Critical Friends


Work friends are the best. Some of the most superb humans I’ve ever known have come straight out of staff rooms in Tegucigalpa, Jakarta, Manila, suburban Chicago, and, for a brief time in my early ’20s, downtown Chicago cubicles. Work friends are also unique because they tend to represent a wide range of people I wouldn’t necessarily have met otherwise– they have been artists, athletes, adventurers, curmudgeons, Suzy Sunshines, professors, class clowns, and everything in-between. All of these people have enriched my life and made me a better person in some way or another. The very closest friends I’ve made along the way, however, fall into two main categories: “You’re the BEST!” Friends and Critical Friends.

I would describe “You’re the BEST!” Friends as those on whom you can rely to tell you that you’re the BEST! You’re so RIGHT! You are NOT wrong! They don’t question your actions, they’re not concerned with the complete picture and whether or not you really did mess up or act less than stellar in a situation. Their main concern is to support you and make you feel good. Who doesn’t love and need these friends?! I act as this type of friend to some people, I have some people who are this kind of friend to me, and I’m sure you have this type of friend, too. They’re who you go to for venting, when you need a strong dose of self-confidence, and maybe when you know you’re wrong but don’t really care or want to acknowledge it in that moment– you just need someone to tell you how awesome you are! Who does this for you? Aren’t they the best?! These friends are important– like I said, we need them to give us a boost now and then. If they’re the only type of work friend that we cultivate, however, we are short-changing ourselves and missing out on an opportunity for growth.

The other type of work friends I’ve made along the way are Critical Friends. The Glossary of Education Reform defines a Critical Friend as: typically a colleague or other educational professional, such as a school coach, who is committed to helping an educator or school improve. A critical friend is someone who is encouraging and supportive, but who also provides honest and often candid feedback that may be uncomfortable or difficult to hear. In short, a critical friend is someone who agrees to speak truthfully, but constructively, about weaknesses, problems, and emotionally charged issues.

While Critical Friends can actually be a school-wide protocol, complete with official structures and formal Critical Friends Groups, for the purpose of this blog I am referring to informal friends who act in a Critical Friend way. Do you have someone like this in your work life? I can think of two friends who fulfill this role for me– Nick and Kari. Critical Friends are different than mentors, the importance of whom I have also written about here, in that they don’t need to have more work experience than you, or be in a higher place on the organizational chart. They simply have to provide you with honest feedback, thoughtful questions, and with a lens to view your blind spots. The other crucial components of Critical Friends are that there is a very high level of trust involved, as well as the belief that this person cares about you and is acting in a manner designed to help you become the best person/employee/colleague/leader possible.

An area that I have personally invested a lot of energy and have experienced growth over time is my ability to ask for and accept constructive criticism. I won’t say that it’s still my favorite thing in the world, but I also know that no one is perfect and that all we as humans can do is try our best to grow, and question, and fail forward. In Radical Candor — The Surprising Secret to Being a Good Boss, Facebook COO Sheryl Sandberg’s honest feedback to her then-employee, Google director Kim Scott, is described. Sandberg told Scott that saying “um” every three words during her otherwise-successful presentation to Google executives made her sound “stupid.” Harsh, right? This is what a Critical Friend can do. They can point out your blind spots and give you really pointed feedback like this because trust has been established and it’s understood that the person giving the feedback has only the recipient’s best interests at heart. When I was working on my Failure conference presentation a few months back, I asked my friend Nick for his feedback. He and I circled back several times during the process, all the way up to the night before my presentation. His early feedback was fairly brutal– but ultimately correct. He could see the weaknesses in the presentation’s structure and was able to articulate them to me in a way that made sense and allowed me to move forward in a better direction.

He and Kari have also helped me navigate a variety of work issues, large and small. I go to them when I truly want to know what they think of a situation. Did I address this in the right way? What could I have done differently? What could that person’s motivation have been? They don’t indulge me– instead, they ask thoughtful questions that help me re-frame how I think about things. I like to think that our Critical Friendship is mutual, that I help them in these same ways.

Not everyone can be a Critical Friend, and that’s okay. But cultivate these friendships, and look for them if you don’t have one at the moment. Take a risk and ask a trusted colleague for their honest feedback– or offer that to someone you think might be receptive to it. Together you can go farther than you’d ever imagined.

