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The Ultimate Guide To Engaging the C-Suite

Engaging C-Suite Executives

No matter what the size of your organisation, for a sales team the opportunity to engage with and develop relationships with C-level executives is a huge opportunity.

In this article, we explore what it means to engage the C-Suite, why the approach differs when you move further up the value chain and we offer specific advice and guidance on how to build relationships in the right way.

There are also plenty of mistakes that can be made along the way – sometimes fatal to the relationship. Through this article, we show you how to avoid the most common and kick off any relationship with the end in mind.

Let’s start with the fundamentals.

What is the C-Suite?

Members of the ‘C Suite’ or ‘C Level’ are those in the highest-ranking positions of a company. They are the people who fill executive roles regarded as the most influential, such as the Chief Executive Officer or Chief Financial Officer. (The “C” in C-Suite relates to the term “chief”).

Due to the C-level executive’s authority and influence over making key decisions within their organisation, they are perhaps the most daunting prospects and clients to engage with, but also carry the most influence.

Given their status, it is vital to understand the right way to engage these executives to forge strong connections and win the bigger, more transformational deals they offer.

What role does the C-Suite play in decision-making?

The executive committee is a slightly different world from any other.

There are three key elements within the business the C-Suite has control over:

  • Creating strategy
  • Creating budget
  • Creating sponsorship

Bearing this in mind, a C-level executive can fill their schedule five times over with action items. They are the epitome of busy and time-poor.

What this means is the person with whom they choose to begin a new project and with whom to have a working relationship is going to be analysed intensely to ensure a successful outcome for both parties.

With the limited time a C-level executive has in any one day, they will ask the question: is this relationship worth the time and effort?

Why is it important to communicate with the C-Suite?

The reason that makes engaging with the C-Suite so important is multifaceted and, because of this, it is often met with great trepidation.

We are all very aware that it is hard to attain high-level contacts and establish solid communication. The process of engaging with and developing high level relationships with C-level influencers can take a long time, often months and years. For many, it can feel like a risk – placing a lot of time and focus on a long-term play that may lead to them missing out on other opportunities in the meantime.

Understanding the difficulty in navigating that journey leads to the question: why bother?

Influential opinions

The most important reason for engaging with the C-Suite is not for their budget holding, as they will delegate that. It is primarily for the influence they offer to you.

The influence of the C-Suite is two-fold:

  1. Positive Influence. If a C-level executive has an insightful and helpful experience working with you, they are more than likely to be an advocate for you and provide valuable sponsorship. It may seem obvious but making a strong impression can be crucial for your reputation.
  2. Negative Influence. The adverse effect is if there is no “noise”. Whether it be a bad experience or a completely forgettable one if a C-Suite exec is asked for their opinion of you and they have nothing to report

A well-established relationship

As well as the external influence the C-Suite can have, the other important part of having a well-established relationship revolves around potential problems.

Ultimately, a win is the start of a project and with the start of a new project comes unavoidable issues. When things go wrong, it is incredibly important to have senior sponsorship to support you. Therefore, you must have a strong and well-maintained relationship at this point.

This maintenance of engagement will help you ‘win’ multiple times over, as it means you are closer to that executive in every moment you might need them.

The correct way to build a connection

Given the authority, influence and importance the C-Suite holds, how you engage with them must reflect this in the intricacy of your approach. The advisor that C-level executives want in their inner circle is “somebody of interest” somebody they want to spend a bit of time with and someone who will always be of value.

You have to tick all of their boxes and to do so you must consider the client you are addressing. You need to think about their voice as well as what it would be like to stand in their shoes. You must also be able to adapt in the moment of your meeting and have every tool available for unanticipated conversations.

There is a correct way to build a connection that will bring the best outcomes for you both. This means taking your mindset and your energy to a different place.

Initial Encounter

It is essential to remember that in your initial encounter with a C-level executive, you can quickly push them away if you are not focused fully on them.

As we have established, it is a long road to get to this first point of contact and you can easily find yourself preoccupied with all of the time you spent preparing, all of your thousands of questions and every piece of information you wish to attain.

