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How to Harness the Power of Questions w/Shane Metcalf, Chief Culture Officer of 15Five - Ep# 97

By Anthony Taylor - April 14, 2021

Shane Metcalf is the co-founder & Chief Culture Officer of 15Five, a people and performance platform that empowers people to become their best selves, wherever they work. Named one of the top 100 software companies by G2Crowd, 15Five combines employee engagement, continuous performance management, and manager effectiveness software with education, services, and community for customers including Capital One, Credit Karma, Hubspot & more.

On this episode of the Strategy & Leadership Podcast, Shane joins us to share his advice for leaders and discuss the power of questions, self-reflection, and much more.


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Here's a breakdown of our conversation:

  • The journey of creating 15Five

Shane spent his early career in private equity. He hated it, and ended up quitting. From there, he decided to dive into the underbelly - the world of transformation, culture, coaching and workshops. He noticed communities involved in self development, relationships, communication, authenticity and more, and realized this was where he needed to be.

He met a mentor who trained him to become an executive coach by the age of 26, and his journey began. He then met someone named David Hassel, who he began exchanging ideas with. David had the idea of asking questions at scale that could lead to better conversations and business results. That product would go on to become 15Five.

  • Be aware of leadership hierarchies 

"A lot of work is coloured by fear and obligation".

Shane explains that humanity has been based on hierarchy for a long time, which has caused a lot of harm. In a dysfunctional hierarchy, leaders don't care if their people agree, only that they're doing their job. As an employee, your intrinsic motivations don't matter. We have some un-conditioning to do. to eliminate the subtle and subconscious war between employees and employers.

Today, leaders need to flip the script and say "I'm in service of you", rather than the other way around. This creates a situation where the people want to be in service to the leader. As Shane says, "switch from authority that's based on fear to authority that's based on trust"

  • Questions for leaders to ask themselves 

Especially for leaders who are early in their career, the opportunity for developing self awareness at the stage is invaluable. Asking yourself what your strengths are is a big part of developing that self awareness, which means don't be afraid to experiment.

Another key question to ask is around communication and how effective you are. Developing your ability to communicate (especially by public speaking) will reveal some of your deepest insecurities. Shane mentions that what helped him in the beginning is assuming that people are interested in what he has to say, instead of the other way around.

Going deeper, there are questions you need to ask yourself around sleep, hydration, nutrition and exercise. By ticking these boxes, you're putting yourself in a better spot to function at a higher level.

And finally, a great metaphor from Shane: Would you rather cut a tree down with a dull axe, or stop, take 10 minutes to sharpen it, and proceed to cut the tree down with ease?

  • Questioning the role of the manager 

The role of manager is not the same at every company. Shane explains that the first thing to do is get on the same page about the role of the manager at your company. What do you expect your managers to do? What's the job of being a people manager? If it's their job to care about their people and get the best out of them, then they might have to commit to caring deeply about their people and having check-ins, one-on-ones, and other meetings.

Unfortunately, there are way too many managers that don't actually get trained on how to lead people, so ask yourself how you can help them.

  • His big challenge right now as a leader

Shane shares that as a 200 person organization, people come into the company with very different experience of work. He's challenged be asking himself how to reach the people that deep down want an environment of growth and development, but have so many layers of resistance that they're convinced it's inauthentic. Not everyone that's hired is interested in a transformational culture, and some are even skeptical of what he's doing, so the challenge is getting through to those people. 


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To learn more about Shane and 15Five: