In Progress
Unit 1, Lesson 1
In Progress

Pitch a Plan, not a Promotion

As a programmer you’re not just responsible for developing code; you’re also in charge of developing your own career. And that means ensuring that you regularly have opportunities to take on new roles and challenges.

Unfortunately, in the software industry, career advancement all too often means moving to a new employer every couple of years. But it doesn’t have to be this way. In today’s episode, guest chef Brandon Hays joins us to explain a new perspective on pursuing job promotions that, frankly, blew my mind a little bit. I hope you find it as eye-opening as I did. Enjoy!

Video transcript & code

Pitch a Plan, Not a Promotion

Pitch a Plan, Not a Promotion...

Scene: HR office

"Officially, we're going to say it's not a fit, rather than firing you for cause. That's so you can file for unemployment." My boss didn't look me in the eye, and the HR rep was polite but firm.

Scene: Exiting office door, head low, holding box

The security guard escorted me to my desk where I piled my trinkets into a cardboard box, and then I trundled out the door.

Clearly, that afternoon fifteen years ago wasn't what I'd expected when I had put in for that promotion to manager.

Scene: Imagining promotion as trophy

I had thought that the promotion would be my reward for a job well done. I made my frustration clearly and widely known when it went to somebody else.

Scene: Front door of home, head low, holding box

And now, instead of being promoted, I found myself trying to drive home through stinging tears. In between sobs, I worked on ways to tell my spouse that I'd lost my job.

Obviously, looking back, this was the best thing that could have ever happened to me.

The two lessons

There were two key things I wish I'd learned before that day: First, if I had actually wanted to move up, I needed to pitch a plan, not a promotion. And second a promotion isn't a reward at all, it's a totally new job.

When were you passed over?

Your story of wanting to move up may not be as dramatic as all that, but I'll bet you have one. Maybe your performance review came and went without the raise you expected.

Maybe you talked to your boss about moving up and they told you to be patient for an opening. Then when an opening did come up, they hired someone from outside the company instead.

Sometimes it's easier to "move up by moving out"

And if you work in the tech industry, there's a solid chance you've never received a promotion. A lot of people in tech have only ever moved up by moving out, and into a new job.


Getting Unstuck

It's pretty common to feel stuck in your current position, without very many options. You can...

My options...

First, you could be polite and wait for your manager to see your good work. Second, you could go in to your manager and just ask for what you want. Third, you could quit your job and get a raise by going somewhere else.

Most people do some combination of these. They patiently wait for recognition, meekly ask about a promotion, and then leave when it doesn't happen the way they hoped.

My options (highlight 4th)

But there's a 4th option: If you really, clearly knew what your boss and organization wanted, you could work out a solution that benefits everyone.

Pitch a plan, not a promotion

I'd like to outline a framework for understanding how to pitch a plan, not a promotion. The goal is to provide such clear additional value that the promotion is just the side effect.


These are guidelines, not set in stone

This framework is based on my experiences managing people for the past 6 years. It's not set in stone: this is just a guide.

Two phases: Do the Homework, Have the Conversation

There are two main phases: the homework phase and the scary conversation phase. These will both take a bit of effort, but taken together, they will most likely have a big impact on your trajectory.

The framework itself consists of six steps:


  1. Take Inventory
  2. Find Your Leverage
  3. Clarify Expectations
  4. Address Limiting Factors
  5. Pitch the Plan
  6. Follow Up and Iterate

Step 1: Taking inventory

The first step is knowing what you already have in inventory, stuff that you need to make your case. Here are a few questions that can help you assess what you have:

Questions for inventory assessment

  • Do I have access to my boss? Or the person who decides where I am in the organization?
  • Are my contributions visible to my team and my boss?
  • Does my role have a clear track to move up?
  • Do I have the flexibility and room to take on new job responsibilities?

If you don't have some (or any) of these things, that's OK. You'll have to add it to your own inventory, which we'll talk about in step 4.

One inventory item though is so special it gets its own step: finding your leverage in the organization.

Step 2: Finding your leverage

Leverage means the power you bring to the negotiating table. The process of understanding your leverage is crucial, and I wrote more about it in a separate blog post that you can check out if you want.

Finding your leverage: Blog post link

But to summarize, there are two kinds of value you need to be aware of. You need to understand your marginal value. That's the clear business value you provide, right where you are. You'll also need to know your market value, which is what someone else would reasonably pay you to offer your services elsewhere.

Chart: increase in marginal value && increase in mkt value

Your best bet is to spend your time on things that increase both types of value. You could learn a new programming language or technique. Or more impactfully, you could teach it to your team. Or even better, you could dive in and understand how the software you write directly affects the business.