Ask yourself, where is the spotlight? In these early stages of the engagement, the spotlight should always be on the other person, not on you. And the executive will pick up on this quickly.

With this preoccupation comes the over-playing of self-orientation. An experienced executive will sense within a few moments if the spotlight has been moved away from them and their business. They will begin to wonder why they have invested their precious time with someone who is not aligned with their needs.

That is why it is key that you are in tune with the C-Suite’s language, their tone, their focus, and their highest needs. Being ‘in tune’ allows you to gain the intelligence you need to be ‘in sync’ with what they are looking to achieve.

A peer-to-peer mindset

It’s easy to finally get the meeting you’ve been waiting for and then make the mistake of coming across as over-enthusiastic in an attempt to build rapport. Worse is adhering to the old-fashioned idea that you should win over your client by trying to become their best friend.

This can jeopardise the relationship before it’s even begun as you deny yourself the status of a peer.

It is important to avoid the pitfall of subordination. It is not what C-Suite individuals want. They want to have a mature conversation with someone who can challenge them.

Some executives may want this kind of relationship but many want an appropriate connection for how they operate. This must be a relationship that has empathy, but empathy is different to rapport.

Rather than playing a subordinate role, remember that you are there as a professional. Try to enter your meeting with a “peer-to-peer” mindset and have the conversation they expect at a C-Suite level.

The voice of the client

The first major thing to consider in your efforts to engage the C-Suite and win your business is the voice of the client. The concept of peer-to-peer interaction links us directly to the clear advantages of understanding the voice of the client and being in tune with the individual to whom you are selling.

The client is a human being

The fundamental thing to remember is that the client is a human being and every client you meet will be a different type of human being.

With this in mind, the first thing to think of in preparation is how this particular individual might be feeling, how they are wired and what they may be thinking about as you step into the meeting room. Then, once you have those foundations established, you can go into strategy and consider:

  • How is the client’s business positioned in the market?
  • Have they got a competitive advantage?
  • How are they positioned for the future?
  • How are they going to win?

(These are just a few things to think about amongst many others – business model, financial model, rhythms and relationships in the executive committee and where they are amongst their peers, the list goes on.)

Most importantly, your understanding of the client’s role, their ambitions and how aligned they are to possible power shifts will directly influence the client’s opinion of you as you engage with them. If you haven’t considered and researched these issues beyond the basics of industry, market or corporate issues then you are not going to get close.

A higher-level agenda

For most senior executives, there is usually a higher-level agenda going on in their heads. Sometimes it is unspoken and a skilled advisor can figure out what that higher level is.

It could be about a business transaction, a relationship with the shareholder, current trading performance or it could be something outside of the business. Being able to decipher exactly what the C-Suite is focused on without directly questioning them is a great skill to have.

Being in the moment

The second element of engaging the C-Suite is your ability to always be in the moment. As we have established, every client is different and the meeting you are expecting to have may take a very different direction depending on how that particular client is feeling on the day. Understanding this and being prepared for a change of direction will give you the adaptability you need to impress the C-Suite in whatever turn of events.

Confidence is key

The first step to being in the moment is to be genuinely confident. As we have previously mentioned, feeling comfortable in your own skin and being capable of engaging in a peer-to-peer conversation is vital when forming a relationship with a C-level exec. To project this mentality you need to be self-assured.

Operating at the C-Suite level, one could assume that people naturally exude huge amounts of confidence but that isn’t the case. It is a big event and, understandably, anxiety and nerves can easily stunt your ability to communicate well. At this point, it will become nearly impossible to listen and this will affect your general behaviour.

