Key Questions to Create Teamwork w/ Pessimistic Teammates | #Teambuilding

Working with very pessimistic teammates is tough on morale. It’s also tough to produce results with these naysayers as their drag slows the team’s momentum. Pessimistic teammates are not the same as skeptical team members.

Skeptical teammates have concerns about certain aspects of a project or idea. They ask probing questions to move things forward with a greater chance of success. Pessimistic teammates believe nothing will work. They are the constant naysayers and complainers. Yet, leaders and teammates can move them forward with some thought-provoking questions.

Pessimistic Teammates: Image is towing and dragging.

Key Questions to Create Teamwork w/ Pessimistic Teammates. Image by Ben Tesch via Flickr Creative Commons License.

Image by Ben Tesch via Flickr Creative Commons License.

Thought-Provoking Questions to Ask Pessimistic Teammates

You get frustrated with pessimistic teammates who rarely have anything positive to offer. Moreover, they often tear down your positive ideas and the team’s momentum. Well, the good news is you are not helpless in this moment. Ask them these thought-provoking questions. Over time, it can change their outlook.

  1. What is one thing you would like to see changed? Notice here that the question doesn’t ask them to change something. It asks them what they don’t like (which they can easily answer). Then, you can discuss how to get there.

  2. What do we have to lose by trying? They may initially say, then why bother. But you can then say, “because we have a chance at gaining a lot.”

  3. If we move ahead with this, what happens to us? This question often uncovers the fears of pessimistic teammates. You can then address these specific concerns.

  4. Buddy-Up

  5. What if we share the load and the credit? If nothing else, we will learn together. This buddy approach can move pessimistic teammates forward. Sometimes they see what’s possible with and through others.

  6. How do you feel when things change? If you are doing a team building event, this question helps all team members share how difficult change is. When pessimistic teammates see that most team members find change difficult, they sometimes learn how to move through it instead of resisting it.

I Challenge You to Stay Positive w/ Pessimistic Teammates

So now I ask you, why not ask these questions of pessimistic teammates? You have nothing to lose in doing it and everything to gain. It may take time for them to be more positive. However, instead of getting frustrated with them, realize that your efforts will succeed over time. In the meantime, you and your positive teammates will continue to enjoy each other’s energy, ideas, and mutual success!

What success have you had in working with pessimistic teammates?

From my professional experience to your success,
Kate Nasser, The People Skills Coach™

Related Post:
Make It Easier to Innovate Than to Complain
Chronic Complainers: Ways to Ignite Their Contributions

©2021 Kate Nasser, CAS, Inc. Somerville, NJ. I appreciate your sharing the link to this post on your social streams. However, if you want to re-post or republish the content of this post, please email for permission and guidelines. Thank you for respecting intellectual capital.

Kate Nasser, The People Skills Coach™, delivers coaching, consulting, training, and keynotes on leading change, employee engagement, teamwork, and delivering the ultimate customer service. She turns interaction obstacles into interpersonal success. See this site for workshop outlines, keynote footage, and customer results.

Get more inspiration and actionable tips for high engagement results!


Buy Kate Nasser’s new book Leading Morale (


4 Responses to “Key Questions to Create Teamwork w/ Pessimistic Teammates | #Teambuilding”

  1. Hi Kate,
    I like these 5 questions especially #1. I have found that many times the problems stem from “trouble” employee’s concerns not being heard or taken into consideration. sometimes all they need is a sounding board to vent the frustrations that we all get from time to time.

  2. Alli Polin says:

    Great questions, Kate! I have also found that many pessimists don’t want to be a part of the solution but are willing to let others “take the fall.” I like to ask: “What do you think we should do?” It takes them out of their complaining/ pessimist mindset to owning the problem and coming up with a solution. Like Steve wrote, it also gives them a chance to be both seen and heard which is often a central issue. It can be so painful to work with a pessimist. You give leaders a great place to transition the conversation.


    • Kate Nasser says:

      HI Alli,
      Your suggested question “What do you think we should do?” is a great one. What you and Steve are underscoring is to keep including the pessimists — giving them a chance to discover problem solving. The temptation for many people is to tune pessimists out to keep things moving forward and lower their own frustration. Yet, when we honor them (not their pessimism) with questions to discover what they may contribute, we achieve something more than just the desired end goal. We activate full participation and that produces long-term success.

      Many thanks for adding to this discussion.

KateNasser on Facebook KateNasser Blog KateNasser on Twitter KateNasser on LinkedIn KateNasser on Pinterest