Requalifying for Your Job

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I recently listened to an interview between Harley Finkelstein and Tim Ferris. There were a number of good takeaways from that interview. One that stuck out to me in particular was this principle of “requalifying for your job”. This simple maxim distilled a concept I have implicitly adhered to but hadn’t yet been able to put into words so elegantly and succinctly. 

The principle goes that professionally you need to be continually elevating your performance to outpace the needs of the organization. Harley talks about how at all times he needs to be the best possible option for the role of COO (now President) at Shopify. And to do that he can’t just follow the growth trajectory of the organization, he needs to outpace that growth. 

This resonated with me. I’ve been working professionally for about seven years now and have always carried a level of anxiety about being “replaceable”. I learned this principle early on through competitive athletics where your role on the team is based on expected future performance not past performance. Yes, past performance is an indication of what can be expected going forward, but it isn’t assumed. One of the most formative experiences I can recall came in my last year of playing collegiate football. I had started every game since I was a freshman but coming into one of our last games in my senior season I had a bad week of practice – not catastrophic, but not great. In that same week, another guy on the team who was not a starter had a great week of practice. When the depth chart came out that week, there I was, second string. For the first time in over 30 games I wasn’t on the first team. It didn’t matter that we were playing the last place team in the league, or that for four years I had started every game. That week I wasn’t the guy. That hurt at the time, but looking back I am thankful the coaches made that decision. It hardened in me this principle of “requalifying for your job”. My job that week was to play corner and in that week I didn’t requalify. 

Netflix describes this experience in their culture deck:

If you think of a professional sports team, it is up to the coach to ensure that every player on the field is amazing at their position, and plays very effectively with the others. We model ourselves on being a team, not a family. A family is about unconditional love, despite, say, your siblings’ bad behavior. A dream team is about pushing yourself to be the best teammate you can be, caring intensely about your teammates, and knowing that you may not be on the team forever.

In any organization – whether that is a sports team, your professional team, or a volunteer team – if you are occupying a role, you need to be the best option for that role. 

One of the core values at Kik (the place I’ve worked for the last seven years) is: we look at all the options. 

I love this value. It encourages ideation and collaboration. It sets a framework for problem solving. And it pushes us to explore non-obvious options that might seem crazy but sometimes lead to unexpected outcomes. 

For me, I’ve also applied this value to my role on the team. I am an option. For the team to be operating at its highest capacity it should be always evaluating me as an option for the role I fill. I think about this every day. Just like it didn’t matter that I was a starter for 30+ games over four years (+ hundreds of practices), it doesn’t matter that I’ve been on this professional team for almost seven years. Am I the best option right now? 

This doesn’t mean that every single day I have to have my best day. That would be maddening and an unhealthy amount of pressure. But I do think that directionally I need to be getting better, and getting better at a faster rate than the company needs right now. My job is not to keep pace the company, as a leader my job is to help set the pace of the company. 

The key, I have found, is to find a healthy balance of the anxiety I mentioned earlier and productive forward momentum. Anxiety can sound scary – and for good reason. As soon as anxiety becomes debilitating it becomes unproductive. But channelled effectively, anxiety can be one of the best things for us. That may sound counterintuitive to a culture that values zen, however, these two things are not mutually exclusive. 

The feeling of anxiousness triggers our body’s fight-or-flight response. This response causes our body to create more epinephrine which leads to increased production of cortisol and adrenaline. The goal is not to live in a state of anxiety that induces fear, the goal is to harness this. In fact, Dr. Mihaly Csikszentmihalyi, renowned psychologist, dedicated his life’s work to human performance and talked about this principle in his seminal work: Flow: The Psychology of Optimal Experience. 

