Crafting Courageous Conversations: 5 Maxims for Everyday Leaders

As educators, we are in the people business. Yes, we deal with curriculum and instruction daily but the currency of our profession is founded in relationships. We are also in the continuous improvement process daily and that include coaching others and having those conversations that many may feel inclined to shy away from. We can all remember that first difficult phone call or conversation with a parent. It wasn’t easy, but we survived. But, what happens when the “issue” is with a colleague?

By and large, educators are pleasers, and we don’t seek out confrontations. College may have prepared us with the theoretical constructs on many educational issues, but somewhere along the way we all missed the class on giving and receiving constructive feedback.  Yet, real understanding in how to approach, prepare for, and execute courageous conversations with others is crucial for the success of any leader.  In educational leadership roles with several decades of experience we have found “5 Maxims for Courageous Conversations”. If you are a leader you can’t avoid them.

Maxim #1: A Courageous Conversation is about crafting constructive communication, not collisions.

This first maxim is based on a presumption of wanting to see others and yourself get better, it’s all about continuous improvement.  Courageous conversations are often not welcomed, but they have the power to transform a relationship. Rather than seeing an impending collision, find the benefit in dealing with an issue head on and up front. Yes, it may be uncomfortable to discuss a problem with another person, but when it comes to the “why”, we need to have the conversation considering that the positive outcomes will outweigh the negative ones.  When sitting down with another person, be certain that your own personal intentions are grounded in finding common ground, keeping your sight set on solutions and creating a shared dialogue. ~Jeff

Bottom Line: Courageous conversations avoid creating winners or losers. You will both gain relational credibility with one another.

Maxim #2: A Courageous Conversation is one in which leader takes his/her work personally and leads with heart.

Advice to leaders entering difficult conversations is typically filled with maxims like “don’t take this personally” or to relax and “not take yourself so seriously.”  In the book Fierce Conversations, Scott asserts that these suggestions are misguided.  She, instead, urges leaders to take themselves and their work personally and seriously.  Leading courageously is “seriously personal” business.   When leaders take their work seriously personal, they come out from the behind the conversation, that is the safety of pleasantries and the futile efforts to placate others, and make it real.   

When leaders step out from behind the conversation and passionately cement their spirit at the forefront, people recognize it and respond.  Because it happens so seldom, people are touched and influenced by leaders who courageously show their true selves.  They are willing to get behind a leader who is passionate and authentic.  They are willing to take his/her words and transform them into action. ~Paul

Bottom Line: Courageous conversations are ones in which the leader takes the work seriously personal, showing his/her true self and influencing others to take action.

Maxim #3: A Courageous Conversation is grounded in clearly defined and communicated core beliefs.

Many times, leaders find themselves in a position of regret wishing they would have communicated expectations or actions earlier in a process.  Then, they find themselves in a position needing to “back-track” to the intended purpose or intention.  In his book Focus, Mike Schmoker shares the importance of being “explicitly clear” in communicating the expectations up front and throughout a process.  When the leader explains his/her core beliefs, it makes it easier for others to anticipate direction and intent of leadership decisions. ~Neil

Bottom Line: Courageous conversations about beliefs up front avoid uncertainty or misconceptions among the team.

Maxim #4: A Courageous conversation is listening for understanding, not listening to reply.

We have all been there, having that conversation with someone and feeling like they are looking past you wondering if they are even listening. Your body language, where your eyes go,  and tone in the conversation is a key indicator of if you are listening. Having a courageous conversation is about allowing both sides to give input. In order for this to happen effectively, you must resist the urge to respond to every comment or explain yourself. Every time you redirect the conversation back to you, you put the focus, well, back on you. -Jeff

Bottom Line: A courageous conversation is about active listening.

Maxim #5 – A crucial conversation is essential if we want to bring about lasting change to our school culture and school community.

In School Leadership That Works, Robert Marzano describes the difference between first and second-order change: first order is incremental, and in many cases, it can be easy and manageable.  It’s something like changes to playground supervision schedules or school dress code policies.

