Because Customer Success is such a new industry, most Customer Sucess leaders don’t come from an executive background. They don’t have decades of experience selling their ideas up the chain. Customer Success (CS) hasn’t been around that long! So, one issue we’ve seen come up over and over again is how unprepared CS leaders feel as they make the transition to higher rungs on the company ladder. This problem goes both ways. Executives don’t always understand what CS is for or what it does. If you’re stepping into a situation like that, the prospect of educating up the chain can be incredibly daunting.

Unfortunately, this results in CS leaders getting so wrapped up in what they want to say (and how important it is!) that they forget the other half of the equation – asking the question, “What is the best way to convey this information so that it gets absorbed by my audience?” There is no one correct answer to this question. You need to understand your audience, their preferences and personalities, and tailor the message to them.

In this paper, we’ll outline practical methods for tailoring your approach to your audience. We’ll also discuss strategies to discover your C-suite’s sweet spots and give you CS-specific ideas to integrate into how you communicate up the chain of command – from emails to full-blown presentations.

Why should I care about my C-suite’s personality types?

The evolution of Customer Success

Today, leading companies recognize the critical role Customer Success plays in the overall health and growth of their business. They involve CS in high-level conversations. They have Customer Success leaders in strategic senior roles. They bring those leaders in to present their insights to the C-suite and the board of directors. In short, as XaaS businesses have grown, so has the influence and maturity of Customer Success.

It wasn’t always this way. In the beginning, many leadership teams didn’t pay close attention to Customer Success. More often than not, they would lump CS in with Support (we know better now!) or view the group through the lens of their specific charter, usually onboarding or adoption. As the industry gained momentum, we all learned what Customer Success is truly capable of – driving strategic growth across the entire business. Now, CS organizations are more likely to tie their metrics to revenue goals, and 61% carry expansion as an organizational charter. This is up significantly from 49% just last year. The 2021 Customer Leadership Study found that 48% of CS organizations outright own up-sell/cross-sell opportunities.

VPs and above lead 60% of Customer Success teams, and 54% of Customer Success leaders report directly to the CEO. With greater responsibilities come more opportunities to shine, but it also means more communication with these high-level executives. So, we have the C-suite’s attention. How prepared are you to capitalize on it?

Executive communication is a whole new ballgame

Different people require different messaging strategies to maximize their retention and engagement with the information they’re receiving. Giving presentations or finding the best ways to package a vital message can be tricky, even in the simplest of circumstances. You can run into communication challenges with anyone – your team members, colleagues, other managers…the list goes on. Talking to the C-suite poses even greater challenges. Their perspective can be quite unique. They care about different things. They operate on a much larger scale, both in long-term strategy and in the benchmarks they use to measure success. Customer Success leaders need to be prepared to connect and engage at an entirely new level.

According to a new article on managing up by the Harvard Business Review, “the key to selling your idea up the chain of command is to understand the psychology of higher-ups – to get inside their heads.” By presenting to personality types, you’re going to have a much easier time getting your message to sink in. You’ll feel more confident about it too.

You need them to care

Customer Success leaders care. They care a lot. (Cue the Care Bears song.) The bottom line here is that you need your executive leadership to care, too. You need them to understand what your organization is accomplishing and what you are doing as head of the CS organization to facilitate those accomplishments. Before, it was all about aligning CS to revenue growth. As Customer Success has evolved, it’s become about even more than that. It’s about how CS strategy can impact revenue and growth company-wide. The stakes are high. If you can’t influence minds up the chain, you risk stagnation. You may never unlock Customer Success’s full potential.

As the role of your own CS team expands, you’ll inevitably begin impacting the entire customer lifecycle. You’ll be working with other departments, building bridges, sharing data, and improving the way everyone works across the board. Whether you are stepping into a new role or actively steering the Customer Succuss ship into greater ownership of customer growth, your communication skills up to your company’s top leaders are vital. Don’t leave this up to chance!

The best way for CS leaders to communicate up the chain: Presenting to personality type

The personality spectrum: Black & white to technicolor

There are many different systems for breaking out personality types into categories: DiSC, Myers-Briggs, and the Keirsey Temperament Sorter, to name a few. Regardless of the system you use, we find that it helps to look at personalities in terms of a spectrum. One side of the spectrum is black and white, data-driven, with less emotion. At the other end of the spectrum are full-color, story-driven minds that thrive on emotional input. The middle is where a balance of these two styles can work best.

Executives, like the rest of us, can fall anywhere along this spectrum. While they tend to require direct and to-the-point data, the way you package it is important. Some may even prefer more robust presentations chock full of supplemental information. The trick is to figure out where each individual falls along the spectrum and then craft messages that speak directly to them.

So, how do you find out where the individuals at the top of your organization fall along this spectrum? Luckily, we have the answer! We’ve come up with a crazy tactic that you might just have overlooked. The answer is to – ask! That’s right, sometimes the first step is just asking what type of information sharing they prefer.

