We have ten days between a cold 10-hour video shoot and the launch of a month long campaign. Twice a day we review content, edits, transitions, copy and general vibe in our self-imposed bubble. The general tone is relaxed but the work is always serious. Always honest. There’s no such thing as ‘good enough’ and we will never be finished. We will run out of time.

After one of our reviews our Creative Director Jon Lopez asked if one of his critiques was too harsh — both in direction and tonality. As usual the feedback was shared with our entire team on our Frame.io app — because it allows everyone to learn and grow together.

This particular feedback was a continuation of a prior concern before an edit that had fully matured so the push was more intense. Our CD isn’t always in the bubble so the day-to-day intensity is different for him. The verbal concern from Wednesday became paragraphs of notes on execution, technology, storytelling and pace.

Living outside of our bubble with a baby on the way while home shopping is stressful, so one might understand the added pressure. But we had four days to launch and less time to revise. The paragraphs were legit, but it was a lot.

“Too much?”, our CD asked after I questioned him about some of the details.

Teachers Learn

I’ve always had a soft spot for both the follower and the leader. There’s a common understanding for the struggles of the Davids in stories, but rarely do people take time to understand Goliath’s point of view. Rarely are parents, principals or bosses discussed with empathy. I doubt that Will Smith could make a popular ‘Kids Just Don’t Understand’ without hurting a few feelings.

Unfortunately most of us spend all of our time learning how to do a job and none of our time learning how to help someone do their job.

Overall, we are all suspect bosses.

Learning to be a good teacher or a leader or a boss takes as much training and practice as doing the job itself. From books to experience we can all get better, but the pain is that real practice takes place on real people with real lives and real paychecks and real careers.

Progress > Perfection

Like any other skill, some people are naturally equipped at leadership. Like any other position, some people have been groomed through their experiences to be good leaders. Like any other job, there are tons of educational resources to help anyone become a responsible leader.

We all must understand that the leader needed for a business, an industry, a situation and an employee may all be different. As an employee, there are times when your happiness is far down on the priority list for your boss.

But a good leader should understand the situation and set expectations. Coaching a team with championship caliber is different from coaching a team fighting relegation. Learning to coach through both experiences takes time and guidance.

The Ceiling is the Roof

If I’m being honest, most of my years as an employee were under below average leadership. Sometimes it was my boss. Sometimes it was overall leadership. That’s a lot to take in considering the successful businesses I was lucky to be a part of.

But the reality is that most of the organizations I was part of were dismantled after the team moved on and many of the leaders found lesser roles. You feel a certain way when you watch people get exorcised years after you saw their heads spin.

Strangely I think most of the people I worked with would make the same general statement because finding good leaders in good positions that fit your personal growth curve for any amount of time is difficult.

Early on Caprice Neely told me, “If you ever get to work for a mentor, do it! Because they will always prioritize you.” And every mentor I’ve ever had as a boss did just that.

Even when I was far from the best employee.

There were a handful of universally celebrated leaders at Nike and even they had their struggles. But the people who worked for them knew that they were as valuable as the quarterly report or the next Air Max.

In business, that’s not always the priority from above.

So the business succeeds. The brand triumphs. The train keeps moving.

But the people may struggle.

The Question

Ultimately, my measure of whether my boss was good for me came down to one honest point of self-reflection.

In my opinion the toughest leadership position is not a Fortune 500 CEO or country President. The heaviest coaching position of all is Parent (the one’s who don’t understand). The responsibility of developing, clothing and caring for an employee 24 hours a day with the hope that they will remember to take out the trash and call their grandmother is a lot. Whether you’re a couple with a 12 year old foster child or a single mother with three kids under 5, the priority of managing the day-to-day operation while promoting growth and stimulation is never ending.

And every good parent I know asks themselves one simple question daily: Am I doing this right?

Time and time again I’ve watched amazing parents of amazing kids — and not-so-amazing kids — ponder if they were making the best decisions for their kids future, well-being and happiness.

Too much internet? Too few vegetables? Too much AAU? Too little one-on-one time? Too many college applications? Too little punishment?

The mere act of wondering whether they are doing a good job and asking their peers and even children is a sign that they know that they don’t know if what they’re doing is right or enough or relevant. That inclination that maybe they could be better is always present in the parents I look up to. The mere act of worrying if tomorrow might be an opportunity to be a better parent is a common thread I find in great parents.

The two-sided coin is the high expectations we put on our parents versus the eventual realization that they likely had us five years younger than our current self without a podcast to give them direction. My parents were 20 when they had my oldest brother. And they were 41 and divorced when they had me.

But I expected them to get everything right every single day.

So as an employee I can now appreciate those moments when my not-so-amazing boss gave me a good day or a good month. It was my responsibility to take those good moments and stretch them into a great career.

But I further appreciate the folks in leadership who ask me as a peer or as my boss how they can improve, how they can be more helpful, how they can do more.

When I was elevated to a formal leadership position at Nike, Scott Portzline, a former boss, congratulated me with “welcome to being part of the problem” and I never understood anything in corporate America more clearly.

Mid-level management is a juggling act that I don’t wish upon anyone. But the skills you learn over time can get you from below average to above average if you let the names in boxes above and below yours on the org chart inform your growth.

High Expectations

After the dust in the bubble settled on the feedback I checked in on the team to see how the editing was going. Turns out the feedback was taken positively and helped improve the project as intended. Our Creative Director’s concern about tone was unwarranted in this particular case, but his empathy toward the potential harm is testament to his strength as a leader.

The immediate hope is that today’s project will get better tomorrow and our team will grow now— in skill and in business. But the larger impact is that everyone on the team gets to see the way leadership is a skill to be developed, checked and rechecked because good people are as much of our end product as anything else.

Good things.