Second-order change requires more than just talking about a problem…it requires action…and it can be emotional.  This is why crucial conversations are so vital…they bring to the surface the uncomfortable and the difficult, and they ask us to address them in a way that will impact our school’s culture.  This is the type of change that people fight against because it is going to go against the adage of “that’s the way we have always done it.”  Bringing this level of change can be paradigm-shifting, but it can also lead to the most resistance and reticence from nay-sayers.  Thus, it requires us to reflect on whether or not this is “the hill we are willing to die on.”  If it is, this crucial conversation must be undertaken if it is going to positively impact kids and their learning. ~ Todd

Bottom line:  A Courageous Conversation is one that brings about second-order change.

Bringing It All Together

Courageous conversations are powerful opportunities to influence lasting change in a person. You should end the conversation asking if there is anything additional that they may need for support or to move forward. Your goal is to set that person up for success. When engaging in this work we need to be mindful to check our motives, remembering our goal should never be to take something from the other person but to add value.  Peter Drucker reminds, “Leadership is not magnetic personality, that can just as well be a glib tongue. It is not “making friends and influencing people”, that is flattery. Leadership is lifting a person’s vision to higher sights, the raising of a person’s performance to a higher standard, the building of a personality beyond its normal limitations.”


This piece was a collaborative effort on the part of the co-leaders within LeadUpNow & #LeadUpChat – Jeff Veal, Dr. Neil Gupta, Paul Erickson, and Dr. Todd Schmidt. Though we serve as administrators in four different states our commitment is the same. Together, we are committed to changing the tone of education and building capacity in the everyday leader whether in the classroom or conference room. 

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Jump Start Growth

Jump Start Growth

Recently, a mentor I respect greatly said something that deeply resonated with me. It was as if he said it just for me and me alone. He put words to something I often feel, but shrink away from admitting out loud. He declared, “I often feel weighed down by my own disappointment over my past failures to grow.” I thought to myself, “Yes… me too!” So often, I have such grand intentions about committing to growth in the form of stacks of enticing books to read, professional journals to digest, podcasts to explore, and past professional learning experiences to revisit.

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As I thought about my mentor’s admission, I was reminded of this truth: Past disappointments don’t determine future outcomes. Anything is possible if I want to change! Andy Stanley wrote about truths associated with change in his book The Principle of the Path. Mr. Stanley explained, “To get from where we don’t want to be to where we do want to be requires two things: time and a change of direction.”  

As I continued to reflect on these ideas about change, I was inspired to brainstorm a plan to jump start my own growth and came up with the steps below. I hope these steps may help you on your own journey towards continual personal and professional growth!

Jump Start Growth

Set a goal with milestones – A good idea is just that, an idea, but a goal with tangible milestones is attainable.  When considering a growth goal, set out steps that lead to the goal. Those steps serve a guideposts to where you want to go.

Celebrate small winsIn her blog, Meg Selig explains that, “Charles Duhigg used the term “small wins” in his book The Power of Habit to refer to modest behavior changes that can set off a chain reaction of more and better changes.”  When you accomplish a small win along the way toward your goal, celebrate! Plan to treat yourself to a pedicure with a friend or a special meal out. Share accomplishments along the way and enjoy the satisfaction of small wins knowing that small wins add up to big wins in the long run!

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Be Accountable – Reach out to a trusted individual and tell them about your goal for growth. Ask this person to help hold you accountable to your commitment and empower them to check in on you at scheduled, agreed upon times. Be sure to communicate what your milestones are along the way, what you hope to gain on your journey of growth, and invite them to celebrate your accomplishments with you be it the small wins or the big kahuna!

Share your learning and growth – What do you plan to do with the learning you acquire and the growth you experience while on your journey? Your growth will be so much richer if you will commit to sharing your learning with others! Do this by tweeting one thing a day related to your goal, blogging your experiences and sharing out your blog, or creating a face-to-face forum such as a small study group to reflect with as you grow.

Seek opportunities to apply new learning – Look for new and different venues where your learning may take you. Could your learning be leading you to meet new people, to try new things, or go to new places? Achieving your milestones along the way requires applying what you are learning to reach your goal for growth.

Invite others to join you on your journey – I have found that my most meaningful times of growth have happened when I do it on a shared journey rather than strictly on my own. When I decided to go back to school to get my masters in Educational Leadership, I knew I did not want to do it alone. I found a colleague who was ready to tackle grad school too and we dove in together. My learning was so rich and profoundly deep because I had a friend to reflect, debrief, work, and laugh with throughout our courses. Spur others to join you on your journey and enjoy the added bonus of learning and growing in community with others.

