As a manager, you know how challenging it is to navigate a mix of personalities, working styles, and backgrounds on your team. This medley can be your team’s secret weapon, as long as you know how to ignite everyone’s individual and collective potentials.

Enter the personality workshop.

Personality workshops are a dynamic exploration designed to uncover the nuances that make your team tick. They come in my different flavors – DISC, Myers-Briggs, Enneagram, or working with me docs. This guide will explore best practices for unlocking the inner workings of your team members' minds, where you'll gain insights that go beyond the surface.

The Frameworks

There are many different ways to run a personality workshop and different frameworks to center on. Each has its benefits and drawbacks – choosing the right framework depends on your team and what you’re hoping to learn.


The DISC test sorts people into four categories (Dominance, Influence, Steadiness, and Conscientiousness) based on their behavior. It's a simple tool used in workplaces to understand communication styles and teamwork.


  1. Easy to Use: Simple and accessible for everyone.
  2. Improved Communication: Helps teams communicate better and reduces conflicts.
  3. Practical Insights: Provides practical information to tailor tasks and teamwork.
  4. Team Building: Useful for building teams with complementary skills.


  1. Oversimplification: Some say it oversimplifies personalities.
  2. Limited Depth: Doesn't delve deeply into personalities.
  3. Static Nature: May not reflect changes in behavior.
  4. Cultural Variations: Might not cover diverse personalities in different cultures.


The Myers-Briggs Type Indicator (MBTI) classifies people into 16 personality types using four pairs of preferences. It helps individuals understand their tendencies in areas like extraversion/introversion and thinking/feeling, providing a detailed picture of how they perceive and interact with the world.


  1. Detailed Typing: Offers detailed insights into 16 distinct personality types.
  2. Career Guidance: Often used for career development, aligning strengths with suitable work.
  3. Deep Exploration: Encourages a deep exploration of individual traits for a holistic view.


  1. Reliability Concerns: Individuals may get different results on different occasions.
  2. Limited Predictive Power: May have limited ability to predict behaviors and outcomes.
  3. Inflexibility: Might not capture the fluidity and flexibility of personalities over time.


The Enneagram is a personality test that categorizes individuals into nine distinct types, each representing a unique set of motivations, fears, and behaviors. It delves into deeper layers of personality by exploring how individuals navigate challenges, forming a comprehensive understanding of their core motivations.


  1. Detailed Typing: Provides detailed insights into nine unique personality types.
  2. Motivational Insight: Offers a comprehensive view of what motivates individuals.
  3. Personal Growth: Encourages exploring deeper layers of personality for personal development.


  1. Subjectivity: Interpretation can vary, relying on subjective self-reporting.
  2. Complexity: More intricate than some models, potentially overwhelming for some.
  3. Scientific Validation: Limited scientific validation compared to other personality frameworks.

Working With Me Doc

A Working With Me doc is a dynamic, flexible document that allows individuals to share their preferred work styles, communication styles, strengths and gaps, personalities, and more. Different than personality tests, these docs are open-ended and allow introspective team members to share different aspects of themselves without much structure.


  1. Flexible / Dynamic: Allows individuals to decide what to share and how to share it.
  2. Depth: Empowers individuals to go into more depth about aspects of their personality and working style.
  3. Personal Growth: First-person writing can be a good tool for introspection and personal growth.


  1. Self-reporting: Risk of self-reporting inaccuracies.
  2. Lack of Structure: Open-ended framework can be more intimidating or confusing.
  3. Time: Can take longer to put together.

The Workshop

Running a successful personality workshop hinges not just on the workshop itself, but on what you do before and after. Here are best practices:

1. Get your team’s buy-in:

Discuss the personality workshop with your team ahead of time, share why you’re doing it, and what you’re hoping to get out of it. Center your team around how the workshop can help them. Ask them for ideas and feedback ahead of time so you can tailor the workshop to their wants and needs.

2. Pre-work:

Have everyone on the team (including yourself) fill out your chosen framework. There are plenty of free and paid options to choose from. Make sure your team has at least a week of lead time to do this.

3. Sharing results:

At least a day before the workshop, have everyone on your team (including yourself) share their results in a shared doc. Ask everyone to read through the entire doc and prepare insights about their own results and what they’ve gleaned from their team members’ results.

4. Guided workshop:

Prepare a list of reflection questions to discuss as a team. Make this your own, tailored to your team’s needs and culture. Here are some of our favorites:

  • What’s one surprising or interesting thing I learned about myself?
  • What’s something surprising or interesting I learned about someone else?
  • What can we do to integrate these learnings into our ways or working?
  • Can you identify specific scenarios where knowing these results would have been beneficial in the past? How might things have played out differently with this insight?
  • Reflecting on your own personality type, what strengths do you bring to the team, and how can you leverage them more effectively?

Post Workshop

Investing in a personality workshop is only useful if you can continue to reference your team’s results and incorporate learnings into your day-to-day work.

Here are some ideas for tools you can use to easily reference results:

  1. Add to Candor profile: Create a full Working with Me doc within Candor or include other personality test results as responses to Takes in the Candor profile.

A candor profile showcasing highlights from a "working with me doc"
A Candor profile showcasing highlights from a “Working with Me” doc

  1. Knowledge Base: Include your team members’ results in your team’s knowledge base, like Notion or Coda. Make sure the docs are easily accessible to other team members.
  2. Slack profile: Have everyone on your team include their personality test results or a link to their results in their Slack profiles.

Here are some ideas for ways to continuously reference results:

  1. Onboarding: Incorporate the personality workshop into your onboarding process for new hires and make sure the rest of your team engages in that process.
  2. Slack emojis: Create custom Slack emojis to celebrate different wins or learnings related to your team’s personality results. For example, if your team tends to lean “Thinking” vs. “Feeling” in the Myers-Briggs personality test, create a “Feeling” emoji and react to positive examples of team members incorporating things like emotional empathy in their work.
  3. Meetings: Create a tradition of checking in on team members growth areas either in 1:1s or as a team.

That’s a Wrap!

In embracing diverse personalities through workshops, managers can get more from their team. From DISC to Myers-Briggs and Enneagram, these insights shape a collaborative culture. Your team will walk away from your personality workshop knowing themselves better and feeling equipped to work together towards your team’s mission.

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