5 Must-Answer Questions BEFORE You Collaborate

by Dave Hamilton, Director of Programs, EXPLO Elevate  
This is Part 1 of Designing for Collaboration: Read Part 2 HERE

You are 20 minutes into an hour-long meeting. The only thoughts running through your head are, “What am I doing here? What value am I adding to this group right now?”

Collaboration is a powerful force, and yet all too often, the work we hoped would feel collaborative and energizing ends up feeling flat, inefficient, or worst of all, unproductive. Even among well-structured teams, collaboration rarely just happens. It is a design process all its own that begins well before the “real” work ever starts. As you plan for productive group work, start by answering five essential questions.

Question One:

“Why are We Doing This Together?”

If you do not have an immediate answer for this question, chances are the meeting, task, activity, or happening you are planning is not a good candidate for collaboration (and that’s ok). At the risk of stating the obvious, the first step in designing for collaboration is determining whether what you are designing will benefit from collaboration. Just because you work on a team does not mean all the work is teamwork.

You might not have an immediate or clear answer for, “why are we doing this together?” and yet you still feel the urge to collaborate. When this feeling occurs, test your instinct against the following checklist:

  • The work is complex or has multiple tasks.
    Perhaps the most common need for collaboration is, you need help. You are facing a large job. There are many steps and, as they say, many hands make light work.
  • Time is tight.
    Having help often (though not always) gets the job done faster. Sometimes, too many people means too many decision-makers, which means… delays. If time is tight, ask for help when the tasks are straightforward and actionable: “Please move these boxes onto the truck.” “Place one red sticker on every folder in this stack.”
  • The work will benefit from a variety of viewpoints.
    Gathering a variety of viewpoints at the outset ensures a diversity of answers and possible approaches. It also helps you check your own unconscious bias and assumptions.
  • There is an opportunity for productive debate.
    Good collaboration should challenge your thinking. Invite others to work with you, especially when you feel a little too confident in your decision or when the path seems too obvious. In these moments, invite disruption by reaching out to people who think and work differently than you do and who are willing to call you out.

If you checked at least one of the four bullets above, we can move on to question 2. If not, ask yourself if you are forcing collaboration onto a task that is better left alone.


Question Two:

“How Many People Do I Need?” 

Before you invite anyone to a meeting or work session, set an ideal group size. (You may adjust this size later on but for now, pick a number.) Plan your group size based on the types of jobs-to-be-done rather than the number of tasks. A project may have multiple tasks, all related to organizational skills. If one person on your team is an efficient organizer, you may only need a group of two.

On the other hand, the project may have many different kinds of jobs. You might benefit from a manager, a creative, a questioner, an editor, and a spokesperson. In this case, you need a group of 5.

There is no one “right” group size. Smaller groups have less diversity of members, fewer viewpoints, and more work per member but are easier to coordinate because you contend with fewer schedules. Larger groups benefit from more diversity of voice and less workload per member and are more challenging to coordinate. Start with 3-5 people and remember the Two Large Pizza Rule often credited to Jeff Bezos: never invite more people than you could feed with two large pizzas.


Question Three:

“What Are My Team’s Assets?”

Once you know how many people you need and who you will invite, determine the group’s strengths. What do you have to work with? What does each team member bring to the team? Remember to look beyond a person’s job description. Your school’s Director of Teaching and Learning may also be an accomplished musician. Your administrative assistant may dabble in floral design. Perhaps the Chair of your History department also organizes the most memorable dinner parties. As you think through the team’s strengths, pay attention to how and where these strengths intersect. In what ways does each teammate complement one another?

In addition to human assets, what other assets are available? Think about the spaces where you might work. What tools do you have? What resources are nearby? What services are right at hand?


Question Four:

“What’s Missing?”

Identifying and naming your assets is a two-for-one exercise. It also reveals the gaps. Another way to think about this is, “Who else can help us?” If you have several people on the same team with similar strengths, determine whether each person is needed. Having four graphic designers working on one presentation may result in the world’s most dynamic slideshow or graphic gridlock. 

If you have three big-picture thinkers, the team is sure to excel at 60,000 ft exercises and might struggle when it comes to “landing the plane.” Your goal is to build a team that has a good balance of different work preferences and approaches. If your team collaborates on projects regularly, ask all members to complete a team profile evaluation such as this one.

If your team has an abundance of one strength and a lack of another:

  1. Replace an existing group member with someone who offers complementary skills.
  2. Increase the size of the group to add that complementary voice. Remember, adding people also adds logistics.


Question Five:

“What’s the Measurable Outcome?”

To create the conditions for productive collaboration, each team member must understand three things: 

  1. The purpose of the project 
  2. His/Her/Their role on the team 
  3. How the team depends on that role

Remember that meeting at the beginning where we wondered, “What am I doing here?” When we experience that question, it’s usually because we don’t understand these three conditions. Maybe we know the purpose of the project, but unless we see how we can help and how that help is critical to the project’s success, even the most enthusiastic among us tend to check out.

In the book Strategic Doing: Ten Skills for Agile Leadership, the authors offer three excellent guiding questions to help name measurable outcomes:

  • If successful, what will we see?
  • What will we feel?
  • Whose lives will be different and how?

“Who’s lives will be different and how” feels (perhaps) a bit lofty. Should we expect every collaboration to be life-altering? Maybe not. But it does offer a way of reframing Question 1 from our list: Why are we doing this together? By naming the measurable outcomes well, we also answer the shorter question, “Why are we doing this… at all?”


Note: If you have answered the five questions listed above, you are now at collaboration’s doorstop. In our next blog post “Designing for Productive Collaboration Part 2,” we will open the door and offer suggestions for how best to structure the group work ahead.