Goal Setting

I'm a big proponent in New Year goal-setting; I like the "fresh start" feeling that comes with retraining your brain to write "2023" instead of "2022", and every year, my spouse and I celebrate January 1 with a set of goals for the rest of the year.

I see a lot of organizations adopt goal setting during this time as well, but it doesn't always go as planned. For new members of an organization, it can be hard to determine what a good goal will be. Some people set too many goals; others set too little (or none at all). Some organizations use goals as a central part of their performance review process; others treat them as unrelated to the day-to-day.

I find goals pretty useful as an individual, but as a manager, they're game-changing. There's no better way to find the maximum overlap between what my team members want to be focused on and what the organization needs than with a strong set of goals.

So it'll come as no surprise to learn I'm pretty invested in making good goals the norm. If you're in a spot where you're about to set goals, but aren't sure how to make them useful, these are the principles I follow.

A good goal...

...is meaningful. A goal should be something that matters, either to you personally or to the organization(s) you are a part of (and ideally, both). Your goals might reflect what you want your career path to be within an organization, or the type of impact you want to have on a set of users. The goals could be tied to a particular initiative, or reflect a general desire to improve in a particular area. The more meaningful the goal is to you personally, the easier it will be to keep that goal moving forward.

...has an easy way to evaluate progress. Not every goal will have a clear end-state, but for a goal to be useful, it should be possible to see when you're headed in the right (or wrong) direction. This is particularly true for long-term goals, where the elements you're thinking of today probably don't reflect all of the steps you'll need to take to be successful.

Career progression goals are notorious for not being easy to evaluate progress. If you're hoping a promotion is in your future, finding & setting goals for the specific ways you will be evaluated for that promotion ends up being more successful than a general "get to the next level" goal.

...might not be achievable. And that's a good thing -- if you're only setting goals that you know will be achievable, you miss out on the big-picture opportunities that come from places of uncertainty. The key is to distinguish between the aspirational goals and the concrete goals, so you aren't accidentally committing to something that ends up being impossible.

If you're part of an organization with toxic patterns around goal-setting (e.g. missing your goals gets you fired), exclusively setting predictable goals might be the way to go -- but if you have a chance of changing that culture, take it. Organizations that don't give room for exploration and failure tend to end up failing themselves, much more catastrophically than a handful of missed goals.

...has a clear expected timeline. This doesn't necessarily mean a due date; there are plenty of meaningful goals that reflect a spirit of continuous improvement, and are therefore never-ending. The goal should reflect its own time-boundedness or lack thereof, so it's clear to you (and if applicable, your manager) what timeline expectations can come from this goal. Even if a goal has an infinite timeframe, setting finite subgoals makes it easier to measure progress.

...is useful for you. This is where I see most corporate goal-setting initiatives fail. If creating or updating goals feels like a burden or a waste of time, most people aren't going to invest in creating or maintaining strong goals. While it's rarely fun to keep your goals up to date, the less it feels like a chore, the more likely goals will be able to shape your day-to-day for the better.

If you're in this boat, good news: this is one of the problems Skippering can help solve! Any updates you make to your goals are also automatically collected when it's performance review season, making reflection on the progress you've made a breeze.

Goal Frameworks

There's many different frameworks around goal setting that you might find useful (or not). Generally, these frameworks have the properties I listed above, but have more specific structure around how you write the goals. Some organizations also choose to standardize around a particular framework, making it easier to parse goals across individuals.

My general rule of thumb on frameworks is, if they're useful, use them; if they're burdensome, change them or drop them. I've summarized the two I see most frequently below, but if you're interested in exploring more, some alternative frameworks are CLEAR, SUCCESS, or FAST (among many more).

SMART / SMARTER These goals are intended for more of the tactical side of goal-setting. I've seen different takes on what the letters stand for, with the most common version being: "Specific, Measurable, Achievable, Relevant, Time-bound (+ Evaluate, Re-evaluate)". SMART(ER) goals are most useful for milestones that have clear steps to achieve those milestones, but are less useful for large initiatives that have many pieces (and/or uncertain aspects) that need to be in place to be successful.

I find SMART goals to work well if you have to set goals for the sake of performance reviews. They're still meaningful, but it should be very clear from the time you set them that they are achievable by the time you're evaluated on them.

OKRs A lot of organizations use OKRs to determine strategic priorities, which can end up affecting individual goals as well. OKRs (which stands for Objectives and Key Results) are an extension of the principles of SMART goals, with a consistent timeframe for evaluation and adaptation (usually yearly, quarterly, or monthly). Unlike SMART goals, the objectives in OKRs are often aspirational, so it's not uncommon for the same objective to be used for multiple cycles of the OKR process.

OKRs are really good at initiatives with lots of different people contributing lots of different types of work. They're designed to fit-together as a kind of chain, so the goals you set as an individual help your team achieve their goals, which in turn helps the organization achieve their goals. In smaller initiatives, OKRs tend to add more baggage than benefit, so for personal goals that don't ladder up into an OKR system, I'd avoid them.

Kip's Approach

I've built up a system that works well for me, where I distinguish my goals by intent and timeframe. This ends up looking like this table¹.

	Personal	Professional
Short Term	Take a long weekend away before March	Gather feedback from 10 different customers by the end of Q1
Long Term	Write a book by the end of the year	Have 500 paying members by the end of the year
Habits	Take a full-day off from work every week	Write a blog post every week

I particularly like having habits separated from the rest of my goals, because I track my habit building very differently than I update the rest of my goals.

I share all of my professional goals with my team (and my manager), but I evaluate goals differently depending on the timeframe. Short-term goals are generally either complete or not. Long-term goals are measured by progress. Habits are measured by the percentage of time where I kept up the habit. And when I am being evaluated on my goals, it's only on the short-term goals within my control.

What did I miss?

Goal setting is one of the most popular topics for people to have lots of strong opinions on; what did I misrepresent from your point of view? Feel free to give me feedback through Skippering!

Footnotes

1. These are pretty close to my real goals for 2023, albeit a little vaguer. ↩