6 months in to my first sales job and I was struggling
Getting people to meet is hard
Those of us who frequently collaborate and communicate with others know the importance of a face-to-face, video, or phone meeting with a prospect, client, or coworker. These interactions give us an opportunity to share ideas or information, build connections, and understand the other’s perspective. They are also the critical times when we get an opportunity to make a pitch, negotiate and get on the same page. However, meetings seem to be unnecessarily frustrating to set up.
With an abundance of new communication technologies at our fingertips, it can be difficult to convince someone to invest the time necessary for a meeting.
Earlier in my career, I was introduced to a more experienced startup executive, who we’ll call Susan, as a potential mentor. I was eager to meet with Susan and get her advice on some of the challenges I was working through. In her first email she said she would be glad to meet, but it seemed to be exceptionally difficult to get something on the calendar. I repeatedly offered a list of potential dates and times, but Susan would take nearly a week to get back to me. She also had a habit of replying at the last minute and saying something like “I’m free now, want to talk?” By that time, I was always busy in another meeting.
She seemed willing to talk to me, but when it came to scheduling, we just couldn’t connect.
Though we did eventually meet, I cannot help but wonder how much time and energy could have been saved if we had just been able to get on the same page. Why is it that something as simple as setting up a meeting can be so difficult? Why are some people more willing to meet at the last minute, while others like to set things up well in advance?
To better answer these questions, we must first understand how personality plays a role in interpersonal dynamics.
Historically, the only way you would be able to fully understand someone’s personality is by either getting to know them really well, which takes lots of time and emotional intelligence, or having them take a personality test. Both of these approaches require that you have an established relationship with the person, which doesn’t tend to work in the world of outreach communication, since we are often trying to connect with new people who we have never spoken with before.
Thankfully, there is a new technology that unlocks another way to learn about someone’s personality without an assessment - Personality AI. We wrote about this in detail in another ebook titled, Personality AI (which you can download for free). This new technology analyzes publicly available information on websites like LinkedIn to predict someone’s personality, using artificial intelligence and machine learning. We built our product, Crystal, to harness Personality AI and enable anyone to identify personalities online to improve their communication and build stronger relationships, all based on the core principle of empathy.
We built our product, Crystal, to harness this technology and enable anyone to identify personalities online to improve their communication and build stronger relationships based on empathy.
Without getting too technical, when Crystal’s AI predicts personality, it uses a framework called DISC to classify personalities into a few categories that we refer to as D (dominant), I (imaginative), S (stabilizing), and C (conscientious). Each of us has a primary DISC type in one of these categories and sometimes a secondary DISC type in another. To keep things simple, we separate these categories into easy-to-remember labels called Archetypes.
You can see them all on this graphic called the Personality Map:
Below is a breakdown of common personality traits within each of the categories in DISC.
D Personality Types: Captains, Drivers, Initiators, Architects
• Motivated by control over the future and personal authority
• Tend to prefer instant, concrete results and having an advantage over competition
• Communicate clearly and succinctly
I Personality Types: Influencer, Motivator, Encourager, Harmonizer
• Motivated by innovative, unique, creative ideas and excited by the future
• Tend to prefer building new relationships and experiences
• Communicate in a casual, expressive way
S Personality Types: Counselor, Supporter, Planner, Stabilizer
• Motivated by peace, safety, and others’ wellbeing
• Tend to prefer security, reliability, and trust
• Communicate in a friendly and genuine way
C Personality Types: Editor, Analyst, Skeptic, Questioner
• Motivated by logic, information, and problem solving
• Tend to prefer accurate information and quality solutions (quality over quantity)
• Communicate in a business-like, fact-based way
These differences are extremely important for your approach in every conversation with a customer or prospect. For example, someone who is a warm, people-oriented Supporter (S) is less likely to engage in a discussion about facts and data. They’d usually prefer to engage in more personal, get-to-know-you conversation. An Analyst (C), on the other hand, tends to enjoy learning more about specific, concrete information. By identifying someone’s personality type, we can learn how to best relate to and communicate with them.
Schedule a meeting with anyone
Most of our communication differences come down to our unique personalities. Some people like to focus on what they’re meeting about, while others want to know more about the person they’re meeting with. Some like to follow certain formalities when setting a time, while others tend to wing-it. By using personality tools and insights to understand people’s different preferences, we can connect more easily and more effectively schedule important meetings. By using personality tools and insights, we can connect more easily and more effectively schedule important meetings
Scheduling a meeting with D-types
Straightforward, decisive D-types tend to prefer when people get right to the point. When inviting D-types to meet, don’t tiptoe around the subject or draw out the conversation. Instead, concisely share why you want to meet and request a specific day or time.
