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Everything started 2 days ago. All of a sudden, it became real. The names I had previously provided were now being seriously considered for termination. I felt both angry and disappointed in myself.

I was angry because when they first asked for the names, we agreed no layoffs would be made yet. I agreed to share names even though I thought the process of performance evaluation was severely flawed. I was disappointed in myself for being so stupid and naive, for not anticipating this outcome.

On the day of the event, I asked myself, “What is my job today?” And gratefully, “A harbinger of dignity” popped up in my consciousness, and a sense of peace immediately cascaded through the pores of my body and soul. I felt centered.

I don’t completely know how I feel about the whole thing. I feel numbed. I feel bad, sad, stupid. I feel like a fraud. I think I am lying. At the same time, I am not depressed. My mood is actually stable. I am relieved too, because on the day of the layoffs, I managed to get them to announce my resignation.

This whole experience has been… interesting. In many ways, I think it’s a failure. Sometimes, I catch myself wishing ill for the brand. But I quickly correct myself, reminding myself that I’ve never been good at predicting outcomes in this situation, nor do I have any solid evidence or experience to bet against their success.

The best thing I can do is leave it alone. I shouldn’t try to make myself feel better by indulging in wishful cursing. Instead, I need to accept that I wasn’t effective in this environment—that I was more fearful and reserved than I wanted to be—and be okay with that.

Still, I hate knowing that I can only succeed in very specific environments. That I didn’t succeed here gnaws at me. My past achievements should be enough to remind me that I’m not completely useless, but I can’t help feeling like a fraud. That said, I’ve faced this imposter syndrome so many times now that I’m starting to laugh it off. “You again? Seriously, bro?”

So, here I am. What an interesting journey.

Have you ever had a “tough love” kind of boss? Do you remember how they made you feel? One thing I noticed about them was almost the reverse of the above Cantonese saying. “They are actually kind at heart.”

What I think these tough love bosses do well is revealing their kindness instead of sabotaging their kindness. In other words, they are tough first, love second, instead of love first, nasty second. When I first came across this observation, I wrote it off. Then I read in the book “Thinking Fast and Slow,” and things started to make sense …

Daniel Kahneman, the author of the book, “delved into the remembering vs. experiencing self. He described an experiment where people were asked to experience pain by placing their hand in a bath of ice cold water for a duration of time. There were two scenarios – holding the hand in for 60 seconds, and holding the hand in for 60 seconds, and then an additional 30 seconds where the bath was warmed slightly. People consistently said the second scenario was preferable and they chose to repeat that rather than the first scenario, even though they were experiencing more pain and discomfort in the second scenario.” But Kahneman said it was the end pain that mattered the most. In other words, how we remember an event trumps our actual experiences of it, and we seem to form our memory of an event from how the event ends.

Applying this to our tough love bosses, they are very good at making us remember their love and kindness by ending our interactions with them with care and support. Almost counterintuitively, it might make sense for us to start with the tough feedback, and invest our effort and time to close out all interactions with love and care.

(This was also posted on my LinkedIn page)

Let’s start with {Level: 99} Discussion:
How did you feel after having a great discussion?

To get to a {Level: 99} of anything you’ll need something extraordinary. World-class conversationalists, from Chris Voss to Dale Carnegie to Krista Tippett, said that in order to be uncomfortably stretched, we must “edge-ride” on extremes:

(1) STOP TRYING TO FIND COMMON GROUND
A discussion is more than about what we can agree on. It should be about gaining an understanding of why the other side believes what they believe. It is to accept the value in relating to each other without rushing to a common ground. 

In fact, the desire of coming to an agreement put pressure on truly understanding each other.

(2) IT’S ABOUT THOSE YOU DISLIKE
A good discussion is whether you can acknowledge what is good in the beliefs of someone you disagree with. Better yet, can you imagine the perspective of someone you dislike? 

So, can you forget about finding common ground when discussing with someone you dislike?

Dr. Lee is a renowned family therapist. I took her courses because they offered live sessions for us to observe.

I THINK YOU ARE RIGHT

A wife complained about her husband’s lack of involvement. When asked how he saw the situation, after a long silence, the husband muttered, “I was too tired from work …” As the wife fired back, Dr. Lee cut her off, “I think he is right!”

Dr. Lee taught us the use of personal judgement should be delicate, and this was one of her tricks to “give voice.” From a supportive nudge to a timid child to a stern demand to a rebellious spouse, “Our role is to give voice and revive dialogues.”

