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Agile Practices 101


5 Things I Wish I Knew Before I Started Facilitating Retrospectives

Retrium Team

“So many of us are sitting on the sidelines with valuable information, precious insights, and experiences that only we can share, and We are waiting on the invitation that is not on the way.“

Executive Director of Full Circle Inspiration and storyteller extraordinaire, Leslie Riley shared some of what she has learned in the webinar, 5 Things I Wish I Knew Before I Started Facilitating Retrospectives.

In this webinar and Q&A, Leslie shares some of the pivotal moments from her time at West Point, life in Corporate America, and experiences running her own business that helped to shape her as a facilitator and how she helps others have more effective meetings. Ultimately providing five strategies to overcome some of her biggest facilitating challenges. 

Tip 1 Pull Before We Push

Going from meeting to meeting - or life event to work - in just a few moments can be jarring. You have barely finished one thought before you are thrust into a completely different headspace. This can happen to everyone. As participants to retrospectives log-on or walk-in, their minds may already be full of information. 

As a facilitator take a moment to check-in with your participants. 

“Allow them to push out other thoughts before your push the primary agenda”

So how can you do this? 

One activity Leslie recommends is to “take a minute.”

Put on a timer or use some type of timebox for 1 minute. In that minute have participants write down everything they want to remember from their last meeting. Or just take a deep breath. Or whatever the participant needs to do to get into the mindset before the retrospective. 

Doing some form of check-in activity before each retrospective can also help participants feel present at the moment and engaged in the meeting at hand. These activities can be a simple question or a more robust activity, as long as it gets participants involved it is a great way to start your retrospectives. 

Lastly, you might ask a question to help pull out those thoughts. One of Leslie’s referred questions is, “What needs to be said so we can be focused for the rest of the meeting?”

This allows participants to air any concerns or preoccupations that need to be addressed and helps the team move forward in a productive manner. 


Tip 2 Silence Is Golden...With Enough Guidance 

As Leslie explains, silence oftentimes terrifies facilitators. Leading to self-doubt and questions like, “are we too far off-topic?” or “are they working on something else entirely?”

But silence with a purpose can be an important tool to help teams break up cyclical conversations, or reflect on what can be added to the conversations. 

If you have ever seen -or been in- an argument where people can’t see how much they agree,  or participants debated over a detail that can be better mapped out at a different time, you could have benefited from this tip. 

An example Leslie shares come from a time she was on faculty with the Agile Coaching Institute. A group of business stakeholders was asked to prioritize 30-40 different user stories. With that many decisions to be made, it would have been easy for the group to start arguing over small changes to prioritization, and spend hours on the final list. Instead, the facilitator only gave the group 7 minutes to prioritize as much as possible. And the group had to work in complete silence. What was the benefit? 

Instead of having the opportunity to have a full discussion over each card, the groups were able to come to a quick decision on most. Those user stories that kept being moved and could not be silently agreed upon were then placed to the side for further discussion. 

With this activity, 7 minutes of silence allowed the group to focus on which user story actually needed deeper conversations, and which were already agreed upon and did not need any conversation at all.

A few caveats though! 

Providing context is important in creating buy-in around silence as a tool. Creating a timebox around the length of the silence, and explaining the benefit of the silence is integral to having the team use silence effectively. Or else you really are just staring at blank faces. 😬

“The question is not, do I feel comfortable with silence. [It is] would the group benefit from it?”     

Tip 3 Stop Fearing Disagreement & Dysfunction. They Can Be A Catalyst to CHANGE!

If you are looking for ways to stop all disagreements and dysfunctions. Leslie has some bad news for you. 

“You can’t.”

Instead, she explains, you want to find a way to find value in the dysfunction. How can you do this? 

When you as the facilitator notice dysfunction occurring, pull back and ask, “why might that be happening and what is driving that behavior?” Understanding the “why” behind disagreements and dysfunctions can help you and your teams better understand systems that are working against them. 

Leslie shares the story of a time she was actually a dysfunctional problem. 😱 

She had been called in to help a team create a plan of action. As the time ticked away, the group kept arguing over choices over courses of action. Leslie, in frustration, slams her hands down and says, “if you all don’t make a decision in the next five minutes, I’m out. Because I am not going to sit here watching you circle the drain for another hour.”

So when the facilitator is getting frustrated there is definitely some dysfunction. So how did Leslie turn this moment into a positive? Leslie  took a step back and asked, “why?” She pondered if she was feeling anxious and nervous, there is a chance that others were also feeling this way. Giving them a chance to examine what habits were leading to these feelings of anxiety. 

When you think you are about to walk into a meeting that is about to experience some disagreements or dysfunction, one tool Leslie recommends is to create a chart. The chart should contain three columns: who is attending the meeting, what is the anticipated dysfunction, what is the strength behind the dysfunction. 


Now you have a more positive perspective, and a way to lean into strengths while examining ways to dial back the dysfunction. or - at least- make it more productive!

Tip 4 The Power of  “I don’t know”

Raising engagement is often one of the most difficult issues facilitators face. And one of the best ways to raise engagement? Give your participants a chance to answer their own questions. 

When a team faces an issue, it is easy to want to give your answer or solution -especially, if you have a story that relates. 

However, facilitators that are constantly providing their own answers, fail to give their teams a chance to develop new ideas! 

Leslie’s solution: “I don’t know, what do you think?”

Send the question back to the group! If towards the end of the conversation, you still think the team could benefit from your insights, then share your insights.

If your idea gets stated by another team member, you can give the idea validation with your agreement. Encouraging that team member to engage further in the conversation. 

Stating “I don’t know” also builds psychological safety in the team. By showing vulnerability, you help to create an environment focused on experimentation and learning instead of getting the correct answer quickly. And when you are focused on generating ideas instead coming up with answers, creativity is allowed to flourish. 🪴

Tip 5 Develop Your Own Facilitation Style

If there is a common thread in all of Leslie’s stories, it is the importance of playing into your strengths. 

Leslie explains that everyone has unique strengths. While some facilitators take a more formal approach, and others prefer to use crayons and markers to start conversations. As the facilitator, you need to feel confident in facilitation. And the best way to feel confident? Create your own style by watching and learning from other facilitators and developing a style that works best for you!

Check out the full webinar and Q&A for more fun stories from Leslie including how she uses Team Radars to check-in with her teams and some updates she makes to tip #3! And if you'd like to download Leslie's slides, you can do that by clicking here.

About Leslie Riley

A sought after speaker and trainer on the topic of team communication, Leslie built her career by answering the number one question she was asked, “How do I fix the dysfunction on my team?”  After training and facilitating teams inside organizations across the globe, from SoCal to Sweden, Leslie realized she not only saw the same dysfunctions happening in almost every team around the world, but also inside every individual as well.  This discovery led her to reenvision how she speaks & trains leaders, at all levels of an organization - so they can create cultures where it’s safe to share the stories that previously felt un-tellable and in doing so, achieve goals that previously felt un-reachable.  Leslie has shared her passion for leadership through better communication in such places as Adobe, Fidelity, VISA, Disney, CapitalOne, Procter & Gamble, Honda, and even her alma mater, the U.S. Military Academy at West Point. 

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