The Team of One

Isabel Gan
Aug 31, 2018 · 12 min read

One of my absolutely favourite writers, Tim Urban, mentioned this about tribes (or as he describes it, a group of people linked together by something they have in common, similar to a team): “Humans crave connection and camaraderie.” Which makes complete sense: you see your coworker, Jenny, way more than you’d see your spouse, roommate or family member in a day. You’re spending 8 hours in an office with Jenny as compared to someone you’d see at home for 5 hours in the evening. In recent years, there has been a shift towards a new type of organizational structure and culture: one that’s highly collaborative and tight-knit.

This is where my story comes in. From May to August 2018, I had the rare opportunity to intern at Klipfolio, one of the biggest digital dashboard company in Canada. I joined the Business Development team in May 2018. That is, a team of one. It isn’t surprising because after all, a rapid-growth organization, like Klipfolio, has increasing demands that requires new resources would be constantly creating new roles for new teams.

In our sleek new office, after we had our Beta launch of “Trends”.

I’ve had a couple of “grown-up” office jobs before this, but have always been in the corporate sector with a massive bureaucratic structure.

*I know that it’s supposed to be “stoked” not “stoke”. But I’ve deleted the Photoshop file, so that really sucks.

I’ve always hated boxes and have cultivated a dislike towards micromanagement. I’m a massive fan of trial-and-error and am trying to steer clear of dogmatic thinking.

Working in a team of one was like winning the golden ticket to Willy Wonka’s factory. My manager was Allan Wille, the CEO. Best manager you can ask for: patient, humble, wise and respectable. We only had 30-minutes a week for our one-to-one session, so I had to figure a lot of stuff out on my own.

So what does “figuring a lot of stuff out on your own” look like?

PROS:

  • Tons and tons of autonomy
  • An opportunity to fail fast, fail forward
  • Ship things without external pressure
  • Define your own expectations and set your own boundaries

CONS:

  • Not properly integrated in the company (in the initial first few weeks)
  • Steeper learning curve
  • Harder to build rapport and gain credibility with coworkers (I’m a massive extrovert)

As Brian Tracy says “there are no limits to what you can accomplish, except the limits you place on your own thinking”, it’s about finding a way to work around the cons, and turn them into positive experiences.

Here are a couple of “rules” I’ve set for myself to make my internship experience an unforgettable one (not that it wasn’t awesome enough already):


Define your purpose and goals from the start

Tackling a massive strategic problem in a team of one goes something like this:

You and your manager want to build a house. But not just any house; This house can host dinner parties, massive events and a luxurious getaway. Your team’s excited. The house sounds pretty cool. You take the idea back to your desk and start sketching.

“Wait a second, I know what the house is supposed to do but I don’t know what goes into the house. And my manager’s gone for the weekend. Does he want a pool in the backyard? Does he want themed rooms? How many bathrooms does he want in this thing? And oh god, the colour scheme- what’s the colour scheme?”

So you spend your first week doing this:

… Not so feasible after all. So you go back to the drawing block, back to square one.

This “house” that we wanted to build was similar to the BD project I was assigned with. So many options, so many ideas. Ultimately, I realized that I needed to make my objectives clear and to thoroughly understand the company’s vision and existing challenges. This is done through interviewing many people from other teams, zooming in on the company’s website and platform, and most importantly, remembering the reason why I wanted to “build the house” in the first place.

I think a lot of people struggle in quickly shipping their projects, because ideas can always get in the way of the real problem at hand. We can get so caught up in testing all the possibilities than sitting down to rationally decipher which possibility is the most effective. Once we’ve fully and deeply understood the “why” behind the goals we set for ourselves, we can then carefully and efficiently plan the next steps in tackling the big problem.


Give yourself certain constraints

When we think about constraints, we may think that is means putting ourselves in a tight vacuum-sealed creativity box which prevents us from taking our role to the next level (think The Bureaucratic Box in point #1). That’s not true. The Cambridge dictionary says that a constraint is “something that controls what you do by keeping you within particular limits.”

Limits aren’t always bad, annoying things. Limits (or constraints) are important and extremely useful as long as we apply first principles thinking into the mix. During my time at Klipfolio, I gave myself constraints that were grouped in the following categories: Deadlines, resources and time blocks.

