Lessons Learned - Transitioning from IC to Leadership

Prologue

So many lessons are learned when you begin planning work across many different organisations and people. I share my experience thus far in this article, my hope is to keep this a living document for myself.

My best lesson thus far:

Adopt diplomacy instead and piss some people off. They’d forget about it in the coming week anyways ;-).

Lessons Learned

Speed is critical

At the beginning of any project, speed is key. Being able to traverse through problems faster than anyone else is the easy way to gain leverage and visibility. You must see your deadlines as suggestions, not timelines but work towards them with a sense of urgency.

The confusion here I seek to clarify is that speed must be met with care, take your time and balance execution with precision. No one remembers your best days but they will always remember your bad days.

Delivery matters (more?)

Your ability to deliver will always be met with speculation, that Godfather style “sizing you up” will happen across different people you engage with day-to-day. Whilst it benefits you to appear faultless, it is an almost impossible outcome with high expectations, you will make mistakes.

Adopt instead the approach to work on your delivery, improve your ability to meet different stakeholders where they need to be met. This will over time take skill but it is your job to understand your audience before meeting them.

For more notes here, check out my article on this topic: Delivery matters (more?)

Keep your stakeholders aligned, not happy

A common mistake I made early was thinking I could make my stakeholders happy, I collected their feedback and tried to find ways to merge it all into a “go-to-the-moon” happy plan. This however brought frustrations as it appears there was never a stable moment with the “happy plan”, their point of happiness drifted faster than the second timer on my watch.

Keeping stakeholders aligned means meeting them at a point you can deliver at and a point they can accept, there is no happy path when multiple people are concerned with a problem.

Adopt diplomacy instead and piss some people off. They’d forget about it in the coming week anyways ;-).

Set expectations very early

This might appear the same as “Keep your stakeholders aligned, not happy” but setting expectations is for everyone around you. Your perception is your reality and setting expectations is something you must realise from day 1.

• Want to be the chill guy who is great at mentoring and open to ideas? Go for it.
• Want to be the uncompromising lunatic on attention to detail? Be my guest.
• Want to be the coaster who comes around when folks are done arguing? Here’s an extended lunch break.

Teams are not a one-fits-all approach but setting expectations is the best way to ensure that when your skills are needed, leadership knows who to call to handle those problems.

A good path here is to read DHH’s article on Commit to competence in the coming year

Let others fight your battles, know your pay grade

As an IC, you have probably been cushioned with the ideals of code solving your problems. In my transition, I found there is this inflection point when you have to stop keeping yourself oblivious to politics and understand the lifestyle around change management and the (unspoken?) dynamics of the organisation.

Once you transition into leading initiatives, you will at-some-point meet a random bloke who does not like you because your boss pissed them off some years ago and you’re now stuck driving the far end of the stick the wrong way.

Believing you’re responsible for a solution here is the false case of ownership, this is far beyond your pay grade and requires context you are rarely going to understand. Leave these alternating problems for upper management to figure out, they get paid to do it for you.

Understand where the dead bodies are buried

“Understand where the dead bodies are buried” is a concept of realising the unspoken biases about how business decisions are made. Your belief that the folks making decisions are rational is correct but subjective, they’re not on the front lines with you day-to-day and that skews their understanding of the problems.

Knowing the paths to success is dependent on the organisation, its history, culture, “highschool frat cliques” that require you pay homage and several other internalised processes that make no sense. Avoiding them may save you a lifelong deal of problems but this will be very short lived – know them before you go diving into landmines every one knows but no one talks about because “you should know about it”.

People bring themselves to work

A star player shines when the sun goes down, we all have seasonal moments laced with ups and downs that the four walls of the business will probably never hear. Always remember that there’s a sense of humanity when working with people simply because you don’t know them – their feelings at every moment will influence their ability to work with you.

Over time, life will happen to everyone and you sadly must deal with the consequences of it, emotional reactions and every other thing attached to being human. Do the right thing at these times, respect is earned and being a decisive (not exactly good?) person should come first in your decisions.

And, finally…

Remember work is a means to an end

As far as work goes, work is a lifestyle but it is a means to an end. It pays the bills and gives you satisfaction but it not the intention of your self-worth. Balance the scales and enjoy the moment, you’d live longer.

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