Prior to founding Willful in 2019, Erin held senior roles at BetaKit and wrote for various publications including The Globe and Mail and Business Insider. She also led her own creative marketing agency, Eighty-Eight, where she worked with clients like Lyft, Telus, and Sony Pictures Television. 

Erin recognizes that empathy, awareness, and connection are key aspects of being a compassionate and empathetic leader, whether it be a service-based or product-based business. Listen to this episode (or read the transcript below) to learn how important our actions are as leaders and how they directly impact our teams and company culture. 

1 Who has been your favorite or most memorable boss?

My favorite and most memorable are both the same person, Sarah Yvette. My second job out of university was working at a startup called Sprouter, which is a social network for entrepreneurs. Sarah was a really strong example of a female entrepreneur and she really made me fall in love with startups, which previously hadn’t been an industry I had known much about. She was always super supportive of me, and she still is to this day, and I credit her for shaping my career path and leading me into the world of entrepreneurship. 

2 What are some things that you would have adopted from what you’ve learned from Sarah? 

Sarah was always someone who encouraged autonomy versus micromanagement and encouraged resourcefulness and she always encouraged people to figure out things on their own instead of holding their hand or breathing down their neck. She always made an effort to hire people that were great at their craft, and she didn’t micromanage anyone and she was successful in this because she was very clear about setting the goals that we were working towards as a company, and we always knew what her expectations for success were. I appreciated her approach of letting people do what they do best and stepping in when she was needed and that definitely something that I’ve applied to my management style. 

3 What are some of the differences between managing teams at an agency versus a technology startup? 

It’s so interesting to look at the differences between a service business and a product business. At the agency, our entire day and company was dictated and driven by external factors versus a product company where everything is driven by internal factors and when I made the shift from the agency to Willful I was almost lost on day one, because I was so used to having clients dictate my daily agenda and all of a sudden as a product CEO I had the freedom to dictate my own daily agenda and my time became my own but you also have the pressure of making sure that you’re focusing on the right things. 

At an agency, you don’t always have the opportunity to dictate how your team feels because sometimes you might have a really difficult client that sets the tone and that can be difficult and I was often stuck in a hard place because we needed our clients to pay the bills but we also wanted to try to keep our team happy and make sure they were being respected. 

When I moved to Willful, the things that I wouldn’t do are things like tracking time and judging someone’s output based on their billable ratios, and how many hours of client work they were doing a week and one thing that I did at the agency that I definitely haven’t brought forward is managing all of the performance reviews myself. At willful, I’ve really taken the approach of building up the leadership team and empowering them to do a lot of the things that I might have previously done as the leader at the agency. There’s also a lot of stuff that I have brought over and a lot of it has to do with culture and education

4 Can you expand on investing in people’s skills within your organization? 

For a team member to feel good about their direction at the company, they have to feel aligned with the larger company mission and feel like they know where it’s going. They also have to feel like they know their direction and where they’re going personally while learning and progressing and ensuring that they won’t remain stagnant in their careers

It can be really hard in small teams, especially if you’re less than 20 or 30 people because you can’t always promote people right away because you don’t necessarily have somewhere to promote them to or you might need someone to be doing the job that they’re doing, and you don’t have the budget to replace their role. I found over time that the best way to show that career growth when you can’t necessarily always be putting people into different roles is helping them grow their skill sets through training or education. At the agency and Willful, I’ve always had a $500 annual education budget for each person that they can use on whatever they’d like that relates to their role and we also do semi-annual training programs for the majority of the team. There is a really amazing grant in Ontario called the Canada Ontario jobs grant that offsets the cost of training for employees, and I apply to that grant every six months like clockwork.

5 Why do you think having a positive outlook is so important?

I’ve always just been an unfailing optimist. I view positivity as a choice. How you’re going to walk out the door and carry yourself is your choice and I choose positivity, and it has become even more pronounced for me in the workplace. Because I was already a positive person, it was natural for me to carry that attitude into the office. Your employees are looking at you all the time as a barometer of how they should feel about the company. If you come in in the morning and you had a really bad sleep, and you’re in a terrible mood that sets the tone for the rest of the office. As a leader, it’s your job to provide a sense of consistency because your team is relying on that to feel confident. 

6 How do you deal with losing your biggest account? Do you still have a positive attitude? 

Positivity isn’t pretending that bad things don’t happen or pretending that you don’t have bad days. I think it’s important to highlight and be transparent especially with my leadership team about days where I’m feeling off because no one is infallible or perfect. 

When sharing that news, it’s always framed in the context of what we can learn from it, right. If there’s a setback for the team, if we miss a revenue goal, if we lose a big client, it’s always okay, this sucks, it’s not ideal, but there are positives. There is always a silver lining. 