#protip: Gather Outside Counsel!

You probably can't see these very clearly by yourself. It helps to get some outside perspective from experienced friends. Tell them about your situation. Ask them to help you see where you stand on each of these kinds of value, and how you might increase it.

Step 3: Clarifying Expectations

The next step is to clarify expectations with the person who makes decisions about your place in the organization. That's usually your manager, but not always.

It's surprising how often people have no idea what their boss is looking for. This is actually pretty easy to clarify by asking for feedback and advice:

How am I doing? What's going well? How can I improve?

"I'm wondering how I'm doing in my current role. What's going well? What are some ways I could improve?"

What advice do you have for me to get to where I want to go?

"I'm looking to grow in my career to do X in the near future. What's one piece of advice you'd give me?"

The goal here is to understand how you're currently performing and how you might add additional value in the future. Be open to creative solutions in this conversation.

Step 4: Addressing limiting factors

Step 4 is to uncover some factors that are holding you back from your goals. This will probably happen pretty naturally as a result of your prior conversations.

This can be painful. It's also crucial.

Keep in mind, this constructive feedback can sometimes be painful to hear, but it's also crucial. You must not skip this step or you won't have the data you need to improve.

Backfilling your inventory

Back in step 1, you also created a list of external factors that are missing from your inventory that you can't fix by yourself.

You'll need to work with your boss to ask for help overcoming them. You may need them to talk to HR to create a new position, or just have them add clear expectations to existing promotion tracks.

Step 5: Assembling & pitching the plan

Now, when you go back and and assemble the data you've gathered, some patterns emerge.

The job: title, expectations, salary

You can now actually describe the job you're looking to move into. You write up a rough title, description, expectations, and a desired salary range.

Promotion != reward, Promotion == new job

That's when it becomes clear: this promotion isn't some reward for a job well done. A promotion is not a trophy, it's an entirely new job.

Promotion == a step up, not a huge leap

It's also important to make sure this new job is a reasonable step up, not a huge leap. Even if you did manage to make the leap, I can promise being promoted too quickly is not worth the stress.

Index card plan: continue doing, improvements, new responsibilities

A good plan should fit on an index card: it's a few things that you want to continue, one or two areas of improvement, and one or two concrete additional responsibilities you can take on.

The plan: continue doing, improvements, new responsibilities, needs

You'll also have a couple areas where you need your boss's help, such as opening up a role with HR, or helping you delegate parts of your current job.

The plan: continue doing, improvements, new responsibilities, needs, timeframe

Lastly, you need a reasonable timeframe, usually somewhere between a few months and a year, depending on how ambitious your goals are.

The plan: The job you want

The plan is designed to get you to where it's flatly obvious that this is your new job. If you were to apply for it, you'd ace the interview.

After getting some more feedback from your friends, you're ready to pitch it to your boss.

You'll know your plan is on track if you can easily summarize it like this:

The pitch

"So if I do A, B, and C, I'll qualify as X with a salary increase in the Y range , and Z months is a reasonable timeframe, is that correct?"

Boss says... ?

The good news is that your boss helped you design this plan.

Boss says...? Thumbs up!

So after just a little back and forth, you successfully negotiate your plan. Way to go!


This is an action plan

But you don't want this gathering virtual dust in some email inbox. This is an action plan. It's time to follow up and iterate.

Start the feedback loop

A key component of the plan is a good feedback loop with regular check-ins. In my experience once or twice a month is about right.

Check-in agenda

Your check-ins should be pretty simple and focused on your original agreement. A basic framework might look like: - Here's a reminder of the goal... - What's going well? - What could I be doing better? - Am I on track? - What I need from my boss...

Win book

Your best bet is to document your progress and achievements along the way and bring these to your check-ins.

Adapting the plan

Some things are going to work right off the bat, and some won't. Over time, you'll need to adapt the plan.

Now you've done all you can

Now you have a clear goal, a roadmap, a timeframe, and an up-to-date picture of your progress. From there, it's up to your boss to keep up their end.


This all might sound like a lot of work. But in fact, most of the work is about making one shift in your mindset:

You are in charge of your career.

Your boss and company are not in charge of your career. You are.

So many jobs in tech are quit because people don't know this.

I wonder what younger me would have done if I'd had these two concepts:

The two lessons

  • To pitch a plan, not a promotion.
  • That a promotion is not a reward, it's a new job.

I wouldn't change the past, but I like to think I might have taken charge of my career sooner. Maybe I'd have spent less time feeling frustrated and powerless.

My hope for you

I hope no less for you as you apply these ideas in your own career. Happy hacking!