How to Sell Teamwork to a Skeptic

Teamwork is not always an easy sell – especially to a “skeptic”. As a person who takes pride in being an independent thinker, they usually don’t believe something is true until they see clear evidence.

And when you need people who may never be friends in real life to find a way to work together successfully, but the skeptic keeps seeing what “isn’t working”, it makes sense they distrust the teamwork process. 


  • So what do you do when you have to sell teamwork to a skeptic who does not trust easily for any number of reasons? 
  • How do you help teams push past the resistance that emerges in team-based work, and define the common obstacles with clear solutions from a neutral place? 
  • What are some ways teams can build healthy connection and communication habits that evolve as they grow and change together? 


It starts by offering the people on your team a mindset that’s rooted in neutrality. Why? More often than not, teams start off with at least one of the five core dysfunctions which are manageable, but need to be seen and understood by the team as a whole. It’s key to the process of building courageous communication and trust within a team – and gives the skeptic the insights they need to get invested. 


According to Patrick Lencioni, author of The Five Dysfunctions of a Team and pioneer of the organization health movement, the five dysfunctions are:

Absence of Trust – Teams who lack trust conceal weaknesses and mistakes, hesitate to ask for help, jump to conclusions about the intentions of others, hold grudges and dread meetings.

Fear of Conflict – A lack of trust leads to the fear of conflict. Employees worry more about politics and personal risk than solutions. Meetings only cover non- controversial topics.

Lack of Commitment – When teams become conflict-avoidant, a fear of failure develops. They have difficulty making decisions and second guess themselves in terms of their specific roles and responsibilities. 

Avoidance of Accountability – Second-guessing and a lack of common objectives then leads to an inability to develop standards for performance. Team members miss deadlines and deliver mediocre work.

Inattention to results – When teams lack focus and clear objectives, team members stagnate, become distracted, and focus on themselves.


Now that is a lot of little disconnects that can create a very mismatched mindset for each member of a team, when leaders are focused on generating a sense of connection and collaboration. It’s important to review these elements as a manager, understand what you see happening on your own team, and gather their feedback, then move onto simplifying and clarifying team dynamics. 


Simplify and Clarify Current Team Dynamics 

Absence of trust is the key “spark” that leads to all the dysfunctions of team dynamics. Which means, when we loop back to understanding how to sell teamwork to a skeptic, we need to start with simple, clear ways to get the skeptic to move beyond doubt and into a space of trust. 

This can be even more challenging than usual due to the recent shifts in the way we all work during the global pandemic, including the fact many team members are now working from home and doing a mixed work week, or online only. 

“Edelman’s 2021 Trust Barometer  illustrates the pandemic has put trust to the test, and societal leaders including government leaders, CEOs, journalists or religious leaders, are trusted to do what is right. In fact, 56 percent of respondents believe that business leaders are purposely trying to mislead people; and the credibility of CEOs, Boards of Directors and even regular employees receded.

The Trust Barometer also found that although only 12 percent of people will believe communications from employers the first time they hear new information, 49 percent of people will believe it after it is repeated once or twice.” 

Which is great news! 

It’s also what makes trust and effective communication more important than ever. Communication must be thoughtful, well planned, executed across several types of content delivery platforms, and blended with humanity, empathy and transparency. It’s how leaders can build fresh cultures of trust within a team or company a little at a time. 


3 Ways to Build Cohesiveness and Convert a Skeptic to a Team Player, On Their Terms 

At Willow North, we encourage leaders to build a healthy, simple starting point for changing team dynamics by guiding team members to revisit these core values when facing a challenge or conflict within themselves or with another. 


  • Be curious with yourself, others, and the situation at hand. Ask yourself some introspective questions to get a better sense of where you are feeling friction and what might be sparking it. Listen to feedback and insights, and understand it’s more important to learn then be “right” or smart. 
  • Explore and find common ground between you and team members in daily work, and especially when facing conflicts. Get out of an us vs. them mentality by asking open ended questions, and explore how you may be alike rather than different. 
  • Appreciate the differences between you and your team members, and how powerful it can be to combine individual strengths and generate a positive outcome for all. Challenge the idea of “what is normal”, and practice empathy as best you can in each situation – it’s not a “one and done” type of behavior. 


It’s also important to remember that love and belonging is key to teamwork and collaboration – the lynch pin of Maslow’s Hierarchy of Needs and a guideline that applies to the human in all of us. 

At the end of the day, coworkers are people looking to share their skills, interests and values with those who are excited to do the same. A skeptic just needs a simple foundation to find personal clarity within the teamwork process to discover the path of powerful teamwork for themselves, rather than feeling like it’s being “sold” to them. The more this concept is talked about and reinforced for a skeptic so they can see it’s useful, the more powerful it will be for leaders and employees alike! 

As a manager, what are some common ways you’ve been able to get a skeptic to come around? 



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