The concept of flow is that we as humans experience most enjoyment not from relaxation but when we face a challenge and overcome it. An excerpt from his book states: 

Even the simplest physical act becomes enjoyable when it is transformed so as to produce flow. The essential steps in this process are: (a) to set an overall goal, and as many subgoals as are realistically feasible; (b) to find ways of measuring progress in terms of the goals chosen; (c) to keep concentrating on what one is doing, and to keep making finer and finer distinctions in the challenges involved in the activity; (d) to develop the skills necessary to interact with the opportunities available; and (e) to keep raising the stakes if the activity becomes boring. 

This describes the process of “requalifying for your job”. This is why I have so much fun working, and genuinely enjoy it. I’m constantly challenged in the work I do, and I hold myself accountable to outpace the needs of the team. And this is why you hear Harley talk about his role at Shopify with such joy. It’s fun to contribute to a team and it’s fun to consistently challenge yourself to elevate your performance. 

The most fun comes when the rest of the team shares that same mindset, where everyone wants to collectively elevate the performance of the organization. That’s how new ground is broken. And that’s why I feel blessed to be a part of a team that is aligned to this principle. We live on the bleeding edge and we expect high output from each other. 

It’s also important to have grace for yourself. As I mentioned, not every day can be your best day, and not every week can be your best week. The ability to manage these retractions and recalibrate is an important embedded principle of requalifying for your job. We want to hold ourselves to a high standard but to manage the micro volatility in the broad arc of the macro trajectory. This is something I have had to learn as well. 

In that game I was demoted from starter, I was dejected at first, but as Coach V would tell us: “You can visit a place of self loathing but you can’t live there.” I showed up to that game waiting for an opportunity, and an opportunity came. I got in the game and ended up playing one of my best games of the season. It took some self coaching to get there, combined with a supportive team of coaches and players. 

That’s the beauty of a team. Yes, we might not be a family of unconditional love, but we support each other and work together for the collective goal of the organization. If someone isn’t matching pace we work together to elevate that performance. But it starts with the individual. It must be self directed and it must be self motivated. 

A simple framework I’ve implemented to do this follows three core principles: 

1. Align on Mission

In many organizations it may be impossible to know exactly what the destination is. Innovation is the process of discovering the future before anyone else and pulling that into the present. That discovery process is often messy with lots of fits and starts. As an individual contributing to an organization discovering the future your role will likely evolve significantly as the organization evolves. Requalifying for a job that is undefined in the medium-long term requires you to be both proactive and flexible. The most effective people don’t just keep pace, they set the pace.

You hear often that a company is a “Mission Driven Company” which can often sound like a trope, but it actually is an important principle for companies building the future. This is the guiding context on which individuals base their development. Harley said in his interview that he wants Shopify to be known as “The Entrepreneurship Company”. This gives context to individuals within the organization to base their development. Everyone should be thinking about how they can most effectively drive the mission of Shopify to be The Entrepreneurship Company. Senior leaders will set roadmaps to push this forward which then cascades all the way down through the teams. As an individual, aligning to the mission of the company, and the mission of your team will give you the requisite context to base your personal development objectives. From here, you need to take ownership of your development. It is good to get feedback and iterate with others on your team, but don’t expect to be told what to do. Professional development isn’t like school with a predefined curriculum. You need to set your curriculum. 

2. Set Your Curriculum

Within the context of organizational mission, the next step is to define the highest leverage areas for your personal development that will best serve the organization. As I noted above, this is something you need to take ownership of yourself. It doesn’t mean you do this in a vacuum but you need to own this. 

The most effective way I have found to do this is to find projects that challenge your development. Sometimes these might be forward looking projects within the organization, or sometimes this is looking outside the organization to challenge yourself. There are three ways I’ve found most effective to accomplish this: 

Side project: If there are things you want to get better at, do those things. Experimentation is the process of discovery and there’s no substitute for getting your reps in. You can’t just watch a bunch of videos of Tiger Woods swinging a golf club, study the biomechanics and the physics, and then go out and shoot par. You need to get your reps in. A side project is a great low-stakes way to dip your feet in the water and start experimenting. This could be constructing a mock investment portfolio if you’re into finance, this could be building a portfolio if you’re into art or design, this could be starting a blog (hint hint) if you want to become a better writer. Just start it and get going. 

