TCW #027 | Turning a dead-end job into a career catapulting growth roadmap

How to co-author a roadmap for career growth with your manager as an ally.

Jul 27, 2023

Hey, it’s 📣 Coach Erika! Welcome to a ✨ free edition✨ of The Career Whispers. Each week I tackle reader questions about tech careers: how to get one, how to navigate them, and how to grow and thrive in your role.

If you’re not a subscriber, here’s what you’ve missed in the last few weeks:

My guest post in Lenny’s Newsletter (🎉 currently the 8th most popular Lenny’s Newsletter post of all time!)
TCW #023: Defrosting a low-trust relationship at work 🥶
TCW #024: Clarifying unclear expectations with your manager, systematically 😎
TCW #025: Helping your helicopter manager let go (of their tight grip on your career) 🚁
TCW #026: Dealing with unfair treatment at work (including harassment, discrimination, and retaliation) ⚖️

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This week, we’ll talk about what you can do if you’re facing a dead-end job but don’t want to leave your current company.

We’ve all been in a dead-end job at some point (or we will be, trust me). It happens for a variety of reasons, including:

you hit the ceiling in our role and there isn’t an opening for the next level up
your current role/team/company can’t offer you new challenges for growth
there are growth options, but you’re struggling to get your manager’s support

Dead end jobs are not ideal. But you can break free!

This week’s post will focus on how to collaborate with your manager to:

get on the same page about your career
co-author a roadmap for your growth
and become an ally to break you out of a dead-end job

Let’s dive in.

☠️ The Dead End Job aka No Opportunities for Growth

I first introduced the The Dead End Job workplace dysfunction in TCW #022: “The 6 dysfunctions in manager-employee relationships.”

Below is a quick refresher:

The Dead End Job happens when employees feel like they can’t get opportunities for growth. Some common signs or symptoms include:

Different Page, Different Book: You and your manager need to be on the same page about where you are in your career, how you’re performing, and what comes next. If any of these is misaligned, your manager might not actually know how to find growth opportunities for you, or they may not believe that you’re ready for ones that exist.
Boredom and Loss of Productivity: Over time, you may feel bored and disengaged from your work if you don’t see a pathway for growth.
Frustration: If you’ve brought up the feeling of being stagnant multiple times with your manager with no progress, you may feel frustrated.

You don’t want to stay in this loop for too long. Being disengaged from your work or frustrated with your manager is no bueno for your zen.

Let’s talk about how to turn this dead-end job into a career roadmap that aligns you and your manager and lights that fire in you once more ❤️‍🔥

Get into the same book: Where you’re pointing your career

At the end of the day, 95% of managers want to see their team members grow. If you’re not getting growth opportunities from your manager, it’s likely one of these three issues:

Your manager doesn’t understand how you want to grow your career (and thus can’t provide the right opportunities for you)
Your manager doesn’t think you’re ready for more challenging work
Your manager is unable to give you the growth opportunities you want (they may be constrained by headcount, scope, budget, or even a sense of agency)

Your goal is first to know what you what.

Some questions to ask yourself before bringing your manager into the conversation:

💡Tip: Radical self-awareness and candor will go a long way toward helping you understand and confidently articulate what you want (and the constraints or challenges you must overcome to get there).

What brings you joy (and a state of flow)? What are you passionate about? What kinds of problems are you most interested in solving or owning? What was the last project you worked on where you got lost in the work and achieved a blissful flow state?
What are your career aspirations? Do you want to be an individual contributor or prefer management? Do you prefer a big company or a small company? Do you eventually want to start your own business? What skills might you need to develop now to open those doors?
What are your long-term and short-term career goals? What do you want to achieve in your career in one, three, five, or even ten years? I find that thinking of this in terms of tangible achievements works best. Try this prompt (or something like it) to get the juices flowing: “In X years, I will have achieved <this>, <this>, and <this>.”
What growth is needed to get there? What key skills have you already mastered? What skills do you need to strengthen? What growth areas do you need to develop from scratch? Ask these questions based on the goals and achievements you’ve identified over the one, three, five, and ten year timeline.

Now, bring your manager into the conversation.

This first conversation isn’t going to be the whole enchilada, ok? Our initial goal is simply to get aligned at a high level — getting into the same book with your manager and speaking the same language about your career.