For example, let’s say you’re an insurance agent looking to set up a phone call with one of your clients, Phil, who is a D-type. An effective template for emailing Phil to ask for a meeting:
For example, let’s say you’re an insurance agent looking to set up a meeting with one of your clients, Phil, who is a D-type. An effective template for emailing Phil to ask for a meeting:
If you’re scheduling a meeting with Phil (or other D-types) in person or on the phone, try using phrases like:
- Should I bring anything?
- It shouldn’t take too long...
- The main thing I want us to do is...
- It will be worth your time…
D Personality Types Captains, Drivers, Initiators, Architects
- Offer to do the prep work for them
- Mention that the meeting will not take too long
- Quickly summarize the goal of the meeting
- Use very concise language
- Schedule any more time than necessary
- Show up late
- Provide too much information about what to expect
- Be unclear about the purpose of the meeting
Scheduling a meeting with I-types
Outgoing, excitable I-types generally like to establish a personal connection before getting to the heart of the matter. They tend to like casual requests that feature optimistic, inviting language. They often love to have meetings around food, so suggesting to meet over lunch or coffee is usually a good idea. Avoid setting the meeting too far in advance.
In this example, if you were looking to meet with an I-type coworker, Wendy, to discuss potential marketing ideas, you might send an email like:
If you’re scheduling a meeting with I-types like Wendy, try using phrases like:
- Let me send over a calendar invite now...
- This should be a fun conversation!
- I think we will enjoy this discussion...
- Do you have some time to talk about it now?
I Personality Types Influencer, Motivator, Encourager, Harmonizer
- Send a calendar invite while you are on the call
- Mention that the meeting will be fun or enjoyable
- Use a warm, inviting tone
- Mention the most intriguing thing they can learn
- Expect them to have a very rigid calendar
- Communicate too much in writing before the meeting
- Ask them to do the scheduling
- Give them a long list of things to prepare
Scheduling a meeting with S-types
Personable, caring S-types like to take more time to feel comfortable before committing to a meeting. It’s important to not pressure S-types to meet immediately and with only a small base of knowledge about you. Take time to build a sense of familiarity by introducing yourself and sharing details about your purpose. Once S-types feel comfortable, they are likely to enjoy an in-person meeting or scheduled call.
For example, if you are a sales rep looking to set up a meeting with Ross, a potential client with an S type personality, in hopes of sharing more about your company to convince him to purchase your product, you might send an email like this:
If you’re scheduling a meeting with an S-type like Ross, try using phrases like:
- This should help you become more familiar with what we do...
- I’d love to get some time on the calendar...
- I’m available for any questions before then...
- We can take as long as you need to discuss this…
S Personality Types Counselor, Supporter, Planner, Stabilizer
- Mention how the meeting will help them become familiar with you and your company
- Use a calm, friendly tone
- Let them know that you are available for questions before the meeting
- Let them know that you will take as much time as they need
- Use overly concise language
- Set a hard end time for the meeting
- Wait for them to propose a location or conference line
- Focus too much on what you want from the meeting
Scheduling a meeting with C-types
Reserved, analytical C-types tend to prefer meeting requests that are clear and specific. Focus on giving them a thorough overview of what will be discussed in the meeting, how long it will take, and what they should have prepared for it. Be ready and willing to answer questions.
Let’s say you’re looking to meet with your C-type boss, Jane, to discuss potential strategies to save on company expenses. You might format an email like this:
If you’re scheduling a meeting with an C-type like Jane, try using phrases like:
- Before we meet, please prepare…
- Let’s schedule a meeting so you can learn…
- Here’s what to expect from our discussion…
- Let’s meet one-on-one first...
C Personality Types Editor, Analyst, Skeptic, Questioner
- Tell them what they should prepare beforehand
- Mention that the meeting will help them learn
- Set their expectations for the meeting discussion
- Keep meetings one-on-one when possible
- Push them for an in-person meeting if they prefer phone or email
- Expect them to have an open calendar
- Use overly casual language
- Share unnecessary details about your own schedule
Avoid the hassle
Setting up a meeting shouldn’t be a struggle, especially when they are so crucial to make a pitch, collaborate on a project, or resolve a conflict. By making an effort to communicate in a way that reaches the other person, you can avoid spending unnecessary amounts of time and energy on countless ineffective scheduling attempts. Whether you’re setting up a meeting with your boss, a coworker, a prospect, or a client, suggestions provided by tools like Personality AI can help you feel confident in your approach.
To learn more about how to lead an effective meeting, check out our free ebook:
Improve Your Calls and Meetings