How productive are you? How often do you surprise yourself and defy the odds? When was the last time you accomplished something truly remarkable?

OKRs can be your secret weapon to getting more done and creating magic in your organization. 

I first learned about OKRs in the book Measure What Matters which is our Mastermind book for September and October 2019.  

OKRs stand for objectives and key results. In many ways they are like the tried-and-true SMART goals many schools utilize. 

Both OKRs and SMART goals are specific, measurable, and time-bound, but like Vygotsky’s zone of proximal development, OKRs are better because they stretch organizations to accomplish far more.

The first part of an OKR is the objective: this is WHAT will be achieved. It’s as simple as that.

The second part of an OKR are the key results: this is where I get excited. This is the HOW you will accomplish your objective. Key results are measurable. Accomplishing all key results should equate to accomplishing your objective.

OKRs are an amazing tool to use because they identify your priorities. Many schools (and leaders) think everything is important.  

Everything is not important.

If everything is important, that is why you are stagnant in creating massive value for your organization. 

Elite performers share a number of qualities. One such quality is an uncanny ability to prioritize and focus.

If everything is important, nothing is. 


The Four OKR Superpowers

According to John Doerr, the author of Measure What Matters, OKRs have four superpowers.

  • Superpower #1: Focus and commit to priorities.
  • Superpower #2: Align and connect for teamwork.
  • Superpower #3: Track for accountability
  • Superpower #4: Stretch for amazing

Superpower #1: Focus and commit to priorities

One of my favorite quotes I share on the podcast has to do with the importance of vision: 

“If one does not know to which port one is sailing, no wind is favorable.”


Said another way: “Where there is no vision, people scatter.”

The first superpower of OKRs is that they clearly articulate what the organization is about. OKRs say, “Here is where we are sailing.” There is no ambiguity in a well-written OKR. Everyone knows exactly what the mission is and where the organization is going. 

The often used metaphor in leadership is that of a row boat. Two people are inside. One person decides to row east and the other decides it is best to row west. 

They quickly go nowhere, rowing in circles. 

This leaves the two rowers exhausted with nothing to show for their effort. 

This is the norm for low and mid performing schools.

Everyone can articulate the goals within a great organization. 

On that note, if I asked anyone in your school: an AP, a teacher, a counselor, a janitor what the most important goal is and how they plug into that goal, what would they say?

Would you be pleased with their response?

If not, OKRs are the answer.

Superpower #2: Align and Connect for Teamwork

How motivated is your team?  

Measure What Matters cites a recent study which surveyed 1000 workers in the USA. The study found that 92% would be more motivated to achieve their goals if colleagues could see their progress. 

Another study cited in the book claimed that only 7% of employees fully understand their organization’s strategy and what is expected to them.  

These two studies tell me:

  • Both goals and progress should be public 
  • We can do a much better job communicating goals and how our people can help us achieve them

OKR Superpower #2 helps schools get everyone on the same page. 

Like the rowing metaphor shared in Superpower #1, OKRs articulate not only where an organization is going, but how each individual can get us there (e.g. everyone row east).

Superpower #3: Track for accountability

Any goal-setting system worth its salt will have some sort of scoring component. Ever since reading, The 12 Week Year, I have been measuring my execution of daily tasks mapped to my major goals. 

Measure What Matters doesn’t specifically call for daily scoring (although that works for me personally and helps me stay accountable to myself and my team). Instead Doerr argues that teams should have frequent check-ins — at a minimum monthly and preferably every week. 

Tracking is made up of three parts: Scoring, self-assess, and reflect


OKRs are regularly scored during a check-in:

  • Green indicates an OKR is “on track.”
  • Yellow means “needs attention” and something should be adjusted.
  • Red symbolizes “at risk.” This kind of OKR may need to be dropped.



During check-ins direct reports and teams should be encouraged to self-assess. These are guides, not grades. 

Quantitative data doesn’t share the whole picture. What is the picture of better effort: scoring green on an easy to attain goal or yellow on a stretch goal?

I’d rather come up short on an audacious goal any day of the week versus achieving a goal I knew I’d always achieve.

This part of the OKR cycle asks everyone to add some qualitative data to the numbers. It puts the “meat on the bones” so to speak and provides a clearer picture of performance.


During a check in a leader would ask her direct report:

  • How are you progressing on your OKRs?
  • What do you need to be successful?
  • Is there anything getting in the way of attaining your objective?
  • Do we need to adjust, add, or eliminate anything?

At the end of a cycle the team might reflect on:

  • Did I accomplish my goal? What contributed to my success?
  • What were the barriers and obstacles?
  • If I rewrote the goal, what would I change?
  • What have I learned that I can apply to the next OKR cycle?

Since OKRs are stretch goals (Superpower #4) they are dropped from time to time. Great risk can lead to great reward. OKRs are not about playing it safe. 

Failure is also an amazing teacher. Conducting a post-mortem on a red OKR can teach an organization some valuable lessons. What did we learn about this failed OKR that we didn’t foresee at the beginning of the quarter? How can we apply these lessons in the future?