7 What have you learned about hiring people and what do you look out for when hiring?

I think it’s important to note that I’ve worked with HR consultants, but we’ve never had a full-time HR person at any of the startups or small teams that I’ve run. It’s been me, in many cases, doing the hiring and I’ve definitely made every single mistake in the book. I’ve hired people for sharing the same hobbies as me and I’ve hired people when I didn’t have a good gut feeling and they ended up leaving a few months later. 

I realized that trusting my gut, really looking for company alignment, not personal alignment with someone that you’re interviewing is really important. I also always look for resourcefulness. I don’t necessarily hire for skills; I hire for resourcefulness. I don’t care if you have the answer, I just want to know that you can find it on your own and get from A to B. I’m looking for someone that is willing to get their hands dirty. Resourcefulness is kind of a barometer for what you’re looking for in startups, you often do get people who are really flexible, and who work hard, and who are able to work within various constraints.

8 How do you figure out if someone is resourceful?

A lot of it is being upfront about what the job and the environment is like before you even bring them in for an interview.  I really tried to start being extremely upfront in the job description, but also in interviews about all of the bad things about the role. We just hired a marketing specialist and I was very upfront, I told them they would have a very small budget, and that they would get almost none of the product and engineering team’s time. I also told them this would be a huge opportunity. When you paint the picture, you’re almost forcing resourcefulness, because you’re telling them you’re not going to be set up for success unless you’re the type of person who can work within constraints and find a way to get stuff done without the perfect set of conditions.

The other way we do that is also through tests. I’m not a huge fan of having candidates do hours and hours of work but one simple writing test or coding technology test can find all of the other pieces of the pie that they need to solve the problem after I’ve given them a small snippet of information and that can be really helpful in understanding if someone is the type of person who is resourceful in finding answers.

9 Do you have any tips for people that want to enhance their personal productivity?

Productivity is a choice and so is organization and some people are naturally organized whereas others aren’t. For example, my husband, Kevin, is definitely more of a creative entrepreneur. He’s the one who had the idea behind Whirlpool and organization doesn’t come easy to him. Over the years, I’ve been telling him that you can either call yourself a disorganized person who’s just never going to have those systems in place, or you can try to work against your natural tendencies and input systems that actually do the work for you. 

So, for me, that’s been things like religiously adhering to to-do lists and productivity software. I live and breathe by our team Asana boards, and by my own personal Asana board that has everything from today’s to-do list to this week’s and next week’s quarterly priorities, and personal to do’s, you name it and if it’s not on that list, it doesn’t get done. I also am a big fan of time blocking. So, putting time in the calendar for heads-down work against some personal tasks. 

I’m also a big fan of the Sunday organization session. I take a couple of hours every Sunday and clean up my inbox, set up my to-do list, and reorganize it for the week by time blocking my calendar. It’s been a really great way for me to go into the week with a really clear sense of what needs to happen. 

10 How do you build systems to make sure the whole team gets more done?

I like to start off Monday feeling organized and go to bed Sunday feeling organized, but you could absolutely wake up on a Monday and just block two hours in your calendar to do exactly that, clean out your inbox, review your to-do list, and time block for the week. Everyone on a team has their own personal organization system that works for them. 

The engineering and product team uses Pivotal, which is similar to JIRA, and the marketing operations and partnership side of the business uses Asana, and I think that helps keep everyone on the same platforms and speaking the same language. 

11 How do you balance transparency in a startup environment? 

We have quarterly OKRs as a company and those are really the focus and anything else is typically shared through our monthly town halls. We also have a team-wide meeting every month where I keep everyone in the loop on the other stuff that’s happening like fundraising or any special projects that we’re working on.  The idea is to balance transparency and I’m very passionate about making sure everyone feels confident about our financial status. As a company, balancing that without providing too much information that actually ends up being detrimental and hindering their ability to do their jobs. 

12 Why do you think it’s important to coach as a manager? 

I’m a very empathetic leader so caring about my team on a personal level and caring about them on a professional level just comes naturally. I remember speaking to someone and empathy didn’t come naturally to them as a leader and they said they had to train themselves to ask somebody at the beginning of a meeting, how they were doing and how their weekend was because it was their nature to get into a meeting and immediately dive into the task at hand.

I used to really fight my empathetic leadership style and a business coach that I work with a few months ago said if you came into the office and screamed at everyone, everyone would be like who is this? This doesn’t align with her leadership style, so I’ve started to lean more into the empathetic side of my leadership and recognize that it’s actually not a bad thing. 

13 What tips, resources, or advice would you share for leaders that are looking to get better at their craft? 

Melissa and Jonathan Nightingale have a course called managing 2020 and it’s a very affordable online course. It’s all about managing through uncertain times because and I would definitely recommend it. I’m also a big fan of the ask a manager blog, which is all about employee conundrums and how people should tackle them. I’m also a big podcast person and really love the Radical Candor podcast which is all about the idea of radical transparency within an organization and how to leverage that as a manager.