On Achieving Goals

Achieving your goals, in its most basic form, can be a very simple process. The recipe is:

  • Create a good goal; have an owner for the goal
  • Make sure that the owner runs regular check-ins that cover two things:
    • Goal status
    • What do we need to do if we’re not on track

People and teams and companies around the world fail at this every day, constantly, disastrously, by not following this simple equation. The main reason goals fail is simply the lack of one of the above elements, i.e. you have bad goals or bad check-ins.

Bad Goals

Bad goals are one of the following:

  • Not valuable
  • Not a priority
  • Ownerless

Not valuable

Your sprint velocity increased, you got all the tickets done, you got 70% of your OKRs done instead of 62% - who cares? Absent other context, these are just numbers that have nothing to do with business value.

Valuable goals have obviously valuable outcomes. The more people and teams and companies shift to second order outcomes, the more your company is headed towards a bureaucracy where storytelling is valued more than impact.

You should have a constant existential itch that can only be scratched by confirming your goals actually matter. Rechecking that your goals matter is often faster than you’d think, and time well spent.

Not a priority

Another main problem in goal setting is choosing goals that aren’t actually a priority.

Common prioritization patterns/heuristics include:

  • There’s no free lunch - assume every goal will require major effort. If it doesn’t require major effort, why is it a goal?
  • Having a recurring goal that always fails means it’s not important and should not be prioritized. If you find yourself aw-shucksing every quarter around some metric, it’s likely it shouldn’t be a goal. Sometimes this can be a hard truth for things people aspire to change but never resource.
  • A team shouldn’t work on more than 2 goals actively at the same time.
  • Company-wide goals need exec level owners.
  • Your CRO’s goal will always be sales and your CMO’s goal will always be pipeline.

Ownerless goals

If you ask “who owns this goal” and the answer is “we all do” - you’re in trouble. When everyone owns the goal, nobody owns the goal. Success will have everyone taking credit and failure will be an orphan.

Someone must own the goal. That person must do the check-ins. That person must have a first name, last name, and email address that we all know. It can’t be “everyone,” but it also can’t be “the project manager” or “whoever is running X.” That person must plot the course and correct it when it strays and they are held accountable if it misses.

Bad Check-ins

Bad check-ins are everywhere. Really smart, senior people screw up check-ins all the time. Ways they do this include:

  • Not checking in
  • Not checking in enough
  • Not checking in with the right people
  • Not running a good check-in

Not checking in

The simplest way people screw up check-ins is by not doing them.

One version of not checking in is never doing check-ins from the start, e.g. “people at this level don’t need hand holding”. Everyone needs check-ins.

Another version of not checking in is check-in atrophy: you did a few check-ins, then they lost steam, and suddenly they just disappeared. This is often a self-fulfilling prophecy - once you miss any check-ins, check-ins become less useful, and then it becomes easier to cancel future ones.

Automated check-ins are also a great way to fail at check-ins. Automated emails without human interaction are digital toilet paper. The power of the check-in is actually checking in.

Not checking in is always a mistake, it’s like coaching a basketball game without ever talking to your team.

Not checking in enough

A classic naive move is the team that thinks they’re special and wants to do standup once a week instead of once a day. This is almost always a mistake. A check-in is a chance to take stock and course correct holistically, which almost never happens organically.

Doing too few check-ins is like a basketball team saying they’re happy to just have less timeouts.

Not checking in with the right people

Another classic failure is partial attendance:

  • This is a super important goal and 7 VPs are allegedly accountable
  • Those VPs periodically miss the meeting
  • The check-in now only ever has partial attendance
  • More VPs start skipping because it’s a lame meeting..etc.

You need to hold the check-in meeting every single time with full attendance. If people can’t make it, reschedule.

Not having the right attendance in a check-in is like a basketball team having a timeout without their point guard there.

Not running a good check-in

Ok, so let’s say you have a good goal, with an owner, and periodic check-ins, in a meeting people attend - by far the biggest failure from there is just having a bad check-in meeting. This looks often like:

  • Not doing a status update on a goal
  • Not actually talking about how to course correct
  • Awkward truths
  • Prioritization issues
  • Round-robin check-ins
  • Lack of ideas on how to fix problems

These are all symptoms of trying to “get through” a check-in meeting instead of actually using a check-in to audit and change outcomes.

Not doing a status update on a goal

Every check-in should have a status check-in on the goal, something like: we’re behind, on track, or crushing it. Say the status out loud and get alignment on the status.

Not saying the status of the goal in the meeting is like playing a basketball game without ever looking at the scoreboard.

Not actually talking about how to course-correct

It introduces cognitive strain to actually think about getting a goal done; people would often easily spend 40 hours doing stuff they know how to do than 15 minutes thinking about how to do things differently. Check-ins exist to course correct and introduce the energy needed to do so.

Once you know the status you must ask how to fix things that are going off course. The plan should be compelling. If you can’t figure it out, keep trying. Good basketball teams make changes when they’re losing; bad teams just keep doing the same thing and wonder why they lost.

Awkward Truths

Sometimes people avoid doing real check-ins because an honest accounting of the situation would surface an awkward truth, like the fact that a person or a team is not pulling their weight. The answer is absolutely not to ignore the situation. The healthiest solution is to just be transparent and clinical. Maybe a low performing engineer is stuck on a ticket - better we can say out loud they need help than all pretend they don’t and miss our goal. The more you can destigmatize honest evaluations, the more you can manage effectively.

Prioritization issues

Another common pattern is that the mere effort of earnestly trying to hit a goal - check-ins, meetings, follow ups - reveals that people don’t actually have the time to make something a real goal. This often happens with executives who try to delegate goals that they don’t personally have the time to hold people accountable to. If you don’t even have the time to check in on a goal, you shouldn’t be telling people to do it.

Round-robin check-ins

The worst kind of check-ins go around and ask everyone what they’re up to. Imagine a timeout in basketball asking everyone for their thoughts on how it’s going.

Good check-ins often include everyone giving updates, but the updates are specifically in context of how we’re going to hit our goals.

Lack of ideas on how to fix problems

Sometimes everyone agrees we’re off target but nobody has any good idea on how to change that. Here’s a standard list you can use to prompt the meeting:

  • Should we de-prioritize other things to focus more?
  • Can we get help? To avoid the Mythical Man-Month kind of fallacy, the best help is often not just adding people, but consulting with very knowledgeable people.
  • Can we cut scope?


One of my favorite movie quote comes from Michael Clayton where the lead character tells his son “You’re not gonna be someone that goes through life wondering why shit keeps falling out of the sky around them.” That quote reminds me of all the times people wonder why goals aren’t getting done. Then you zoom in and see that the infrastructure for their goal (or lack thereof) destined it for failure from the beginning. Hopefully with this guide, you too can not go around wondering why shit keeps falling out of the sky around you.