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What Motivates Your People to Do Their Best? Interview with Jeremy Bailey

By Anthony Taylor - April 24, 2017

Jeremy Bailey, the Creative Director for Product at FreshBooks, (an online accounting system for small businesses) joined us to chat about strategy, leadership and culture and how these help influence creativity and customer service. Jeremy shares insights on how critical thinking and team building can help organizations align their teams with their mission, empowering them to make decisions, as the organization grows. 

Jeremy also shares author Daniel Pink's views on managing teams. Built on the three pillars of: mastery, autonomy, and purpose, a leader can guide their team towards empowerment and help them to make the best decisions for the client base, and in turn, the organization. 

Other key insights that Jeremy shared include:

  • The importance of reflecting on assumptions and following up with customers 
  • The knowledge that what is right today may not be right tomorrow
  • Understanding how to include your team in the organization wide strategy, from the bottom up
  • Focusing organizational goals on what can help the customer, rather than just bottom line profits
  • How team and leadership feedback can foster the growth of each team member

Listen to the full podcast below: 


 Interview Transcript: 

AT: Hi there everyone. Anthony Taylor with the strategy and leadership podcast. Today I’m joined by Jeremy Bailey, who is the creative director for product at Freshbooks.

Can you tell everyone a bit about your background and yourself? 

JB: I’m creative director of Freshbooks, which means I lead, and inspire, and manage our design team and practices here. I also work as an artist, part time. I think you were commenting on my Twitter profile. If anyone visits my Twitter profile, you’ll see that I don’t look like your typical creative director, and that’s because for the last 10 or 15 years, I’ve acted as a famous new media artist online. I have a mixed life as a “self-proclaimed famous new media artist”, and that’s a satirical title, and creative director at Freshbooks. Surprisingly, there are many similarities between these two roles in a lot of ways. 

AT: Can you give us a quick blurb about Freshbooks, what it does, and you just released new Freshbooks, so I don’t know how deep we can get into the strategy and the process of that launching. That might be a whole other conversation, but just tell us a bit about Freshbooks.

JB: Freshbooks, the best way to put it is, if you hate accounting and you’re running a business because you have a passion and not because you like to do your paperwork, we’re here to help you out. We’re an accounting platform and software, available across all your devices, but we’re really focused on getting out of your way and making it really easy to do this thing that we know a lot of people consider a headache. This is what most software products aim to do; take a pain in the world and try to make it better.

We know a lot of people, with a lot of pain, just in regards to their accounting. Simple accounting, for most people who we serve, usually freelancers or small business owners, a lot of it is around getting paid, billing, and simple expense tracking.

AT: You’ve been with the company almost seven years now, is that correct?

JB: That’s right. Yeah.

AT: You’ve definitely seen the evolution of product and been through different stages of that product: art director, creative director, and now more focused on the product side, or I’m sure some overlap within that?

JB: I joined about seven years ago, and there were about 30 employees at that time, and since grown to about 300. It’s really not about the number of employees, because that just allows you to do more stuff. I always feel like there’s way more we could be doing. It’s part of the job, but [we] also have built up the team, and all the processes, and learned to become a pretty good manager I think. There’s always more to learn and that’s a big part of my philosophy for management and running a team. It’s really about learning constantly. 

I’ve learned a lot. One thing I would say is every time you get to a peak it’s like you can see the next mountain peak just ahead. The more I learn, the more I realize I need to learn. I think the team has that attitude as well. We’re growing and learning, and we have really amazing customers, kind of like you, who have a similar mindset I think, quite often.

AT:  What would you say are your two to three best practices for leading strategy?

JB: It’ll be hard to narrow it down to two to three. Maybe it’s only one I start and we kind of dig in. I lead as a designer, first and foremost, or from a design perspective. This might not be the way you’d want to do it if your company is oriented a different way. Freshbooks happens to be very customer centric. When I joined the company, at first I thought, “Is this a cult?”

People, the CEO and the people here, they were just so emphatic about spending time with customers, getting to know them. Our strategy starts there as well. All of the design processes I’ve built are about spending more time with the customer, getting to know their needs. The biggest strategic mistake I’ve seen in my life before, and even when we’re off track here at Freshbooks, is when we don’t really include the customer’s voice and we start to rely on our own opinions, rest on our success, or our opinion about what we think will be the right thing. 

