How to Close Sales in the Age of “Always Be Helping”


A pushy salesperson isn’t good for anyone.

Sales today is about helping people solve problems like a doctor or a consultant — not slamming deals like a used car salesman.Social media didn’t exist decades ago, but today, 75% of all B2B buyers (including 84% of C-level and VP-level executives) use social media to research their buying decisions. If you’re consistently too aggressive while closing deals, you’re setting yourself up for bad press and damage to your reputation that can last a long time.

For more advice on closing, check out The GSD Show — tips for salespeople, by salespeople.

To excel at modern sales, reps have to juggle a multitude of activities — learning their product, listening actively, handling multiple stakeholders, and mitigating curveballs — all while remaining professional, helpful, accommodating, and staying in control of the process. Setting the right expectations and helping people are important parts of selling today and will likely grow in importance over the next 20 years.

But wait — isn’t sales harder this way?

Maybe, but we have no choice. The rules have changed and you have to change with them. The days of taking prospects golfing to close deals are over.

At the same time, you still have to hit your quota. So what happens if your prospects take their sweet time to make a decision or are spending a lot of time in education or exploration mode?

The key is to manage your deals and sales process in a way that helps prospects move along at a steady clip without being a jerk. The seven strategies below help me exceed my number month after month while still being a helpful, consultative sales professional.

1) Manage a broader pipeline with more deals.

Some of your deals will roll to next month, or next year, or not close at all. Accept that as part of the reality of being a salesperson. In an age where strongarming prospects into signing a deal this month is no longer a viable sales strategy, you have to manage a broader, longer-term pipeline so you have enough volume to hit your number.

Part of managing this pipeline is understanding how to manage your prospects. If your prospects need to delay their start date for a short period of time, that’s fine — but you can’t forecast based on hopes and dreams. Always be as specific as possible when a deal rolls to next month by establishing a specific date and time to follow up. There’s a huge difference between “We’ll start next month” and “We’ll execute the payment link on Thursday, December 17.”

2) Only spend time with prospects who have real business pain.

Good prospects have real business pain. Your job is to help them formulate a good problem definition. Both are necessary for a purchase, and so my priority is finding and defining business pain.

I’m not above saying, “That doesn’t sound like real business pain to me,” to a prospect. After all, it’s more productive for me to offer to stay in touch and periodically send resources to a prospect in education mode if it doesn’t sound like they have thought through what they need. It’s wasteful to spend calories bringing them through the entire sales process, only to have the whole thing go belly-up because their need isn’t acute enough to buy.

But just because your prospect doesn’t fully grasp the pain doesn’t mean there isn’t any. A top salesperson can dig deeper to see if a mere nuisance right now is caused by an underlying problem that will mushroom into something problematic down the road. You are doing your prospect a huge solid if you can help them anticipate future problems.

3) Identify your prospect’s stage in the buyer’s journey.

The modern buyer’s journey has three stages (awareness, consideration, and decision), and buyers have three corresponding modes: education mode, evaluation mode, and purchasing mode. If you treat all your prospects like they’re in purchasing mode and try to aggressively close them, you’ll lose deals and waste time.

Instead, learn to diagnose what stage your prospect is in. For example, if they tell you they need to achieve a certain goal by March 2016 and are speaking with reps at three different companies, they’re clearly in the buying stage. But if they’re still researching what could have caused below-average performance in their last fiscal year, it may be too early to present them with product options.

If the prospect isn’t ready to buy, let Marketing work them instead of Sales. Send them information and then drip them free resources through predefined workflows and have them reach out to you with questions. As they educate themselves on their problem, reach out every few weeks or months to stay connected and check on their progress.

4) Create a buying plan with the prospect’s needs in mind.

In my experience, prospects tend to forget that their journey doesn’t end the day they make the purchase. In fact, the hard work has just begun. To help them understand this, a good technique is to start with their business goals and work backwards to the date they’ll need to implement by to see their ideal results.

The most valuable way to approach this exercise is to have your prospects talk through the timeline themselves and supplement their plan with your knowledge. Having them draw conclusions on their own is far more powerful than telling them what you think, even if you’re right.

Remember to always focus on the implementation, not the purchase, and back up the plan with as much data as possible to create a sense of urgency.

5) Expect curveballs.

Some of your deals will inevitably get delayed or fall through altogether, and there’s nothing you can do about it. Don’t get emotional — understand that at least 10% of people will be irrational or that life will get in the way. I’ve had deals delayed due to car accidents, last-minute vacations, and illness. Eventually, you’ll experience all these things too.

The key is to not get emotional. Many prospects are afraid to call you back when curveballs rear their heads because they don’t want to have a difficult conversation or be strongarmed into doing something they can’t or don’t want to do right now. So always react calmly, and mutually come to next steps with your prospect so they don’t feel attacked.

