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Sales prospecting is one of the foundations of business, but sales reps often do not receive training on how to approach senior-level executives. In this post, we hear from sales expert Matt Conway as he shares his insights on why this happens and the skills needed to get the attention of C-level prospects, such as CEOs.

In this article:

  1. The Basic Principle of CEO Prospecting
  2. C-Level Prospecting: Why Make the Decision Makers Your Potential Customers
  3. Two Skills for Effective Prospecting
  4. How to Start a Change in Mindset
  5. How to Speed Up CEO Prospecting
  6. Writing a Prospecting Letter

Prospecting Ideas | How Sales Reps Can Skip Mid-level People and Close Deals with CEOs

 

The Basic Principle of CEO Prospecting

The Basic Principle of CEO Prospecting | Prospecting To CEOs | Skills You Need According To Matt Conway

Hi, my name is Matthew Conway, and I am an expert in C-level sales prospecting. I help sales reps get the attention of CEOs and convert them into customers.

My career started in inside sales before I moved to field sales, leadership, executive, and go-to-market strategy. I’ve been head of sales in Microsoft. I was a general manager (GM) of Nokia back in the good old days when they were successful. Also, I did consultant marketing strategy in the UK. I’ve had a good career in sales and sales and company leadership. However, I have always had a passion for developing the next business, and prospecting is my particular strength.

Some people may ask me, “Matt, I’ve seen some of your stuff. Just a quick opinion or guidance on how to move my career forward.” I always remember what my mom told me. Back in the day, I was a frustrated young inside salesman doing cold-calling every day. I was pretty miserable and bad at it if I’m being honest.

She said, “If you want to achieve anything in your life, go high. Talk to those who make the decisions.” So if I’m talking to a new salesperson or even to mature salespersons on how they can take the success to the next level, I would just say, “Go and talk to people whose core motivation is to introduce change. Don’t waste your life on people who can’t say yes or no.”

C-Level Prospecting: Why Make the Decision Makers Your Potential Customers

One of the things I believe I’m good at is spotting patterns and making connections. I realized early on, every salesperson, sales leader, executive, fast-growth or immature company, business, and sales organization I’ve ever worked at seems to be missing certain things.

Everybody wants to speed up their sales cycle, and they want to grab opportunities and make their proposals win. Yet why is the same problem happening time after time?

When I started to go high, my own activities began to decrease, but my results kept getting bigger and bigger at the same time. I call it the invisible elephant that’s been stalking boardrooms and sales floors all over the planet.

There are three things, the trifecta of sales and their performance, that could be the problems:

1. Their Sales and Boarding Are Backward

Because of that, the message we send to the target market or prospective clients when we’re prospecting is backward. We get people onboard by product marketing, and the message shoved to their throats is “Why choose us?” “Why should you pick our service our company?” “Why are we the best in class?” It’s we, we, we. The prospects don’t like it.

You’ve got to invert the whole thing. When I was a sales leader, I didn’t put my people in the “Why change, why now” framework. It’s in your client’s best interest you do something different. All sales are selling behavioral-approaches change. I think the sooner the salespeople recognize they are in the change game, the faster the paradigm shift will start to happen.

2. Salespeople Are Prospecting and Selling Too Low to Mid-Ranking Executives Who on Paper Look Like Their Ideal Client Profile

We have built personas or personality types. My belief is we create most of the ideal client personas while looking into a rearview mirror. They’re brought to the organization as incoming leads. Something is happening in the organization that prompted them to reach out to them in the first place. What’s the trigger event that’s going on? Where is it coming from? Sales reps are often introduced to a mid-ranking person tasked to do something different. If something is not working, then they go out and find a solution.

When you ask a CEO who they should contact if they want to do business with other companies, they’ll go, “No doubt, it will be the CEO.” For what reason? “Well, that’s who make the decisions to change fast.”

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If that’s the case then, why are companies letting or telling sales professionals to contact mid-ranking people who operate on a status quo — who can’t say yes or no?

3. Nobody’s Teaching Sales Professionals How to Prospect Right to the CEOs

Sales reps do not receive any prospecting training on how to approach C-level executives in ways that cut through the crowd and get their attention.

People in sales should be going higher, but one thing that doesn’t really work is how they’re being taught about it. They’re pushed toward the mid-tier person versus the CEO. They’re not equipped to approach the latter.

People say, “Look, the CEO doesn’t have the time, and I can’t get through to him. I can get this influence and build my business case, and they’ll take it to the CEO, but that certainly takes a long time. In the perfect world, I would just call up the CEO, but I can’t get him.” In reality, it’s a combination of mindset and skill.

Two Skills for Effective Prospecting

Two Skills for Effective Prospecting | Prospecting To CEOs | Skills You Need According To Matt Conway

It’s fun to be working with a group of people with whom you can see the lightbulb go on. You can see that little shift in mindset.

One of the most common concerns of sales reps is what they’re going to talk about with the CEO. “I’ve never been a CEO. I don’t know what to talk to them.” The motivations of the CEO are simple and easy to understand: how to make more money and how to save more money. Everything fits into those two buckets whether it’s speed to market or mitigating risks. If you’re going to hit those two key points, you’re probably pretty good.

This reminds me of the millennials, those young ones straight out of college. They are so lucky. They didn’t grow up with the sense of deference. In my generation, we viewed CEOs as “We’re not worthy. They’re superhumans and superachievers.” Millennials don’t have the kind of deferential baggage we have. They just look at them as human beings, which is precisely what they are.

