[ How to Become a Coaching Manager and Have an Outsized Impact on Your Team ]

I spent the early years of my career working in politics. I raised money for candidates and managed day-to-day operations for campaigns. I loved the pace, the team environment, the magic of a small group coming together around a few folding tables and working crazy hours to achieve a huge goal. But there were drawbacks, too — an unsustainable lifestyle and feeling stuck in my own development — and after four years I decided to go back to school to pursue an MBA. After diving into the world of startups as a leader in the Entrepreneurship & VC Club and an intern at an early-stage fund, I’ve found that the things I loved about working in politics are at the center of day-to-day life at a startup. Both political campaigns and startups are scrappy, low-budget, crunched for time and cash, and staffed with folks wearing a lot of hats. Both pride themselves on hard work and no fluff. And both rely heavily on the quality, flexibility, and rapid growth of their people and teams. Helping small, hardworking teams pursuing big, crazy goals by implementing what I’m learning about managing people and teams at school and bringing in my experience from campaigns has made me think a lot about how leaders in both fields can, and must, motivate their teams to improve and grow. On teams like these, the quality and growth of each individual matters more than any other factor in achieving rapid success. However, there’s little time or money to invest in those people. Large companies and organizations can afford to pay for leadership and management coaching or to fly their managers on fancy three-day retreats; startups can’t and won’t. And yet it’s in those environments that a little coaching can make a world of difference — on the individual, on the team, and on the company’s bottom line. Enter the “coaching manager,” a term I’ve only known for a few weeks, but that has fundamentally changed the way I think about leadership and management. Just before COVID-19 lockdown forced the move to a fully-virtual grad school experience, I took a one–week Intensive Learning Experience course called “Coaching High-Performance Teams and Individuals” taught by Evelyn Williams. Professor Williams is an experienced executive coach and an expert on leadership development who consults with Fortune 500 companies. In just 40 hours of class and another ten spent cringing through videos of ourselves in meetings and conversations, she swept us through the theories and methodologies of coaching, simulated meetings to analyze our own performance and our peers’, and left us with a toolkit to approach daily workplace interactions through a coaching lens. We learned and practiced the skills needed to become a “coaching manager” and make individuals and teams rapidly change behavior and improve outcomes — that is, how to help the people you work with, ranging from the people under you, to your peers, to even your boss, realize what they’re doing right and wrong and get better, all while on the job. Here are three ways to incorporate coaching into everyday workplace conversations: 1. Start Every Meeting and Conversation with Self–Reflection Every conversation should begin with the meeting leader asking all participants for their thoughts on how things are going and specifically how they themselves are doing. This gives the coaches agency to shape the direction of the conversation, and provides the manager insight into their thinking. I once managed someone who spent hours on unimportant tasks, like choosing catering for company events, leaving her no time to do the actual important work. It was only after months of frustration that over happy hour she revealed that she thought our boss cared about what was on the menu above all else. Asking for her take on her performance and priorities at the start of our conversations, instead of launching into a speech about how she needed to better allocate her time, would have gotten me that answer a lot sooner. 2. Ask “How? and “What?”, Not “Why?” or “Yes/No” There’s no scarier question to receive from a stern looking boss than “Why did you do that?” Suddenly, you rethink every decision you’ve ever made, including why you wore those stupid shoes and also what made you think you’d be good enough to do this job. This is unfortunate because often what the boss is actually trying to ask is — how did you arrive at this decision, which perhaps is different than the one I would have arrived at? What factors did you consider, that perhaps I’m missing? Restating the questions to be open ended and start with “what” or “how” lowers the stakes and turns the conversation into one focused on process, as opposed to one with only wrong answers. I remember anxiously walking into the office of my campaign manager at the start of a new job, certain that I was about to be chewed out for something I’d done. I sat down on a rickety folding chair, nearly shaking but prepared to defend my decision. He started the conversation by asking, “Can you walk me through your thinking on this?” I immediately exhaled. It felt like letting the air out of the balloon inside my chest. I was able to calmly explain my thought process instead of trying to figure out what mistake I had made, and we had a productive discussion about how he was thinking and where our views diverged. 3. Use a Task, Process, Relational (TPR) Approach It’s helpful to approach big, messy topics — especially those that can be sensitive or difficult to talk about, such as dysfunction on a team — with a framework. The Task-Process-Relational framework breaks down an individual or team’s performance into those three distinct areas. To analyze the task, you’d ask “Did we accomplish the goal? Did we achieve the best outcome? In terms of process, you’d ask “Did we use an efficient process, or did we waste time agreeing on how to organize our discussion and thinking? Did we account for potential biases, or did we seek consensus over the best outcome? To evaluate the relational aspect, you might ask “Did we make sure everyone was heard and invited to participate? Did we echo each other’s comments before moving on, or were we all just waiting for our own turn to speak?” I think of myself as a people person with high EQ. But through this analysis, I realized that in work settings, I’m very quick to jump into a plan of attack and immediate execution of the task, without taking a breath to connect with teammates and synchronize our watches. I was all T, no P or R. Since finishing the course, I’ve been trying to spend the first five minutes of every Zoom meeting agreeing on agenda, goal, and timeline. I’m also working on responding directly and echoing my teammates ideas before jumping into my own monologue. Not only has it made me a more pleasant person to work with, I’m actually finding that a little time and effort spent on process and relations results in meetings that are faster, more efficient, and produce better results. Managers who use these tactics to structure conversations can shift into a coaching relationship, where they help their team members share their thinking, improve their performance, and develop as individuals as well as employees. Small tweaks convert to big investments and outsized impact. These opportunities are key for any team, but especially those that are small, scrappy, and seek to grow rapidly and make magic. — — — Welcome to the Squadra Blog. Each week we’ll be sharing advice, stories, and how we make hard decisions as we work with our portfolio companies to build extraordinary teams and companies. Interested in talking to our investment team? Fill out our form https://squadraventures.typeform.com/to/lYvbTDEh