6) Be comfortable “firing the prospect.”

Know when to say “when.” I’m happy to offer help to any prospect, but it’s illogical to spend a lot of time on a deal that doesn’t exist or is going to be too hard. I’ve had prospects who have asked me for help over five distinct sales pursuits over several years and just can’t pull the trigger. After a certain point, I have to realize that prospects who aren’t ready to buy after multiple sales processes aren’t ever going to be ready, or I’m not the right person for them to work with.

You have to know your own limits for what makes sense — for me, it’s two sales processes that go nowhere. Whenever this happens, closely review the process to determine what you could have done differently. This way, you’ll learn to spot the signs of a prospect who will forever drag their feet and won’t repeat your own mistakes.

7) Ask happy customers for referrals.

Remember when I said earlier that bad actions can destroy your reputation? Your professionalism and excellent sales execution can do exactly the opposite. By leveraging your existing network of customers, you can make future sales easier.

Whether it’s asking your customers to write you LinkedIn recommendations, having them serve as references for prospects, or blogging about your product, your customer base can help you do your job. After all, there’s nothing more valuable to moving a sale along than having someone who’s gone through the exact same process explain how easy it was.

Ultimately, sales is like dating. Ideally, you’ll find a prospect whom you’re a mutual good fit with, and you can close the deal. But if you find a prospect who isn’t ready for you yet, you have a choice. You can force the relationship and have a hard breakup where you’re left with the person you care about bad-mouthing you. Or, you can let the deal go and accept that it’s just timing or other external factors that are off.

Sales is human, but buyer behavior isn’t personal. All too often it can feel that way, but the best sales professionals remember to keep their heads cool so they can be as productive as possible.

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Source: How to Close Sales in the Age of “Always Be Helping”

6 Secrets to Getting a Response From the CEO


Imagine you’re a pilot landing a plane. A long runway is obviously better than a short one since it gives you more wiggle room to adjust your approach. When you are tasked with landing on a short strip of runway, you must be far more meticulous about your movements to bring the plane down safely. I often use this metaphor to describe the difference between reaching out to a manager- or junior-level buyer as opposed to a C-level executive. When a salesperson sends a message to a lower-level prospect, they can afford to try a stronger ask at first, and then tweak it or scale back as necessary. But when you’re pitching to a CEO, you really only have one shot to engage them. Bungle the ask and you miss the runway entirely.

With this in mind, salespeople must be deliberate and thoughtful in how they approach CEOs if they hope to receive any kind of response. Here are six tips that can help your pitch land smoothly with the chief executive officer, and maximize your chances of getting a reply.

How to Get a CEO’s Attention

1) Use a gentle ask.

CEOs are extremely busy, so in my outreach, I’m not going request a meeting or a conference call. Deploying an overly strong ask in the initial email or call will pretty much guarantee never getting a call back. And at this stage, a response is all I’m after — not a signed contract.

CEOs aren’t usually willing or able to give of their limited time. So instead of trying to think of the magical sentence or statistic that will prompt the executive to drop everything and meet with you, I encourage salespeople to consider what CEOs are willing and able to give. In general, CEOs are friendly and outgoing since they’re constantly representing their companies to a variety of audiences. They’re extremely savvy when it comes to social dynamics and credibility.

Take this information and play in their wheelhouse. Rather than a meeting or call request, soften and socialize your close by asking the CEO for a referral or a connection to more information. Not only do these asks require significantly less time and attention, CEOs actually like giving references and information.

For example, an email using this approach might read something like this: “I want to make sure I don’t sound foolish when I call your organization about X issue. Where/from whom can I get the best information on this topic?”

Instead of coming to the CEO as a credible sales rep, you’re now approaching them as a curious student, and you’ll likely find that they’re much more willing to engage on this level. And once they start to engage, you can ramp up the relationship bit by bit.

Another benefit of making it ridiculously easy for the CEO to respond to your message: Getting any sort of response automatically boosts your credibility with others in the organization. Maybe you’re trying to book a meeting with the VP of HR. You think it’s more likely they’ll agree to your call when you say “Well, I got in touch with your CEO last week, and she said X … “? Instant credibility earned.

2) Write emails on your phone.

CEOs are constantly on the go, which means nine times out of 10, they’re reading email on a tablet or smartphone. If an email from an unknown recipient requires them to scroll, it’s not getting read.

Bearing this in mind, write any email intended for a CEO on a smartphone. That way, you see exactly how it will appear to them when they read it. Salespeople often make emails to C-level buyers overly long and complex, because they think they need to sound smart and impressive. But when it comes to getting a response, short and simple is always better.

Don’t sit in front of your desktop computer and fill up the screen with a novel. Get out your phone, type out a few brief sentences, and send.

3) Don’t dismiss the EA.

