Sales strategy for selling to CEOs: HOW TO GET A MEETING WITH THE C-SUITE

Developing a sales strategy for selling to CEOs is something that is very close to my heart. So close that I’ve spent the past 6 years building a business focused on extracting actionable customer insights. This article will reveal the most successful strategies.

I interviewed a customer recently, as part of a workshop I was running for a client in the Technology industry. One topic they asked me to talk about was how to harness the ‘Voice of our Customer’ and get inside the head of a C-suite executive.

Greg* was an open book, answering every question I put to him in an honest, thoughtful and often humorous way. Questions like:

  • Could you share your observations about the evolution in the IT industry, during the course of your career?
  • What’s your perspective on the changing needs of customers buying technology solutions today vs 10 years ago?
  • Can you share some stories about the good, the bad and the ugly of engaging with IT vendors, over the course of your career?
  • What advice do you have for young sales people, just starting out, who want to add value and be relevant to the customers they serve?

At the conclusion of our interview Greg was gracious enough to stick around a while longer and take questions from floor. A couple of the insights he shared really struck a chord with me. When one of the audience asked Greg how a young sales person could engage with or add value to him, Greg explained that he never picks up his desk phone, rarely responded to unsolicited emails, but always responds to an introduction made by someone within his peer network.

Find someone to introduce you

As tools like Linkedin and Facebook continue to demonstrate on a daily basis, the power of our networks is extraordinary and often underutilised. Overtime, your network should become the most valuable asset that you have in your sales arsenal…assuming you know how to extract value from it of course.

One of the world’s leading authorities on the power of networks is an incredibly interesting and gifted communicator called Kingsley Amis, who I had the pleasure of meeting in Sydney late last year. Kingsley gives a fascinating TedX Talk exploring the power of building personal networks and diasporas, both locally and globally. A couple of his tips which really stood out for me included:

  • Build lots of weak connections
  • Develop plenty of social capital
  • Take the time to audit your network
  • Be high-tech and high-touch
  • Talk to strangers

For younger sales professionals or those transitioning from one career path to another, building a strong network can seem an impossible task, but believe me it isn’t. Here’s a few tips of mine, to add to Kingsley’s great ideas.

  1. Focus on creating a small number of strong connections first and then leverage those to begin building a larger number of weak connections.
  2. Give freely of your knowledge and insights and always have the heart of a teacher
  3. Be authentic and open in your communications
  4. Share valuable content with your peer group as often as you can. The more relevant and personalised the better.
  5. I’ll start you off, any young sales person reading this article is welcome to reach out and connect with me and see who I’m connected to. But please don’t send a bland Linkedin connection request or email take the 30 seconds to write a real note to introduce yourself.

Don’t be intimidated

Selling to the C-suite typically makes sales people uncomfortable because of the stigma of the these senior executives being unreachable or intimidating. Another interesting insight from this workshop, was just how intimidated many of the group felt, reaching out to someone very senior in a customer or prospect. So much time and effort is expended on how to get these meetings, while often not enough time is spent focusing on how to have an impactful conversation and earn the right to progress the discussion.

The good news, as Greg was quick to remind us, is that senior executives were also starting out in their careers once and they aren’t necessarily as unreachable as you might think. As he explained, it’s his job to make the company more profitable or help it run more smoothly. So if a vendor proposes an interesting or innovative way to do that, any senior executive worth their salt, will take the time to listen. The bad news as we all know is that most C-suite execs are exceptionally busy people, so your window of opportunity is likely to be small.

Master the Art of Listening

My advice for selling to the C-suite is the same as my advice for selling to anyone at all: Listen. A CEO will listen to you because she’s hoping you can solve a problem for her or present her with some new information. Take the time to really understand what the problem is, talk to the CEO in the language she uses in her business and show her through your words and actions, that you understand. Then and only then, can you even consider proposing a solution or offering an insight.

Takeaway: Let listening become your bedrock sales skill and you’ll build a successful career

But also . . . honor their time

“Wise men speak because they have something to say; fools because they have to say something.”  Plato

Whether Plato actually said this or not, it’s perfectly applicable to sales, particularly when you’re dealing with very busy CEOs who see a lot of vendors.

  • Do your research and prepare well
  • Be clear in your own mind what you are hoping to achieve with each interaction (and ‘making the sale’ should not be your only goal)
  • Be succinct
  • Be aware of your time constraints and structure your content accordingly
  • Most of all be yourself

Takeaway: In sales and in life, time is our most precious commodity, use it wisely and guard it

Make a connection with the gatekeeper

My advice is to never try to trick or circumvent the Executive Assistant to gain access to a senior leader. Why? Because the CEO has charged this individual with guarding their precious time. In the unlikely event you do manage to bypass the executive assistant, the CEO is likely to reprimand them for not doing their job properly and you’ve just made an enemy for life. The best strategy is to actually create a relationship with the gatekeeper.

When I wanted to interview the CEO of a large multinational for a business book I was writing, I started by ringing his EA and asking her about his availability, his preferred method of interacting with interviewers and whether I could send her some information. I didn’t make any demands on her during that introductory phone call and she wasn’t put in the position of having to say yes or no to a meeting request. But a couple of days later, she took the initiative and contacted me to suggest a couple of dates when the CEO would have some time free to meet with me.”

Takeaway: Gatekeepers serve an important purposes, respect them, don’t circumvent them

Be Honest

The Hollywood stereotype of a salesperson is a slick, smooth-talking, snake oil salesman. In real life, that’s called being a con-man and thankfully the world of B2B selling is slowly but surely ridding itself of these type of characters.

Many salespeople feel the need to stretch the truth or avoid saying no to a prospective customer, either due to insecurity in their own knowledge or from fear that the prospect will walk away. A far better strategy is to highlight any potential risks, difficulties or stumbling blocks early on in your interactions. Not only will this serve to address concerns that may arise further down the track, but it will also inspire trust and confidence in you, which is a critical quality for closing sales. If they walk away, then you have done both them and you a favour, because they never would have bought in the end.

If a prospective customer wants something you can’t deliver, be up front about it, while letting them know what you can deliver instead. CEOs know when something sounds too good to be true. If you don’t make it necessary for them to separate fact from needless optimism, they will respect you for it.

A solid sales strategy is a simple strategy

These tips may sound basic, but that’s ok. Despite what some sales experts might like you to believe, selling isn’t rocket science, it’s been happening in a variety of guises for thousands of years. Sure the tools, techniques and terminology may have shifted a little (although less so than you might think) but in this author’s opinion at least, the fundamentals are still exactly the same.


* Greg’s name was changed for this article

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Cian McLoughlin

Cian McLoughlin

Cian McLoughlin is the founder and CEO of Trinity Perspectives, a boutique sales consulting and advisory business. He is passionate about the world of enterprise selling and committed to improving the negative perceptions of this industry.

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