5 Questions to Sell to C-Suite Execs

Posted on May 3rd, 2024 to Uncategorized

If you’ve ever found yourself preparing to sell to C-suite execs, you know it’s not just another sales call. 

Selling to executives is a high-stakes strategy that differs significantly from other sales interactions. 


When you deal with executives, you’re not just addressing immediate problems — you’re aligning with broader corporate initiatives and goals.

They’re making decisions that have a sweeping effect on the whole organization — and so the agenda you set and the questions you ask need to reflect their level of thinking.

In this post, we’re diving deep into the nuances of how to sell to C-suite execs. By the end, you’ll have learned that by asking five key questions, you can significantly enhance your ability to make impactful connections with the leaders at the helm of the business. 

Let’s get into it.

Two Main Strategies for Reaching the C-Suite

Before we discuss how to lead sales conversations with C-suite executives, let’s explore a few ways you might find yourself in these conversations. 

1. Taking the Elevator Up

Most of my clients usually enter into a sales process with someone at a lower level of the organization through a warm lead or a Champion. 

Through strategic effort and nurturing relationships, you’ve gradually ascended to higher levels of decision-making. 

This approach is like starting on the ground floor and taking the elevator up, level by level. 

It’s about building long-term relationships and proving your value at every step, ultimately earning you a ticket to the top.

The second circumstance is what I call the helicopter drop.

2. Helicopter Drop

Sometimes, you might find yourself with a direct line to sell to a C-suite exec — this is what I call the helicopter drop. 

Instead of taking the elevator up, you get dropped right into the corner office.

For most small business owners, these direct C-suite connections happen less often — but for my clients, who practice the relationship lead generation strategies I prescribe, it’s a more common occurrence.

This direct opportunity requires advanced skills and tactics, mainly because the stakes are immediately high, and there’s less room for error.

Regardless of how you land the opportunity, it’s key to understand the executive perspective before the meeting. 

Understanding the Executive Perspective

Whether you work your way up or get dropped off on the roof, the approach to sell to C-suite execs must distinctly differ from interactions with others in the company.

For these high-level executives, it’s not just about solving a problem — it’s about steering the entire organization towards its long-term goals.

Executives operate with a wide-lens view, overseeing all aspects of the organization, much like managing a six-lane highway. 

In contrast, non-C-suite roles typically focus on a single lane, concerned primarily with their department’s metrics and immediate responsibilities.

When engaging with executives, you should focus on becoming a strategic partner. Executives don’t meet with vendors; they meet with advisors. 

You can do this by:

  • Delivering value
  • Demonstrating a clear understanding of the broader business landscape
  • Explaining how your solutions align with the company’s overarching objectives

In the following sections, we’ll explore how to accomplish this by setting an agenda that addresses five executive-level questions and then the questions themselves.

Preparation for the Conversation

Before you even step into the room (virtual or otherwise) with a C-suiter, it’s crucial to have a clear and concise agenda prepared and tailored to top-level concerns. 

An influential agenda sets the stage for a productive meeting by highlighting key discussion points that align with the executive’s strategic goals and allows for unexpected turns in the conversation.

By meticulously preparing for your interaction with C-suite executives, you not only increase your chances of a successful outcome. You also strengthen your position as a trusted advisor capable of meaningfully contributing to the executive agenda. 

As we move forward, we’ll delve into the questions to include on the agenda to make the most impact, uncover any tensions and get the information you need to move toward a deal.

Question #1: Is solving this problem mission critical?

When engaging in a sales conversation with a C-suite executive, asking, “Is solving this problem mission critical?” is a rich starting point for a few strategic reasons:

1. Alignment with Executive Priorities

C-suite executives are inundated with various challenges and potential projects. By asking if a particular issue is indeed a problem that needs solving, you’re helping the executive assess and affirm its relevance to the organization’s overarching goals. 

This question ensures that the conversation is aligned with their current strategic priorities, making the discussion immediately more relevant and compelling.

2. Efficiency and Respect for Time

Executives value efficiency and concise communication. By directly addressing whether the issue is significant enough to warrant attention, you respect their time and demonstrate your understanding of their need to focus on high-impact initiatives. 

This approach shows that you’re more than just there to push a service but to engage meaningfully on issues that merit executive attention.

Asking this question does put you at risk of hearing a no, but it also engenders a significant amount of trust in you from the executive. 

Plus, it saves you from going down a road with expectations that might not lead to anywhere.

Once you’ve established the answer to this question, it’s time to lead them to the next: What are the options to solve the problem?

Question #2: What are our options?

