Who Will Tell You When You’re Being an Idiot? (Challenge #49)

One of the things I talk about a lot on the Kind Leadership challenge is the way in which leadership is a team sport. Creating Collaboratively is one of the three core skills of kind leadership, because all of us need people who can help us get out of our own heads and expand our perspectives. However, there is also such a thing as too many cooks in the kitchen, and too many perspectives can just leave you in a muddle. When a hard decision needs to be made but you’re not sure you’re seeing the whole picture, what do you do? I’ve had success over the years by identifying a very small set of trusted advisors who I know beyond any doubt have the same goals as me, even, or perhaps especially, if they might have different ideas about how to get there. And today, I’ll share a great way to figure out which of your colleagues would be a good addition to your inner circle.

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 Welcome to the Kind Leadership Challenge, the podcast that empowers educational and library leaders to heal their organizations! I’m Dr. Sarah Clark, founder of the Kind Leadership Guild, where I use my PhD in Higher ed leadership and nearly 2 decades of experience in academic libraries to coach leaders like you who want to build a better world without burning out. 

Kind Leaders aren’t perfect, and we don’t need to be. We’re learning how to make the tough decisions without becoming jerks. We’re designing systems that enable our teams to make a big impact without unsustainable workloads. And we’ve realized that when we stop controlling and start collaborating, even the most ambitious vision can become effortless. It all sounds pretty simple, but that doesn’t mean it’s easy. So if you’re up for a challenge, stick around for the next 10 minutes as I teach you how your school or library can create a resilient, thriving legacy that will strengthen your community long after you’re gone.

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Here's the thing. Leaders, like everyone else I’ve ever met, are idiots from time to time. We get high on our own visions. We get so excited by a new project that we don’t think about whether we have the resources to accomplish it, or we see some process that doesn’t seem to make sense, and decree it needs to be changed without first determining WHY things are the way they are. I’ve learned and shared a few strategies to minimize a leaders odds of making idiotic decisions, but every so often, we’re going to roll the dice and they’ll all come up as ones. That is why you need a few selective people in your life who have both the courage and perspective to tell you you’re being an idiot while there’s still time to change course. 

The challenge in finding these people, of course, is that we’re leaders. We often have fancy titles, strong personalities, or both. Pretty much my whole life I’ve gotten occasional feedback from friends and colleagues that I can be a bit intimidating. As an overthinking geek who podcasts about kind leadership and worries a little too much about smoothing the awkward edges of her personality, I don’t totally understand that perception. But in some ways, I kind of do. I’m a very determined soul. When I settle on a vision or goal, I will do whatever it takes to get there. I will argue my point even if I’m the only person in the room who sees things the way I do. I am also willing to bruise a few egos in service of the greater good. I can’t change that about myself, and as a late Gen Xer settling into middle age, I’m not sure I want to change that about myself.

So, if you’re a leader who is nodding your head along with my description of my own leadership personality, you probably know it’s hard to find advisors who both understand where you’re trying to go and have the strength of personality to recommend course corrections. Here’s a four step process I’ve found handy in identifying and nurturing my relationships with my trusted advisors.

Has a colleague or a team member every said something so provocative and contrary to your ideas that you find yourself seething hours later? Well, I hope you didn’t rip their head off in the moment, because that can be an indicator that they told you something you needed to hear. That’s an important ability in your advisors. It indicates both that they have a different enough perspective on the situation that they could provide you with useful information, and that they have the guts to express that perspective. Maybe they didn’t do it in the best way possible, but that can be easily addressed with a bit of practice. 

Which leads me to the second step of my process for identifying trusted advisors: Can they listen? I’ve worked with many an ambitious, talented professional over the years who’s perhaps a little TOO invested in the rightness of their perspective to understand the full complexities of the problem at hand. Effective decisionmaking is a weird tightrope that requires being strongly confident in your own perspective on a challenge while being willing to see that there are other valid ways to understand that challenge. I dig into this a bit more in episode 15 when I talk about the importance of using multiple lenses to understand a leadership challenge, but for our purposes today, you need to see if a prospective advisor can see the value in your lens while also providing you the information they see from their vantage point. Share your perspective on a situation, explain why you disagree, and observe whether they’re more interested in understanding or just arguing. 

If your prospective advisor’s passed that test, then it’s time to see if they understand the conversational dichotomy I explored in episode 30: Does your advisor understand the difference between providing comfort or solutions, and are they as least basically capable of providing both as the situation requires? As much as I prefer to process my emotions about a tricky leadership situation on my own, sometimes the loneliness of the situation becomes a bit much and I’ve got to ask one of my advisors for help. A good advisor will have the necessary empathy to give you a bit of reassurance or commiseration you need to get back on your feet, but also has the inner strength and boundaries needed to give you a firm but friendly kick in the butt and start you moving toward whatever unpleasant thing needs doing.

Finally, it is only fair to ask someone to be a trusted advisor if you are willing and able to do the same for that person in return. We all need someone outside of the chatter in our own brains who can point out the things lurking in our blind spots. Don’t force yourself on someone, as they may already have a fully stocked advisory board and don’t need any more cooks in their kitchen. However, make sure the welcome mat is always there if you can return the favor for some helpful coaching that your advisor provided you. And who knows? Although I am adamant that your coworkers cannot and should not be like family, I’ve had plenty of advisors and advisees over the years who I’ve come to think of as friends. And given that we spend half our waking lives working in our schools or libraries, that’s a pretty nice thing to have in your work life. 

So here’s your challenge for this week. Who are your advisors? I currently have three people in my personal and professional life that I would consider my main counselors, with one or two more who seem to be growing into that role. Five’s about my maximum, but as I also tend toward introversion when working through a sticky decision you may do well with a larger advisory board. 

If you’re in need of an advisor, or simply want to improve your working relationship with an advisor you already have, try the four step process I just discussed! Look for people who have the perspective and the guts to challenge you, test out their listening skills, see if they can learn when best to provide comfort and solutions, and check in with yourself to see if you have the wisdom and bandwidth to become one of their advisors in return if they so wish. Identifying your advisors can be time consuming, and sometimes the trial and error process doesn’t work out. But when you’re chasing some pretty butterfly of a vision that could transform your organization, you’ll be able to run after it with more confidence if you know you’ve got someone along side who can stop you before you charge over the edge of a cliff.

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Thanks for listening and for taking action to become a kinder leader. If you found this week’s episode insightful, 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.