ISN’T IT INTERESTING

Before each live session, Dr. Lee would prep with therapists who referred the clients. She was adept in spotting patterns of situations, yet she remained genuinely delighted by the unknown. “Oh, isn’t it interesting? ” She would exclaim. “The more cases I see, the less certain I am. Isn’t it interesting?!”

THE CONTEXT WE ARE IN

“How can you help a deflated spouse discover her reality? What questions uncover the context of why he feels he doesn’t have enough attention? This is critical because how you see people in context influences how you communicate to them. It’s not what you say that matters.”

During these first 6 months, a few very courageous souls and start-ups gave me the chance to beta-testing the corporate rah-rah I have hoarded over the years. Here are few observations:

1. “High-Performance; Low Potential”: Too often we divest from someone (or ourselves) because their potential is “limited.” No one lacks potential. We merely need to break down leadership traits into approachable blocks and hone them. I am more convinced than ever that a practice-based coaching approach would steer and motivate us to work diligently, patiently and persistently. Yes, we are all bound to be successful

2. Founders, young leaders, and executives all share a similar challenge: the language to articulate ourselves. Business jargons often confuse rather than clarify, and the work on listening from within deserves a lot more attention.

3. It seems difficult for many to evaluate the value of coaching because coaching qualifications and quality don’t always stack up neatly. After all, unlike fitness coaches, we don’t have the muscles to show for. Yet great leaders invest in leadership coaches: Gimlet’s Alex Blumberg and Matthew Lieber, Google’s Sergey Brin and Larry page, SoulCycle’s Elizabeth Cutler and Julie Rice, and more. Clearly we coaches have more work to do

My Practice-based leadership coaching dojo :

Enliven Works — Practice-based Leadership Coaching

“Yea, video-tape your axx all you want. You think Kobe Bryant got great by only by watching VHS?”

6 months ago I decided to end my 20-year corporate career and started my own leadership coaching gig. There was one person that I blame this whole mid-life crisis on: One of my bosses at Nike. This was in the late 2000s. He was an ex-NBA player, and he was the first person that forced practice-based coaching at the workplace on me.

One fall, he started dragging me to join the executive leadership team meetings. I would be asked to present parts of our business unit’s strategy, or participate in debates around quarterly priorities. As a member of the executive team, he would always be in the room to observe me. In the first meeting, I struggled mightily. During our next one-on-one, he went straight in.

“You sucked. You need a lot of work.” He said. “Do you expect a basketball player to not work on his or her weaknesses?” He continued.

He forced me to come up with things to work on. I listed a bunch of things, from the excessive hand gestures to the pathetic incoherence of my logic.

He then asked, “Which one of all these stupid habits of yours is foundational?” I must have looked perplexed because he just continued, “A foundational skill is the bedrock of a set of skills. You first strengthen that skill, and all the other skills can then be stacked on top of it. If a basketball player can’t play with his off hand, what should he be working on first? Is it his left-handed shooting, going to the hoop with his lefthand, or dribbling with both hands?”

I rolled my eyes (in my mind). It was trite to be reminded that we should be aware of our weaknesses, we should commit to practicing new skills, and it was important to know which one to start with. “Duh.” I fired back (in my mind).

“Do you know what made you look nervous and shouldn’t have been let into that room? You know what made that tiny ugly desk outside of my corner office your perfect home? You said ‘really really’ a lot. ” He said.

“The consumers really really engaged with us.” “It is really really important that we focus on activation.” “The team was really really excited about the mission.”

I didn’t think that would be the first thing I should work on. There must be other far more significant flaws I should be tackling instead, I thought. I reluctantly took on the challenge and decided to work on it.

The behaviour itself was easy to overcome. In addition to “really really,” He suggested me to find two other words to rotate through. I chose “incredibly” and “very.” He threw in “really x 1” just to annoy me.

This really really habitual behaviour of mine was an unconscious coping mechanism to nervousness. The simple new habit of alternating adverbs made me become more aware of the moments when nervousness struck. I started to notice my incessant pacing, my distracting hand gestures, and other really really annoying reactionary reflexes. In the past, even if I knew I was nervous, I didn’t know what to do. As I progressed, I started to get better at pausing and creating this tiny mental gap between feeling nervous and reacting.

Tackling this single behaviour turned out to be a foundational change of the relationship between my emotions and my reactions. After having micro-successes in replacing “really really” with … “really x 1”, I gained confidence in my ability to widen the gap between an emotion and taking action. This ability evolved into an anchor for me to work my composure. This gap began to become available when I was flustered, when I was annoyed, when I was defensive, when I got too excited.

Another thing that he did for me was he would always observe me in action. Similar to a real sports coach, he was always sitting at the “courtside” to watch me “play.”