DEADLINES

I’ve always been jealous of the product team’s sprints. For those who don’t know what a product sprint is, a period of time is allocated to specific work that must be made complete and ready for review. Sprinting sounds fun.

So I decided to create my own one-person sprint: mini projects with deadlines.

Like a sprint, a specific time allocated to planning is necessary. I intentionally park my meetings immediately deadlines I’ve set for myself, so that I am on a time crunch to present a completed set of work to my managers.

RESOURCES

Being data-driven is important, but being able to critically question the source of data is equally important too. When I started off in Klipfolio, it was like going into an all-you-can-eat buffet with the goal to leave the restaurant extremely full. Since we’re a data-driven organization, it makes sense that we have tons of internal data sets that we use (i.e. Salesforce, Marketo, our data warehouse). Starting off, I tried to use every single data set we had in the organization and fit it into a massive spreadsheet. The spreadsheet was packed with information and had tons of information in it.

After presenting it to numerous stakeholders in the company, more questions were raised and nothing made sense. It was information, yes, but it wasn’t accurate information. One of my awesome coworkers gave me this incredible advice that made me come to a complete halt: “I feel like you’re doing too many things. Focus on the one or two, and dive deeper”.

I pushed the reset button and looked at all our internal resources with skepticism and caution.

When analyzing information, it is important to critically question how the data was generated. By weighing the pros and cons rationally, we need to understand the motives behind the data, and why we are getting it from that particular source.

Otherwise, it may result in more inaccurate decisions, and in turn, negatively impact your organization.

TIME BLOCKS

I’m a huge fan of the Pomodoro technique, and yes it was named after a tomato. Not an actual tomato though. A tomato-shaped timer. The way the Pomodoro technique works is simple: when faced with a huge task or project, the Pomodoro technique breaks the work down into short, timed intervals (25 minutes) that are spaced between short breaks (5 minutes). It has drastically improved my attention span and concentration abilities after doing it for months.

In order to keep track of my progress, I use the Productivity Planner by Intelligent Change. It helps to make the daunting goal less daunting by breaking them down to increments of achievable short-term goals using the Pomodoro technique.


Be clear in your ask

One of the most significant moments of my Klipfolio career was when I had a 15-minute meeting with one of our C-level execs. After spending 5 full minutes elaborating on the project’s execution and what I’ve accomplished so far, he just stared at me and asked, “well I still don’t see what you’re trying to get at.” This led me to another 5-minute reiteration on what I’ve accomplished so far.

“I still don’t see the question here.”

“So… What do you think? Am I on the right track?”

“That’s a vague question. What do you mean by ‘right track’? What are you trying to answer?”

Truth was, I didn’t know what the question was either. Looking back, I should have started with assumptions I had, instead of yapping away about the data I found.

I realized that it was okay to be wrong because he would have just nudged me in the right direction. But if I had no clear direction, he couldn’t provide any answers.

More meetings does not mean increased productivity. In fact, it might be the opposite. Keeping meetings short and concise clarifies the purpose in meeting almost immediately. It takes away the ambiguity of the goal between other decision-makers in the organization and gets you the facts you need to quickly start taking action.


Be a frequent planner

I’m going to insert a cliche quote by Cornelius Fichtner here: “Planning without action is futile. Action without planning is fatal”.

During the four months, it was a priority of mine to start my week with 1-hour allocated to pure planning. Notebooks became my best friend.

I found it easy to focus on the doing instead of the reason behind it all, so it was important to make sure that everything I was doing tied back to the big goal that was set from the beginning.

The reason why I’m able to jot down these learning lessons so clearly after 4-months is also because I found the importance of journaling; I found it important to write down the thought-process behind all the doing, to justify conclusions and provide clearer updates for my manager.

P.S. this article was initial meant for personal use, but my peers were telling me that this content was useful, so I’m sharing my learnings.


Always get feedback and support

I look at one-to-one meetings as mentorship sessions, and have found it to be extremely useful in steering me back to the right path. While working for a team of one, it’s easy for people to forget you exist (because everyone else has their own set of worries and problems they need to fix, and not in a malign way at all). It’s your job to insist on weekly one-to-ones with your manager and make sure that you come prepared to every meeting. It doesn’t have to be long.

