Smart Risk Taking

To put a close on the Boston Tech and Learning Leader Event I wanted to take time to reflect on the learning, the opportunities, the connections made, the reconnection with EdTech Leaders, the fun with friends, and the risks taken (# poetry_slam). The poetry slam made me think of the Henry David Thoreau quote I read often before trying something new

If one advances confidently in the direction of his dreams, and endeavors to live the life which he has imagined, he will meet with a success unexpected in common hours

So, after reflecting on the event, I wanted to share my thoughts on risk taking because many of us took risks at #TLtechlive in different ways.

It also got me thinking…..What can aspirational people do to keep growing? 

My answer: The encouragement to keep taking risks.

Now we didn’t go skydiving or swim with sharks at the Tech and Learning event, but we did step out of our comfort zones. That may have been participating in the Keynote, or leading a session, or running a playground, the poetry slam, or for some it was their first event as an EdTech leader and participation was stepping out of your comfort zone by collaborating with some peeps you only follow on Twitter.

I know, there have been hundreds, if not thousands, of articles that have been written about how making mistakes is one of the keys to success.

However, As I reflect on that thought, my issue is that thought is emphasizing the outcome (the mistake) rather than the type culture we would like to create. It’s not the mistakes that leads us to success, it’s the culture of risk-taking. As leaders, we need to be cultivating a culture of smart risk-taking. A culture where people understand what risk taking is, what’s is a smart risk, and then feel comfortable in proposing or even taking risks.  

For example – our poetry slam.

  • Six of us participated

Screen Shot 2018-04-29 at 8.38.21 PM

  • Carl Hooker sent us an invite.
  • Our choice to participate.
  • He provided us some exemplars.
  • He checked in often to make certain  we felt supported.
  • He also gave tips and encouragement along the way.

It was that supportive culture that allowed us to take a risk. Thank you Carl!! This post will be an expansion of my thinking about risk taking for growth.

I think there are two types of risk

  • Smart: clear, calculated, planned and rational (based on sound analysis and facts)
  • Reckless: blind, frivolous, undisciplined where you must rationalize the risk (justify the action, not based on facts)

So, to use at the poetry slam  – we were smart and rational with a load of support. Not only from Carl but from each other.

So how do you judge or measure risk?

I think by:

Knowing the risk – You are able to describe the change or risk you are considering taking and why. 

What does it take to participate in the risk – You are able to detail what needs to happen to get there while focusing on the planning. 

Reflect and GO– Once you decide to take the risk – make it happen 

Once that you are a “Go” – how do you to proceed with taking a risk – I say with preparation and safeguards.

Preparation and Safeguards

  • Avoid unhealthy/reckless risks
  • Don’t risk everything – taking a risk is for growth
  • Know what you want and ask/plan for it
  • Execute
  • Practice and learn from errors
  • Don’t stop and Don’t worry about what others think

Once you have made the decision to “Go” with stepping out of your comfort zone and then preparing to take the risk – it is time ACT.

Carl created that environment for all of us.  

So how do leaders do that for others? School leaders are the architects of the social, emotional and intellectual organization of the school. Promoting and cultivating healthy individual and collective learning and achievement culture in schools is essential. This culture will drive how teachers feel about their work and how they think about themselves as professionals and increase their resiliency for taking risks. Leaders must support educators’ imperfect first attempts by applauding the participation and continually supporting thought a culture of encouragement and care.

I believe success won’t fall in my lap — I must pursue it and work at it.  Success not LUCK – its effort and stepping out of my comfort zone.

How do leaders create this culture of risk taking?

Define Smart Risks and Set Limits

We need to define what we mean by smart risk.  I tried to lay that out above, as much for me as anyone who reads this. The last thing we want as leaders is for every staff member to just take a risk for the “hell of it” and jeopardize student learning or educator confidence/growth.

Demonstrate Risk-Taking

Find something at which you’re good at and let your staff see you do it. Make the point that regardless of your current performance, you will never improve at that activity unless you are willing to push yourself to the point of making a mistake. Part of my entrance into the poetry slam was to lead risk taking. I wanted to demonstrate it.  For some of the educators I try to push to keep taking risks, I shared drafts of my poem and talked through my thinking.

Be Willing to Fail

Leaders can’t just show staff what they are good at, they must be willing to try something at which they are not good at so your staff observe and celebrate your willingness to try

Model Risk-taking Behavior

Leadership defines culture, and if we want to create a culture of acceptable risk taking, then we need to display that kind of behavior.  We also need to be transparent about the risks we are taking, explain why we are taking them. People learn from watching and if they can understand our smart risk-taking approach it can help them develop theirs.

Identify Some Risk-Takers and Encourage Them 

Risk taking is a behavior, not a process, so identify who your possible first risk takers and encourage them to take smart risks. The more people modeling smart risk-taking behavior, the quicker and easier it will be to create that culture. 

Create A Safe Environment For Risk Taking

We need to create a safe environment for risk-taking; this means not punishing people who take smart acceptable risks and fail but supporting them.

Reward Smart Missteps (I don’t like the word failure in risk taking since it is a success to even try)

Set up a structure that reviews missteps and celebrate the best attempts, as this will show that the school is serious about risk-taking. What gets rewarded gets repeated, so we need to reward the best missteps as well as success as this will send a strong message to the school.

Effective leaders design plans in the spring and summer that will produce success academically within the first few weeks of school. Why not create plans for encouraging risk taking and celebrating attempts? Recognize effective effort and practices simply and clearly throughout the year will encourage more of the same efforts. When staff understand what smart risk taking is, they will understand their comfort zone and be able to deal with anxiety and uncertainty more easily.

Create a culture of risk taking starts with preparation, vision, and taking a risk to do it!!

So, my time to walk the walk.  Below are my attempts from the most recent to when I started. They are my drafts/practice attempts leading up to my actual live poem.

Click here for My 3 minute Poetry Slam in Boston – had a BLAST

Click here  for My last practice of the Poetry Slam in Boston (This helped me watch and hear myself to work on timing)

Click here for my first attempt

Below are some of the notes I made after watching my first attempt and getting feedback from Carl. Check out the date…the event was 14 days later.  Smart risk taking is ….well planning and being smart.

Screen Shot 2018-04-29 at 9.56.39 PMScreen Shot 2018-04-29 at 9.58.02 PM



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