Now, you might ask your senior leadership what they like, adjust accordingly, and fall totally in sync with them from now on. That would be fantastic! Unfortunately, we know things are rarely this simple. If it were, we wouldn’t be writing a whole paper on this topic! There are actually many variables to consider when it comes to fielding attention from the C-suite. In the next section, we’ve built out a list of questions with explanations and examples to help you as you go through the process of tweaking your approach till you’ve reached a point of harmony between your communication style and theirs.

Different strokes for different folks

Here are some examples of different opportunities to learn more about your leaders’ communication styles and methods you can take into consideration to adjust your approach to better match their personalities. And remember, these lessons can apply to other levels of the CS organization! If you’re a CSM, asking these questions can help you manage up to your Customer Success leaders, too.

How do they communicate with you?

Sometimes the best way to decipher what a person wants to hear from you is how they like to talk to you. Communication is a two-way street. If your CEO is constantly answering your emails with one-word responses, you might be dealing with someone on the data-heavy end of the spectrum. They probably desire clear, specific information that gets right to the point. On the other hand, if you have a Chief Revenue Officer who likes to have walking meetings where they spout off ideas as they move, you might be dealing with a story-driven personality. This individual likely needs you to keep up with them and filter their thoughts into cohesive actions. They benefit from talking things through, and if your style doesn’t match theirs, you may want to remember to schedule extra time in meetings for them to have the space to do so.

How do they want to be reminded?

Another critical factor for communicating up the chain of command is how and how often you should follow up with them. You should definitely ask your leadership how they would prefer you send them requests, notifications, or information. These days, the options for information sharing are abundant. Some closer relationships might require a texting exchange. Others might text you but expect a lengthy email in response. Some personality types require phone calls or in-person meetings. Find out and try to accommodate it.

How often to send reminders is just as important. One VP may want you to send the same email over and over and over again, five or six or more times, so they don’t forget to answer you. Another may explode if you send more than one reminder email. So, don’t be afraid to ask: How do you want to receive information from me, and what happens if I don’t hear back from you?

When do they want to process the information?

Your meeting could end up being a real head-scratcher if you’re presenting to someone who needs time to process data but you’ve neglected to give them the materials in advance. Someone falling in the middle of the personality spectrum often needs a balance between the two extremes. They need logical ideas presented with a bit of color well ahead of a meeting or presentation, so they have time to think about and engage with the material. You might be thinking the solution is to always send details ahead of meetings, but no. Some personality types hate to be bothered with a bunch of facts and figures ahead of time. They like to receive information in the moment. So, be sure to factor this into the communication equation.

How fast do they want to move?

Lightning speed or slow and steady? Everyone’s seen the type who drives meetings like a horseback rider in the Pony Express. Get them the bullet points, be prepared to offer them choices to make a quick decision, and for goodness’ sake, pick up the pace! Many CEOs are like this. They want to keep things moving in meetings. They crave energy. They rarely dawdle over data. Then, another type requires time to think and doesn’t want to be rushed into potentially rash decisions. This is the person who will stop in the middle of a presentation to run numbers. It might drive the movers and shakers crazy, but this is what they need to do to feel comfortable enough to move forward. This tends to be more common among CTOs and CFOs. Simple observation of your leaders’ behavior should send clear signals to determine your pace.

What is most important?

Asking which metrics are most important will make a big difference in how the higher-ups receive your message. If we’re talking C-suite or board of directors, they care about Net Revenue Retention (NRR) and possibly only NRR. Loading your presentation up with lots of other KPIs will only distract from what’s most relevant to them. In this vein, also find out how much information they want to receive. Some people love to pour over intelligence and analytics (hello, black and white side of the spectrum!), while others just want you to tell them their options to make as fast a decision as possible.

In some cases, you might want to leverage the AREA technique to give concise, well-thought-out responses. AREA stands for Answer, Reason, Example, Alternative. It’s an excellent method for engaging individuals who rely on data and for those who fall towards the center of the spectrum. In other cases, you may need to amp up face-to-face interactions to convey your most important messages.

What resonates the most?

Getting into the big “P” – Presentations! For the big daddy of executive communication, Customer Success leaders have many tools at their disposal for tailoring a presentation to resonate with various personality types. If you have access to them, customer interview highlight reels are excellent storytelling devices for conveying critical messages to those on the story-driven side of the spectrum. Of course, there are reports, dashboards, and pivot tables for those who need a more dispassionate approach. A more balanced style could include customer testimonials, use cases, or case studies.

You might not discover what resonates best with the C-suite on your first try. Nobody really falls into a neat little box where X always equals Y, and people’s preferences can change. But we know how good Customer Success leaders are at testing and refining strategy over time. This is a process that you can gradually fine-tune. The important thing is that you are trying out new approaches, developing trust, and building a stronger rapport with your leadership that will help you take your organization into the future.

Ready or not, Customer Success leaders are in the spotlight. It’s up to you to communicate all things CS up the chain, make important requests for your organization, and ensure company leadership truly understands the impact Customer Success has on the business. Presenting to the C-suite doesn’t have to be intimidating. By putting in the effort to learn more about who your executive leaders are as individuals and presenting information to them based on their preferences and styles, you will build stronger relationships that enable you to effect meaningful change across the entire organization.

Originally published as an ESG White Paper