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Thank you to the 1,400 leaders who’ve generously done the 7 questions!
I hope reading

helps you in your leadership.



Jonno White

7 Questions with Kyle Havlicek-McClenahan
7 Questions with Kyle Havlicek-McClenahan

Name: Kyle Havlicek-McClenahan

Current title: CEO

Current organization: Scales Technologies

Originally from the San Francisco Bay Area, Kyle has spent the past decade studying, working and (emphasis) living in Switzerland, France, Alaska and Norway. An avid hiker, skier and naturalist, his passion for the outdoors contributes to a deep sense of connectedness with the ecosystems around him, including social, collaborative and community ecosystems. This fascination with how we interact led him to build Scales, a platform that fundamentally reimagines how people, process and knowledge connect in organizations and across communities and networks using automation and artificial intelligence. In his free time, Kyle loves to read, cook and spend time in nature.

7 Questions with Kyle Havlicek-McClenahan

1. What have you found most challenging as a leader of a small or medium enterprise?

Allowing myself the time to engage in nothingness - not free time spent on hobbies or with friends and family, but the absence of something entirely. Every leader should be putting an hour of their work day on the calendar to engage with nothingness. Whether that means meditation, guided or unguided mindfulness, a walk without purpose - the point is not what you do, so much as the emptiness you must afford yourself. It's in the liminal space between emptiness and a return to work where I find the most valuable insights appear.

2. How did you become a leader of an SME? Can you please briefly tell the story?

By accident, insomuch as a pandemic wasn't planned! The first lockdown in March 2020 was the green light to allow myself a "drastic" departure from what I had been doing before. It's not so much that I needed the change, or even wanted it, but I knew that by letting myself explore I could never lose. It was an accident that it turned into a fast growing startup, and quite a wonderful one at that!

3. How do you structure your work days from waking up to going to sleep?

I block time as much to preserve deep work as to avoid work entirely. Being a remote-first software company and defining my own "hours", I have that luxury. Some nights I have to be working from 5am and others 11pm to account for time zones, workload, etc. What this means is that I don't sweat while taking breaks. So my structure tends to be an anti-structure, in some senses, as anything non-essential is treated as such. Going with the flow and learning to be effective asynchronously are two incredibly hard to train but invaluable skills that I'm still trying to perfect.

4. What's the most recent significant leadership lesson you've learned?

Stop asking questions, start asking feelings. People often need a loving nudge, not only to share how they're doing or what they're thinking, but to actually understand it themselves. Engaging proactively in dialogue is so incredibly important.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

The Tao Te Ching by Lao Tzu

The Witter Bynner translation available free online here:

6. How do you build leadership capacity in an SME?

Will someone let me know when they find a good answer to this question? Asking for a friend...

7. What is one meaningful story that comes to mind from your time as a leader of an SME so far?

It's not so much a story as a pattern that plants the seed for so many stories. Ask. Be real, communicate your truth, and ask. People want to be kind, want to help, it's a matter of whether or not they perceive you as genuine that defines the degree to which they will go out of their way. Another way of saying this is to ask: to what degree are you giving of yourself in the professional interactions you have each day?

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