5 Methods to Determine Your Executive Leader’s Personality Type

February 22, 2022

Marley Wagner

Category: Customer Retention, Customer Success as a Service, Customer Success Maturity, Customer Success Strategy

The Customer Success industry is coming into its own. We’re in the spotlight now, baby! The 2021 Customer Success Leadership Study found that 54% of CS organizations report directly to the CEO. 75% of Customer Success leaders have a seat at the executive table. And CS leaders are increasingly placed in top roles at their company.

But, uh, wait a minute. They’re paying attention to us!? We’re going to have to talk to our executive leaders more? What we say has an impact? This means we’ve got to work even harder to ensure our messages are received, and (crucially!) we have to make sure they are interpreted correctly. That’s a lot of pressure!

The C-suite’s attention can be a bit of a double-edged sword. As a CS leader, you (of course) want them to value your organization and understand what you’re capable of achieving. But engaging with head honchos is a whole new ballgame. You’ve got to level up your communication skills to build a rock-solid foundation of trust with your leadership so that you can accomplish your short and long-term goals.

So, we asked Chief Churn Crusher Anita Toth and our own Sheik Ayube to put their heads together and come up with a strategy that could help CS leaders develop better relationships with their executives. We’re talking deeper connections that allow you to effect meaningful change for your Customer Success organization and the business as a whole. Sheik and Anita wrote a new paper: Executive Communication: A CS Leader’s Guide on Presenting to Personality Types that I definitely encourage you to read, if you haven’t already. Here, we’re going to talk about five methods you can use to first determine your executive leadership’s personality types before diving into the how-to of presenting based on each person’s type and style.

The best methods to determine your leadership’s personality types

1. Take a personality assessment

You can analyze individual personalities in a number of different ways. At ESG, we actually brought in a consultant last year to help identify our leadership team’s individual personality types in order to maximize our communication with each other and our clients. This exercise was extremely enlightening, and I’d absolutely recommend doing something similar if you have the time and budget. We each learned a lot about the driving forces behind our personalities and how to enhance our effectiveness as a team.

Another good alternative is to take a self-administered personality assessment. There are quite a few free and paid options to choose from like DiSC, Myers-Briggs, and 16Personalities. I found a fairly comprehensive list here to help you choose the best one for your goals. If you can get your leadership to do it with you, then you’ll know a lot more about what makes them tick.

Bonus tip: Even if you can’t get your leadership to do a formal assessment, it can help to do one yourself. Knowing your own style will give you the confidence to play to your strengths as you sell your ideas up the chain of command.

2. Get an example of what they like

One of the best ways to figure out what resonates with your leadership is to ask them to send you examples of past presentations that they’ve really liked. I recently heard from an executive that a great presentation can bring a tear to their eye, so if others are like her, they should be able to relatively easily recall the ones that stood out. But if they are too busy or if this feels awkward, you can try to find the pitch deck from an idea they’ve already greenlighted, either from the person who originally proposed it or an internal company resources library.

You can also learn a lot by simply paying attention to your leaders’ body language during in-person or virtual meetings when other people are talking. When do they lean in, ask questions, and stay engaged? What kinds of materials grab their attention, and what makes their eyes glaze over? Whatever they respond to the best will signal to you where they are in the spectrum from data-driven to story-driven personality types.

3. Extrapolate from how they communicate with you

You can glean a lot of information about a person by how they communicate with you. Big talkers and people with high energy are very different from introverted, quiet types who don’t like socializing. Does your CRO like to have long, walking meetings where they talk through their ideas with you? Does your CFO respond to your emails with one-word answers? If you’re paying attention, you can learn a lot about how they like to be communicated with from how they interact with you.

4. Speak to the folks who work with them all the time

Even in larger enterprise companies, there will be people who work with the C-suite all the time. Administrative or Executive Assistants, Chiefs of Staff, or anyone in a close, supportive role could be a wealth of knowledge on what the executives love, like, and hate. If you’re newer to a higher-level position, you could ask your colleagues about the personalities you’ll be communicating with at the top of the chain of command.

5. Just ask!

One extraordinarily simple method for determining your executive leader’s personality type that you may be overlooking is to simply ask! CS leaders have so much going on, and they wear so many hats, it’s easy to forget that sometimes you can just ask for the information you need.

Asking also helps you develop trust in the relationship. Imagine having a meeting with someone who just doesn’t have a clue how to engage with you, but, after the fact, they ask how they can improve in the future. You’re naturally going to be more open to what they have to say the next time you meet – because you know they are making that effort to do better.

Customer Success impacts the entire customer lifecycle and, therefore, CS leaders are a treasure trove of information about the health of the business. Your executive leadership needs to hear what you have to say – whether we’re talking emails, phone calls, or full-blown presentations. Determining their personality styles is the first step towards engaging with this unique audience that will make an impact in the long run.