Landing a meeting with a top exec is no easy feat. With their busy schedules and armies of gatekeepers, gaining access to these decision makers only comes with a well-developed network, intelligent networking, a successful cold email, or by sheer luck.

But getting the meeting is just the beginning. After successfully navigating through a series of assistants and lower-level decision makers, you have one shot to impress the top leader in this organization.

Play your cards right and you’ll end up with a big opportunity and a shortened sales cycle. Fumble, and your odds of ever selling to this prospect or account disappear faster than ice cream on a warm summer day.

There are a lot of great posts out there that will help you prospect senior level people and strategies for landing the appointment. We’ve even written posts about how to get past the gatekeeper. But in this post, I want to cover how you can maximize the odds of that meeting going well and successfully closing a big deal.

1) Preparing For The Meeting Ahead of Time

Before even entering the executive’s office, it’s essential that you’ve done your homework. A few things to do ahead of time include:

Research the company’s goals and objectives

Whether this executive makes the final decision or needs to run a proposal by the CEO/CFO, they’ll only be interested in your business if you can clearly define how partnering with you will benefit their bottom-line through one or several KPIs.

Although you can ask the executive during the meeting for more details around their product, prices, and the LTV (lifetime value) of their customers through the discovery process, if you can discover these details before the meeting you’ll have more time during the conversation to go into more detail regarding their needs and your service.

Deduce the executive’s professional goals and interests

While the executive you’re meeting with is certainly invested in the success of the organization, your research shouldn’t start and end with their business. Dive a little deeper to discover what the executive’s own goals might be.

From moving up within the organization, to establishing themselves as an industry thought leader, to building a healthy professional network, executives are ambitious – and finding a way to help them achieve their next win can result in substantially more involvement on their part.

Yes, this win may come from delivering mind-blowing results after implementing your product – but it could also be through a new connection, speaking engagement, or any other opportunity that you’re able to assist them with. The more you know about the executive directly, the more value you will be able to contribute during the conversation.

In order to gain the respect and potential business of an executive, you need to be an expert. This doesn’t mean you need to know more about the industry than the exec, but you should have a grasp on what’s going on and be able to share a view novel insights.

Thanks to Google it doesn’t need to take long to establish yourself as an expert. Simply:

  • Spend a few minutes doing a quick overview of the industry.
  • Read one or two niche pieces about the industry that’s relevant to the executive and your business.
  • Develop your own perspective on the issue.
  • Run your perspective by someone else in the industry to ensure that it’s logical, relevant, and thoughtful.

By entering the meeting with the ability to speak on issues that are important to the executive, you’ll reveal both an interest in their success and present yourself in a way that shows you are capable of helping them achieve their goals.

Plan out the conversation’s major milestones

You should view the conversation with an executive more as a journey than a bullet-pointed list of to-dos. While you should have a clear starting and ending point, along with a few must-visit destinations along the way, be sure to include plenty of room during the conversation to allow for pit stops or detours that come up as the meeting progresses.

Ago Cluytens shares that it’s essential to know how to start the conversation. What questions, topics, and interesting facts will you launch the conversation with? While much of the conversation can flow, it can be helpful to have a scripted intro and conclusion to ensure that you are clear and succinct where it matters most.

2) Managing The Meeting Effectively

Once in the meeting starts, there are a few things you can do to keep the conversation efficient and beneficial for both you and the executive…

Remind the executive who you are

Most executives have a full schedule and often forget why a specific meeting’s on their calendar. Take a moment to quickly remind the executive who you are, how you were introduced, and why you’re meeting.

This will bring the executive up to speed so they can spend the rest of the meeting engaged with your message rather than trying to play catch-up.

Start the conversation on a personal note when appropriate

Although executives are busy, they’re still people – and when time permits they enjoy connecting on a personal level. Read the situation (and perhaps ask their assistant ahead of time) to decide how likely they are to engage in small talk, but don’t hesitate to make one or two comments that provide them with the opportunity to engage further.

Do they have an interesting photograph on the wall or book on their desk? Ask a quick question about it. If they open up, feel free to sidetrack the conversation momentarily. If, on the other hand, they seem to shut down any further discussion, respect their busy schedule and cut straight to the point.

Begin the business conversation in a way that establishes your credibility

Ago Cluyten believes that there are four key points to hit when beginning your conversation with someone in the c-suite:

  1. Come across as an expert.
  2. Build the relationship.
  3. Stroke their ego a little.
  4. Discover their agenda.

Ago recommends that you do this by making the most of the research you’ve done ahead of time to develop a succinct paragraph that hits all four of these points, such as:

“Hey John, I was struck by one of your comments in the Q3 analyst update. When you talked about your firm’s expansion into emerging markets, it seems you were very successful at capturing market share in Asia-Pacific. Our own research has shown that the real challenge is often not just capturing market share, but maintaining it over time. I wonder: what are your thoughts on that?”

