Jonathan Kirschner on Practicing Empathy as a CEO When You Can’t Please Everyone

Woden
6 min readSep 19, 2018

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Dr. Jonathan Kirschner is the founder and CEO of leadership development consultancy AIIR Consulting, which is dedicated to fostering strong leadership in organizations around the world. Jonathan long ago learned that, as a leader, you can’t please everybody, but it’s still important to foster a strong capacity for empathy.

Did you have any fears about becoming an entrepreneur?

I definitely didn’t know what I was getting into. At the beginning, it all looked good and felt good in the imagination of my brain. I am really good at dreaming things up and mapping them out, but this was the first time I actually put a big idea into motion that contained risk. The progression of AIIR was very much this theoretical concept that progressively grew in size over the course of many micro-decisions and some very consequential decisions in an incremental way over time.

When you’re in it, you don’t necessarily see that progress. There were certainly moments of dread. You’re fighting all these little battles to stay alive and don’t see the progress because growth can be so incremental at first. But in the rare moments where you’re able to get out of the day-to-day immediacy and step back, that larger view always provided the hope and encouragement to offset fear.

What has been your greatest triumph in your founder’s journey thus far?

There are moments during those all-hands-on-deck team meetings when you step back and say, “Wow, I launched this in my basement nine years ago surrounded by a bunch of psych books and now I’m in a really nice office that we built with an incredible management team and a global bench of over 80 consultants.”

A notable aha was after creating a new functionality for our coaching platform calendar. The feature would allow a user to see any coaching engagement going on at any given time within the organization. … When we got this feature working for AIIR engagements, I was clicking and scrolling to next week. On Monday at 8 a.m. we had several sessions in New York and Dallas, then a coaching session later that day in San Francisco, and then a session in London at 9am the next day, which would occur while I was sleeping. I recall just thinking to myself, “Holy cow, this is unbelievable; there’s client work going on while I’m sleeping!” To trace that back to the very beginning of AIIR when it was just me and my idea was a huge, fly back in your chair moment.

What has been your biggest sacrifice?

One of the big sacrifices is realizing that there will be people that aren’t going to like you. … It’s been hard for me as someone who thrives on likeability and harmony. There’s going to be people out there that don’t like you or what you’re doing, that may even try to attack you. On some level, what I have learned, is that if everything is rosy for an extended period of time, you probably haven’t done that much. It’s a hard reality to accept and embrace, but part of the necessary development as a leader is making bold decisions in the service of the organization, even if it ruffles feathers and stirs conflict. The big sacrifice has been having the ability to dial down my pervasive niceness and know how to toggle between being the peacetime CEO and the wartime CEO.

What has been your biggest failure?

The biggest failures are when I become so passionate as a Founder/CEO that I don’t take the time or build in for the capacity to properly empathize. So there are moments in the very fast-paced environment we’re in where assumptions can be made, comments can be flung impulsively, and can create bruises and cuts. Those are the moments that I aspire to learn from in my own personal development. How does one engage intensely and passionately while at the same time maintain incredible discipline in the ability to empathize with others consistently?

Did anyone in your life try to dissuade you from becoming an entrepreneur?

Many people were supportive, though I think there was a fair amount of underlying skepticism. [They’d say], “That’s a cute idea, but … let’s see where he goes with this.” … There have been people that have come and gone, particularly in the early days. … There was not enough writing on the wall that this would be winning concept to preserve confidence of many people. As great as the idea was on paper, I was terrified of selling and getting traction was an extremely painful learning curve! Keeping the lights on required a fair amount of irrational behavior on my part when there were so many individuals and signals that questioned the long term viability of AIIR.

What’s been extremely valuable for me to get me out of ruts is having a mentor. Not just a mentor who was an executive, but who understands, experientially understands, what it’s like to start from scratch and build. There are a number of fellow entrepreneurs in my life that I draw support from. I also take my own medicine and have a coach. Coaching forces me into a 30,000 foot view of myself and AIIR. Coaching has been invaluable.

Is there anyone who was especially supportive?

My father was very much in support and continues as our Chairman today to be huge advocate and source of support for me. … And my mom has been a huge supporter … She really keeps me in check. My wife has been there and willing to trust in my vision- even when AIIR bounced a check in year 2 and had negative $200 in the bank. In the first 5 years of AIIR, I never took a salary. For at least the first three years, AIIR was in the red. My wife Larah supported us and was just — she believed in me, had conviction, and was willing to put in a tremendous sacrifice for the vision to play out.

How is your work-life balance?

I’m not quite sure when it’s going to stop, but there’s an intensity to being an entrepreneur and founder that would be atypical to a standard job. What I’ve come to appreciate is the importance of carving out time and protecting it like crazy. For me, every weekend I commit for a 24 hour period — Friday night to Saturday night — no phone, no electronics: this is my Sabbath. I’m Jewish, and it’s a very important part of my identity. Shabbat is a sacred time for family and to refuel and recharge.

I’ve also started playing ice hockey again recently. … Hockey has gotten my mind outside of the business. Entrepreneurs have all these plates spinning. The plates don’t slow down; they only speed up. Having an activity can help channel a lot of energy into something other than business has been very helpful.

Did you ever come close to giving up?

I’ll never forget early on when a Fortune 100 organization responded to a cold-call email I had sent. He emails back and says, “You know what? We have someone great for your model. This is going to be an engagement. I want to learn more.” I remember literally crying from joy. This validated the cold-call strategy and validated the company, the fact that a total stranger saw value [in AIIR].

When that fell apart two weeks later, I remember thinking, “This is hard. This is really, really hard.” Rejection after tremendous amounts of work and unpaid time and effort to bring in a sale is like a punch to the gut. Particularly in the early stages, when the fate of the company relies on that. Getting punched in the gut, successively and particularly within a short period of time can be the most challenging aspects of being an entrepreneur. For many, it’s just too painful and not worth it. For others, they learn to cope, and over time, build resilience.

What would make you feel as though you accomplished what you set out to do with Aiir? Does such a moment or goal exist for you?

No. It’s how I think. Whenever I get to a goal, my mind goes right to what’s next.That’s the torture of being me. It doesn’t mean I don’t celebrate [successes as they happen], but it never stops. I don’t have an end point that I would say, “If I reach that, then I know I’ve made it.” For me, it is about the journey, not the destination. I’m in love with the journey.

Check more of these honest conversations with founders pursuing what they love at capturinglightning.com. This is a project of Woden, you can check out what we’re all about at wodenworks.com.

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