How to Challenge Teams to be Better

Photo by KC Alabanza

Photo by KC Alabanza

Through training classes and conference workshops, more Scrum Masters and Agile Coaches are learning about professional coaching skills and practicing them with their teams. I think it’s fantastic.

That being said, sometimes we’re so focused on asking powerful questions that we may neglect other coaching skills that can also help us serve teams well: articulating what’s going on and challenging.

Cherie and I introduce those coaching skills in our Powerful Coaching presentation, which I had the pleasure of leading at AgileCamp Dallas last week.


A development team had worked for many months on features before they were released, and a few issues popped up in production that necessitated them turning off the functionality. Naturally, the business stakeholders and Product Owner were interested in exploring changes that would allow customers to use the functionality and wanted to know rough estimates so they could determine the return on investment for the effort before proceeding.

The team spent time reviewing the problems, brainstormed options, outlined what would be involved effort-wise, and created a plan to present. There would be three areas to be addressed, and the team decided they would work on all three at once.

Hearing this last part, I said to the team lead, “I’m confused by the decision to start working on all three fixes at once. Your manager has been encouraging the team to limit its work in progress and focus on the most important thing. What’s happening here?”

The conversation continued, and we talked about how the team had wanted to change its practices for a while but had been feeling stuck trying to meet a timeline. Their collaboration had been stifled and the work had been stressful. Now they were about to propose more timelines without improving a thing!

“Your stakeholders are asking for reasonable estimates, and you have management support to do what you think is right to ensure a quality product. The team keeps thinking that the time to improve will be soon, and yet it doesn’t seem to happen. Right now the work is important enough to be done in a better way. Are you and the team willing to make changes now rather than keep waiting for a day that won’t come?”

Honestly, I felt like I was being belligerent by this point. I reiterated that the team had the ultimate decision on how they would work and that I was challenging because I believed in them. When they were reviewing the issues and brainstorming options, it was exciting to see each team member contributing ideas and asking questions; they were motivated and engaged in trying to solve business problems. And now they were on the verge of settling into old behaviors rather than championing the better ways of working that they’d wanted to try.


Coaching is more than asking questions. Teams need someone willing to reflect back what is being observed and heard so they can process it more deeply, and they benefit from having someone challenge them to be greater than they may think they’re capable of in that moment. Practice articulating what’s going on and challenging in addition to asking powerful questions for more effective coaching.

Allison Pollard

I help people discover their agile instincts and develop their coaching abilities. As an agile coach with Improving in Dallas, I enjoy mentoring others to become great Scrum Masters, coaching managers to grow teams that deliver amazing results, and fostering communities that provide sustainability for agile transformations. In my experience, applying agile methods improves delivery, strengthens relationships, and builds trust between business and IT. A big believer in the power of community-based learning, I grew the DFW Scrum user group significantly over the five years I served as an organizer. I am also a Certified Professional Co-Active Coach, a foodie, and proud glasses wearer.