Being prepared

Preparation is the key thing that gives you the confidence and insight to act accordingly in the moment. Before you engage with the C-Suite here are some tips for being well-prepared:

  1. For a half an hour to an hour meeting, you should spend at least three to four hours preparing and learning about the client. This refers back to the voice of the client. The more you know the less likely you are to be blindsided in case of a direction change.
  2. Think about what you will be doing fifteen, ten and five minutes before you go into the meeting. This timeframe is when you need to get yourself into the correct mindset. Don’t enter the meeting room distracted, it will not go down well.
  3. Think hard about the first two minutes of the meeting. What are the best questions that you can have ready for a strong start? These first few questions are very important and if they’re pitched too low or don’t sound particularly interesting you risk losing your client’s attention.
  4. Don’t drag out the niceties. The best thing to do is to get to the point. Come equipped with some facts and figures and try a conversation starter that will get you exploring what is going on in the market.
  5. Aim to end with an even stronger finish- this is something we will come to later in the blog.

Example scenarios

So, you are prepared, you are confident and you are ready for your C-Suite meeting.

There is a particular project you expect to talk about and you have rehearsed and researched intensely. You walk into your meeting and begin your pitch. Out of the blue, your client says:

“I don’t want to talk about that today, I have an issue elsewhere…”

This is where all of that preparation is going to serve you. This change of pathway in a meeting can be triggered by anything, from your client’s mood to a topic-changing question and at this level you have to be able to go wherever your client wants. You have to be able to judge this moment and adapt, do not try to force your own agenda.

Another scenario to be prepared for is if there wasn’t a specific purpose set up for the meeting. In this scenario having three or four topics prepared means you have plenty of reserves to fall back on if you are in the driving seat.

Winning the Inner Game

Reaching this level of confidence and preparation has been dubbed ‘winning the inner game’ by the Win Academy. You can learn even more about it, and many other topics covered in this blog, by engaging in Win Academy programmes.

Offering and gaining insight

The third key part of engaging with the C-Suite that we will cover in this article is the offering and gaining of insight. This comes through the questions asked and answered in your C-Suite meeting. The quality of these questions and how well they are being exchanged is often a fantastic indication of how a meeting is going.

Having said this, the Win Academy has found that the weakest area in the pursuit of winning business is the quality of questions. When put on the spot it is concerning how limiting the types of questions are that people ask. They can be too obvious, too operational and quite often they are not expansive enough.

One of the most powerful skills you can have is the ability to ask questions that no one can answer.

It prompts thought and consideration from the buyer and takes the engagement to a new level. One of the most valuable things you can do is offer your client 100% of your attention and you do this by asking these types of questions.

Low-value questions

If someone can ask you more questions within a nanosecond of you finishing your first question, or, they can’t wait for you to finish what you’re about to say it means they have already formulated the answer. This indicates a low-value question.

You have to ask yourself, as the questioner, for whose benefit are you asking these questions? Are you there because you are trying to gain insight for yourself?

Although you are gathering intelligence and information, the issue with questions that begin with “how many”, “when”, “who” and “what happened” is that they are looking largely at the past.

You should most likely know about the past and the client knows about the past too. Although you are showing an interest in their business, they are questions the client will have answered many times over. Instead, you want to ask high-value questions the client hasn’t necessarily thought of before.

High-value questions

An example of a high-value question is one that may involve a challenge. For instance, if you question your client’s transformational plan and how it could be made better, that is the type of question that lingers.

By reframing questions they were expecting into ones they hadn’t previously considered you become a person of interest and somebody they want to invest time into.

Avoid using uncertain language within your questions. Using terms such as “depends” shows a lack of assertiveness and can diminish the confidence your client has in your decision-making and planning.

Some of these challenging questions require courage to ask. They aren’t the questions that naturally build rapport and they might stretch the other person in a place you may not have thought you were comfortable doing so. However, if you’re not going to be courageous or comfortable asking high-value questions then you aren’t going to be memorable. If you’re not a person of interest then you’re not going to get the next meeting.

Emotional connection

The type of questions you put forward in your meeting relates to the kind of relationship you wish to build with your client.

Although clients are unlikely to be looking for friends, having an emotional connection with your client is fundamental. It demonstrates you are keen, you are excited and you are a peer. This connection comes from your likability.

Alongside good body language, confidence and solid preparation, likability is directly linked with the questions you are willing to put forward. This is where you can gain your client’s respect. By asking these provocative and in-depth questions of value you are far more likely to create a stronger emotional connection and encourage them to trust you and your ideas.

