Caring for your direct reports as if they were your children

Caring for your direct reports as if they were your children

Management as a form of parenting

📸: greensboro.com

Becoming a manager is a huge responsibility — you are being entrusted with someone’s career which, in turn, affects their broader lives. It reminds me a lot of parenting — a demanding, 24/7 responsibility, but with personal rewards that extend well beyond the traditional relationship.

To succeed at management, you have to give a damn. You have to obsess about your direct reports and think about their roles and well being at all times. While the conversations will often be around work and career, they will undoubtedly extend into the personal arena — breakups, conflict, tragedy, therapy to name a few.

To obsessively care about one’s employees, you to understand where they came from and where they want to go. Said differently, management is not just a point-in-time (or near term) relationship — instead, it covers a vast continuum of the employee’s life.

Understanding how the employee got to this role is the first part of the process. Yes, their “major milestones” were presumably teased out during the interview process but that just scratches the surface. Like any good relationship, understanding the transformative events in one’s life require time, deep listening and compassion, and trust. But developing that rapport and understanding these events form the fundamental basis of the employee’s life and thus will inextricably be tied to their performance and behavior at the company.

While there’s no playbook for building this relationship, a few themes come to mind:

  • Nature of important relationships (parents, but also friends)
  • Childhood experiences
  • Passions and hobbies
  • Travel and cultural perspectives
  • Insecurities

This is by no means a comprehensive list, but you can quickly see that that asking the question “What are your insecurities?” will not lead to a trusting and fruitful relationship.

I love the Tony Robbins quote “The Quality of your Life is measured by the Quality of your Questions?” All relationships require effort and an investment from yourself — the manager-employee relationship is no different.

The second piece is understanding where the employee wants to go and providing them with the tools for them to be their “best, authentic selves.” Here is where I disagreed with many of my management peers. Being your best self is independent from the company in which you work. It is naive to think that an employee will work at your firm for their entire lives, thus equally as naive to believe that you must give them the tools to succeed only at the company.

But there’s a healthy tension here, notably that culturally the employee will feel like they must behave as if the company and job is the only one they ever want to have. (This cultural paradigm may be beyond the control of the manager themselves, especially within a large company.) Again, with trust originating from deep listening and compassion, the manager can create an environment in which the employee will feel comfortable being authentic and sharing their true ambitions and passions more genuinely.

This is where I think many managers (and companies) fail. By not letting their direct reports be authentic (due largely to the unreasonable expectation that they will work at the company forever) the employees put on a mask and have dual selves.

More specifically, as a function of a lack of trust, they hide their true ambitions and passions from their manager (and consequently often from themselves). If you asked a direct report — what do you see yourself doing in five years and they answered with “being the best [insert current role extrapolated five years forward] I can be for the company” I call bullshit. This answer is a huge disservice to both employee and company as it reeks of disingenuity.

I saw this very specifically with business school applications. Many of my industry peers tried to dissuade their top performers from applying because they didn’t want to deal with the ensuing huge hole that would arise. But this selfish calculus would undoubtedly backfire down the road. What kind of message does this send to the employee about their long term prospects with the company?

This reminds me of a story of Coach Dean Smith at UNC’s Men’s Basketball program. If a student-athlete had a high likelihood of being a lottery pick (~top 10) he would encourage them to go pro after one year in college with the ask that they return to college post-NBA to complete their degrees.

Woah. This pissed off boosters and fans alike — ushering their best talent out the door after just one year? But think about the message this shows to young players and recruits — we care about your well being beyond that of the program. A secondary (and more nuanced way) of looking at it (from Smith’s perspective) is that there is an exchange (a “reciprocity” in going back to college) that, once again, optimizes for the student athlete being their best authentic self.

I don’t need to tell you the impact this philosophy had on the long term success of the UNC Basketball program, we’ll leave that to the history books. This loyalty to the student is a form of abundant thinking, where the student and the program reach their full potential.


Another way to break from the “dual self” paradigm is by understanding and supporting an employee’s hobbies and passions. Again, I observed in my industry peers that hobbies were viewed as “taking away from the core mind space” of getting the job done and were ignored (and sometimes even discouraged). I recall a friend’s direct report who had two passions — teaching history and coaching lacrosse. I urged the friend to stay on his report to make sure that he nurtured these passions, even offering to introduce him to members of my network.

Passions are not second class citizens at work — they are what makes each individual unique and nurturing these passions will bring out their best selves. It is incumbent and necessary that a manager do that and the byproduct will typically be a high performing employee.

So how does one implement all of the above? There could (and will) be a string of follow-on posts to address this. But the first principles are: compassionate listening, asking good questions, and caring beyond the role.

Andy Grove talked a lot about the 1:1 check-in meeting; his approach was a check-in a week, per direct report, limiting the number of reports to 6–8. He also made it very clear that these check-ins are the employee’s meeting and the manager’s sole role was as listener.

Another effective approach is to leave the office. Stroll the areas where employees are working, at different hours of the day, observe, ask questions and notice the patterns and energy. This may sound obvious, but many managers fail to do this.


Like parenting, you can’t fake it — well, you can, but do you really want to know the consequences? I always loved hearing my older friends discuss how they loved getting all their kids and grandkids around a huge dining room table. Wouldn’t it be fun to extend the family?

🤔🏄🖋⏲3

Reflect, flow, write, with a timer, Day 3


I’m experimenting with a daily writing process, focusing on just ideas and nothing else.

Khe Hy
[email protected]

Khe Hy is the creator of RadReads.