Why Mastering Challenging Conversations is the Key to Kind Leadership (Challenge #22)

When people join the Kind Leadership Challenge facebook community, one of the entrance questions is: What is your biggest kind leadership challenge? 

The answers to these questions have inspired their share of posts and episodes over the years. I was reading over some of those questions earlier today and I was struck by something I’d never noticed before. Almost all of the challenges our community members describe could be resolved, or at least start to be resolved, by having a challenging conversation. And today I’ll pull out a few examples and explain why that’s the case. 

Welcome to the Kind Leadership Challenge, where I empower educational and library leaders like you to detox your organizations! I’m Sarah Clark, founder of the Kind Leadership Guild. My PhD in higher ed Leadership, my experience coaching, consulting, and presenting to library leaders all over the world, and a career working in academic libraries from the front desk to the Dean’s office taught me that leaders don't have to be perfect to build a better world. And now I want to share those same lessons with you.  

Here's the deal. You give me the next few minutes of your day. In return, I'll share short stories and simple challenges designed to heal yourself and your school or library, so you can get back to making the impact you wish to see in your communities. By embarking on each week’s challenge on your own or with the community of over 1000 kind leaders in our private facebook group, you and your team will begin growing humanely, managing effectively, and partnering collaboratively, and your school or library will build a more informed and educated world along the way.

Hey, did you know I also do online and in-person presentations, keynotes, and workshop facilitation? If you need an expert on library and educational leadership issues for your next conference, webinar, or staff development day, email me at  sarah@kindleadershipguild.com for details. I can only do a few engagements a semester between my day job and my other Kind Leadership projects, so contact me as soon as you can to find out more, and get on my calendar.  

So in this episode, I’m going to pull out a few kind leadership challenges reported by our facebook group members, and briefly explore why mastering challenging conversations can help a leader solve those challenges in a kind manner.

Leadership challenge #1 is “Constant interruptions, I don’t do well with this and feel I’m spinning my wheels all day and can only really concentrate outside of work hours but am too tired”. This Leadership problem can absolutely be solved with a challenging conversation. Really two conversations. First, you need to have a conversation with yourself about what boundaries you need around interruptions in order to get your work done. Then, conversation 2 is with your interruptors, where you can brainstorm some ways they can accomplish what they need to accomplish without interrupting you as often.

Leadership Challenge #2: This was a succinct one: “Entering union contract negotiations”. Now, before I tackle this one, I want to make clear that I’ve never worked or led in a unionized setting. (Side note, if you have been a leader in a unionized school or library, contact me! I’d love to have you on a future episode of the podcast). 

But back to my point. Why (and how) can mastering challenging conversations help with navigating contract negotiations in a kind manner? Well, the first thing that came to my mind are the pre-conversation checklists I created as part of the free Mastering Challenging Conversations guide. The checklists help you clarify your goals for a conversation as well as the stories each person may have about the other, so you can maximize your chance to have a fact-based, mutually respectful negotiation and agreement that honors both the needs of your labor force and the organization they work for. That sounds like kind leadership to me!

Now for Leadership Challenge #3—and I feel this one. “New leader in a health science library and a baby librarian to boot! And a career changer! Yikes!”

If I were talking to this leader, after giving them some reassurance that they were hired for a reason, I would tell them the one simple thing they need to do in this situation. They need to pick the most accomplished and respected member of their team. The one who everyone acknowledges as the hardest worker and most skilled librarian. And they need to have a conversation where they ask that slightly intimidating person to honestly tell them where they need to improve. And at the end of that conversation, they need to ask that person for help. 

I am well aware that this sounds terrifying. I said it was a simple conversation, not an easy one. But by placing your trust in this well-regarded team member and taking on their guidance, you will most likely earn their trust in return. And as that trusting relationship grows, other team members will probably follow their colleague’s lead. And in that way, a single leap of faith can be the seed of a trusting, psychologically safe, and creative team culture that can handle any challenge that comes its way.

In the premium video version of the Mastering challenging Conversations guide, I discuss how to have this kind of conversation, as well as other common leadership conversation scenarios. Go to https://kindleadershipchallenge.com/conversations  to get the free version of the guide, and then select the upgrade on the next screen to get the premium version with the 90 minute video course. It’s currently only $20, or one or two Friday lunches out.

Let me know if you liked this slightly different episode format! I enjoy talking about other folks’ leadership challenges as well—makes me feel a bit like the educational and libraries version of Dear Prudence or Ask a Manager. If I can gather up more listener challenges and questions, I may start doing Q&A episodes like this more often. And one other new episode format I want to let you know about—we’re going to start doing monthly-ish interviews! These interview episodes will be a little longer, probably in the 30 to 45 minute range. That said, as a busy library leader myself I will continue to respect your time, and work hard in the editing room to make sure you get all of the good stuff but none of the fluff. 

Next week you’ll be hearing from Alvina Peat, a consultant and trainer who’ll be talking about how anyone, in any position, can learn to lead from where they are. It’s an important message for all of us whatever our job titles may be, and I’m excited to share this conversation with you. 

Thanks for listening and for taking action to become a kinder leader. If you found this week’s episode insightful, give the show a rating or review—or even better, tell your fellow leaders!  Never doubt that day by day, you’re building a better world, even if you can't see it yet. So until next time, stay kind now.