Don’t ‘Waterfall’ Your Career

February 9, 2022

Right now I’m working with five different members who are ready to quit their jobs.

To help them think about what it might take to stay, I’m using lessons from my upcoming book, Never Search Alone.

The bottomline of my book is this: 

You wouldn’t use waterfall to build a product.

Don’t use waterfall to build your carer.

Instead, remember that your skills and experience are your product and, with that in mind, engage in an iterative process that gives you market insights about the intersection of what you want and what the market wants (what I call your “candidate-market fit”).

Be smart. 

Be iterative. 

Be market- and customer-focused.

– Phyl 

P.S. For more detail on how I helped a CPO decide to stay (and get the resources and support she needed), then read below.

Five Steps to Help Sarah Stay

1. Ask for help

No surprise,  #1 rule is to not do this alone. 

Ask for help – especially if you are a CG member, you have this whole community ready to help you. Start by reaching out to me.

Sarah, a Chief Product Officer at a Series C SaaS company in San Francisco, did this recently when she realized her equity was way below industry standard and was ready to leave.

I asked her what would it take for her to stay? Was there anything the company could do?

She said that if they brought her equity up that would help and she would like more budget to build a better product management organization and really tackle the transition from single product to multi-product company. 

I said OK, let’s do this. 

2. Positive Politics

After a member tells me what they might need to stay, I then talk about what I call “positive politics”, which is the theme of the meetings in Chicago – more on that soon. 

The point of positive politics is to figure out what positive change you want to lead that will help your company and its customers. This is important, especially when asking for a promotion, pay raise, or more budget – because you want to be grounded in the larger picture of what’s important and not just focused on your personal career or salary.

I reiterated this with Sarah and confirmed that one of her main objectives is to lead the multi-product transition.

3. Job Mission and OKRs

With the objective of the positive politics campaign spelled out, I then shift to talk about creating a job mission with OKRs. Job missions are not job descriptions – rather, they are actionable OKR-oriented documents that describe the results you are going to deliver, and the budget and resources you need.

When working with job seekers, we create these once things start to get serious with a potential employer.

With folks in current roles, like Sarah, we create them as soon as possible.

Sarah’s company is not yet using OKRs, which was all the more reason I suggested she do this. She agreed to create one and I sent her the additional resources from my next book, including a Google Drive folder of 10 examples of job missions with OKRs (these are anonymized versions of real job missions that CG members have created and used in their negotiations).

4. Listening Tour

Then it’s time to go out and listen to and do some discovery work on yourself.

Remember, you are the product so don’t create the strategy without iterating through your thinking with the market.

This is what no traditional job search methodology does. 

Again, you wouldn’t simply sit down by yourself and think up your “dream product” and then go build it.

So, why would you do that with your career?

Back to Sarah.

Once Sarah had created a job mission with OKRs, we reconvened to talk about how to conduct a listening tour to help her think about her budget request and her equity request.

She had arrived at her company just before the Series B transaction (and her role was an important part of the pitch to investors) and she helped grow it through the Series C that closed last year.

I connected her to a few members and she got some market insight (including reference to a VC database on salaries) that confirmed that her equity should be much more, and gave her some additional support around her budget request.

5. Permission-based conversations

With all this work done, Sarah was ready to talk to her boss, the CEO. So, we met and discussed what I call “permission-based conversations.”

One of the key rules about permission-based conversations is that you *create* the environment for listening to happen on both sides. 

So, I asked Sarah to first tell the CEO she’d like to meet and talk about the focus for the next 12 months of her work, the budget she’d like to ask for, and the equity she’d like. 

In other words, be clear about the agenda and get agreement to meet on those topics.

Then in the meeting, I suggested she ask permission again – this time to share her focus on the transition to multi-products, the budget she wants to make that happen, and, importantly, the equity she deserves.

Get his agreement not on your ask, but on *listening* to your ask. 

This doesn’t guarantee you’ll get what you want, but it does help to create the possibility the other party will listen.

In Sarah’s case, her boss agreed to listen, was then impressed by her job mission and OKRs, agreed to her budget, and agreed to work on adjusting her equity.

She left the meeting with a clear understanding of where she stood and, as of this writing, is waiting to hear back on the equity, but it’s clear that he’s going to do something more.

This simple process has helped a number of CG members stay and be more effective (and thereby helping a lot of CG member companies retain key talent).

If you are feeling burnt out or you don’t have what you need to stay in your current job and you want help, then give me a call. 

I’m happy to help you take a more agile approach to how you navigate your career inside or outside your current company.


P.S. I’m also planning to turn this into a talk for companies — aimed at helping employees think about how to find a way to stay and be happier, more effective, bring more impact. Let me know if you want to find out more about that.

About the Author

Phyl Terry

Phyl Terry, Founder and CEO of Collaborative Gain, Inc., launched the company’s flagship leadership program – The Councils – in 2002 with a fellow group of Internet pioneers from Amazon, Google, and others. Thousands of leaders from the Internet world have come together in the last 15 years to learn the art of asking for help and to support each other to build better, more customer-centric products, services, and companies.

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