn’t in the sales force, it made me realize the pent up power the sales force’s knowledge represented for the entire company. 

But submit real information, and be stunning in your preparation

Make sure you also train your team to get and share information that’s real — that makes sure your product is deployable in a way that works for the customers. That your product and this deal is likely to grab their company and move it forward in a way that it wasn’t before. Listen for what real business transformation might be, and think deeply about how you answer that problem.

After meeting and working with 100,000s of employees, and 10,000s of sales reps, the sales reps that impressed me the most were the ones who understood the entire financial profile of the company, its actual public and private business issues, the latest hires and how they fit, and so on. That type of preparation makes it a lot easier to ask great product questions of the prospect. As one of my former VPs of Sales used to say: 80% of winning is the preparation before the meeting! That makes you a very welcome party, and your listening is accelerated, and the prospect will trust you because they should: you have respected them and their time by knowing what the business needs and what is going on.

Don’t pretend to be Steve Jobs: What fantastic product managers do

Finally, process that information and leverage it to build a more competitive, better product as you build it. Too often, in new companies, there’s a soft underbelly of people who think they know 100% what’s right; it’s the psychology of a well-educated, highly intelligent product manager who sits alone in a room deciding what the right product to build is and then decides, I’m gonna build that. Unfortunately, that kind of process is very nebulous to leadership and customers, not to mention it sells to customers too late.

Many of those PMs tend towards the belief, even if well intentioned, that “I’m like Steve Jobs; I know what they want without their having to say what they want”. But the truth is, most of us aren’t Steve Jobs (to say nothing of the fact that Jobs worked 30+ years to become… THE Steve Jobs). Often, people hold on to this Steve Jobs myth about themselves because, on some level, they’re avoiding hearing what other people have to say. It’s hard to listen to others. Not to mention there’s no challenge to you doing things your way with no input. Listening to the feedback that will stream back from a trusted, engaged, listening sales force — and incorporating that into your strategy — will not cause anything to be taken from you in terms of creativity or vision. You’re still building the project. You’re just building it better.

You decide how and when you take the inputs in: That’s not to say that you necessarily have to incorporate and act on all the feedback and information you get from every sales rep and every interaction. In fact, you might decide NO action is the right action. I would gladly accept a product manager coming to me and saying, “I’ve listened to 1200 hours from the field — but I’m not accepting that info. I have a different vision for this and here’s why”. When the work has been done, that calculated approach as a product manager, articulated convincingly and credibly, can actually become reinvigorating for the entire company and give confidence in the roadmap.

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Last, but far from least, there’s a human upside to all this. Creating a culture of an always-listening sales team and organization turns what can be an adversarial “us vs. them” dynamic into one that imbues the people selling your product with a sense of greater ownership, purpose, and fulfillment. It turns being a cog in a coin-operated grind into being an invaluable part of the core strategy — creating a virtuous cycle of better feedback, better direction, and better focus. It also empowers the development team, the product and engineering teams, and customer support, because they get what we all crave: data and insight. They know — no longer have to guess or learn in isolation — what worked and didn’t work, and the entire company can tie it all together if there’s a process. THAT’S when the magic happens.

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