Quite often your assumption about what you think is right, is wrong. A lot of what I would consider strategy, is mitigating those false assumptions, those risky assumption. The best way to mitigate them is really just to get out of your comfort zone, get out of your building, spend time with customers, and also bring customers into the building; we do that in a number of ways here, and include them in the process of designing your product or your strategy.

AT: I get the underpinning part of your business strategy is really making sure you understand who your core customer is, what their needs are, and being attached to your mission. Is that correct?

JB: Yeah. The mission wasn’t invented out of thin air. Nor is our brand, or anything else or anything else that comes out of this company. It is all a reflection of the customer. That can sometimes be difficult, because you have different customers with different priorities. We’ve done our best, wherever possible, to focus on a specific customer. That’s another strategic error, I think a lot of companies make, is they try to be all things to all people. A good strategy is choosing your customer, and really going after them, and doing things for them that are really quite specific to their needs. That’s a challenge, especially as you get into consumer software. The spectrum or segment, whoever you consider your customer segment, might grow, you still need to serve the original early adopter customer, and then maybe a new customer segment comes along.

Sometimes you add features that hurt another customer segment … Anyway, all of that ends up becoming more and more challenging. We certainly don’t want to start out trying to be the next Instagram. It’s really hard to do that. I don’t know if you’ve talked to anyone in that space. We started out with creative professionals, I’ll put it that way, and then we expanded that to include consultants and marketing professionals. More recently we’ve started to see, by accident, people in the trades industry starting to use our product, legal professionals, but we always remind ourselves that we, first and foremost, we built the product for this specific customer, and then we modified things to allow more and more people to use the product.

AT: I’m trying to put myself in your shoes and understand your process. How do you then, as an organization, or you personally, translate that strategy and direction to your people?

JB: Process is actually a big part of that. The process that we use for design is really a bottom up process. One of the things that I’ve worked over the last seven years to do, is get out of the I can do everything heroes team … I might hire a team of independent contributors who work in silos and are just heroic figures. That was why I was hired here. I was hired as an art director to fix everything. I could do a little bit of everything, but I realized that’s not very scalable. As we grew, we had to investigate processes for distributing decision making, and making decision making and strategy happen from the bottom up, rather than the top down.

One of the ways we do that at Freshbooks is we use what I think a lot of other start ups might use, but we use it as a mature company as well, are lean start up methods. There’s a great book I can recommend that has revolutionized and refined a lot of the way we work. It’s kind of an old classic now, but it’s Ash Maurya’s Running Lean. It’s a book, the book that came out after lean start up. Hopefully people have read Eric Reis’s Lean Startup. If you haven’t, it’s a great book as well around efficiencies, and strategy, and management. Basically, the premise is the individual contributors are in contact with customers, but they’re always contacting them with a hypothesis.

When I said include the customer, it’s no good just to have a customer come in and tell you what to do. What you really want to do is write down your assumption about how you think they’re behaving, or what you think they need; write that as a hypothesis, and then design a test or a scenario in which … That would be an interview. There are ways to do that. I can get much more specific if you’d like, but a test in which you can validate those assumptions. Like I said, a lot of times, we just go ahead with the assumptions and build those things in software, and that’s a very expensive way to develop a strategy: find out if you’re right after you’ve spent a million dollars. Not a good idea.

The cheapest time to validate your strategy is when you just have an assumption: what you think, who you think the customer might be, and what you think the problem might be. Our designers, for example, would just call up some customers or go visit them at their offices, and talk to them about, “Hey, we think these are your problems,” and they would do what we call a problem interview, as a first step. They would find out: is this the right customer, and do they have the problems we have? Usually they’re wrong. Usually we send them out into the field, or they come back and they’re like, “Actually, this was right, but these two other things were wrong. The customer that responded the best is actually not someone we originally identified. It’s this other person.” There’s a lot of that. The strategy emerges over time. We progress through stages. Confidence increases over time. We don’t come out with a refined strategy, or work behind closed doors on our strategy. We build up a strategy over time. We might know roughly, here’s a market opportunity, let’s go investigate that. Then within that market opportunity, a strategy would emerge through this process of negotiation with our customers.

AT: Most interesting in that is the bottom up approach to strategy. We advocate top down, as in you have the leaders of the company create the strategy in a way, send it down to the front line employees, get their feedback on it, and then send it back up. It sound like that’s what you’re doing, and then in addition you empower all of your employees. I wouldn’t necessarily think of a designer traditionally to be on the phone with a customer. You would just lock them in a room and they could start coding. It sounds like that’s not your approach to things. You really make sure that your employees are all involved in all parts of the business. Am I understanding that correctly?

