Well happy Sunday, and more importantly, happy Fathers’ Day. It’s been quite some time since I’ve published a blog post, such is the nature of my desire to write. Sometimes I’m addicted to it, other times I don’t want to be anywhere close to a keyboard once I push back from work.
Lately, I’ve had a lot of thoughts on a lot of issues, and I need to commit to writing for at least a half hour each day, so this is the beginning of that. My goal is to post at least weekly.
So with that out of the way, I want to talk today about leadership.
Catching you up - why leadership?
The last time I was writing prolifically was during my chemo treatment (one year and 4 months in remission and feeling stronger than ever by the way), which at the time was a necessary outlet that produced some writing I’m quite proud of (check it out in the older posts if you’re curious). At that time, professionally, I was on a bit of a journey. Those of you who know me well know that 6 years ago, I was a freelance opera singer and voice teacher who used day jobs to fill the financial gaps. I made the pivot to working for EF Educational Tours in Feb of 2019, moving into a sales role.
I fell in love with the place pretty quickly, and I’ll save the full story of my EF time for a post focused on it, but long story short, I invested in my career there, built strong mentoring relationships to intentionally grow my skill set, and started investing that mentoring back into my circle amongst the folks that, over time, started to look up to me.
Right around the time I was diagnosed with the Lymphoma, I was starting to feel ready for a shift into leadership within the organization. I’ve always been good with people, and my sales and strategy skills were starting to catch up to that innate talent, so the path was beginning to feel right. As I finished my treatment, and we approached Summer (which for our organization is a big time of restructuring), I started to ping my network about opportunities. One of my closest mentors suggested a switch into a smaller product within our organization than the one I was working in at the time (switching focus from international travel to domestic). I remember being kinda mad at her at the time, as that wasn’t the path I wanted. Spoilers, as usual, she was giving solid advice.
To get through the preamble and cut to the chase a bit, I met with a member of the senior leadership team from the domestic product, and we hit it off. He made the pitch to me that I’d be able to flex my newly developed leadership muscles in a profound way within this product, and that my impact would be fast and measurable. I was convinced.
In May of 23, I signed on the dotted line and began working as the manager of our newest employees within that product. My job would be to help these new employees transition from either college, or a previous career, learn our product and our sale, become proficient at it, and then graduate them onto our regional sales teams. I started out with a team of 10 direct reports, that, due to the timing of my start and our hiring cycle, quickly ballooned to 28, across three different office spaces. I suddenly found myself managing staff in Boston where I’m located, and remotely via our Austin office, and about 10 fully remote employees scattered across the country.
Those of you who work in management might understand just how big an ask it is to ask someone new to management to be responsible for not just 28 humans, but 28 humans who all are “high-needs” as they are brand new to our organization. It was incumbent on me to create a working environment where they could learn and grow quickly, and to set the tone for their early experiences of our organization. Failure would be costly (a stat that floats around is that the average cost of a failed hiring decision is about $300k), but I felt confident. I had benefitted from strong mentoring, an incredible leadership development program, and I had fantastic support among the overall leadership and training team, so I got to work.
We had some early successes in terms of re-structuring the nature of the role of our new hires to fit both the immediate business need, and my idea of how the role could be better tailored to meet that need. I was proud of my vision, but even more proud of my ability to give all 28 of those humans enough of my time to make them feel valued, safe in their roles, and comfortable stepping out of their comfort zones and trying something new.
Before long, I had the opportunity to bring a colleague of mine into the management space, to create a shared leadership model and spread some of the load of managing these folks out. She was a bit more junior than me, had been through less leadership training specifically, but she was a great add to the team with a different perspective and style than me in a lot of ways. I had the opportunity to sort of “big-brother” her while we built out our team together.
We had a great year together, success after success with this team, we even had a new start class of new hires in November, changed our goal structure around, and smashed through all of our targets. One year later, we’ve had so much success that when an opportunity to fill a recently vacated director role arose, I was tapped. I’ve started working with that new team officially, and was able to participate in the hiring of my successor.
So, that’s where I find myself today; about to take on a new challenge in the leadership space, a level up and a year sooner than I had anticipated. I’ve also had the opportunity to reflect on this past year, and what I think it means to be a “good” leader through the course of the hiring process for my replacement. That reflective process, along with content I’ve been plowing through lately (I’ll give a reading list later), has me starting to develop some ideas of what leadership can look like in today’s market, what I think it should be, and how I am going to target my own growth within the overall “leadership” umbrella. That’s what I want to write about.
So, now that we’re caught up…
Man, that feels like a lot of preamble for me to get to the point where I want to start actually saying something, but here we finally are.
I’ve been successful so far in my leadership roles, and I am excited to continue growing. What I’m going to start to write about is why I think that is, and what I think makes a “good” leader.
Let’s start with a hypothetical, have you ever found yourself in this situation?