The common perception among salespeople about executive assistants is that they handle C-level professionals’ calendars and block others’ access to them. End of job description.

Maybe that was the case 20 or 30 years ago. But in 2016, executive assistants are extraordinarily competent in a plethora of areas, and their duties extend far beyond administrative tasks. Beyond keeping their boss’ calendars, EAs also represent their managers at internal and external meetings and sometimes even make decisions on their behalf.

Because of this, I think of the executive assistant as the CEO by proxy. Instead of trying to bypass the EA, work with them to get the information you need and indirectly engage the CEO. Sometimes interacting with and posing your ask to the EA is more beneficial then accessing the CEO. For example, if I was building an ROI calculator to strengthen a presentation and needed data from the CEO to complete it, getting it from the EA is just as good — and much faster. When it comes to any other ask besides signing the contract, I don’t distinguish between the CEO and their EA due to how closely they work together.

It’s also a good idea to call the EA and pick their brain before you reach out to the CEO — after all, they know more than anyone else what works with their boss and what doesn’t. However, EAs are busy people too, and they won’t just give you the information you want simply because you asked for it.

Keeping in mind that EAs get countless calls from salespeople pitching “value and benefits” for the CEO, differentiate yourself from other reps by showing your vulnerability. For example, here’s how you might kick off your call with the EA:

“Hi, Mike. I’m going to be reaching out to Wendy soon, and I don’t want to look stupid … what’s the one thing I definitely shouldn’t say?”

Ah — now you’ve got their attention. The EA can be critical in your campaign to reach the CEO, so don’t shoot yourself in the foot by dismissing them.

4) Draw on the college connection.

Salespeople often try to find common contacts, interests, or employers when reaching out to prospects. This is a smart technique, but it can be tailored even further with CEOs.

The most powerful connection you can use with the chief executive isn’t their current company, their former company, or any of their colleagues past or present. It’s their college. In general, CEOs are extremely involved with their alma maters, and if you went to their school or know someone who did, use that as an in. Reminiscing about college days can quickly become talking about current business.

5) Call late.

Common sales wisdom holds that salespeople should call executives early in the day, before they get too busy. But in my experience, connect rate (which I define as a phone call over 60 seconds long) is notoriously low in the morning hours. Why? When a CEO gets to their office, they might not have gotten in the swing of things quite yet, but they’re distracted — thinking about all the tasks they have to get done that day. Not the ideal time to hear from a salesperson.

The end of the day tends to be a better time to call the C-suite — think 5 to 8 p.m. local time. Later in the day, you’ll find that the person on the other end of the line is less distracted, a little tired, and in an overall better mood.

You might be concerned that a late call will be a bother to an executive. But to me, this is a non-issue. If your call comes at a bad time, they simply won’t pick up. Not to mention that what a CEO finds “bothersome” has little to do with your timing and everything to do with your message. If you have a good message, they’ll be interested in what you have to say — even if it’s a bit late.

6) Use a 45-day cadence.

Industry standard is five touches in 30 days. For CEOS, I advise five touches in 45 days.

CEOs’ schedules rarely exist on a monthly cadence. They think about quaters, not months. Most prospects are available sometime within a month. No matter when I reach you, there will be sliver of time in four weeks that you’re available — even if for two of those weeks you’re on vacation, sick, off-site, working on a major proect, and so on.

But many CEOs will disappear for an entire three weeks at a time, depending on what they’re doing.

A CEO can’t stay away from her company for an entire 45 days, which is why I recommend an extended calling schedule.

Want more sales tips? Subscribe to my quarterly newsletter “The Deal Doctor™” to receive my latest tips, techniques, and strategies to achieve greater sales.

Editor’s note: This post was originally published in March 2015 and has been updated for comprehensiveness and accuracy.

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9 TED Talks on Effective Communication That Will Help You Close More Deals


Effective communication helps you forge strong connections, collaborate with internal and external stakeholders, close deals, and convince people to share your views. It’s critical to your success, whether you’re a sales leader, manager, or front-line rep. So what makes you an effective communicator? You must be able to explain complex ideas simply and clearly, speak in your own voice, tailor your message to your audience — and that’s just to start.Improve your communication skills by watching these nine TED talks. They touch on every aspect of communication, from what we say, how we say it, whom we say it to, and equally importantly, what we don’t say.

9 TED Talks on Effective Communication

TED Talks for the Workplace

1) “Listen, Learn … Then Lead” by Stanley McChrystal

If you think the United States Army is a rigid organization where decisions and orders come from the top and must be followed without exception, you might be surprised by former U.S. Army General Stanley McChrystal’s TED talk.

In this talk, McChrystal — who joined the Army at age 22 — shares the different leadership styles he encountered as he rose through the ranks, then shares the lessons he’s learned as a general. As the armed forces changed, McChrystal found himself leading groups of people who had vastly different experiences than himself.