Now that you’ve established the problem and confirmed that the leader needs to solve it, your next job is to lead them through some options. 

By leaning into your experience and expertise, you can show them the available opportunities they can employ to solve the problem beyond the obvious surface-level solutions they may be aware of. 

For example, suppose the CRO is facing a sales problem. 

In that case, they might want to explore different solutions, including revamping the sales strategy to target new markets, implementing advanced sales analytics tools to better understand customer behavior, or redesigning incentive programs to boost sales team motivation.

Each solution offers a different approach to solving the underlying issue and could significantly improve the organization’s sales performance.

You’re establishing yourself as a valued and trusted advisor by helping the CRO see the path to the solution, including who they might need to call upon. 

Question #3: Who can help us solve it?

As you’ve probably noticed, you’re taking a leading role in this conversation by helping them diagnose the problem, explore their options and map out the path to getting it done. 

This is a massive win because one of the biggest barriers to selling your services is the overwhelm about how to implement the solutions. 

By laying it all out, you’re doing what it takes to sell a deal. 

As I often say, for subject-matter experts like you, the deal doesn’t rest on how good you are at what you do (they know your capabilities); it’s about what’s getting gummed up internally.

So, when it comes to who can help the C-suite executive solve it, you’ve already laid the important groundwork and established yourself as a solid candidate.

And you can help them see who else can contribute to solving it, including those on internal teams and the outside help available to them. 

Question #4: What resources do we need?

Determining the necessary resources is a pivotal step when engaging with a CEO to tackle significant challenges. 

This part of the conversation should encompass a thorough assessment of the people (as detailed above), time, and budget needed to execute the solution effectively.

Let’s look at each in detail. 


Estimate the solution’s implementation timeline, including key milestones and deadlines. This helps set realistic expectations and aligns the project timeline with other strategic priorities within the company.


Assess the financial investment required to mobilize the necessary resources and achieve the desired outcomes. This includes direct costs like hiring additional staff or purchasing new technology and indirect costs such as training and potential disruptions to regular operations.

By discussing and defining these resources upfront, you can ensure that the plan is feasible and that the CEO fully understands the commitment required to address the problem effectively. 

This clarity helps secure the necessary approvals and support, and also positions the project for success by aligning it with the organization’s capabilities and strategic goals.

This process also helps proactively avoid any obstacles to your deal getting done or problems with executing your plan. 

Question #5: Where might this go wrong?

Discussing potential pitfalls is critical to any strategic conversation with C-suite executives, especially when decisions could have sweeping implications for the company. 

Whether implementing a new tech system, undergoing significant cultural changes, or reshaping core business processes, recognizing and planning for these potential issues upfront can significantly mitigate risks and set the stage for a smoother execution for you and the company.

When we’re laying out the possible pitfalls, one key thing to hash out is when these issues might pop up. 

It’s in your best interest to diplomatically pose the question: do they want to tackle this head-on early when you can manage it better or later? (After the middle-of-the-night panic attack!)

By asking this question, you can help manage any immediate fears and provide reassurance about handling any bumps or risks more effectively. 

Client Case Study: 7-Figure Deal

Last year, I coached a client who had been consulting with a company for many years, mainly working with leaders just below the C-suite. 

She had been nurturing internal relationships and delivering solid value when she got the call to meet with the CEO about a specific scope of work.

Despite knowing the organization inside and out, my client knew that this meeting required a different approach. We jumped on a call to strategize how she would lead the meeting based on the five questions I’ve outlined in this post.

The company had regularly renewed 300-400K contracts, but after she impressed the CEO in the meeting, the CEO signed a nearly $1 million contract for an 8-month engagement.

Recap: How to sell to C-suite execs

Wrapping it all up, selling to a C-suite execs isn’t just about presenting a product or service—it’s about stepping into their world and aligning with their broader vision for their company. 

Whether climbing the corporate ladder “elevator-style” or parachuting in via “helicopter drop,” the key lies in framing the conversation. 

You’re not just solving immediate problems but helping steer the ship toward long-term success. 

By setting a strategic agenda, asking the right questions upfront, and being prepared to dive deep into discussions about potential risks and the resources needed, you position yourself as more than just a vendor—a trusted advisor.

While asking these questions might seem counterintuitive to signing a deal, by doing so, you make yourself indispensable by demonstrating your understanding of their world—overseeing the entire “six-lane highway” of their organization. 

And in the world of high-stakes executive sales, being indispensable is the ultimate goal.

Join the next Sales Roundtable for more high-level sales insight and discussion.

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