Co-pilot: For near-term development I have found it effective to try and be a co-pilot on a project with someone who is proficient in an area you want to grow in. It’s important to find a way to add value to the process and not come with an expectation that someone is just going to take you along for the ride and teach you. Take ownership. For example, I wanted to become more proficient in design so I started doing some individual work through reading, online courses, etc. to get a base knowledge and then I approached a designer at work to see if there was an area of a project that I could contribute to. She gave me the task of working with the product manager to create basic wireframes (design outlines) and then from there she turned that into clean mock-ups which she brought me along for the journey on. This was a win-win-win. I helped speed up the process with the product manager and the designer, I got to work within that team, and I learned the process and basic principles along the way. 

Volunteer: For longer-term development something I have found to be most effective is finding volunteer opportunities that challenge my development in areas that I want to pull into my professional life. For example, I started leading a volunteer team at church while I was still an individual contributor at work. This challenged my development and made the process of moving into a leadership position professionally less of a shock. This was a win win. 

3. Create a Tight Feedback Loop

The third key principle in development is to create a tight feedback loop. As I noted above, you need to take ownership of your development – you can’t expect to have someone, even your manager, walking with you every step of the way telling you what to do. That part is largely on you. But at the same time you do need feedback to know you are growing and growing in the most high leverage areas. That is why creating a tight feedback loop is also something you need to take ownership of. 

You can see the central theme in the curriculum development is learning by doing. I have found this to be the most effective way to learn, and with the amount of resources available today it is easy to learn on-demand. To make the most of this development practice of learning by doing you want to get the feedback quickly. 

The most effective way I have found is to have multiple sources of feedback. Some of the best sources of feedback won’t come from an individual, it will come from measurable outcomes. If you can, work on projects that create feedback from their output. Create something and release it to the world to see what kind of engagement you get. This will give unbiased measurable feedback. And don’t stress about it being perfect, remember, this is part of your development. This blog post in itself is an exercise in my development. I want to become a better writer, so what better way to do that than to write often and publish to see what kind of engagement I get.

There is also value in getting specific feedback from individuals but you can’t expect any one person to be so invested in your development that they will be omnipresent. It’s not an indictment on any individual, it’s just the reality that people are busy. And even if you did have an omnipresent source of feedback, there is value in the diversity of thought that comes from a group. The key here is to find ways to add value in your development journey such that those sharing feedback see value in doing so. The best way is to be developing by doing and have the feedback come as part of the process ie. you’re working on a project with people who are all contributing and you’re refining as you go. In the design example above. I didn’t go to the designer with something I was working on that she had nothing to do with, I worked on something with her that she had to get done so her feedback helped refine a product she was contributing to. 

Don’t make work for people. Do the work and find ways to add value. 

In the earlier stages of development you want these feedback loops to be as tight as possible to get you going in the right direction. This is most effective by doing small projects or tasks with tight turn arounds and as you build more proficiency you can take on bigger projects.

Closing Thoughts

This is by no means a clean playbook for professional development. I have found this formula to be most effective for me. It keeps me moving forward while affording time for reflection and refinement as I go. There is little time to remain stagnant – the key is that every week when I sit down to assess last week’s performance I ask myself: was that the best you could do last week? And when I finish that assessment and move on to next week’s goals I ask myself the corollary question: is this the best you can do this week? 

Everyone is going to look different in their journey. As you become more senior in an organization the expectations of your development get higher and the level of ownership you have to take in that development gets higher. But that is the fun part. As Dr. Csikszentmihalyi noted, challenging yourself is the first step to optimal experience. 

This post outlines the principles I apply to the process of requalifying for my job. I have found this to be both a productive and enjoyable experience. I hope you can find that same enjoyment in what you do. 

Note: I wrote a post about habit building here, and productivity here that build off of this post. You may find those interesting too.