From Feedback to Trust: The Real Skills of Great Bosses
It’s so much more than meetings and deadlines
I’ve had a lot of bosses. Some have been excellent. They pushed me to learn and grow and achieve more than I thought I could. Some have been cool. One used to talk to me about punk shows in the 80s and would use bad words while he trash talked the company we worked for. Some have been bad. Stern, inattentive, disorganized, absent, demanding, and straight-up mean.
Nowadays, as a freelancer, in some ways I don't have a boss at all, and in other ways, I have dozens of bosses.
I worked with Dallase in a previous sustainability role before I went to grad school. Now, seven years later, I am back working with her team part time. True to the culture Dallase created on our past team, and now at Trust, we talk a lot about the intentionality of how we do our work, including working together as a team. One of those conversations was about about the whirlwind of a time I had with my supervisors since we last worked together. In the name of increasing the number of excellent bosses out there, I wanted to share some of the insights of our conversations with you all.
Meetings & Deadlines Matter (But Not As Much As You Think)
The management side of staff management is just like following a recipe. The ingredients are given to you (SmartSheet, Asana, weekly check-in meetings), and the instructions are clearly defined (finish quality work on time). Assign tasks to teammates with clear, achievable deadlines. Ensure staff has the tools they need. Hold weekly check-in meetings to address roadblocks. Make sure you use all of the ingredients and complete each step of the recipe and voila! you have yourself a shepherd’s pie (or a successfully delivered project)!
But hold on a minute, I know each of you can think right now of someone in your life who just can’t follow a recipe for the life of them. They have the right ingredients, but somehow their shepherd’s pie comes out of the oven looking more like a cow pie. They used high heat instead of low heat to saute the onions, the ground beef is watery, and the mashed potatoes on top were burnt under the broiler.
Same goes for some managers. They hired a team of subject matter experts and built beautiful schedules, but they overbooked their staff’s time and never checked in on how they were holding up with the demands of their roles. Most of my supervisors have been like this. Their teams have a lot of success and they are highly regarded within the company, but their teams are burnt out. Because of that, they have high staff turnover rates.
So, while your supervisor may check all of the boxes of staff management, no one thinks back on their time on their team with any positive feelings. In fact, they tried to flee as quickly as possible. While its hard to be a good boss without checking those fundamental staff management boxes, being a great boss requires a more intimate approach.
Feedback Is A Gift
We all say that we want feedback, but as soon as someone says something even remotely negative we want to run for the hills. Turns out its hard to be vulnerable! But the best bosses give and receive constructive feedback. Constructive being the important word here.
I used to think being a boss meant doling out tasks and correcting employees. My worst supervisors critiqued me endlessly but couldn’t handle even the smallest piece of feedback (like suggesting they run a spellcheck before sending emails to clients). But I’ve learned that feedback isn’t a critique, its a gift (when done right).
The best boss I ever had started asking for feedback from me on Day One. She encouraged me to give both positive and constructive feedback. And she would do the same for me. I watched her ask for feedback from everyone in the office, from interns to board members. She gave feedback directly but without judgement and took feedback with grace. Her body language was calm, and she never reacted explosively. If she ever wanted to push back, she did so thoughtfully and in an even tone. This mutual respect made me feel safe to approach her about anything, whether I had made a big mistake or I had suggestions for improvement.
Receiving feedback so frequently, and by someone who showed genuine interest in my growth, helped me accomplish so much more in my role. I was able to tap into my strengths and target my skill gaps because I wasn’t shying away from them. I felt like I had the space to be creative and take big swings because I was encouraged to be innovative, and I knew that it wouldn’t be long before I was reigned in, if need be.
When my supervisor and I built a relationship where our strengths and weaknesses were out in the open, we were able to attack projects more efficiently. We could divide and conquer based on our strengths and interests, while slowly improving our weaknesses as a team.
Be a (Good) Person First
What we remember about all of our good bosses is how they made us feel and what they taught us, even if those lessons aren’t realized until years later. And in my experience, those lessons have more to do with living and leading than about the content of our work.
A colleague told me about a friend of hers who has a super organized, highly regarded boss who still can’t pronounce her supervisee's name correctly despite multiple reminders. This boss presents very well to clients but is not well-thought of by her team. They feel overlooked and only like cogs in the machine. Even if her team is high-performing, the supervisee learned that her identity is not as important as the work at hand, leaving her dejected and unmotivated.
On the other hand, one of my favorite bosses of all time was very busy with other projects and had to reschedule a lot of our meetings. But, despite how busy or distracted he was, he always made sure to ask about my classes and the score of my roller derby game that weekend. He also shared with me his candid concerns about the work we were doing and what was going on his personal life. I felt like I actually knew him as more than a giver of tasks, and he actually knew me as more than a task completer. Ultimately, I was there to complete tasks. And I did. But, because we had rapport, I never felt I was just checking boxes. I was able to find the inherent value in my work and took pride in working hard to support my supervisor’s mission.
Sometimes, building a relationship that goes beyond work talk helps us better understand each other. I was able to let some of my supervisor’s less-than-perfect days slide because I knew how busy he was with other projects and his family. Other times, it helps us work from a more focused standpoint. When we vented about the staff meeting for 20 minutes at the top of a weekly meeting (check out the Trust Chat Live about Office Gossip to learn more about constructive gossip), we could actually focus and get difficult work done for the next 40 minutes.
When I sum this all up, it seems simple: Ask for and give genuine feedback, focus on the people not the tools, and be a good person. In truth, its very complicated. Because we all know the guy who is really fun to work with but his team never gets any work done. On the flipside, there are countless experts who have incredible success but everyone dreads working with them because of their lack of bedside manner. There is an art to finding the balance of empathy, vulnerability, diligence, and structure that leads to being a great leader. Shifting your mindset from the structure and business of management to the relationship and trust building of leading people is a great place to start. Get to know each other so that you can get to structure and business with the least amount of tension and roadblocks.
Looking to become a better boss? The Growing Trust Series helps teams practice exactly this kind of leadership—where empathy and structure coexist, and feedback fuels connection.
Julia Weeks is a writer and editor who previously worked in sustainability. She worked with Dallase at GreenerU from 2017 to 2019, when she left GreenerU to pursue a graduate degree from Emerson College. She graduated with an MFA in Creative Writing in 2022. Since then, she has worked as technical writer and editor for federal contractors creating trainings, fiction and nonfiction authors, visual artists, journalists, and more.