Superpower #4: Stretch for amazing

How do you add muscle? You lift more than you can easily lift! 

The secret to adding muscle to your frame is the same as being an elite performer or creating a world-class organization. All of these entities do the same thing: they accomplish more than they thought was possible. 

When I started getting serious about my fitness I was regularly in a lot of pain. That’s because I had to challenge myself to lift more than I thought was possible. 

OKRs are just like muscle. Lifting too much and you get hurt (and demotivated). When you add just the right amount of challenge, that is where greatness lives.

As educators we know this. It’s called the zone of proximal development.

Jim Collins called it a Big Hairy Audacious Goal (BHAG).

One of my favorite guests on the podcast is Ryan Jackson. He has been on the show two (maybe three) times and at least one of his shows is always in the top twenty five podcasts.

One thing that Ryan often talks about is the idea of self-actualization made famous by the psychologist Abraham Maslow.

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Maslow argued that once our basic needs are met, it is self-actualization that truly fulfills human beings. Dan Pink would agree. In his book Drive, Pink says that mastery motivates. Humans want to get better on work that matters. 


By stretching workers, OKRs create an environment where humans are happier, more fulfilled, and motivated to be their best.


Some Tips for Writing OKRs


  • Objectives are the WHAT and key results are the HOW.
  • Less is always more 
    • 3-5 objectives
    • 3-5 key results per objective.
  • Model what you want. Leaders should also engage in OKRs and share their progress with their organization


“When you’re the CEO … you’ve got to say ‘This is what we’re doing,’ and then you have to model it. Because if you don’t model it, no one’s going to do it.”

Coach Bill Campbell



My First Stab at OKRs


After finishing Measure What Matters, you can say I was fired up. 


Below are examples and pictures of all the OKRs I created for the remainder of Q3 2019 (eight weeks). Depending on how it goes, I can see myself adjusting or rolling-over these OKRs into Q4.


OBJECTIVE: Help more school leaders level up







  • Ship 2 SEO optimized, value-packed blog posts a month
  • Ship 6 podcasts a week (BLBS & SLS)
  • Write 2K words a day or 1 hour a day for book #2
  • Record all SY 19-20 podcast episodes August 1.
  • Ship Authenticity course in Go! Community by August 30.

And since a picture is worth 1000 words, here are all my OKRs. I use Trello to build the cards and track …


I know the context in which you lead is different than mine, but goals are goals. If you want to take your leadership and your organization to the next level I encourage you to experiment with OKRs for the next twelve weeks.

After that, see what you learned. Make the process better. Add more value to the community you serve.

Q3 Results & My Takeaways

I wrote the first draft of this post while setting up my Q3 OKRs. I published this post at the end of the quarter. Here is what I learned and also my results.


According to the text:

“The simplest, cleanest way to score an objective us by averaging the percentage of completion rates of its associated results.”

Google uses the following scale, so I stole like an artist and used it too:

  • 0.7 – 1.0 = green (I delivered).
  • 0.4 – 0.6 = yellow (I made progress, but fell short of completion).
  • 0.0 – 0.3 = red (I failed to make real progress).


OBJECTIVE 1: Help more school leaders level up [43%] (.3+.9+.1 = 1.3/3)


  • Launch Kelly’s mastermind cohort with 10 members by August 30 [0.3].
  • Maintain 60 members in my mastermind by Sept 13 [0.9].
  • Add 200 members to the Go! Community by Sept 27 [0.1].


OBJECTIVE 2: Create amazing content [76%]


  • Ship 2 SEO optimized, value-packed blog posts a month [0.5].
  • Ship 6 podcasts a week (BLBS & SLS) [1.0].
  • Write 2K words a day or 1 hour a day for book #2 [0.3]
  • Record all SY 19-20 podcast episodes August 1 [1.0].
  • Ship Authenticity course in Go! Community by August 30 [1.0].


OBJECTIVE 3: Increase brand awareness [57%]


  • 50K downloads a month for BLBS by Sept 27 [0.6].
  • 20K downloads a month for SLS by Sept 27 [0.5].
  • 5K visitors a month to website by Sept 27 [0.6].
  • Grow email list to 5K [0.6]. 


OBJECTIVE 4: Plan live event [100%]


  • Identify and sign location by September 20 [1.0].
  • Sell 20 early bird tickets by September 18.
  • Create agenda by July 31 [1.0].
  • Personally invite 100 leaders by September 17.
  • Ship live event landing page by September 16 [1.0].


OBJECTIVE 5: Improve fitness [46%]


  • Weigh myself every Friday [0.6].
  • Eat healthy 6 of 7 days [0.4]
  • Abstain from chocolate and dessert every day [0.2].
  • Crossfit 3x/week; Heavy Lift 2-3x/week [1.0]
  • Decrease body fat < 14% [0.1].



