
How To Plan For Uncertainty
08/07/20 • 19 min
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We live in uncertain times. My friend Andy posted a photo of a sign from 2015 today that asked “Where do you see yourself in 5 years?” Well, I seriously doubt that any of us would have answered “living through a global pandemic with an uncertain ending.”
No matter what your role, it’s important that you learn to plan for uncertainty. You can’t predict what will happen, but you can prepare yourself to deal with unexpected events in a more productive way. On this episode, we share three core principles for planning for uncertainty:
- Ask better questions. Many people don’t ask questions because they don’t want to know the answer. However, it’s only when things go awry that you fully realize the quality of the questions you’ve been asking. In this episode, I share how to ask the “what’s the pin in the grenade?” question to help you prepare for unexpected negative events.
- Build your runway. You need to know that you have the resources needed to bridge from here to there. Many businesses will go under during this pandemic because they weren’t able to survive the downturn, but those who make it through will be far better positioned on the other side to take advantage of the rebound.
- Protect the main thing. Mission is king. You need to adjust and adapt in whatever way is necessary to protect your mission and abide by your values.
Uncertainty is inevitable, but how we deal with it makes all the difference between a successful outcome and a disastrous one.
Mentioned in this episode:
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Butcherbox: Butcherbox.com/accidental EarnIn: Download EarnIn on the Apple app store or Google Play
Please Support Our Sponsors:
Butcherbox: Butcherbox.com/accidental EarnIn: Download EarnIn on the Apple app store or Google Play
We live in uncertain times. My friend Andy posted a photo of a sign from 2015 today that asked “Where do you see yourself in 5 years?” Well, I seriously doubt that any of us would have answered “living through a global pandemic with an uncertain ending.”
No matter what your role, it’s important that you learn to plan for uncertainty. You can’t predict what will happen, but you can prepare yourself to deal with unexpected events in a more productive way. On this episode, we share three core principles for planning for uncertainty:
- Ask better questions. Many people don’t ask questions because they don’t want to know the answer. However, it’s only when things go awry that you fully realize the quality of the questions you’ve been asking. In this episode, I share how to ask the “what’s the pin in the grenade?” question to help you prepare for unexpected negative events.
- Build your runway. You need to know that you have the resources needed to bridge from here to there. Many businesses will go under during this pandemic because they weren’t able to survive the downturn, but those who make it through will be far better positioned on the other side to take advantage of the rebound.
- Protect the main thing. Mission is king. You need to adjust and adapt in whatever way is necessary to protect your mission and abide by your values.
Uncertainty is inevitable, but how we deal with it makes all the difference between a successful outcome and a disastrous one.
Mentioned in this episode:
Please Support Our Sponsors:
Butcherbox: Butcherbox.com/accidental EarnIn: Download EarnIn on the Apple app store or Google Play
Please Support Our Sponsors:
Butcherbox: Butcherbox.com/accidental EarnIn: Download EarnIn on the Apple app store or Google Play
Previous Episode

3 Questions To Ask Right Now
You need other people in your life to help you see yourself fully. You only see a certain perspective, but people around you can help you see opportunities for growth and advancement that are invisible to you.
But right now, community isn’t naturally coming to you. You have to go to community.
On this episode, we share three questions that you should be asking someone in your life you trust. If you are a manager, these three questions can help you unlock areas of growth for yourself and your team, and can illuminate places where you’re slipping into ruts or over-controlling the team. The three questions are:
- What am I doing right now that I should stop doing?
- What is something obvious that you don’t think I see?
- How can I be of help right now?
Mentioned in this episode:
Please Support Our Sponsors:
Butcherbox: Butcherbox.com/accidental EarnIn: Download EarnIn on the Apple app store or Google Play
Please Support Our Sponsors:
Butcherbox: Butcherbox.com/accidental EarnIn: Download EarnIn on the Apple app store or Google Play
Next Episode

Navigating Through Failure
Everyone loves to win. The accolades, attention, and rewards are addictive. However, if you’re trying to do the work you’re capable of doing, you’ll eventually fail. If you’re leading a team of capable, driven people who are stretching themselves creatively, you’re probably going to fail often to hit your mark. You will eventually fail.
If you’re not failing every so often, you’re probably not trying hard enough.
After a failed project, many teams simply move forward to the next one, without a postmortem. This is a huge mistake. It’s important that you seize those failures and mistakes and turn them into growth moments for your team. Otherwise, people are likely to commit the same mistakes again. Some of the biggest coaching opportunities you’ll have are in the moments when an individual or the team has failed.
Mike Krzyzewski, the legendary head basketball coach for Duke University, said in an interview: “My defining moments have usually been something where I’ve lost or where I’ve been knocked back.” At the end of the 1983 season, Duke lost by 43 in the ACC tournament. The program was in disarray and many thought that Coach K’s career was over. At dinner that night, someone raised his glass and said, “Here’s to forgetting about tonight.” Coach K stopped him and ordered him to put his glass down. Then he raised his own glass and said, “Here’s to never forgetting about tonight.”
The following season, when the team arrived on October 15 for the first practice, the scoreboard over the court read 109–66, the final score of the tournament loss to Virginia. Players recounted that Coach K wanted them to never forget how it felt to get beat so thoroughly and to use it as fuel to give their best every day. Since that day, Duke has emerged as a premier basketball program, and Coach K largely points to that defining moment as the turning point.
If you’re not failing every so often, you’re probably not trying hard enough.
Here are a few questions to ask shortly after experiencing a failure. It’s very important that you couch this conversation as a desire to learn from the experience and grow, not as a trial of competence:
Why do you think you/we fell short of our objectives? Stop to consider what happened, and strive to ensure that the team is telling a consistent story about what actually happened. Often, team members will have different perspectives on what led to the failure. Make certain that there is a common understanding of what contributed to the failure to hit the mark.
What did we learn from this experience? Try to capture whatever was learned from the shortcoming so that you are able to institutionalize that learning and prevent the same mistakes next time. Were there any assumptions that were limiting your thinking? Were there any faulty lines of logic that led to miscommunication? Whatever the problems, make certain that the team understand where things went off the rails.
What will you do different next time? Failure is only a huge problem if (a) it takes you out of the game, or (b) it’s repeated in the same way more than once. Strive to never fail twice in the same way. Failure the first time is inevitable, failure twice in the same way is a function of poor leadership. Was the failure one of effort, decision making, or skill? How can you avoid it again? (By the way, failures of effort require special treatment, because it’s the one kind of failure that is completely avoidable.)
If you were me, what would you do to prevent these mistakes in the future? Solicit input from your team members about how you can prevent the same mistakes next time. Don’t assume that they will share their advice with you unless given explicit permission to do so. After a failure, team members are often hesitant to speak up until they know the temperature of the room. Give them permission to speak truth to you, and to offer their advice for how to succeed in the future.
Strive to never fail twice in the same way. Failure the first time is inevitable, failure twice in the same way is a function of poor leadership.
Finally, avoid the temptation to backward rationalize poor results as acceptable. Some teams try to find the “silver lining” in every situation and rationalize why their supposed failure was actually a success. No. Everyone on your team knows what really happened, and you’re not fooling anyone. instead, highlight your failures and use them as fuel for improvement.
How you handle failure as a team leader will determine whether your team is willing to take risks with their work. Use those moments of failure as a learning opportunity, and treat them as one more marker on the road to growth and success.
Parts of this article were excerpted from Herding Tigers: Be The Leader That Creativ...
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