How do you approach the C-Suite if you don’t have a big brand?

Something that can make this experience even more intimidating is if you are going into the sales process without the backing of a big brand behind you.

Perception is projection

Understandably it is most likely that the big brands will get the first meeting, but there is a lot of capability spread around the market for particular point places and this brings the opportunity to build relationships.

Insecurity regarding this circumstance comes from your belief in why a client would listen to you, who would take notice and where your credibility comes from.

Perception is projection. No matter the brand behind you you have reached this level because you have that expertise. Otherwise, you shouldn’t be there.

At this stage, the client isn’t judging you on your brand. They are judging you on the:

  • Credibility
  • Know-how
  • Experience
  • Strength of content
  • The value you add to the relationship

If you have confidence in these factors and you can clearly articulate your purpose then there is no reason you cannot reach the engagement you set out to achieve.

What makes a strong finish?

The worst way a meeting with the C-Suite can end is in ambiguity. You can also fall into the trap of being so preoccupied with the next meeting that your subtlety in selling becomes obvious. Both outcomes are not ideal and you can lose your client as easily at this point as you can at the start.

When it comes to the end of the meeting these are some things you can do to ensure a satisfying and strong finish:


Bring the focus back around to the actions you have agreed upon within your conversation. Speak about what the next steps will be, the outcomes that you should expect and who owns them. Gain a sense of mutual ownership.


Acknowledge the value of the time you have spent in this meeting and thank your client. By thanking them, and ideally having your client thank you back, you ensure the meeting ends on a positive note with forward-looking energy.


Summarising the content of the meeting means everyone is clear on the point you have reached. You can also talk about something you’ve learnt or something you can send your client in the time between now and your next meeting. The constant adding of value shows your client that you are a person worth investing in.

Follow up:

Everyone knows the importance of follow-up, yet few practice what they preach. Following up after every encounter to continue to add value and demonstrate a commitment to developing the relationship is key to succeeding long-term.

Assess the meeting

In meetings further down a company’s sales cycle, it is understandable that you may need to ask some precise questions about the next step to keep momentum.

But a meeting with the C-Suite is different and, at this point, it could be a beneficial first move to try and judge the meeting for yourself. Debriefing on your own or with someone who might have solid insight, rather than the people you spoke to directly, could bring you up to speed whilst retaining subtlety.


Amongst the plethora of information we have presented in this article when it comes to engaging the C-Suite in your pursuit of sales we can recognise three vital elements:

  1. The voice of the client. This is the understanding of the client’s world and trying to experience what they are experiencing. You can’t possibly completely understand somebody and clients don’t expect you to, but they do expect you to be making a strong effort to understand them.
  2. Being in the moment. This is about the importance of preparation. It also demands you are comfortable in your skin and capable of being in a space where you are peer-to-peer. You aren’t worried or distracted but instead, you are there to focus on the client and add value to them.
  3. The offering and gaining of insight. This is your ability to ask fantastic questions. The ability to be able to offer or ask questions that perhaps other people are not brave enough to do.

This article was developed from the collaborative advice and experience our three of our most experienced Win Academy coaches, including:

  • Martin Coburn, MD and Founder of The Win Academy, has been a speaker and consultant for more than 20 years. He helps sales leaders accelerate performance improvement and unlock the potential of their teams with his willingness to challenge them and provoke outcome-focused discussion.
  • Mark Cheshire is a C-Suite specialist with 30 years of banking experience, including Group CEO of an Aim-listed plc. For the last 12 years, he has been coaching and mentoring clients to reach the “inner circle” in the C-Suite world.
  • Nick Sandall is a C-Suite specialist with 33 years of client-facing experience at Andersen and Deloitte. He has coached, mentored and developed leadership in professional services firms, Fintechs and healthcare companies for the past four years, bringing large sales experience and strong relationships in the C-Suite.

Watch the full conversation here.

Discover how The Win Academy helps develop your sales team to take advantage of more C-level opportunities with our Engaging The C-Suite programme. Click here for more details.