JB: That’s right. The designer is responsible for a lean canvas, which is a business model canvas. Their responsibility is to validate every aspect of that business model. That also includes the user experience, which is where you would typically find design. Before they do that, they need to validate the customer, the problem. They need to validate the solution, what comprises the whole solution in relationship with existing alternatives. The user experience is a small part of that, that comes at the end, but I would say 80% of their time, they’re working on validating assumptions, and then 20% of the time on actual design work, like the way you’d classically consider it visual design.

I’ll also say they’re working alongside a product owner who has more of a business background and more of a strategic thinking background, and they’re both tag teaming on that work typically. They’re working alongside myself, the director of product, and our CTO and CEO are checking in from time to time. They’re out there doing the work. We’re very much making sure that they’re the ones in contact with the customer. In an average year, we talk to about 2,000 customers now. There’s no way I can talk to 2,000 customers.

The number of features that we might be working on are aspects of our product, is in the dozens. Every week we’re getting between 10 and 15 hypotheses out into the world. Companies like Facebook, of course, are testing hundreds of assumptions all the time. As a 300 person company, I’d say we’re testing dozens at any one time. That’s what I mean by bottom up.

AT: I’m definitely going to ask you about how you manage those assumptions in the scope of strategic priorities. Let’s move on to the culture. You’ve got this culture of collaboration. You have a culture of ownership. You have a culture of being people first. You have a culture that’s represented in your brand, the creative professional, for us by us sort of thing.

What are the things, as a leader, that you do on a day to day basis to cultivate that, that our listeners could say, “Oh, I could do that with my team, because I want to develop our culture.”

JB: There was a book that had a big impact on me. There have been several, but the one that I refer to often is Daniel Pink has this book. It’s called Drive, and it’s about motivation. I’ve read other books on management that also echo this, but I really like his principles that there are three things that motivate people. One of them is mastery or craft. If someone’s good at something, you’ve got to let them do it. A lot of times you’ll hire someone, and you’ll tell them how to do their job. Every time I’ve seen that happen, it’s a recipe for demotivation. That person now has no value.

The second thing is autonomy. It’s kind of similar to the mastery piece. Autonomy is giving a person the space to practice their craft and to make decisions. That’s what I mean when I said bottom up strategy, to know and to learn how to make a decision so that we can scale decision making. To give them frameworks to do that, that’s something that I would do. I’ve given the team many frameworks for structured decision making, so they can take a little bit of the guess work out of it, but it’s also important to build that muscle around critical thinking. Critical thinking is absolutely necessary in a world where uncertainty is increasingly the norm.

In an age of acceleration,  as Thomas Freedman would say, is that when everything’s going faster, the person that was right yesterday is potentially wrong tomorrow, and they need to be in a position to challenge their assumptions and think critically. Finally, I think you hinted at this earlier, it’s so important, and this is where the most top down thing can come from is on the third vector, which is purpose. The mission statement does that, but on a team level, you can give your team a sense of purpose by simply having a set of values you work by and a goal that you aspire to have the team develop towards. 

One that I have been public about on my team is, I want us to have an inclusive and diverse team. I want us to be one of the leading design teams in Canada. I want us to produce product we’re proud of and that our customers are inspired to use. By making that part of the DNA of the team, and that’s how we hold ourselves accountable, and remember the team’s also motivated. It’s autonomy, mastery, and purpose that I think are the three things you would want to inject into any team. That’s based on a foundation of peer learning, respect, looking out for one another. There’s a whole bunch of other things you can do to nurture those three pillars, but I consider those the three pillars of inspiring a team.

AT: When we talk about those things, the peer learning, the respect, the inclusiveness, are those hard and set communicated values across the organization? Is that what people embody, they just embody it naturally through your hiring process? You look at culture change, and if you didn’t start off with the start up culture, because that’s one of the things that drives success of these organizations, these lean start ups, is they start with a culture and that drives performance.

Within an organization that might not be so culture focused from day one, what’s the benefit of doing that?

JB: Culture is really huge at Freshbooks. I’ll just give you an example. Yeah, we have the values. Every company should have values. I’m sure you’ve heard that before. One thing we do to indoctrinate people into this customer first mindset, is we spend the first month, each of us, on customer service. Everyone, whether you’re the CEO or the CTO, that’s come in brand new, has to spend your first month on customer support. That means picking up the phones, answering emails, but really it kind of gets your ego in check that we’re all on the same team here. We all have one goal, which is to help our customer.