When they actually get through the CEO, what they find is the conversations they have with someone who’s successful, confident, humble, and it is just that — conversations. Compare that to trying to convince a mid-ranking person. If they make a mistake, the company can fire them from the existing project.

Sales professionals also need prospecting skills. Nobody’s teaching people how to compose an excellent, tight value proposition and send it by email. They don’t know how to convert their prospecting letter into voicemail, let alone articulate it. Yet, miraculously, it’s supposed to appear. No other professional makes it with that level of inefficiency in their career, yet we kind of do that in sales.

How to Start a Change in Mindset

Changing a mindset is not an easy process, but there’s a way to do it fast. The quickest approach is to understand really clearly what is the potential value, outcome, impact, or result their product, service, or solution can create for another human being. When you have a prospecting reluctance, your fingers are pointing at your ego, basically. “Oh, I might get rejected.”

I speak from a great deal of experience. I went through these rejections as a young salesperson. It’s so hard to get over them, right? Here’s the thing: when you’re focusing on how you’re feeling, your attention is on the wrong person. If you’re the person I would like to talk to, I would say, “How can I serve you with your best interest?” If I can help a business improve their sales performance, mitigate risks, reduce supply-chain cost by 12%, and accelerate the time to market, I have a duty of care to let the CEO know I’m here. I can be of service to them. It’s not about me at all — it’s about them.

If you were stuck in the proverbial lift with somebody and the CEO says, “What is it you do for my business?” you should be proud and say, “I appreciate your asking. Last year, we helped you accelerate the time to market in China. We collapsed it by 6 months.” It’s not about you but what you can do for another human being.

When they develop this mindset, then salespeople will go, “Oh, it’s not about pushing or selling my products. It’s being clear on both the professional and personal outcomes I can deliver to another human being.” There’s the mindset shift. It’s not about being shy or selfish but about prospecting.

How to Speed Up CEO Prospecting

As you move from the “me-to-them” mentality, you wonder how you can speed up the sales process. Perhaps you have several years of experience in doing sales. As you made more revenues and lead more people to the sales funnel, you become more confident. Now your goal is how to be more efficient in what you do.

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Whether the salespeople are in inside or field sales, they benefit from the internal tribal knowledge on the results and outcomes your company can deliver for others. The fastest way, therefore, is to tap into that.

You realize you’ve got to peel the onion beyond the nice platitudes and testimonials. “We helped companies accelerate sales performance!” Woohoo. Yet you heard that from everybody. You need to quantify. By how much? Under what situation? What is the XY by when?

Then, you use third-party social proof. With salespeople, we think it’s our job to sell but consider these two scenarios. I sell to someone, “You’ve got to spend time with me. I’m Matt Conway. I’m 6 foot 1, blue-eyed, great-looking fellow.” Then you hear somebody else go, “You’ve got to meet Matt Conway. Great guy, big, kindhearted.” What’s more impressive to you: me telling you how wonderful I am or the other person telling you the same thing?

It’s the stories about the outcomes and the transformations you or the company has driven for others that really make an impression on people. It’s not me trying to convince you that should buy something from me. The storytelling calls to behavioral psychology that says the power of stories or metaphors bypasses people’s conscious objections and talks to their subconscious or unconscious brain.

Writing a Prospecting Letter

Lots of people talk about sales prospecting methods to CEOs. How do you exactly do that? Based on my journey of being a cold-calling salesperson in the UK back in the day, I tried selling to the mid-level people. It was not so successful. It took a long time. There were lots of rejections. It was only when I took my mom’s suggestion it went high.

Nobody, though, taught me how to write prospecting letters. Instead, I read lots of books on B2C copywriting and picked up some of the psychology tips. This is different from the B2C copywriting, however. You’re not selling a product or service. It’s not a long-form copy. You’re trying to sell a meeting. You’re trying to sell “spend time with me.”

Eventually, I developed a system over the years of adapting B2C copywriting and condensing it into a format that works for B2B prospecting. In all my journey, I studied hypnosis and neuro-linguistic programming. This way, I would not only embed the processes or elements for an effective prospecting copy but also overlay them with persuasive writing.

Robert Cialdini says if you use the “if-then-becomes” formula, you increase your compliance by 60-plus percent. What I’ve done is I married 20-plus years of C-level prospecting and how to write a note. Quite frankly, this has helped my clients get better results than I did when it comes to getting a CEO appointment after sending an email. There’s a young sales development representative (SDR) in Lancaster, Pennsylvania, who holds a world record of 38 seconds from an email sent to appointment booked. That’s tough to beat right there.

If you have 20 or even 200 salespeople doing prospecting differently every day, that’s terrible inefficiency. You have to stop doing that. You can get very a standard and effective approach in place quickly. Also, companies try to hire marketers to do sales and prospecting copy. If they haven’t done this job before, it can be terrifying. Be mindful if your marketing is writing your sales and prospecting copy. You have to question why you’re doing that.

 

We hope you’ve gathered helpful tips from Matt Conway on how to empower your team to approach senior-level executives. Change your team’s mindset and train them on the skills needed to talk to the CEOs than the mid-level executives because that’s how you’ll win at prospecting.

What are some tips you can give to help leaders empower their sales team to approach senior-level executives? List them down in the comments section below.

Up Next: Sales Prospecting For the Pros: 5 Secrets to Build a Winning Cadence

 

Editor’s Note: This post was originally published on April 26, 2018, and has been updated for quality and relevancy.