“We’re operating a force that must have shared purpose and shared consciousness, and yet [direct reports] have different experiences, in many cases a different vocabulary,” McChrystal says.

To bridge gaps of understanding, it falls to leaders to build credibility through being transparent, willing to listen, and open to being reverse-mentored, McChrystal says.

2) “Remember to Say Thank You,” by Laura Trice

Productive communication doesn’t require agreement — in fact, some of the best meetings I’ve ever had involved disagreement. And that’s to be expected when you work with smart people who have strong opinions. But in order to have productive discussions and keep your team moving forward after conflict, people need to feel heard and appreciated.

In this TED talk, doctor and life coach Laura Trice poses a simple question — why don’t people ask to be thanked for the value they bring to the table, whether in their personal or professional lives? She thinks it’s because by asking for praise, we make ourselves vulnerable.

In this talk, you’ll explore the value of saying “thank you,” asking to be thanked, and the implications of freely giving gratitude.

3) “The Danger of Silence” by Clint Smith

In this powerful spoken word TED Talk, Clint Smith addresses what happens when we simply don’t communicate. Smith, a teacher and poet, gave up speaking for Lent one year — and realized how much he’d already silenced himself.

How many times do you see something happening in the workplace or your personal life that makes you uncomfortable? How many times do you speak up for yourself, a coworker, or a customer? In his TED talk, Smith argues that the price of staying silent is injustice — and that’s too high a price to pay.

4) “The Secret Structure of Great Talks” by Nancy Duarte

Whether you’re in sales or not, you pitch people every day. Want to hire more people on your team? A promotion? A new project? You have to influence the people around you to get your way — and that’s where Nancy Duarte comes in. Duarte, a presentation expert who helped Vice President Al Gore with “An Inconvenient Truth,” believes that all great presentations follow a specific arc.

As a presenter, it’s your job to tell a story that draws in your audience and convinces them of something. In this TED talk, Duarte shares actionable tips to rework how you tell stories — and hopefully help you get closer to what you want.

5) “How to Save the World (or at Least Yourself) From Bad Meetings,” by David Grady

Communication is a good thing. Transparency and openness are both good things. Pulling people from different teams to give input on important projects is a good thing. So you would think that the concept of the work meeting — something designed to deliver information, gather opinions, and make progress, would be good as well.

Unfortunately, there is such thing as too much of a good thing. David Grady, a cybersecurity manager, believes that we’re being deluged by pointless meetings that waste our time. In this TED talk, you’ll learn Grady’s “No MAS” technique for making meetings more productive and valuable — so that when you’re communicating with your coworkers, you’re only talking about what really matters.

TED Talks on Communication Skills

6) “Connected, But Alone?” by Sherry Turkle

We live in a world where it’s easier than ever to reach out to people across generations, cities, and even continents. Yet go to any restaurant, concert, or even funeral and you’ll find people disengaged from their companions because they’re on their phones, MIT social sciences and technology professor Sherry Turkle says.

Besides the fact that it’s bad manners, this increasingly common behavior is preventing us from relating to each other and self-reflecting. In Turkle’s TED talk, you’ll hear about how being overly connected is actually isolating us from our communities, and what we can do to unplug from our phones and plug back into our relationships.

7) “10 Ways to Have a Better Conversation,” by Celeste Headlee

Words are our primary way of relating to other people — whether it’s building strong friendships, getting into arguments, or persuading coworkers to follow your plans. And yet we suck at it — a Pew Research study found that Americans are more polarized than we’ve ever been.

Radio host Celeste Headlee has some experience using words to move people. In her TED talk, Headlee explores the components of a truly great conversation and shares 10 strategies to improve conversational competence.

8) “The Power of Vulnerability,” by Brené Brown

Of course, true connections can’t be formed if we don’t bring our whole selves to our relationships — no matter how conversationally competent we are. In this TED talk, Brené Brown, who researches vulnerability, courage, and shame, suggests that only by confronting what we’re most afraid of can we truly connect with other people.

In her research, Brown found that her subjects who felt the most love and belonging had one thing in common — they were willing to make themselves vulnerable. It’s not easy to get to that point, but Brown argues that if we’re willing to put in the time and effort, we’ll be able to reach a kinder, gentler world.

9) “Comedy is Translation,” by Chris Bliss

When I was younger, I thought Saturday Night Live and The Daily Show were just funny. And they are, but they’re also shows that delivery commentary in a way that makes people laugh and think at the same time.

In this TED talk, standup comedian Chris Bliss explains that comedy isn’t just about entertainment, although humor is obviously central. The elements of comedy — misdirection, its inherent virality, economy of language, and deliberate juxtaposition of seemingly opposite or unrelated concepts — make it a delightful way to entertain people and convey important messages.

Editor’s note: This post was originally published in March 2016 and has been updated for freshness.

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