As mentioned, come prepared with specific questions, and dedicate 30-minutes to planning before the meeting.

During the meeting, I like to ask about the Trust Battery: “What does our trust battery look like as compared to the last month? If it has increased, what did I do well? If it has decreased, what can I improve on?

Here’s how I usually structure my meetings as efficiently as possible:

1. Updates

“During the past week, here were my goals and here’s how I achieved them.”

I always reminded my managers what my goals were. After all, they were my goals for me to remember, not my managers.

2. Assumptions along with questions that will help steer me away from the roadblock

“During the past week, I ran into these roadblocks. These are the reasons why I thought it held me back. Do you have any advice on how I can work my way around it?”

Sometimes if it’s a big issue, I’ll send them a list of questions that they can spend the day thinking about so I don’t throw them off-guard.

3. What do I need from you?

“I do not have the authority to make this decision. What do you think?”

This is largely for decisions I can’t make on my own, or if I need access to a certain platform that is only available for a specific number of users in the organization.

4. Personal development questions

Some of my favourite questions: “How can I ask better whys? What can I do to make you more successful this month?

That being said, questions should not be limited to the weekly one-to-ones. I’m cool with the fact that I don’t know everything. I actually celebrate it. Because this means I’m going to learn something new everyday, and that means I’m going to grow.

In order to grow, you need to know how to ask for help effectively and objectively. Instead of asking “can you give me [insert vague, generic term here like marketing] advice?”, ask “this is what I’ve done and these are my assumptions. What do you think?” I learned that being specific and making “wrong” assumptions are better than asking vague questions that will lead you to running around in more circles.

When starting out in an organization, I think it is important to research on everyone’s role and identifying who you would be working closest with. Working in a team of one forces you to take the initiative in reaching out to ask for clarification or get new information and answers.

Another P.S. I learned a ton about effective meetings in the past 4 months at Klipfolio, and the past year at Legacy. In the near future, I may potentially write another article some day to zoom in on how to plan effective meetings spanning from one-to-ones, mentors and all-hands.


Don’t be afraid to invite yourself

Working in a team of one can get lonely. Very lonely. Especially for an extrovert like me — who gets social anxiety when having to ask for things.

When I first joined the company, I was pretty jealous that the other co-ops that had the usual “weekly huddles” or team drinks on Thursdays. My desk buddy was also working remotely so she was barely in the office, so I had to find a way to navigate around that.

This means inviting myself to drinks, adding myself to Slack channels, sitting with strangers at lunch. Saying “good morning, how was your week?” whenever I saw someone in the kitchen.

To be clear, Klipfolio has one of the most welcoming, friendly work environments I’ve ever seen, so it wasn’t a massive challenge to get a friendly hello and a good conversation over lunch. It’s important to work for a company that has a culture which aligns with your values. The company also organized monthly lunches, and monthly breakfast outings to make sure various teams are integrated.

Being surrounded by other interns was also a huge support. It consisted of people my age, and/or people who are new to the company. Coworking sessions and after-work drinks was my go-to for a social life at work.


To end, here’s what I think: I think it sucks that talented, driven students in the community don’t know enough about other high-growth companies in the Ottawa ecosystem. It really is a shame.

I’ve had my biggest learning lessons to date (i.e. it inspired me to change programs and realize Accounting was not what I wanted to do for the rest of my life), and I’ve not been able to come up with a single bad thing to gripe about when working for this company. If anyone has the opportunity of working for Klipfolio, you’re in luck. Huge luck in fact. (Klipfolio, you rock.)

I’ve learned to be a better manager, to be a better team player, to be a better mentor and a better ‘mentee’. Klipfolio emphasized on a lean and agile team to make up their organization, and you’re constantly surrounded by people who are smarter than you.

Point is, I highly encourage everyone to look beyond the sexy new companies that make the news 24/7, and look for companies with a culture and vision that aligns with your values. Look at what you will learn from the company, instead of fancy job titles or a company that everyone is talking about, and then go for it.

So what’s holding you back now?

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