A response like this hits all four points and makes it easy to move the conversation forward effectively.

Ask intelligent questions

Each executive has KPIs and metrics that they are of specific interest to them – and you should target your pitch appropriately. How do you know which questions to ask?

To start, simply look at their job title. A CFO is going to be interested in discussing the company’s ROI and bottom-line, a CMO may prefer to discuss their innovations in marketing, and the CTO will love sharing the challenges around keeping up with the latest technological advances.

According to Kevin Dorsey, one of the best questions you can ask is: “What’s the LTV (lifetime value) of a client?”. Dorsey states that he almost never hears this question and it’s one of the most beneficial when determining how much your service is actually worth.

Mold your questions to the specific individual to develop rapport, motivate them to share, and ultimately, discover how to connect your product with their perceived needs.

Asking the right questions can direct the conversation where you need it to go while still allowing the executive to spend the majority of the time talking.

Expect to be tested and critiqued

It’s not uncommon for an executive to ask you hard questions in an attempt to get you to trip over your words or feel intimidated. This is especially likely to happen when meeting with an analytical executive in finance or technology.

If this happens it is absolutely crucial for you to maintain poise and control. Take a few slow, deep breaths and remind yourself that you’re grounded and are perfectly capable of offering an intelligent response.

Most of the time, when these hard questions are asked, the executive is more interested in how you respond then your actual response. Provide a witty response (without being offensive), offer a well-grounded answer, or simply affirm the quality of the executive’s answer and admit you don’t have a good response.

As long as you can stay collected during the conversation, you’ll be able to provide legitimate responses to anything the executive throws your way.

Add value to the conversation

Don’t jump straight to how your product will solve all of their problems. Once you start delivering anything remotely similar to a sales pitch the executive will prepare to end the meeting and move on with their day. You don’t want this to happen until you’re ready.

Offer new perspectives or mention solutions unrelated to your brand that can assist the executive with solving specific problems. Did you have a previous client with a similar challenge? Share how they went about overcoming it – and only mention your product in passing during this story, if at all.

Although you want to end the conversation appropriately, until the end of the meeting you want to maximize the value-add that you’re able to provide to the prospect.

Leave the meeting with a clear next step

You don’t need to end the meeting with a sale, but you do need to close it with a very clear next step. Geoffrey James recommends allowing the executive to decide on where to go next. Meanwhile, Cluytens suggest giving the executive 2-3 potential next steps and allowing them to mold an answer from those (likely merging these ideas into an additional conclusion).

Regardless of which method you choose, make every effort to get the executive making a decision about the next step. This gives you more credibility and clout the next time you call the organization as you can reference the executive’s request.

3) Following Up Appropriately

Just because you successfully made it through the meeting doesn’t mean you’re done. While appropriate follow up is important for any sales pitch, it’s particularly important after meeting with an executive. Maximize the value of your follow up with these three tips:

Quickly deliver on your post-meeting promises

Did you tell the exec that you would provide detailed numbers for her to share with her CFO? Did you agree to make a connection with someone else in your industry or send over a white paper the executive may benefit from?

If so, deliver on your promises right away. As soon as you have time – preferably within a 24-hour window – send over all of the information and details you agreed to. Along with this email offer a thank-you for the conversation and share your enthusiasm regarding your future partnership.

By responding quickly, you show that you are able to deliver results quickly and ensure that you make contact before the prospect completely forgets about your meeting together.

Remain the single point of contact during the sales process

Many sales teams like to toss clients around from one person to another. A sales rep pulls someone in and then connects with with an AE, who may eventually direct them to a more senior AE.

While this may be acceptable when working with lower-level decision makers, the moment your organization lands a senior-level client, allow them to maintain a single point of contact with your company. If you were the one in the meeting, allow them to reach out to you any time they have questions or answers, and strive to be the sole individual reaching out to them.

An executive can quickly lose track of who to call for what issue. By delivering all communication through a single individual, you can save the executive time filtering through emails and searching for contacts. This will show an additional level of respect for the client on your part, and they will certainly be grateful for the communication ease this brings.

Adjust to fit their schedule

Sales reps and account executives frequently cancel and reschedule meetings. And this drives executives crazy!

Not only does this suggest that you view your calendar as more important than theirs, it also reveals a lack of organization on your part. If you can’t keep your promises when making a sale, why should they believe you’ll deliver once you have their money?

Make every effort to fit your schedule around the needs of the executive and they will see you as a valuable partner who invested in the success of their organization – which will ultimately result in you landing their businesses.


If you’ve landed a meeting with an executive, then you’re well on your way to another large client. By investing the appropriate amount of time in preparing for this meeting, you can ensure that meeting flows smoothly and results in a mutually beneficial partnership.

After the meeting takes place (or if you’ve already mastered the art of closing executive prospects) share your experience in the comments below to inspire the rest of us.