You’re working in a job where you have the skills to execute the necessary tasks, but growth will be required to move your career ahead
Your boss is hard to read at best, and absent at worst
You constantly wonder if you’re meeting the standard that will allow you to be promoted
In your darker moments you worry that you’re not doing well enough to keep your job
Every Sunday you get big anxiety about the next week at work.
Ever feel that way? Well, that’s your boss’s fault. A good boss, a good leader, will never leave employees feeling unsure of their next steps, will never leave enough room for an employee to doubt their performance, and certainly will never fire or otherwise terminate an employee without engaging directly with them to make sure they understand where they’re falling short, and how they can pivot towards success.
Seems pretty basic, no? And I suppose on some levels it is, but that situation in the bullets above is shockingly common. So let’s take it point by point, starting with advancing your career.
What’s one of the most common reasons employees leave? It’s lack of clarity on how to advance. The second a job feels like a dead end, talented people are going to start looking elsewhere. That’s why leaders must prioritize career pathing from the outset of a new hire’s career. “Hi, welcome to our intake role! Here’s how you can be successful right away, and at XX tenure here’s the next step for you and how you can build towards it!” Is that putting the cart before the horse? I don’t think so. I think it’s critical that people can see the long term vision for where their career can take them, even right at the outset, so that we can help them achieve it as soon as possible.
What’s more frustrating than not being able to get your boss on a call to help guide your decision when you need them? What’s more paralyzing? Accessibility is a key component of effective leadership. Yes, business leaders are busy people, my calendar is an ever increasing mess of meetings, trainings, 1-1 conversations with employees, etc. But it is my job to make sure that when my team needs my guidance, they’re not held up by it. Oftentimes when an employee is ready to ask a question or run something by me, they’ve arrived at the right solution and just need a little validation, a gut-check. If I make them wait too long for that, then I kill their momentum.
Now - does that mean that I drop everything every time an employee has a question? Certainly not. Do I check teams notifications during meetings with others? No. Well. Sometimes, but I truly try not to. But my team knows, because I have told them — and then followed up on this, that they can leave me a message on teams or in my email, and I will get back to them as soon as I possibly can. They also know where to go if I can’t, because we communicate well with each other and they know who on the team is experienced enough that I trust them with decision-making.
Now on to the “am I meeting the standard” bullets. Look folks - no one should have to doubt that they are performing to standard in their roles. It should be obvious. In the best cases, performance metrics are transparent and immediately available to the entire team, meaning no “secret” performance matrices, no favoritism, no back-channeling. The worst versions of this result in an employee being fired without understanding why, or having the opportunity to address their shortcomings. This undermines employee trust and results in a highly anxious workforce. I think, for me, this is the most directly actionable thing. Leaders must be comfortable with tough conversations, and understand that challenging an employee who isn’t performing up to standard is an act of service. People shy away from confrontation, and that is the worst thing you can do to an employee. It’s much more kind to lay out the feedback you need to give them from a place of genuine care for their career. Kim Scott, in her book Radical Candor, says to “care personally, and challenge directly.” I highly recommend her book by the way, for a quick primer on the book, click here.
A firing when someone has no idea why they’re being let go is the ultimate failure of leadership. We are stewards of other people’s careers, and those people often times have people who depend on them being successful. If we aren’t being transparent, how can we feel comfortable making decisions that can have ripple effects on a family’s economy? I can’t. I need to make sure that we have exhausted every path towards developing that employee towards success before we affect a termination. I think a good leader should be quick to praise, quick to pivot, and very slow to terminate.
Not only do I think the above because it serves the employee, it also fills my cup. There are few things in the past year that I am more proud of than being able to take an employee who is underperforming, help them understand why, guide them to resources that will help them improve, and then watch them flourish. It’s so gratifying to know that someone I work with is happier and more effective at work because of efforts that we’ve taken on together. That’s how I start to measure my impact.
The “Sunday Scaries” bullet I mentioned above kind of goes with all of the above. Instead of talking about my leadership style here though, I’m going to talk about my boss’s. He and I have similar values and styles, one of many reasons we work well together. He exemplifies everything I’ve talked about so far, and consequently, I never wonder how I’m doing. He passes on praise, lets me know when he shares my wins with other leaders, lets me know if I’ve messed up that it’s either consequential and needs dealing with, or not a big deal. In short, I never have to wonder how I’m doing, so I never have to experience the “Sunday Scaries.”
Fathers’ Day Reflections
So this may seem like a pivot, but bear with me. I’m going to talk about my dad for a second.
My dad was in the army. He retired as a Colonel after 30 years, and for much of that time was in a division that specialized in personnel management. He managed teams in developing personnel software for the Army, in addition to many other things. In his 30 year career, he served with people like Colin Powell, Eric Shinsecki, and other names that have become “larger than life.” He was a White House aide for the military during the Regan administration (my thoughts on that one are… complicated). Point is, he both exercised leadership, and was around some of the storied leadership of his generation.
