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Getting your boss's job: 17 questions every employee needs to ask themselves

By Michael Tamblyn • March 09, 2018


When asked to describe my job as a CEO, I have a long answer and a short answer.

The long answer talks about product strategy, markets, customers, performance, fostering culture, knowing when to watch and when to ignore competitors. It takes forever, lots of words. It’s uplifting; inspiring. There are harps and angel sounds.

The short, mostly-joking answer is “Budgets and HR.” Budgets because everything – customers, products, trends, share, strategy – distills down to how we’re performing as a company. HR because it’s people who get us there. Like I said, mostly joking. But still…

One of the things that came from the “HR” side of the job was Kobo’s Kick-Off in January. Every year we get as much of the company together as we can, and we lay out the whole plan. Everything. Numbers, department targets, key metrics, where we were right in the previous year, where we were wrong. It’s a pretty radical exercise in transparency and I love it.

This year it was done as a science fair – employees traveled around the office to hear pitches from each of the departments, with passports that accumulated stamps to get them into a party at the end. After the pitches and before the party was an all-hands Ask Me Anything session, with senior management on deck to answer anything and everything, with questions streaming in on a live Slack feed.

One important question that came through was “How do I get ahead?”, i.e. how do I advance in my career at Kobo? It got solid answers from the leaders on stage, but it was such a big question that I wrote something the next day and slapped it up on my Slack channel, #the-chief.

So, how do you advance at Kobo? (Or anywhere, really).

When I think about people who have really excelled in their careers, the most common characteristic is that they were ready to jump into the fire when their time came. They were ready to do their boss’s job. Or their boss’s boss’s job. Or the job that hadn't been invented yet.


So, let me answer the question by asking questions. My question to you is: Are you?

What’s the gap between what you are capable of doing now and what your boss is doing today, in terms of raw skills, experience, judgement, leadership, decision-making, culture-building, energy, and commitment? What’s the gap between you and your boss’s boss?

Are you thinking and planning on how to close those gaps?

Are you seeking responsibility, creating new things, going above and beyond, hustling, innovating, and driving positive change?

Are you building relationships across the organization that you will need later?

Are you taking responsibility when it’s on offer?

Are you putting your hand up, pushing, trying to find ways to do an old thing better, creating efficiencies, finding savings?

Are you educating yourself on what makes a good manager or leader, or growing skills that you don’t need now, but you’ll need next?

Are you looking for opportunities?

Are you being a great collaborator?

Are you a great listener?

Have you taught yourself how to run a meeting well?

Are you asking for mentorship or guidance?

Are you asking questions about parts of the business outside your job?

Are you just doing your job or are you intentionally striving for excellence?

Am I saying that you have to do all of these things to grow in your career?

Nope. But the more you do, the more likely it will.

Am I saying you should sacrifice your entire life on the altar of work?

No again. Sometimes a situation calls for extra effort, but you'll notice nothing on that list says: "Are you working a million hours?"

Am I saying that if you do all of these things you will automatically get a promotion?

Nope. But you’re a thousand times more likely to get one than the person who isn’t doing any.

It’s worth noting that most of those qualities aren’t delivered by programs or professional development.

They aren’t constrained by budget or resources. They don’t involve stepping on or over people. They aren’t about who you know. They certainly aren’t tied to gender or age or background or ethnicity. And they are all qualities I repeatedly in high performers here at Rakuten Kobo, including many who started in junior roles and are now in the Senior Management team.

If you want that job, that’s how you’ll get there. If you want to run or be a part of a truly amazing company, that’s how you will get there, too.

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