Let's Have a Do-Over

I think we’ve all had those conversations when we just want the conversation to be over. That feeling when we say to ourselves, “This is not going how I imagined.”

More simply, I can think of a lot of things I would have liked to be over. Not that I’m regretful that those things happened, but remembering the undercooked lasagna I baked for Christmas Eve one year, and the laughter my family still blesses me with when we mention lasagna, I’d like to have a do-over on that one, for sure.

When I think about my personal relationships over the last 40+ years, including my parents, siblings, friends, family, and colleagues, I can think of so many times I begged for a do-over.

And let’s be honest, I’m 50% part of the problem when this happens.

But now that I reflect, the many misunderstood words, phrases, and nonverbal interactions, that set the wrong tone for the conversation, I really just didn’t use the tools to make them what I wanted at the moment. Even as a child, unbeknownst to me because of my youth and inexperience, what I thought was a conversation I just wanted to get out of, was really wanting to start things over again. 

In the world of leadership, I believe there are so many opportunities to have those do-over conversations. Yet in the sense of urgency, and sometimes the level of importance, we approach conversations blindly, and find them to be a “one and done” experience. In one of my more recent coaching conversations with a building leader, we discussed just that opportunity: is there a chance for a do over here?

Some things are simple do-overs

Samuel*, a first year building leader, shared his experiences of having post observation conversations with teachers, which I applauded as his commitment to having continuous engagement with his staff. He shared with me, honestly, that the conversations seemed very transactional, like they were dialing it in, waiting for them to be over. He noticed this because of the short timeframe that he was engaging in those conversations (10 minutes), and also the content and depth of thinking that was going into them.

Samuel was previously an instructional coach and a department leader, and knew how enriching conversations could really be. But now, in his role as principal, he found himself with many tight timelines, and not being able to dedicate deep, instructional, and reciprocal conversations with teachers. These are often the cases that I find as well: when a fantastic teacher and coach steps into a leadership role, and just by the nature of the demands on a building principal, they become absorbed in the transactional and procedural parts of their role.

I was proud of Samuel for recognizing how quickly he had fallen into that trap. So when I asked, “If you had to do the conversation all over again, what would you do differently?” the question was enough for him to realize that, although he had not dove into the conversations the way he wanted to, there would be other conversations that he could be more intentional about the reciprocity he found most valuable.

Samuel was previously an instructional coach and a department leader, and knew how enriching conversations could really be. But now, in his role as principal, he found himself with many tight timelines, and not being able to dedicate deep, instructional, and reciprocal conversations with teachers. These are often the cases that I find as well: when a fantastic teacher and coach steps into a leadership role, and just by the nature of the demands on a building principal, they become absorbed in the transactional and procedural parts of their role.

I was proud of Samuel for recognizing how quickly he had fallen into that trap. So when I asked, “If you had to do the conversation all over again, what would you do differently,” the question was enough for him to realize that, although he had not dove into the conversations the way he wanted to, there would be other conversations that he could be more intentional about the reciprocity he found most valuable.

Commitment to Planning

What Samuel and I explored next was just how to plan those quick check-in, post–observation conversations that he found so valuable to teachers and to himself. Because the conversations were only about 10 to 15 minutes long, we determined that using a simple three-step structure to the conversations might be helpful. Also, even though he wanted the conversations to be very organic, sharing with teachers the simple Wins-Challenges-Priorities process was one way to provide consistency to the dialogue he was going to use time and time again, at each post-observation conversation. He was setting the architecture of the conversations early, and reinforced them again when he was in the moment of the conversation.

The Wins-Challenges-Priorities (WCP) structure was framed by Marcus Buckingham’s work with ADP, within the employee engagement platform, StandOut, providing leaders and teams with tools to stay connected. The WCP is a simple, reciprocal process that can be used multiple times throughout the year. It is best that both leader and team member address the wins-challenges-priorities and share them in the conversation. True to form, both parties commit to having the same conversational structure, and it allows for consistent do-overs and connected conversations throughout the year.

At the heart of it, Samuel needed to teach his teachers how to have reciprocal conversations by sharing with teachers early in the year that there would be post–observation conversations at times, and he was setting the stage for the expectations of how they both needed to show up in those meetings. He didn’t do anything wrong, initially, but he needed to reframe the check-ins as opportunities, and to practice better ways to show positive intent, meaningful dialogue, and measurable growth with teachers.