Dad told me a lot of things over the years, but two things stick out the most. One was the old adage “absolute power corrupts absolutely” (thank you very much, Roberts Court…) and the other was that he had “learned as much from the leaders he didn’t want to emulate, as the ones he did.” People remember a negative example, but they also remember the differences that their positive leaders make.
Indulge me in a tangent to my tangent - speaking of differences that leaders make. One of Dad's assignments was guarding the Kurds in southern Turkey during the first Gulf War. I don’t have a lot of first hand stories from Dad of that time, but when I moved to Boston, I met some roommates off of Craigslist. One of those roommates wound up dating a Kurdish guy who was studying at MIT. One night we were chatting casually on our Somerville patio, and it turned out that he actually was at one of those camps. He even had a patch that one of the soldiers had given him, a patch that matched my dad’s division at the time. He told me that the soldiers used to play soccer with them, and that they were kind to them, and that kindness is what inspired him to want to come study in America. Now, I don’t know for certain that Dad was one of those specific soldiers, but I like to think he was. Point is, you never know just how much impact you’ll have on someone in the smaller moments.
Anyway, back to the main subject - leadership. I suppose my point here is that the early foundations in leadership I have come from my father. Dad was the leader of my Boy Scout troop for a while, helped me lead a group of boys in my Eagle Scout project, and achieve a milestone at 16 that has had ripple effects throughout my life.
Now when you think of the “military dad,” you might imagine someone gruff, commanding, harsh. That’s not my father. Dad was a gentle leader with his teams, and he was a gentle father to me.
Last night, we were sitting around having dinner (I made a German feast to celebrate Father’s Day for him, some of his favorites from his time stationed there). I shared with him how excited I am to be succeeding in a leadership position, and how meaningful it is that I get to share it with him, which of course made him choke up. Once his eyes dried, he told me that there are two things that always came up when he describes a good leader: “Positive, and Collaborative.”
What’s profound about that, is that everything I just said in this lengthy post can be summed up in those two words. I believe that leaders should approach all staff with the assumption of good intent, and an antennae to discern negative intent when needed. I believe that every leader’s success is measured in who they collaborate with, and thus shared amongst those collaborators. I believe that a good leader deflects praise towards those collaborators whenever possible, and that they are responsible for maintaining a positive environment in which their employees can flourish. These are all things I’ve come to learn over my past year of deploying the philosophy of leadership I developed through all my mentoring and development, and here Dad was, spitting out two words that encapsulated all of it. Guess he’s kinda smart.
One more thing
The thing I would add to my dad’s brief wisdom (brevity is the soul of wit, no?) is authenticity. Authenticity will get its own blog post, vulnerability and candor are tied up with it, but I want to mention it here as it is a core element to a successful leader. It’s hard to trust someone who comes across as disingenuous. I have the benefit of being somewhat older than most of my cohort at work, as this is my second career. The benefit that affords me is perspective on myself. I know who I am, and I perfectly happy to display that without worrying about reprisal. That allows me to be truly authentic with all of my staff.
We spend so much time trying to fit certain molds, trying to adjust ourselves to land somewhere we think we’re expected to land. Take it from me - as someone who manages staff, if you bring your full, authentic self to work, we will find the right way to make the most of what you’re bringing to the table. It’s when I have to seek for it, to dig to find what motivates you, or who you really are, that I can’t serve you as well as I’d like.
And that brings me to…
In conclusion (for now)
There is one red thread through all of this: service. True leadership is service. Everything I’ve talked about so far is an element of serving your employees; reducing anxiety with direct feedback, rewarding candor, creating an environment where employees feel safe being their authentic selves and thus performing to their max ability, all of it is service. When we keep service at the core of what we bring to our leadership sphere, we will find success with our teams, without fail.
I want to write a great deal more about leadership. I’m going to focus in on authenticity, psychological safety, inclusivity, delegation, and much, much more (including but not limited to: how not to fear the advent of AI, what leadership should look like at the national level, and how we on “the left” suffer from lack of cohesive vision), but I want to add the caveat that I am still learning and growing, so the views I have are not set in stone, and I am open to challenges. I would love to get some feedback in the comments, or if you’re local to Boston, let’s grab lunch and talk about it!
PostScript
I mentioned I’d add a reading list, so here it is.
Books:
Radical Candor by Kim Scott
The Big Nine (currently reading) by Amy Webb
Good to Great by James C. Collins
Podcasts:
Simon Sinek “A Bit of Optimism”
Brene Brown “Unlocking Us” and “Dare to Lead”
I leave you with something juicy to listen to on loud speakers or headphones. Check out this up and coming band from Providence RI:
Comments