Tuesday, 14 July 2015

Career Advice and That Jason Post

Last week Jason Calacanis wrote this post, and I sent a kind of expansion of it to my team.  A few of them came back and told me I should post it, so here goes...

This one stood out from the general noise in ‘career advice tweetstorms’ because, when I read it, I thought to myself holy shit that is exactly how I think of people and exactly how I know my boss thinks about me. That is pretty important intel for anyone hoping to achieve meteoric growth in my kind of company, so I think it is worth you each internalizing what it means for you. Let me break it down a little more first, into some more grounded practicalities:

1 and 2 are items I consider pretty immutable, so just do it. Besides - this isn’t work. If you’re in the right career then this is fun, you’re passionate about it, and you eat it up 24x7 whether you’re paid for it or not. It doesn’t feel like work. Achieving mastery in your craft is its own reward. However I acknowledge that not everyone can be in a job they find personally fulfilling and enlightening and, if you are in a product or technology role just because it pays well, then I’m not going to get all preachy about your motives. Just keep in mind that if you want to stay in that role and keep growing the rewards over time, then you need to do this just as much as (and maybe more than) those who are pursuing their passions. Because they will leave you behind, and they will out-compete you for the best roles.

3 is where Jason and I are going to disagree or – at best – there is a subtlety we agree on for which ‘startup’ is useful shorthand. Where I think we might philosophically agree is that you need to get somewhere where you can be individually visible (not buried in a huge team of homogenous ‘resources’) and your ability to step up and take on more, to exceed the normal boundaries of your primary responsibility, are not structurally constrained. Big, mature organizations tend to be set up such that the system of production (roles/structure, process, inputs and outputs) is defined in the abstract, and pursued ahead of unique or especially talented individuals who may not fit easily into any one predefined box. And, because these things tend to become more rigid over time, it is difficult to exceed one’s personal remit in a constructive way. Pick a business in a growth industry, and pick a team which is big enough to do cool stuff but not so big as to require Vogon-like bureaucracy, and pick a boss who values utilizing (and stretching) individuals where their passions and aptitude converge over having everyone nicely fit into a tidy box with the ‘right’ label on it. Startups are like this out of necessity – that’s why I can agree that ‘startup’ is a compact way to communicate this kind of sentiment – but they don’t have a monopoly on this. It can be a sustainable lifestyle choice in any phase of a business. 

Item 4 is one of the characteristics I have seen in almost every high potential high performer I have had the pleasure of looking after. To what Jason already has there I would add two things; first working hard and taking on more doesn’t mean being in the office 24x7. It just means intensity, urgency, focus, and prioritization. I won’t personally give you any points for being in the office any longer than me – in fact I am slightly more likely to wonder if you need a little extra support. Second thing here is to know your cake from your icing, as a really fabulous CEO I worked for a long time ago told me. Go after more, take on more, over-deliver unexpected surprises, but never at the expense of your core responsibilities. The reason your primary role exists at all is because a lot of customers and colleagues rely on you delivering on time and to a high quality. That’s your cake. And if your cake starts to suffer for more icing – all the extras etc – that marks the difference between a high performing high capacity individual who is obviously in need of a promotion and an irresponsible slacker who doesn’t understand the business needs and is letting the team down. 

I work with a few companies at different stages of growth, and I wish I saw a little more of item 5 everywhere I go. You should actively look for chances to do this, not wait until you’re asked to do a brown bag session or something. The fastest path to true mastery of anything is to have to teach it to another. Or, in career advice terms if you prefer, unless there is at least someone around who is as good as you at what you currently do then this will eventually become a blocker to your personal advancement. Giving you a bigger role is important but creates a difficult rubix cube-esque puzzle, but giving you a bigger role when you have a solid, practiced succession plan ready and waiting becomes a no-brainer. 

6 yup another JFDI. This I would enhance with Postel’s Law. If you practice a kind of ‘human equivalent’ of the robustness principle then you will shut down negativity instead of amplify it and deescalate potential conflict. ‘Assuming positive intent’ is such a powerful tool for keeping everything constructive and feeling awesome about yourself and others. 

I’d read 7 as never be reluctant to ask for things. And not just in reward; also resources, opportunities, mentoring, training, chances to join in senior forums, a place in special projects. Whatever. And I know this town is equity-crazed, and equity is certainly nice, but it isn’t the only way to be rewarded and it isn’t the only path to wealth. Regardless, you should be fairly compensated for the value you create. Amid all today’s rhetoric about leaning in and whatever, just keep in mind that the prerequisite to this is to actually demonstrate your value though real results, consistently over time first. Similar to my addendum on number 4, this distinguishes the merited from the ‘participation award’ crowd who want it all just handed to them for showing up. You own your career. 

8 is table stakes in product. You’re here to define an alternate future, where your company is better tomorrow than it is today. Startups are just one killer feature around which the rest of a business and a complete product emerges, so all the same instincts and behaviors will carry you to success in any product-led business whether or not you might call it a startup. 

So that’s some career advice I think everyone can take something away from. I believe that people achieve more and feel more passionate about the product (and stick around longer!) when they can see how doing so is helping them grow and taking them closer to their idea of success for themselves. That’s why this shit matters to me and it matters that my leadership team take it equally seriously for all my people.

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