What Makes a Leader the World's Best Boss?

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I spend a lot of my time talking to people who lead others.  I also spend a lot of my time thinking about the people who lead others, trying to understand them, thinking of ways to connect with them, motivate them, helping them become better versions of themselves.  I’ve told plenty of stories of the anti-patterns I’ve seen through my experiences - the stereotypical bad bosses; these are tales of egos, tales of misbehavior, tales of incompetence, and sometimes just tales of being a flawed human no different than myself or anyone else in the world.  Today I’d like to tell a different story though, the story of the best boss I’ve ever worked for, a guy who would never actually use Micheal Scott’s “World’s Best Boss” mug (and maybe that’s another sign he deserves it).  I want to tell the story of Todd Dickey. 

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The man, the myth, the leader

TD, as he’s known lovingly within the circles of folks who have worked with him, worked with me during the formative years of my professional career.  I was young, in my mid twenties, working for a company that made blood collection and other medical devices.  Absolutely fascinating machines.  There was so much information to absorb, such cool technology, and a cavalcade of characters; the likes of which would rival the writers of the office.  Todd was the leader of this group, which had some pseudo-managers and formal managers sprinkled throughout, and these folks were all focused on one thing: supporting existing customers and helping them fix issues with things that came up with our software or devices, good old fashioned tech support - albeit in a very advanced (and regulated) environment. 

I have to jump back to the present for a moment to really set what drives my evaluation of Todd as a leader.  I’m not sure at the time I worked for Todd I would have called him the best manager I’d ever had, but now that I’ve spent nearly a decade in the talent management and leadership development space, having started my own company and worked first hand with high performing executives and leaders across various F500 companies, I think I finally have that elusive piece of the puzzle that cruelly evades us during our younger years.  I have perspective. 

What was the TD difference?

The perspective I have is that I’ve learned to evaluate leaders on what matters the most: behavior.  In terms of behavior, when I think back to Todd, here’s a few leadership behaviors we care about and measure today at Rhabit that we know correlate strongly with, not only company performance, but employee retention and growth; behaviors I think Todd showed really frequently. 

1. I observed TD strike a balance between interpersonal warmth with clear, direct communications around expectations. 
2. I observed TD holding people accountable for their performance when it was unacceptable. 
3. I observed TD congratulate, celebrate, and encourage team members openly to the group.  
4. I observed TD push people to grow, to take charge, to learn new things, and to jump into opportunities to stretch themselves. 
5. I observed TD being vulnerable, admitting fault when he was wrong, and supporting others when they made mistakes themselves. 
6. I observed TD being empathetic consistently with the employees under his charge in a myriad of challenging circumstances over multiple years in different situations.  

There’s plenty more, but my marketing team will poke me if I get too long winded here because of SEO or something.  They might even edit that sentence out in post, who knows? My point is - is it an exhaustive list of every key behavior that goes into being an effective leader? Absolutely not.  Are these the representative signals that we strongly correlate with team performance and employee engagement across all of our years of collecting talent management data?  Abso-freakin’-lutely. 

More importantly these behaviors were key in accreting trust - the more a leader is  observed consistently demonstrating these behaviors, the more the team as a whole trusts them, and the more they socialize that trust among themselves.  What this does for high performing work cultures really is something to behold - when everyone genuinely believes that their leader has their back and supports them, that they’re trusted to execute, and that they’ve got someone they can go to if they ever need a person of higher authority than their own - it really makes for a wonderful work environment.   All of those positive affect moments, I like to think of them making deposits into an account of “trust” between leader and employee, and a withdrawal comes from a moment of correction, a moment of demand for extra effort, or a moment of being asked to sacrifice or go above and beyond. Todd reaped the rewards of this as a manager and it went beyond just being “liked”, which he was, but more importantly, he was respected and trusted in addition to being liked, and this is a subtle but fundamental difference that made him an elite leader.

A well balanced (man)ager

Looking back, there’s an additional overall theme here that is worth noting  - the theme of balance.  Todd wasn’t a push over and perpetually jolly.  He was capable of being extremely terse and firm.  I’ve been on the receiving end of a (well-deserved) dress down from TD, but even in those moments he stuck to the facts and never strayed away from the overarching idea that he wanted me to succeed, that he believed that I was capable of being better than I was performing, and that he was pushing me for reasons I stood to benefit from, not because he was threatened, or spiteful, or unnecessarily demanding.  That’s another special thing; that balance; that zen of being able to be fiercely direct without overextending, without misusing that ferocity for something counterproductive and being extremely selective of when to really lean into something.  This is an incredibly difficult skill to master, but one that you see consistently in high performing leaders.  How do you hone this? I think Todd will tell you something similar to my take on this one - you learn from screwing it up a bunch and paying attention to the feedback you get when you do.  

Leadership skills aren’t something you wake up with, and despite what you’re marketed and sold, they’re also not skills that are effectively taught in a classroom environment or through some videos or interactive apps - they’re most effectively taught through real world experience that comes with real word feedback, and that’s why we’re obsessed with feedback at Rhabit.  It is the fundamental element of learning and the key to unlocking the potential of your leaders.  If you’d like to see how we make feedback accessible, meaningful, and down right easy to get - check out our products or book a demo.  Will Rhabit make you an awesome leader like my old boss Todd Dickey?  Hard to say, but I know he’s been a huge influence on how we’ve designed our product and content experiences, thinking about what it’s like to lead teams in the real world and all the challenges that come with it, more so than he probably realizes.  Cheers, TD. 

Are you a leader aspiring to Best Boss status? Read more about leader behaviors, and reach out to us at hello@rhabit.co - we have a special program for leaders like you!