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I have decided, I am not going to let my past disappointments stop me from pursuing future growth and accomplishments. I am recommitting to growth, one milestone at a time. My current goals include reading at least one book relating to professional growth each month and blogging at least once a month about my growth.

 What would you add to these ideas for Jump Starting Growth? I am also curious, what are your growth goals in 2016? 

Leading From the Edge

Many people like to live life in the center, choosing to stay away from the unfamiliar or the extreme. There is something about being in the mainstream, and going with the flow that feels “nice.”  There is a certain comfort afforded with this perspective.  However, what begins to develop over time, especially in organizations, is group think; or worse unquestioned conventional thinking that arises.  It becomes easy to hang out in the middle, not pushing back or making waves.  Questioning is replaced by complacency, an acceptance of business as usual.  In time organizational morale and engagement suffers.

As leaders, our ability to influence growth and change doesn’t happen from the center, but the edge.  Though the edge brings uncertainty, it also has the opportunity to bring clarity when we have a well-defined purpose and established values to lead others forward.  The edge affords a particular vantage point for effective leaders that differentiates them from managers or maintainers.

b2ap3 thumbnail Comfort zone

Vantage Point 1:  People Over Programs

You affect change or culture by impacting people, not programs. We miss when we spend time and money trying to motivate students and teachers through programs. School initiatives come and go, but what will always endure is the relationship potential that walks through our doors daily. Leading from the edge is an uncompromising commitment to develop your top talent.  In the era of high stakes testing and teacher accountability, there is a significant amount of time spent on developing the marginal amount ( 1-5%) of teachers who are in need of improvement.  Leaders should challenge this conventional thinking.

What if we invested the majority of our time in our most effective leaders?  Consider the multiplying effect of influence that result in developing those top people who in turn develop others.  Leading from the edge means-growing people, not bigger programs.  Your number one job as leader is to grow the capacity and skills of your top people.  In turn, as you grow your teacher leaders – student achievement rises as well.

Vantage Point 2:  A Culture of Permission

As leaders, one of the most powerful words we can ever say is “yes.” Our school cultures begin to thrive as leaders give permission and ignite ownership Effective leaders hire well from the beginning, ensuring they have only the best people and BELIEVE the best about their people.  In turn, it is easier to trust teachers to lead initiatives we believe in and can support.  Today’s leaders serve less as supervisor’s and operate more as coach.  Autonomy begins with supporting our people to have not only self-direction but also decision making.  Leading from the edge requires that today’s educational leaders are not managers of people but connectors.  Our job is to help our teams effectively connect, collaborate, and support them with resources necessary to thrive.

In the 21st century, edleaders are rejecting compliance-based systems because they realize how unmotivating it is for themselves and students.  If the goal is for self-efficacy of students and staff then our practice must reflect the rhetoric.  Students and educators alike increasingly want to be a part of a bigger story, to add value.  Leading from the edge means giving up control so that others can thrive, explore, and discover how they can leave an imprint.

Vantage Point 3: Risks Are Rewarded

Our culture does not stand up to celebrate failure.  We give trophies to winners and feel sorry for the loser.  This win/loss mentality is not an indicator of leading from the edge.  We are most effective when we foster a mindset that rewards risk.  As a leader, do you focus more on the problem or solution?  Solution focused leaders identify the issue and develop processes towards a solution.  By asking guiding questions such as –  “What do you need to do next time?  What do you need to do to move this forward?  What do you think we need to do to be successful?” allows an individual/team to feel supported and take next steps.  Great leaders will spend their own capital to support others failing forward on the road to success.

Are you willing to stand on the edge?  Standing on the edge can get windy, even downright frightening at times, but the view is worth it.

#NoArmChairNovember

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Game of Six of the ALCS fans nearly watched the Royals blow a solid 3-1 lead against the Blue Jays when slugger Jose Bautista crushed a pitch from relief pitcher, Ryan Madson.  Royals fans certainly had to feel sickened by this unfortunate turn. They felt sick for their team, who, at the time, was on their way to letting a World Series trip slip away.  The more empathetic fans also felt sick for the onslaught of criticism that Royals manager, Ned Yost, would receive.  The critics were fast and furious with their dissatisfaction in Ned Yost’s decision-making.

