How to Evaluate Job Offers

At some point as your career advances, you’ll get job offers. Often, like waiting for the proverbial bus, three come along at the same time. How do you choose between them and your current role? This is the simple framework I use to evaluate, and more importantly, discard… opportunities that I’m approached with. YMMV.

I have four factors I use to evaluate offers. In order. Pairs nicely with my quarterly assessment of existing roles.

  1. Learning
  2. Impact
  3. Fun
  4. Money

I generally take roles and force rank for these factors (use a scale of 1 to 5). Usually, one leaves the others behind, or, at a minimum, the ranking eliminates one or two from contention making decisionmaking easier.

1. Learning (and Growth)

Despite being later stage in my career, I always try to put learning and growth at the top of my list. If you’re early-stage career-wise, I feel this should be doubly true for you.

If you’re more senior, this factor rounds out your value proposition as a contributor or manager as you progress career-wise. If you’re younger, this is essential experience that grows your expertise and breadth.

In fact, when I interview people, I carefully double-check people who have been too long in one company and one role. Why? I find they tend to become experts in the companies they live in, rather than in being adaptable and being able to get things done in diverse and novel situations. Historically, some of those hires have wilted like hothouse flowers when moved from a rarefied atmosphere like banking into a startup environment.

So, given two reasonable equal jobs I always side on the one that is going to give me a greater opportunity to enlarge myself for the future: teach me something new, expose me to a new skillset in business, taking on or scaling management, or an entirely different industry.

In fact, I’d argue whether you’re a knowledge worker, executive, data scientist, developer, or entrepreneur it’s always a good idea to have a list of skills you wish to pick up and when opportunities presents themselves, map the role to see if one of those skills can be picked up, and choose (or negotiate) accordingly.

2. Impact (and Helping People)

Most roles feel worthwhile because you are helping people in some way. Unless you’re a sociopath, most of us are wired to have our work add value and meaning to society or our customers. It makes us feel good, useful, and like our work is worthwhile.

So, pick good problems to be solving.

The second aspect to this is about how much impact you can have. What sort of real world accomplishment can you potentially make in this role, or count coup on when you’re looking back at the role in a couple of years’ time?

For me, this has increasingly become about creating change in the world that I want to see and I feel that unambiguously helps people. I have a fairly high bar for myself here, but that is a personal thing. There’re many ways to contribute and do worthwhile work: build something worth building, creating an environment where others can do their best work, growing others to become better, or developing expertise in a needed niche capability are all forms of impact that may hew to your particular talents. Figure out what works for you and how to make your work feel worthwhile and go with that.

The important thing is that you feel you are spending your days accomplishing something that allows you to express your unique talents and skills in a way that delivers value to people and society in some way.

3. Fun (and Adventure)

All of my best jobs I’d describe as fun. And generally that has been working on interesting problems with great people. To the point that the best of them almost felt like play.

This isn’t to say some days weren’t hard or difficult in those roles… in fact, I don’t think work feels worthwhile unless it’s often challenging, but there were aspects of the role that made it fun — often, having to push myself to the edge of my skills and deliver on difficult challenges with interesting teammates.

If I had to define what those things were they’d be:

  • interesting problems
  • great people
  • freedom and autonomy to sovle those problems
  • ability to express and improve mastery

Added to this has also been pure adventure. I’ve purposefully slanted towards roles that provided the opportunity for relocation to other countries and cultures where I’d also have to adapt myself to new ways of doing things, a different business environment, and even entirely new languages (one could argue this should slot under learning, but I’ve always felt it’s fundamentally different as it’s about how much I’m enjoying the environment I’m in.).

Even though it seems quaint, fun is a serious consideration you shoudl take into account when evaluating an offer. Do these people seem like they are going to be fun to tackle problems with? Is this an environment and leadership that is going to be supportive and enjoyable to work with, even when things get tough? Do I trust these people? Are there too many people you speak to in interviews you find prickly or a bit difficult?

These are serious considerations as the environment and how much you enjoy it is the substrate on which your days will be built.

4. Money

Yes, I Put money last for a reason.

Far too many people over-value an increase in reward. Despite evidence on diminishing returns on salary increases, most people focus too hard on how much they’ll get paid.

So, if you’re already financially stable and are slowly building wealth, you should carefully consider the actual value of an increase in monetary wealth of an offer versus other factors listed here.

As a further caution from previous posts on finances, you should always be constructing your financial life in such a way as to make money the least of your concerns when looking at job offers. In fact, the other three factors may so heavily outweigh money that you want to take a pay cut, to emphasize learning, adventure, or freedom (and before you call me out on this, I have taken a nearly 50% pay cut and moved to a much more expensive city for an opportunity.).

As an exercise, you may want to try to evaluate monetarily how much each component of of various aspects of a role you’d be willing to give up to gain them. For example, how much would I be willing to go down if I received an extra 5 days of vacation each year? What is the ability to work remotely for 30 workdays (or permanently) worth to me? What is pension/tax free savings matching worth as a benefit (as easy one since it can be calculated directly)?

I’d also caution here against roles which offer too much of a compensation component in stock unless you are early career. I’ve now had three roles daub life-changing stock components at offer only to have them revised down or diluted vastly downwards as VC evaluation bubbles burst. Same goes for bonusing being too large a component of your compensation (I should disclose I personally feel bonusing does not align personal incentives with company interests and worse, creates a culture of bonus time performance heroes versus people continually doing their best for the company if they’re fairly compensated.). Fact is, cash is king. Base salaries in hand are problably going to trump bonusing and stock, unless you luckily land on Boardwalk in your company selection.


And that’s what I use when looking at roles and in trying to choose a direction for where I want my career to go. I hope it’s useful to you and possibly gives you another perspective if you’re trying to decide between various courses of (hopefully) multiple offers or even between something new and where you’re already sitting. I’m always curious to hear how it’s gone for people who may adopt some of these ideas, or hear more about what may have worked (even better!) for you or other things that have made a huge difference for you. Feel free to mention me as @awws on twitter or email me at via email


5a4a526 @ 2022-10-13