Objective data isn’t everything — something schools could learn about standardized test. I’ll get off my soapbox now.

For example, my first objective was to help school leaders level up. My objective score was 43%. This objective needs attention. I barely scraped by an “at risk” waiting but this score doesn’t tell the whole picture.

Why did I score low? Well I didn’t add many members to the Go! Community at all (3 new members. 200 was my goal). I also have 54 members in my school leader mastermind instead of 60. 

 But I did start two new masterminds. One mastermind is for entrepreneurs in the education industry and this group already has 7 members. And I started an “Inner Circle,” a mastermind for Superintendents. This group has 6 committed members.

I’ll take those results any day of the week.

Here is my full self-assessment:


OKR Progress Score Self-assessment
Help more leaders level up 43% 1.0 I didn’t move the needle at all on the Go! Community and my personal school leader had two members “pause” membership to come back in two months. That’s okay because I started two new mastermind for “Edupreneurs” and Superintendents. When I think of impact and profit these two groups have a huge upside and I’m absolutely thrilled I get to serve these two new groups.
Create amazing content 76% 0.8 I didn’t realize the first month working with my web team was setting up the system. I move super fast and had plenty of content ready to go, but we needed to set our system up, gather baseline data, research topics that would offer value before really shipping. The good news is that I’m ahead of the content game and excited where this will lead. Plus, the School Leadership Series podcasts are all done so I can really focus on writing now. Rewrites on one book proposal are taking a lot more work than I anticipated and I haven’t prioritized like I need to. The live event really took over. I also was involved in the altMBA again and Story Skill Workshop so I haven’t even started my second book proposal. And if I’m honest this creative risk is a bit scary to even start. I need to take this serious in Q4.
Increase brand awareness 57% 0.7 I scored this a bit higher than the objective score because the system is now set up for content which I anticipate will lead to increased brand awareness. I’m less keen on running ads to boost awareness. My focus is on creating highly valuable content that leaders want to share. I’m playing the long game, not the interruption game. That’s why you won’t find pop-ups on my website. I used to have them, but I’ve noticed how much I hate pop ups on other websites so why would I do that to a website visitor? If I’m enjoying the content I don’t want to jump through hoops to get to it. 
Plan live event 100% 1.0 I was off in planning to sell tickets. It took longer to get bids, evaluate options, and sign the contract. It was also scary to sign a contract for that kind of money … the live page narrative and links were handed off to the team and will be able to go live for mastermind VIP access in October before “early bird” access to the rest of the BLBS tribe in November.
Improve fitness 46% 0.7 My eating sucks. Well, my meals are okay but I’m going crazy with sweets. I also started a love affair with beers (I’ve been missing Belgian Tripels). I rehabbed a calf and groin injury so I’m back playing footie and I’ve been consistent in the gym. So as long as I add some HIIT training and demonstrate discipline in regards to what I eat, I’ll achieve progress next quarter.


Did I accomplish all my objectives? If so, what contributed to my success?

No. See below. I made great progress and learned a lot.

If not, what obstacles did I encounter?

I picked too many key results and maybe was a bit too aspirational for the first attempt. I was tracking 22 KRs. According to Measure What Matters, 15-25 key results are the sweet spot. 

Another obstacle was my emotions. I felt fear and nervousness connected to my first live event. This was the first time to sign such a large contract that I’m responsible. I haven’t purchased a home and the event, Bollingen Tower, costs more than a car so it really made me think about what I was doing. 

Since I made some great progress on other goals, I don’t anticipate being as spread thin this next round.

I also didn’t consistently map each day and keep score of my progress. That isn’t usually the case. This quarter I really struggled with some habits I usually have locked down. 

If I were to rewrite a goal achieved in full, what would I change?

The only goal that I scored a 1.0 on was the live event. I think I could have made some decisions regarding the emotions and cost of the event ahead of time which would have sped some of the process up. 

This is a good question to ask, but this was a committed goal, not an aspirational one, so I definitely didn’t settle anywhere. 

What have I learned that might alter my approach to the next cycle’s OKRs?

It would help to do this as a team. I anticipate that working OKRs with my sous-chef, Kelly, will build more momentum toward our goals. 

I also want to be mindful about how much I commit to this quarter. 

Your Turn

At the end of the day it’s all about action.

“Ideas are easy. Execution is everything.”

-John Doerr, Measure What Matters

A Japanese proverb talks about action this way:

“Vision without action is merely a daydream.”

Reading this blog post might help you feel productive. That’s different than actually being productive. 

Make a plan.


And let me know if I can help. 

There are three main ways in addition to the podcast / blog of how I can help you level up:

Speaking of help … If you’re the generous type and would love to help me …

If you enjoyed what you read today, please consider sharing it on social media. All of us are better than any of us. Don’t keep this learning to yourself. Let’s get better together. 

Go make Ruckus

❤️ D

PS … If you want to read more about OKRs you can check out this post on coaching I did and my friend Matt wrote a great post on OKRs. You can read that here.

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