Logistics and Mindset

Choose the right time to have the conversation. Do not spring this critical conversation on them as a surprise. Tell them that you want to have a dedicated career conversation, and ask if you can schedule 1 hour to meet with them. Yes, a full hour. Find a time when you're both feeling positive and productive and can be in the mindset to openly discuss your career goals.

Framing is everything. This initial conversation is where you’re going to tell them your overarching career goals, but remember that your manager has OKRs and goals to deliver on today — this month, this quarter, this year. It’s natural for them to be thinking about what they get in the short term. Frame the conversation around creating a shared understanding of your longer-term career goals, and share your desire to seek their advice and support.

Expect candor (which can sound like criticism). If you framed the conversation well, your manager should be thinking on a longer time horizon, but that doesn’t mean that they won’t highlight areas of need or gaps in your logic. Get your mindset primed for a candid two-way conversation that isn’t all sunshine and butterflies. Be open to feedback, even if it can sound harsh or blunt.

Conversation goals

Be specific about your goals. Avoid generalities, like your manager that you want to "move up" or “increase scope” or "be more successful." Use the specific career goals you established with yourself. Share details about what you want to achieve in your career in the next three, five, or even ten years. Get them excited about the vision you’ve created for your career.

Be prepared to discuss your current performance. If your performance is excellent (and your manager agrees), this won’t be a roadblock to the conversation. However, if you’ve been struggling in the role, expect that your manager may be surprised that you want to talk about next steps for your career when you aren’t yet mastering your current role. If you’ve been feeling disengaged or demotivated recently, your performance likely has suffered. Be prepared to own any slips in your performance and to demonstrate your interest in re-engaging in your current role.

Be prepared for some productive scrutiny. It’s best if you first identify some growth areas that you’ll need to fill to achieve your ambitious career goals. Your manager will appreciate the thought and candor you’ve invested, and they may add to your list of growth areas. This is a good thing, because in the future you can ask them to help you find assignments that build on those added growth areas 😁

What good looks like

If you and your manager can align on these two things, you’ve had a wildly productive career alignment conversation:

Your career goals for the next 3-10 years
The growth areas you need to develop to achieve your career goals

If not, keep trying. Sometimes it just takes more time to let things settle in, sometimes you need to take a different angle or approach.

Either way, don’t give up on forging an alliance with your manager unless you are 100% sure they have no ability or interest in helping you grow in your career.

Get on the same page: Co-authoring a roadmap for career growth (with your manager)

Now that you’re aligned on your long term goals and gaps, it’s time to co-author a roadmap that will take you from here to there.

I suggest authoring a rough draft before a follow-up meeting with your manager, but be wary not to get too married to your own ideas. The draft is a shared starting point, not a contract that you’re trying to get them to rubber stamp.

To outline your roadmap, consider the following:

What are the specific steps you need to take to achieve your goals? What skills do you need to develop? What experience do you need to gain? What avenues do you see in your current role/team/company to get that experience?
What resources do you need from your manager? Do you need more training? Do you need more responsibility? More scope? More complexity? More exposure to a certain technology, system, resource, role, or situation?
What is your timeline for each step? When do you want to achieve your short-term goals and tackle each growth area? What’s realistic?

Come to the meeting with reasonable expectations and an open mindset:

Be willing to compromise. Your manager may not be able to give you everything you want right away (some opportunities may not exist yet, you both may need to keep an eye out). Expect to work with your manager over time, iteratively, and flexibly.

Be prepared to move around. Your manager might identify that they aren’t going to be able to take you all the way to the finish line of your roadmap. They might suggest a rotation or even moving teams to get the full suite of experience you will need. Be willing to move around as needed.

Closing thoughts

Sometimes we think of our managers as “the Boss” and don’t recognize them as a built-in ally for our careers. Taking the time to get on the same page (in the same book) as your manager is the first step to building out a collaborative career roadmap. Ideally, this roadmap will help them grow their impact and influence while growing your capacity as the same time.

Breaking out of a dead-end job can be a win-win for your manager, but you have to be willing to have the conversation and face the realities of your mutual constraints. The best manager relationships are a partnership, at the end of the day. Find ways to help them win, and they will do what they can to help you get where you want to go.

🎉 That’s a wrap!

Because working relationship dysfunctions are so woefully common in the workplace — and so detrimental if not dealt with expeditiously — I’ve created a series dedicated to diagnosing and resolving dysfunctional workplace relationships. All posts in the series:

Subscribe to stay tuned!

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