Ross Chapman’s role as Talent Technology specialist at Shopify is at the forefront of the interaction between technology and humans. Talent Technology is exactly what it seems like – it’s about the software used in human resources (known as Talent at Shopify) and other tools in the company’s tech stack. It’s also an interaction between people and software. The balance and the irregularity is an aspect of the job that Ross really enjoys. 

Authentic Leadership

Despite working closely with HR technology, Ross values the human aspect of leadership. He may not directly reference it, but the idea is Authentic Leadership: a concept that has been around a while – going back to the Ancient Greeks. Now, research has shown that employees who report having authentic work relationships have a more positive workplace experience, are more productive, and increase performance/success. 

As a team leader at Shopify, Ross enjoys talking to people, identifying their pain points, and working towards a solution. In a way, it’s the perfect balance of technology and humanity – using technology to help make someone’s daily life a little bit easier. 

“My favourite part of my job is meeting with people across our entire talent organization and understanding what their pain points are, their problems, or exciting new work that they want to do and then partnering with them to do that,” says Ross. “So anytime we ship something new it’s pretty cool. It’s great to feel a part of that and see that work go live.” 

In his role as Talent Technology Specialist at Shopify, Ross embraces authentic leadership in four key ways:

  1. Admitting that you’re not perfect.
  2. Building genuine relationships.
  3. Creating a comfortable space for feedback.
  4. Acknowledging when something isn’t working.

Here’s how Ross explains those four strategies (and puts them into practice):

1 Admitting that you are not perfect

When leaders are authentic, they don’t try to hide their failures or pretend that they have always been perfect. This authenticity creates a space where failure is ok. When you are creating new things every day, it is much easier to innovate when you have room to fail than if you are pressured to do everything perfectly the first time. 

Ross has found that this perspective and mindset has been passed down from the leaders at Shopify. For example, Shopify’s leaders aren’t afraid to comment about things a “younger Shopify” did that probably wasn’t the best idea. It’s not necessarily about the outcome but about the learning, pivoting, and process:

“I think that authenticity creates room for failure,” says Ross. “The reality here is that we have a lot of new leads, but I think when you can create such an authentic environment, there is room to fail. And failing isn’t fun. It’s not easy. It’s not like ‘I’m going to set out to fail today so that I can learn’. But it also creates some of the best learning opportunities. So to have that room to be your authentic self, to be accepted for who that is and to have the space to mess up and fail and fix it and figure it out, only makes us stronger.” 

When Ross was an individual contributor at Shopify, he saw this attitude in the leadership team. Seeing other people embrace the attitude and share what they learned, helped Ross feel freed up to take risks:

“I remember being an IC and thinking, ok, no one here is claiming to be perfect. It’s almost like perfect is a state of being done. There is nowhere to improve from perfect,” says Ross. “Saying that things aren’t perfect and that things can always be improved, and to be curious to look around and make things better .. starts to create that space where you see other people doing it. You’re like, ‘ok that’s a mistake but look at everything that they learned from it’. It’s freed me up to feel like I can take more risk.”

This ties in perfectly to the self-awareness aspect of authentic leadership. As Kevin Kruse describes, authentic leaders “show their real selves to their followers. They do not act one way in private and another in public; they don’t hide their mistakes or weaknesses out of fear of looking weak. They also realize that being self-actualized is an endless journey, never complete.” 

2  Building genuine relationships

For Ross, the key to building genuine relationships with his teammates is to get to know them as people. Sometimes, Ross is able to find a shared interest or something that they are both curious about. The goal is to find some common ground. 

In practice – during his one-on-one meetings with direct reports – Ross tries to share something about his own personal life and be authentic so people can feel like they can be the same. It’s about creating a comfortable space.

Ross gives the example of telling your coworkers about what you did with your kids on the weekend. If your lead is a bit stand-offish and business all the time, then this feels out of place. But if you know your lead on a more personal level, this conversation comes across as more natural. 

“I think that having genuine conversations and getting to know people as people is how you really start to build relationships,” says Ross.  

3 Creating a comfortable space for feedback

Ross admits that giving feedback might not be his greatest strength, but that he’s learned to do it with practice. While he thinks that the best way to improve your ability to give constructive feedback is practice and time, Ross does have a few suggestions about how to improve the feedback process:

For Ross, it’s important to have a strong relationship with the person so that constructive feedback is taken in the right frame of mind. When you know that someone is giving you feedback because they want to see you grow, it’s much better received than if someone comes up to you out of nowhere and gives critical feedback. 

Ross also acknowledges that it is hard to give feedback up the chain to your manager and other leaders in your organization. A way that Ross has tried to get around this is to try and build authentic relationships with his direct reports, so that their relationship doesn’t just feel hierarchical. 

“You want everyone to get better,” says Ross. “I would expect the same [getting feedback] from them. Even with my direct reports, I know that it is pretty uncomfortable to give constructive feedback up. But that’s really the only way that we all get better. So I think that the more genuine you can make that relationship then the better it works for everybody in the long run.” 

As an organization, Shopify uses Fellow to collect peer feedback. Combine this with a self-assessment and a lead review, and it’s easier to identify key themes and move towards a more natural progression. In this last feedback cycle, Ross commented that his direct report’s self-assessments were alined to the peer feedback, showing self-awareness, yet another aspect of authentic leadership. 

4 Acknowledging when something is not working

Ross meets regularly with the rest of the Talent Operations team (including Mobility, Global Talent Expansion, Total Rewards). They meet every three weeks and rotate hosts so that everyone gets an opportunity to lead the meeting. These might seem like unconventional aspects, but it’s a result of a lot of meeting feedback.

In an effort to make the meeting as impactful as possible, the team is consistently iterating! According to Ross, two weeks between meetings felt way too soon while monthly was too far as things at Shopify move fast. Thus, the three-week span was a happy “baby bear” solution like in the Goldilocks and the 3 Bears.

 As for the rotating meeting hosts, it offers everyone on the team (not just the director) an opportunity to lead and plan the meeting. The rotating hosts technique gives people room to stretch out a bit and get to know each other better: 

“I think it’s because we try things and then, when they don’t work, we change them and try again,” says Ross. 

This isn’t the only meeting Ross attends that has been tweaked over time. His weekly smaller team meeting has evolved from more of a stand-up project based meeting to an impactful opportunity to share what everyone is working on. 

After asking for feedback about the meeting, the team realized that they needed to make it a bit more interesting and a little less focused on strictly business. So they decided to incorporate a new section in their meeting agenda (that has helped them get to know one another): “What did you do this weekend?”

Now, they use Fellow for a basic agenda with two “open-mic” slots, where anyone can ask a question or insert a topic. This could be about how a team member implemented a new configuration or sharing experiences in which you pivoted direction. 

The last 10 minutes of the meeting focus on project updates for some of the more impactful projects. Ross describes this meeting as an opportunity to ask each other:

 “Hey, what’s up in your world? And can I learn a bit about it?”

Authentic Leadership is not a new concept, but in the 21st century, it’s become incredibly important. Ross is great at showing his authenticity and showing his humanity to his teammates, allowing them to feel more comfortable to feel the same. 

Gone are the days of the robot-like boss. #ManagementHeroes like Ross show vulnerability, build genuine relationships, and create a comfortable space for feedback and personal growth.