By literally putting you in that position where helping the customer is your only job, you’re not allowed to do anything else during that first month, we set up this mindset. The culture is useless if it doesn’t help you achieve your goal. There are poisonous cultures that somehow lead to achieving a goal. (I’m not sure how Uber or Amazon does it.) At Freshbooks, what we found is when people are passionate about doing the right thing for the customer, about helping the customer, they tend to go out and make the right decisions day to day.

When they’re in a situation where they’re not sure what decision to make, they err on the side of what would be right for the customer instead of what would be right for me or our bottom line. That’s just the compass. What it does is, from a strategy standpoint and an efficiency standpoint, is it makes things much more efficient because people can make the right decision more often. We’re all sort of having the same direction. We have other tools to help people make the right decision, but I would say that’s the primary tool.

AT: Going to the autonomy piece, when we work with teams on their values in their strategic planning sessions, the benefit of having values is that is sets from the outset the behaviours that are acceptable. If you do this, we’ll be happy with you. You know that you will be successful and supported if you act in X,Y,Z way. You said it very clearly that employees are empowered to do things that are in line with being customer centric.

JB: We’ve all been in an organization where we are anxious about the decisions we are making, even though we thought we were kind of good at our job. Every week we were there, we felt a little less good about what we were doing, and we were a little more anxious about the decisions we were making. That’s sort of an exercise in paralysis, a form of analysis paralysis. Relative to your own identity and ability to make change in the organization, if you have to second guess every decision, that’s just not very efficient, and it’s not going to have us all going in the same direction.

AT: Do you have a system for feedback loops for that kind of stuff?

JB: On the design team, I can speak to that. The way we design feedback is peer based. We actually meet at least twice a week. We meet twice a week as a whole design organization. We’re split two ways. The company’s set up as two lines of business. Each line of business meets, all the designers and all the product owners, together for a peer review or critique. Doing that, maybe it’s not a feedback loop on behaviour, but it’s a feedback loop that we use to emphasize we’re building things together. The micro feedback loops happen all the time throughout the week where, by bringing people together and showing them that they’re all working on the same project, they’re also hooking up throughout the week on their individual projects.

Then, of course, I meet with them one on one, if you’re talking about literal management feedback loops, on a weekly basis. One on one, I’m helping them develop their careers, or talking through difficult situations that they might be in. It’s kind of like Brass Tacks Management.

I will say one huge thing that I didn’t recognize until maybe a year or so ago, was that I felt like I had to run all of the meetings and all of the processes. The biggest change that I’ve made that I’ve seen unlock the most potential in my team, is to take the whole organization and assign leadership across each designer. Each designer is leading an initiative that benefits the whole design organization. They get to choose. We develop that focus based on their skills and their career aspirations. That’s really triggered some motivation that I didn’t expect. I didn’t expect to see that they would want to take on that additional work, but they do.

Self management, in that regard, team health and hygiene is now managed by the team itself, which I’ve been really pleased to see have an impact. It’s really big stuff that I would normally hog, selfishly, for myself, stuff I most want to work on. I realize that it would be much more efficient, if I really want to work on something, if I help someone else work on it, I’d be doing my job a little bit better and we could do a lot more.

AT: What are some risks to avoid in the planning process?

JB: Knowing when to tell and when to ask is really important, giving the experience level of your report. I said give them this huge responsibility, but don’t just give it to them and not provide any instruction on how to do it. If they don’t have knowledge, it’s really efficient to just tell them, but then knowing when they have enough knowledge that you can begin to ask them questions, and get them thinking about how they can improve it. That distinction, I think, is important because sometimes I’ve made the mistake of giving a junior person a little bit too much responsibility, and then they’re afraid to ask when they’re in that position. They’re not yet at the critical thinking stage. Coaching them hands on at that time, and telling them, and providing really closed feedback loops …

I mentioned feedback earlier and I forgot to say, feedbacks and one-on-ones are ok, but the best kind of feedback happens continually, in real time, like right after a meeting, or in conversation. “Did you think about this? Oh, I once did it like that.” Right? Think about a sports team. The best coaching happens just after the person gets off the field. It doesn’t happen two days later, or a month later. In that moment they’re primed. They’re like, “How did I do coach?” “Oh. Well, you could have done this. You could have done this, but you really did this well.” You always want to have a five to one ratio, I was always taught, of positive to negative feedback. That kind of feedback and making sure you’re not just asking people, “How should we do this”, when they’re not ready for it, but also giving them the knowledge they need to accelerate.

