The Forgotten Step in Goal Setting

Steven Hancock
The Startup
Published in
5 min readJun 24, 2019

There’s a lot of goal setting frameworks out there. Between OKRs, SMART Goals, BHAGs, or even Goal Pyramids (like Rockefeller’s Strategic Planning Pyramid) you’ll choose some specific goals that are measurable, actionable, audacious (but achievable), and time limited. I’m not going to tell you how to set goals or even that you should set goals (there may be harmful effects). I will, however, tell you that unless you are willing to analyze the results don’t even waste your time setting goals.

The Importance of Reflection

Reflection is key. I challenge you to come up with something that doesn’t benefit from reflection. A big problem with goal setting is the inherent probability that comes with them.

Quickly, what’s the probability that if you roll 8 dice, at least one is a 6 and you finish reading this article?

In Thinking Fast, thinking Slow, a fantastic book that everyone should read, Daniel Kahneman demonstrates that as a human race we suck at thinking with probabilities. The premise of his book is that without deliberate action we think fast and use out intuition. Unfortunately our intuition is horrible at accurately accounting for probability. We suck at understanding expected values, timelines, anything that has a value based on probability. What are goals base on? Probability. Humans need to be deliberate when dealing with probabilities. We need to think slowly and recognize our intuitions are wrong.

A management consultant that I subscribe to, Mark Horstman, has a Chirstmas Rule.

Anything you do rarely and that’s important, you’re never going to get better at.

His Christmas Rule exemplifies why repeated reflection on setting goals is so important. You aren’t going to be good at goal setting until you make it a deliberate practice that you repeat over and over again. We should have a retrospective on every goal (success or failure). Ask why, ask why again, then ask it again.

Better doesn’t happen without hindsight and deliberate action. Here’s some tips on how to be deliberate in your reflection.

Schedule Reflections

Scheduling time to reflect on you goals is your first step in your reflection journey. There’s two distinct times that you will want to reflect on your goals, periodically during the goal’s lifespan and after the goals duration is complete. Go ahead, schedule your goal retros now. I’ll wait.

Reflection Before Goal is Complete

Prior to goal completion your reflection should:

  • Include Status Updates — Where are we at? You’ve already set up some sort of measurement for you goal (right?) so now is time to let everyone who is involved know where you are at. What tactics have been tried? What tactics are you going to be trying?
  • Plan new tactics — You should have already had some ideas on how to accomplish your goal. Perhaps those haven’t worked out as well as you thought they would. Now’s the time to plan new tactics and set yourself up for success.
  • Adjust your Goal — Goals should not be rigid. If you are a week into a 3 month goal and you realize that your goal is more like shooting for Exoplanet EPIC 201238119 b instead of shooting for the moon, you should be adjusting your target. Or conversely, you have already hit you target in your first week, you should be setting a more difficult goal. Maybe you’re an agile type. Perhaps you’ve pivoted your focus. Don’t be afraid to throw out your goal and create a new one.

Reflection after Goal Duration

Within a few days after the goal duration ending it’s time to hold a post mortem. Most of the general rules of running a post mortem or retrospective are applicable here.

The main prerequisite is that this reflection needs to blameless. If goals weren’t obtained it is no one person’s fault (could be one person’s responsibility, but that’s not blame). Blameless post mortems cause an environment of safety where no one will feel attacked for their thoughts or actions. Do NOT use obtainment of goals as the sole means of performance evaluation. Bring in any context that helps you evaluate your goal. When you are forming goals, you do not have the benefit of hindsight. At evaluation time you do! Why wouldn’t you include the extra data that hindsight gives you?

Set the stage to help everyone understand what happened. Did you reach your goals? What was the timeline? Who was involved? Draw attention specifically to what went well, what went wrong, and what we got lucky with. What went well can be surprisingly difficult if the goal was not obtained. An unobtained goal can cast a large shadow. Look for the positives, did you hit any metrics along the way? What was accomplished? Was anything learned? Likewise what went wrong can be difficult if the goal was accomplished. Here you’ll want to find tactics that weren’t completed or metrics that weren’t reached. You’ll want to dig into negative feelings like stress. Getting lucky (or unlucky) is difficult to admit. Did the number of users increase because of great marketing or because a post went viral? Look for things that you don’t have a high confidence that you could repeat if tasked to do it again.

Once you gather information, it’s time to make recommendations and take actions. The recommendations are simple bite sized statements of what you should do differently next time. Actions are statements about what you WILL do differently next time. The distinction is important. You may have a recommendation that states you shouldn’t be so aggressive when setting goals, an action on the other hand, will state HOW you will be less aggressive. If you were writing a tldr; for your reflection the recommendation and actions are all that are needed for others to learn. All other information will be used to providing context, the why to the recommendations and actions.

If you expect setting goals to have an impact at work, at home, or in your community, do yourself a favour and get good at it. Reflect on your goals and become an expect with the uncertainty that comes with goal setting. If you are not trying to get better at goal setting, you will be horrible at it and the goals won’t be as effective as you had hoped.

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Steven Hancock
The Startup

I’m a ‘data guy’ at a fast growing tech company, Vendasta, in the heart of the Canadian Prairies.