Being Mid-Career Sucks: The Context Crisis
Headless employees are no better than headless chickens
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Being mid-career can be frustrating.
It’s not uncommon to feel two conflicting ideas simultaneously:
You’re frustrated that you aren’t getting given more interesting projects and you’re not given more responsibility, AND:
You’re secretly worried that you’re not very good at your job and not providing enough value
Holding these two conflicting ideas simultaneously is emotionally taxing. It’s a vicious cycle that only gets worse - the more you are frustrated with your current role the more you neglect your duties and check out, lowering your chances that you’ll be able to move up and become more senior.
These two feelings conflict and contradict each other - but they share a common source: lack of context.
When you’re more junior it’s ok to take requests at face value. You’re asked to perform a site audit so you look up how to run a site audit in the company's confluence and get to work. You’re essentially following instructions.
But as you get more senior you start to field more nebulous requests. Things like:
“Hey can you prepare a quick summary of SEO in 2021 for me?”
“Can you make a P&L for the SEO team as it stands today?”
“We’re doing 2022 planning and I need your plan and budget for the year”
For requests such as these it can be hard to even know where to begin. The request is ill-defined and there’s no blueprint to follow. You know there’s more context but you just don’t know what it is…
Despite being “senior” in your role you’re googling “P&L template” hoping no one notices you and feeling like a fraud.
The Context Crisis
Here’s the problem with most managers I’ve worked with: they don’t include enough context with their requests.
This causes their teams to be stressed, confused, anxious and demoralized.
Consider one of the requests from above. Imagine you’re the head of SEO in-house managing a small team. Your boss, the VP marketing pings you on slack:
This kind of request instills fear, panic, anxiety, and uncertainty. Is this a summary of work done? A summary of results? Should the format be a presentation? An email? They said “quick” but we’re changing how we report our data right now so should we use the old data format or the new one? Does quick mean they need it today? Are they using this to evaluate my performance? Are they upset with me?
When you look at a request like this there’s so much context missing. Your manager asking for a “quick summary” likely has a crystal clear vision for what they need, but by failing to provide a little more context for their request they’ve kicked off a chain reaction of busy-work and anxiety.
Consider if instead your boss had sent one of these messages:
Ok - now we have some context! Notice how this message provides clarity around both WHY the request is happening (meeting with new CTO) but also the clear OUTPUT expected (list of bullet points).
Or, consider instead if they had said something like this:
Notice how this is essentially the SAME request - but the audience, intent and format are radically different. The way you’d fulfill these two requests would be very different.
And notice how both of these requests allow you to breathe easily - you’re not getting fired. This instantly reduces your anxiety.
Direct & Indirect Context
The more senior you get inside an organization the more you become privy to different types of context. You become aware of not just formal things like what the company strategy is but informal things like “who the CEO displeased with right now”.
It’s easy to forget quite how much context you have as a senior manager/executive - and you have to think carefully about how to share the right level of context when you pass on a request.
First, there’s direct context for your request, things like:
Why you’re making the request
Why the request is more/less important than other projects
What you’ll do with the output once it’s done
Who else will be involved / who else will care about this
What format you need the output in
What key things you need / don’t need
What the deadline is (not just the date, but what’s the deadline for the ask behind the ask?)
But there’s more subtle, indirect context that you have too - things like:
What are the big company priorities right now?
What else is being worked on in the organization?
Changes in the org chart - either people leaving, joining or reshuffling
Is there a crisis or issue elsewhere in the business right now? Which people or teams are underperforming.
As a manager it’s important to remember BOTH types of context as they can easily inform the urgency, rationale and format for a request.
Unfortunately, when you’re mid-career you’re experiencing requests from people who themselves are lacking context. This is a terrible situation and you’re in a bureaucratic version of telephone - where no one is getting what they want and everyone is frustrated…
As the request gets passed down the chain more layers of context are stripped from the request until some poor soul gets handed a headless request - and produces work that their boss isn’t satisfied with, causing a cycle of shame and feelings of inadequacy.
A request without context will make you do bad work that makes you feel bad.
The Impossibility of the headless Worker
As someone who gets given a request from someone more senior - it’s crucial to remember that the more context you are given, the better your work will be.
Asking for context is being good at your job, not being needy and ineffective.
And said another way, if you’re managing people you should be providing as much context as you can:
Providing context makes you a good manager, it’s not micromanaging.
Unfortunately you’ll commonly be stuck mid-career reporting to people who aren’t great managers. Which means you’re fielding requests that lack context - which means you’re doing work that you can sense isn’t hitting the mark… This is the catch-22 of being senior enough to understand there are wider contexts to your work - but not understanding enough or having access to those contexts to get better at your job.
The only way out is to train your boss to get better at providing context. We’ll talk about managing upwards in another email but you should learn to ask questions that explicitly gather context. Things like:
What format do you need this in? What are you going to do with it once I send it to you?
What is depending on this work - what decision are you trying to make?
Is this more important than [project A] that I had planned to work on today? When do you need it?
SEO Requires Context
Every job and every role should be given context - but SEO is especially prone to lack of context. SEO is a complex domain that doesn’t map neatly to the org chart - it requires working across marketing/product/engineering and more - and every time we cross from one team to another we enter a new set of contexts.
This complexity means that context is critical to success. Not just for knowing what to do but knowing how to actually get things done.
So if you’re mid-career and feeling frustrated or if you suspect your boss sucks then become a context hunter. By doggedly requesting and seeking more context you’ll not only do better work but you’ll also find yourself becoming more senior - with a better understanding of how the business works.
Fantastic piece! True for most managerial jobs. Dropping context is one of the biggest problems with cascading management requests and general make-believe work in most organisations.
Great piece! How do you bypass this shitty part of your career as fast as possible? How to get more senior in less time, so to speak