Lessons From the Best and the Worst

Learning from good and bad managers BY DAVID DeFILIPPO

David DeFilippo is chief people officer for Suffolk.
He can be reached at editor@CLOmedia.com.


person’s connection with their direct manager is often one of the most important they have at work, and the quality of that relationship has an impact on their day-to-day satisfaction. In his book, “First Break All of the Rules,” author and motivational speaker Marcus Buckingham notably stated, “People leave managers, not companies.” In my regular review of employee attrition trends, this cause is typically among the top three reasons that employees vote with their feet for any given time period. How can the current and aspiring people managers of the world learn from those bosses who inspired them as well as those who demotivated them and diminished their contributions?

I’ve spent 30 years in the workforce and worked under scores of supervisors ranging from first-line managers to CEOs. The managers who I grew from the most did three things really well: They taught continuously, they provided regular feedback and they flipped the boss-employee paradigm.

I recall my first job as a high school Spanish teacher, where I showed up eager to learn the craft of teaching. It was when my department head handed me the Spanish I and II texts and said “good luck” that I realized I was going to figure out this new vocation on my own. Contrast that experience with one I had several years later when I was learning my first corporate role in an operational position. In that instance, my manager taught me how to do my job while working by my side, demonstrating the aforementioned continuous teaching. He said, “I am going to teach you how to do this job by using the tell-show-do model,” which meant he would explain the task, then demonstrate it, and finally I would give it a try, which ultimately led to — you guessed it — providing regular feedback.

While performing new tasks, feedback is an invaluable part of the learning and mastery process. As I advanced in my career, regular reviews by my managers to continuously sharpen my skills have been an instrumental development resource. For example, some years ago when implementing a significant cultural change, I presented a plan to my then manager who said to me, “This is an aggressive plan and moving in the right direction, but the timing of these changes will be too much for the organization to absorb. Let’s find a way to achieve the same outcomes but pace ourselves.” This feedback was one of those life lessons that spoke to my own impatience and high standards. I still think about it today; it was a significant contribution to my development.

Feedback is an invaluable part of the learning and mastery process.

Building on these first two manager practices, I found that with my best managers the manager-employee relationship and experience was fundamentally different. Those managers flipped the boss-subordinate model and made me believe that their role was to serve and help me. I remember this specifically with a manager who continuously asked me, “What can I do to support you?” This question made me feel supported and also motivated me to solve issues on my own and come back with solutions.

Conversely, I learned equally valuable lessons from those superiors whose habits I committed to never repeat. These include providing vague feedback, constantly cancelling meetings and being a know-it-all.

In the case of feedback, I have found that carefully scripted and vague descriptions of how to improve are confusing and simply not actionable. The best advice I can give is to just say it, don’t overthink it — your people can handle constructive feedback.

Admittedly, I am a stickler for being organized and managing a schedule. Not keeping to a daily and weekly meeting schedule is disrespectful of people’s time and has downstream impacts on others’ calendars. I use the first two days of the week to hold direct report one-on-ones and team meetings that are treated as sacred and therefore never moved.

Last, reporting to a manager who has know-it-all tendencies is demotivating and reduces the opportunity to create solutions and learn collaboratively. As a result, I have practiced the use of listening and questioning skills to facilitate real-time problem diagnosis and reflection to foster self-sufficiency among my team members.

Similar to those moments when we hear ourselves borrow a line from our parents and think, “Is that really me?” we can learn from both our best and worst managers to hone the skill of leading and managing people.