Strategic means being confident enough to fail.
Pick yourself up, brush yourself off, and start again.
What does being strategic mean?
It means being perceptive, future-oriented, open-minded, proactive, working off the front-foot, and making and taking decisions based on evidence and calculated hunches.
To be strategic also means you need to be confident. And confidence is a learned skill. It comes from doing something even though you know you might fail a lot initially. It comes from having the tools and team around you to support you as you try. Confidence does not grow in safe and easy environments.
Have you recently watched someone learn how to ride a bike? There's this beautiful moment when momentum, balance, and self-belief all come into alignment, and off they go. They are empowered to ride a bike.
Here's the thing: I'm sure there's someone in the background of the memory you just conjured yelling madly, "You can do it!" they didn't start with just saying, "You are empowered to ride a bike."
Your story might have training wheels, possibly a steady hand at the back of the seat, someone running beside you - because empowerment comes with actions as much as words. And those actions are based on the teacher's knowledge of the tools you need to find momentum.
As a leader, you need to create "learn how to ride a bike" moments for your team. You'll see magic if they learn how to ride a bike together.
Step one on the path to learning how to ride a bike?
They need a focus point, and you need to be ok with letting them fall.
EXPERIMENT
What's interesting about getting people comfortable with the possibility of falling is you can't tell your team, "I'm ok with you falling." You might believe it's true, but they might not. And the "Optimizing my work, so I don't fail." cycle continues.
Recruit your participant. Ask your team who would be open to helping you with an experiment. You want them to Opt-In first.
Share with them that you want them to share a story of a failure with a different manager in a different role. What is an example where there were concrete negative results? Example: I assumed what I heard from a colleague about a critical element of a contract was what the agreement said. I didn't loop in the legal team to confirm. We made a decision based on that element. We were wrong about our assumptions. It cost the company several $100K. It was not my finest moment.
Workshop the next steps together. Along with your individual, you need to assume the role of the person who made the original mistake.
What did happen?
What do you think should have happened?
Are there other options?
What was the lesson learned?
This collaborative exercise creates trust and confidence between both parties.
AMPLIFY
Amplifying this idea takes some courage from both parties. Make this exercise a collaborative exercise with your team. Instead of having it behind a closed door, have your team listen to the story and watch you both workshop.
Note: They don’t get to workshop the problem with you - this is about reactions to failures, not about promoting their ideas. You should, however, ask them to share how they see the individual’s potential in a more positive light after watching the exercise. This turns a failure story into a potential story, and in doing that, everyone wins.
INVEST
Want to learn how to get your team confident with destructing and recreating?