Make that feedback continuous. Make yourself their partner. My favourite expression that I think someone shared with me once is, “If they have a problem, it’s their problem, but as soon as they share it with you, it’s our problem.” I think as long as I am a manager or a leader, making sure I’m an ally, rather than an adversary, is super important, at least in my experience. Then people come to me earlier with their problems, and I have better awareness about what the overall health of the team is, and I can actually take action and adjust. Surprises aren’t good on either side.

We have really solid retention. We’re always attracting great people, so I do think it works out. The CEO, it certainly matters to him. I learned these lessons from him. I think he has this expression which is, “You take care of the team, and the team takes care of the customer, and the customer takes care of your business”, but really, it starts with taking care of your team. That’s successful strategy right there.

AT: There’s real benefits to it, financial benefits. We’ve already talked about this but …

JB: There are a lot of things you can do. Context and the individual matter. There’s no one right way. That’s one thing I learned along the way, and I’ve read numerous times and it’s absolutely true. It’s true about product design too. The universal truth is humans are unique. You have to take care of the individual, first and foremost. Everyone matters and has their unique idiosyncratic behaviours. To motivate them, you really have to get to know people and care about them. I may be guilty of investing too much emotion in each person, but I find it comes back to me in a form of a place I really want to work, with people I enjoy being around, and who are challenging me as much as I’m challenging them.

AT: As a leader, it must develop you and give you opportunities to develop when you focus on each person.

JB: I’m bad at email and Slack, but what I am good at is walking over to a person’s desk, inviting them out for coffee, sitting down with them for a little while, going on a walk. I started doing a lot of my one-on-ones as a walk, based on psychological research that people are less confrontational when they are standing beside you, walking, and scanning a horizon. There’s all kinds of calming principles there that really work. It’s kind of common sense, and I’ve always worked against this institutional business mindset that business is different from life. I just haven’t found that. Maybe that’s where my life as an artist has taught me a lot.

When you’re creatively motivated, when you’re excited to come into work, and you like your peers, and they’re pushing you, things kind of start to go. I just feel like that’s where I want to work. It’s really just about creating a peer group, closer to maybe a university or something, except there’s a business outcome that we’re really accountable to and that we care about.

The best expression I’ve heard is work/life integration. Instead of work/life balance, we should talk more about work/life integration. How do you integrate in a way where your work is actually pushing your life forward, is part of the richness of your life? You don’t want to end up on your last day thinking, “God. I could have spent less time in that horrible place.” I think the way we hire, and the way we nurture here, what I’m trying to do anyway, and we’re not all the way there, is to create a place where you’re living your life while you’re doing the work you love.

AT: Is there anything else that you would recommend to a CEO or a manager responsible for leading people and leading a strategy?

JB: I think the term CEO-itis is really that meddling too much, the feeling that if only you were involved, people could get to the right decision faster. I think it’s really tempting. I’ve been tempted by this, as a director as well, and feeling like if I could just show them, if I could just push them to do this thing. They need me. That’s how we equate our value as managers and executives. Because we’re not creating anything physical, we feel like our value’s wrapped up in how fast we can get a person to the right answer.

I think it’s really important to give people a place, and create an environment where they can get to the wrong answer, and not be punished, but be advised. They’re like, “I thought it was going to be like this and I was wrong. The recognition that I was wrong led me to the right place. You didn’t need to give me that shortcut”. I would just say get out of the kitchen. Be there when you’re needed. Be available. Create an environment where people are coming to you with their questions, rather than you coming down and enforcing the rule of law.

I used to be an art director, so policing was what I did for a living. “Oh, this is not on the guidelines. This is off brand,” and it was a terrible way to make a life for myself, and also, the teams were never motivated that I was working on. I’ve learned over time that if I could create an environment where people come to me with a question, it’s much more valuable than telling them what to do.

AT: Thank you Jeremy. How can people get a hold of you, and how can people check out Freshbooks?

JB: You can get a hold of me on Twitter, @JeremyBailey. Check out FreshBooks at freshbooks.com. If you don’t like it, I’m really excited to hear from you. If you love it, I’m excited to hear from you too. I’ll put you in touch with a designer. We have customers here in the office all the time, and we’re really excited to hear from you. Try it out and let us know what you think.

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