When Samuel and I met again about this topic, he was pleased at how quickly teachers had begun to engage in the simple structure he provided. Conversations were more meaty, and it actually prompted teachers to want more check-ins, proving to Samuel that the structure was a tactic for further engagement with teachers. I called that a win for him!

Some things you just can’t do over.

I’m glad Samuel realized that he had opportunities to do conversation over, to reset the tone, to set the expectations for engagement, and to find out areas where he was going to measure his own success.

But there are conversations that sometimes we just cannot do over. The heated, triggered, aggressively-reactive conversation that damages not only the opportunity in front of them at that time, but also future interactions, is a whole different beast.

More recently, my conversation with another leader, also a former instructional coach, explored how she had let a teacher treat her with aggression and intimidation during a meeting where she had to offer constructive and critical feedback. That was six years ago; since then, the principal has tiptoed around interactions with this teacher, until the principal and I had a conversation that involved this teacher bullying a new staff member. We determined this was the moment for a long-overdue do-over.

In that example, the principal did not feel there was an opportunity for a do over the first time she experienced the teacher’s aggression, and she may have been right. She may have had some tools in her coaching box from working with teachers, but as a new principal six years ago, she may have been unsure how to use them in tackling this heavy issue. But what should’ve happened shortly after that original heated conversation, was a reset of expectations moving forward. There is more damage, immediately, in the short term, and potentially in the long-term when we don’t remain flexible (or are ready to engage to set things straight), even when we don’t feel like we have to.

In our coaching time, I introduced the SBI model (Situation - Behavior - Impact) of feedback outlined in the Kim Scott book, Radical Candor, and also part of the Crucial Conversations framework. I modeled language for her that demonstrated the flow from S to B to I. She made notes of some key language she wanted to use. I asked her what roadblocks might impede on that conversation, and shared with her that the meeting was going to be short, and with two options: 1) to ask a question to open up dialogue, or 2) to make a directive that reinforced her expectations for professional collaboration.

The next day, the principal texted me that she had the conversation, using the SBI tool with confidence. The immediate response was somewhat surprising, but as in all things, she is still learning that incorporating any new tool to her leadership will take time to get used to, on both sides. I’m proud of her and her commitment to the do-over from years ago. She may not know the respect she earned that day, but my hunch is she will never be treated with disrespect from this teacher again.

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Think with the end in mind

In each of these examples, it was important for the leaders to plan their conversations, but not to the point where every word is scripted. Because they were both new and their roles, and needed to build their own toolbox for feedback and critical conversations, thinking with the end in mind sets the expectation for the intended outcome:  “What are the successes and setbacks that structure in the conversation might have?”

Working with an executive coach, although both of them were fantastic instructional coaches when they worked with teachers, shed light on the immediacy and the importance of planning these heavier conversations. It’s not that they didn’t have those tools already; but knowing when and how to use those tools as a leader, the supervisor, the head decision-maker for many people, made a big difference in how these principals showed up for their teachers.

While the do-over will never go away (thank goodness), and the more we have trusted opportunities to do do-overs (that’s a mouthful), the better we get at the one-time conversations. Keep in mind, every time leaders get it right is getting them closer to the secret sauce of their own authentic leadership. But in the meantime, let’s keep doing it better.

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Interested in learning more about flexibility as a leadership competency?

I’m hosting a free webinar on Tuesday, October 14th at 11:15 am ET.

Register here to join me!

This blog of Coaching Insights revolves around our self-sabotaging voice of judging ourselves too harshly when it comes to conversations that don’t go as planned.

Over the past several months, I’ve had conversations with leaders where they need to give themselves grace, and permission to be flexible in how they move forward from difficult conversations. This is especially true when a leader has just transitioned into their new role. Hear two stories of how the Do-Over gave leaders the chance to free themselves from their own judge, and begin a new path with positive intentions.

As an aside, I primarily work with principals and school leaders, but I hope you find your own connections to these stories because I feel they are universal to just about every leader in every organization.

Hang tight, my friends! 🍂