Five Useful Questions to Ask a Struggling Team Member

As solo entrepreneurs, now and then we have team members (assistants, vendors, contractors, etc.) enter our offices (or email, call or IM us) with dilemmas. The issues may be personal or professional.

We entrepreneur-types are often eager to solve problems quickly.  And although sometimes a team member in crisis seeks an immediate solution, more often than not he or she wants, more than anything, to be heard. Inquiry is an excellent way to help both entrepreneurs and team members understand the situation at hand.  Here are some general-but-useful questions to help foster dialogue before generating solutions.

  • What are you struggling with?
  • Why is this important to you?
  • How might you be contributing to the problem?
  • What support would you most like from me right now?
  • Would you like to schedule a time to talk again soon?

How productive are your team interactions?  Conflicts can often be prevented if team members have a comfortable avenue for discussing their concerns.  By offering an approachable, objective resource, skilled in communication, we entrepreneurs can more effectively identify issues and take steps toward addressing one-off and even systemic problems.

I am passionate about helping individuals find their voice, express their brilliance, and maximize their power.  Over the past decade I have coached hundreds of leaders and their colleagues to communicate to their best advantage.  To learn more about the support I now provide exclusively to solo women entrepreneurs, email to arrange your complimentary half-hour consultation.


  1. Debra Woog

    I appreciate you sharing that. Based on your review of the situation and the article, anything you can add?

  2. Margelit Hoffman

    Thanks, Debra! I had to use this recently–glad I read it back then. Rereading it now to make sure I did the right thing!