#NedYost happens to be one of the worst managers in baseball; Madson has horrible numbers against the #Jays and he has Davis can get 5 outs?” 

#Fourth home run of the season for Madson. That’s almost a fireable offense for Ned. What a foolish, foolish mistake…#yosted

“I don’t know that there is a man I dislike more in baseball than #NedYost, even #ARod I like and respect more I think. #KCRoyals

Ouch. And these are those appropriate for a school leadership blog. Search #yosted if you’re interested in the PG-13-and-more version.  Yikes.

When fans criticize the decisions made by managers and professional athletes, they take the widely accepted role of the “armchair quarterback.”  According to http://www.onlineslangdictionary.com, an armchair quarterback is…

“a person who watches sports and believes one could do a better job than the players or coaches.”

We rationalize our positions as armchair quarterbacks by saying “It’s my right as a fan.” “They’re overpaid, so I can over-criticized.” “It’s not like I’m going to see Ned Yost tomorrow at the grocery store.”

All of that may be true, and it led us to start connecting the phenomenon of armchair quarterbacking to our positions as leaders…

It can be easy to sit in the safety and security of your favorite armchair, bellowing calls at the television or hiding behind social media.  This reality occurs daily in our respective roles as educators–teachers and principals being armchaired by naysayers, arm chairing each other or central office admin, legislators armchairing all of us, educators armchairing parents (yes, we are very guilty of this.)

It’s easy to be a naysayer, focusing on a single call or could have, would have, should have perspective. However, like a great coach, leaders understand the big picture, they have the moral and visionary courage to see beyond one inning or quarter, they embrace the challenge of the whole game. In fact, great leaders know that we may lose this one only to win the next. So we have a challenge to make, a declaration to abandon the practice of armchair quarterbacking others.  Let’s have a moratorium on judgment. We call it #NoArmChairNovember.

The #NoArmChairNovember Challenge…

Be invested in people, not problems

If we are not careful, we can focus on a problem, forgetting that real people are involved. Spend your energy on people, not the problem. Are you spending time with all your stakeholders? Do you truly know your students’ struggles; are you spending time in that teacher’s classroom, having that meaningful conversation with a parent, inviting that district leader to be on your campus? Like all worthwhile pursuits it will require you to invest of yourself and time, but remember it’s not about us, but the people around us.

Ask the right questions

You don’t know the reasons why a decision may have been made. Our first reaction is to question it before even seek to understand the purpose or strategy behind it.  Seek first to ask questions to bring clarity and understanding. As edleaders we have to avoid being expedient, making snap judgments, take the time to understand a situation. Avoid critiques; offer solutions that contribute to moving a conversation forward and being a win for all.

Believe The Best About People

Great teams don’t thrive in toxic cultures. When we believe the best about our people their capacity and confidence greatly increases. Leaders give their best so that everyone around them can be their best. Our call as leaders is to inspire and grow people, many of us believed this when we accepted the challenge to lead others early on, we get to coach others to greatness, and this means less evaluation and more modeling through our own attitude. As leaders, we raise what we praise. Like many a locker room has a saying over the door that players see daily as a reminder, we need to have that same vision for our teams and ourselves.

So embrace #NoArmchairNovember and resist judgment, seeing the best in others and creating a vision of acceptance and optimism.  When we do, we move from the armchair to the field, this is where the real action is, anyway.

The concept of #NoArmchairNovember generated from some friendly sports talk between Paul Erickson and myself.  Three weeks ago, Paul and I were voxing back-and-forth, talking college football and the scrunity under which coaches find themselves.  We started to make connections to the “armchairing” that educators face and the armchairing they engage in themselves.  Sports talk quickly turned into self-reflection, collaboration, and, finally, action….a call to resist the temptation to judge and to instead boldly build others up, believing the best in them and thus getting the best results for your school community.

Paul Erickson, is a lead learner and elementary principal in Kansas, and also a Kansas Principal of the year recipient.  Through Twitter, the #Leadupchat tribe, and Voxer, Paul and I have connected as like-minded educators, pushing each other lead on, lead up!  Thanks, Paul, for working with me on #NoArmChairNovember