“If a coach of a professional tennis player never actually watched her students played, she wouldn’t be much of a coach.” He retorted when I complained the looming pressure I felt when he was in the room watching me.

“Yea, video-tape your axx all you want. You think Kobe Bryant got great by only be watching VHS?” He barked at me after I suggested I could just review video-recordings of my presentation instead of practicing in front of him.

He applied this practice-observe-iterate coaching approach on my other leadership and interpersonal skills, from negotiation to relatability to self-motivation. In my entire career, I grew the most under him.

He was the catalyst of my appreciation of coaching. He was also that annoying voice in the back of my head that pushed me to make the leap and turn my career towards becoming a leadership coach. Even though this new journey is nerve-wrecking, I know what are some of the things I could do to ensure some meaningful progress. One of them, is to stick to a coach.#coachin

Being genuinely humble is such a common challenge. I see that especially in highly capable founders and managers that I get to work with.

I tried to be humble too because humility was such a sparkly clean and powerful virtue: A humble leader liberates the team by personally welcoming the inevitable failures that authentic learning brings. If Commodus in the movie “The Gladiator” had humility, his apathetic Stoic Dad Marcus Aurelius would have approved, and no one had to suffer the pillow of death.

I tried to logically think my way into believing my teammates were capable of better ideas. I would proclaim openness in meetings, where “no ideas were stupid.” Yet I could never hold my thoughts back and would always make one comment too soon. “If he’s so smart, why would he pretend and didn’t just say what he wanted?”

Humility is hard. 1st, humility is an alchemy of honesty, curiosity, and courage. These virtues, by themselves, are some of the most challenging attributes to hone. 2nd, one side effect of forced humility is hypocrisy, the worst trust-destroying adornment that no managers want to wear.

One way to work towards humility is to “fake it till you make it.” The “fake” is to make your learning visible. This means you consistently say out loud to your peers and teams about what you have learned. The key here is you must only share things you’ve learned from OTHERS- Not from a book, not from a management retreat, but another human being.

Why does this work? 1st, it is easier to start by being selfish and commit to your own learning. 2nd, making your learning public hold you accountable. Lastly, by focusing your learning from others, you will start to taste the feeling of discovering excellence in others. As these add up, you might be able to scale up to the acme of all virtues.

One Christmas, a boss gifted us a book on mindful leadership.

“Ok, so you are a mindful jerk.” Someone quipped. 
“I want to reciprocate with ‘The Five Dysfunctions of a Team’ book.” Joked another.

Another time we received cans of artisanal Baltic sardines. Greg the vegan tweeted, “It’s not personal. It’s not personal.”

And those one size only hoodies, branded mugs from the company (budget), still sit in my closet. (It’s rude to re-gift “Breath to Win #TeamMINDFUL” polos)

Gifting is hard, especially at work. But it’s the thought that counts, isn’t it?

Gifting can be narcissistic when it is a mass-AirDrop of virtue signals: My kind of book, reishi coffee, documentary, etc. Similarly, gifting at work can become jabs of performance reviews:

“Dave, 
Great Book — ‘Mindset — Changing the way you think’. 
H.H., 
Your Friend”

In essence, gifting is committing to the “imaginative journey to put oneself in the mind and the anticipation of another”. Kick-ass gifts are delightful, witty, and, yes, loving. Yet gifting is mentally torturing and risky to your reputation. Therefore gifting can become the work to hone empathy and courage.

The thought counts because of “the imagination behind the thought, and the effort in making this imagination tangible.”

*Quotes from David Whyte

“This is so complicated!”

We endure complicated processes, meetings that are littered with “break-outs,” “share backs,” and those damn “parking lots,” and we tend to blame these on our managers.

Then when we become managers, we begin to accept simplicity is merely an aspiration that sits cross-legged at the highest echelons of business ideals: “Simplicity is the ultimate sophistication!” “Life is more complicated!”

Simplicity whispers danger. What if we missed something? Simplicity whispers fear. We tend to reject it, especially when it comes to describing our choices and ourselves: I am complex; therefore I am unique.

In reality, effective simplicity is a spectrum that spans from Steve Job’s four products to Bruce Lee’s “Be Water,” and it can be worked on through simplifying a meeting:

* Remove elements of a meeting aggressively. No fear!
* Build adaptability (observe, feedback, tinker, and adopt) by geeking out on the who (including us), what (resist too many things, as noise will be our biggest enemy), how (smash bureaucracies), and when (how often).
* Turn this into an infinite loop. Consider setting no deadline and strive for patience and grit.

This work is to learn how to ride the wave of becoming simple. It doesn’t end.