“Don’t walk in front of me… I may not follow
Don’t walk behind me… I may not lead
Walk beside me… just be my friend”
― Albert Camus

“Why did you do all this for me?’ he asked. ‘I don’t deserve it. I’ve never done anything for you.’ ‘You have been my friend,’ replied Charlotte. ‘That in itself is a tremendous thing.”
― E.B. White, Charlotte’s Web

Failing Forward, SUP Yoga-Style

“Fail Forward” is a phrase currently ringing through the halls of my school district. We have a new superintendent who has publicly encouraged our staff to take risks, fail forward, and to just “press the button”– specifically when it comes to technology, but I think this message can also be applied more widely. He shared the exhortation to “fail forward” at our first administrator meeting of the year, as well as at the all-staff Opening Day Institute. It was exciting to hear this specific encouragement coming from a school leader. In my experience, most “opening day”/”first meeting of the year” types of speeches tend to be more inspirational than challenging. They often regale us with successes of the previous year, reminders of exciting events that will be occurring throughout the coming year, inspirational quotes and videos, cute student pictures, and motivational stories. I have been part of many schools and school districts (international private, Illinois public, elementary districts, and high schools), and most of these leaders opened with this type of positive messaging. Not to say that this year’s opening message was not positive, because it was. But it also offered up a challenge, and challenges often imply that something is not yet being done. Or at least not being done consistently. So it was exciting to hear someone at the top level challenge us to “fail forward” and to recognize the intrinsic value of being vulnerable in front of our students and one another.

Schools can be high pressure environments. Teachers and administrators feel responsible for preparing students for state and district testing, feel concern for students’ academic and social emotional needs, are anxious about our own evaluations and, let’s face it, can sometimes feel afraid of being judged by our peers. Teachers and administrators put in a lot of work to get to where we are, and most of us feel a sense of pride in our skills and experience. Often, we are known in our schools or districts for being especially competent in one thing or another, and the desire to preserve this reputation runs deep.

It can be hard, therefore, to jump in and try something new– what if, at that moment of failure, someone walks in and observes us and questions our competence? Is it worth the risk? What if we try something, and it adversely affects our students or our job somehow? What if I do it wrong? What if my evaluator sees? Sometimes I forget how real these questions are, because when it comes to technology, my job is to press the buttons. I’m comfortable with technology and love trying new things with it. Unfortunately, this means that I sometimes don’t have as much empathy as I should for people for whom trying technology presents a greater feeling of risk and vulnerability. C’mon it’s easy! Just try it, no risk involved!, I can hear myself saying.

Enter SUP Yoga. I have been practicing yoga for a pretty long time, and very rarely do I have yoga experiences that take me out of this comfort zone. Well, this weekend I had the opportunity to try Stand Up Paddleboard Yoga with my wonderful colleagues Lynn and Marianne. I have SUP’d (is that a verb?) before, but never SUP yoga’d. It was definitely more challenging than regular yoga, as you need to engage about ten times as many muscles as you do during normal yoga so you don’t fall off the board into the water. Near the end of class, we started to have some options for trying more complicated poses– this is where my self-doubt and fear of failure kicked in. What if I try some of these things and I fall in? No one else had fallen in yet, so what would it say if I did? Will it look like maybe I’m not that “good?” Maybe it would be best if I just stuck with the basics and didn’t take a risk, since I couldn’t control the outcome the way that I can in a regular yoga class. Plus the failure would be so public! I mean, imagine the splash?! I admit that these thoughts did swirl around in my head for a bit, but the instructor was incredibly encouraging, and everyone else was just there to do their best and enjoy a beautiful end-of-summer day on the lake, so I just went for it. And guess what? I fell in. A lot. I think the grand total may have been eight times right in the lake.

But I learned a lot from each of those tries– I learned about center of gravity, the importance of grip and core engagement, all feedback I can use next time around. And nothing bad happened. I don’t know what everyone thought of me and all my crash and burns, but it really doesn’t matter. I failed– but failed forward. And I think it gave me a little empathic insight into how others might feel uncomfortable or afraid when I encourage them to try some new technology tool or strategy. The fear of failure is real, but with the right support and mindset, we can all learn to “press the button” and fall in (the water’s fine)!