Overcoming Obstacles

lead with people Nov 06, 2023
Leadership Lessons from "Going on a Bear Hunt"




When my daughter was little, I would read her the book, We’re Going on a Bear Hunt, by Michael Rosen, illustrated by Helen Oxenbury, multiple times per week (once she got over her fear of it being about bears).

In the book, a parent takes their three kids on a bear hunt and encounters a variety of obstacles. I personally think taking children on a bear hunt, or even just going on a bear hunt is a bad idea, but this parent thought differently and was tenacious. On this imprudent adventure, the family encounters long, wavy grass; a deep, cold river; thick, oozy mud; a big, dark forest; a swirling, whirling snowstorm; and finally a narrow, gloomy cave where they encounter a bear, realize their misguidedness and scramble back home.

Despite the fact that this parent is totally insane and exposed their children to life-threatening scenarios, we may be able to learn a few things about leading from them. I’ll spare you the splish splosh and hoooo woooo sound effects.




“We’re going on a bear hunt. We’re going to catch a big one.”

Where are you going? What are you going to do there? Why are you going to do that? Your team is probably craving the answers to all these questions.

In the book, shockingly, none of the kids asked their parent, “Why are we trying to catch a bear?” In the real world, I’m certain you’d need an answer to that question.

The answers to your where, why, and what questions should relate to your vision and be aligned with one another.

Where are we going? We’re going on a bear hunt.

Why are we going on a bear hunt? Our vision is to provide the most secure picnic baskets in Yellowstone, and Yogi and Boo Boo and friends are one of the greatest threats to picnic basket security.

What are we going to do when we find the bear? We will tag it with a GPS transponder so we know anytime it is approaching a picnic area.

If your vision is to sell coffee, then a bear hunt is probably not an aligned strategy.

Be clear and succinct. Leaders who fail to provide a concise mission to their team risk wasting their teammates’ energy on deciphering answers to the where, why, and what questions. If your team is spending energy trying to understand the mission they’re on, they are not spending energy on accomplishing the mission. Left to decipher the mission on their own, your team will likely come to an array of conclusions that may lead them in different directions, robbing your organization of the synergy that happens when everyone moves in the same direction.

Give your team something clear to aim at and act upon.




“What a beautiful day. WE’RE NOT SCARED!”

The time is now, and we have what it takes. Mission is established through a combination of observing external factors (trends, competition, etc.), evaluating existing capacity (skills inventories, financial capital, etc.), and top management team input (vision, values, etc.). If all of these factors are taken into account, then a mission can be created with reasonable expectations of success, and your team needs to hear it.

Be transparent with your team. Very few things will rob productivity from a team more than a lack of trust in leadership decisions. Good leaders take the time to explain their methodology in deciding, possibly even highlighting alternative courses of action not being taken.

This is also a great time to answer the other question your team will surely have: How are we going to do this?

If your decision-making process includes an evaluation of existing capacity, you will be ready to tell your team how you see that capacity will be utilized and calibrated to accomplish the new mission. Assuring your team that you know what they have and that they have what it takes for the mission will give them the confidence to face obstacles that arise.




“Oh-oh! MUD! Thick, oozy mud.”

Henry Ford once said, “Obstacles are those frightful things you see when you take your eyes off the goal.” I disagree. That sort of thinking leads to blame, shame, and being lame.

Obstacles are inevitable because there are other humans in the world and there are natural phenomena like weather and plate tectonics. The leader who assumes a laser focus on mission will lead the organization to avoid obstacles will either blame someone else or feel shame in themselves for lacking the proper focus when an obstacle inevitably arises. Blame and shame will both erode trust and negatively impact efficiency and effectiveness, therefore leading to the aforementioned lameness.

A good leader will lean into the confidence they’ve inspired and help their team expect obstacles. They will proactively work with their team to identify potential obstacles early and develop the agility to overcome unexpected obstacles.

Look, the parent from the book should definitely have known there would be a river that needed crossing. Instead of recklessly fording a cold river in wintertime (remember the snowstorm?), this dummy should have planned a bit better. Maybe the route could have been near a bridge or a rowboat. Anticipating obstacles makes avoiding them possible and makes overcoming the unavoidable obstacles much easier.

Sometimes an obstacle will be unexpected.

The book was written in 1989, before everyone carried The Weather Channel in their pocket, and perhaps this parent didn’t have a TV or radio and was blindsided by the snowstorm. That’s okay because on the mission, obstacles are to be expected. The important thing is that everyone knows what the mission is and everyone has the confidence to accomplish the mission. If that attitude is developed in the team, then the obstacles encountered become opportunities.

Obstacles give mission-focused, confident teams an opportunity to show their mettle by pushing through the storm or innovating in a way that transforms the obstacle to an asset. 




“We can’t go over it. We can’t go under it. Oh, no! WE’VE GOT TO GO THROUGH IT!”

You will probably have more prepositions at your disposal than over, under, and through, but you will inevitably encounter obstacles with options for overcoming them. You’ve laid out the mission, been transparent with the decision process to inspire confidence, and assured your team there will be obstacles that you’ll take on together.

And now you’re here.

Investments didn’t go the way you predicted. The Fed keeps raising interest rates. Rain is preventing you from laying that concrete. Kristin is about to go on maternity leave. You’ve encountered an unexpected forest on your bear hunt.

This is the time where it is best to remember the most repeated word in the book:


Sometimes people have positional authority because of their expertise or experience in a particular field. That does not make them leaders. Leaders do not rely on authority given to them by virtue of their position. Rather, leaders work to build trust, loyalty, and capacity amongst the people around them.

A good leader at the foot of an obstacle will look around them to see what knowledge and skills others have, and they empower people to utilize and combine their skills in search of a solution.

A leader asks, “What do WE know? What can WE do?”

One person may recognize that the grass is too high to go over. Another person may intuit that the cost to go under the grass is too burdensome. A third person may understand that the pliability of the grass allows for the possibility of moving through it. The leader empowers each person to provide their perspective to maximize the number of options and minimize the risk of neglecting the best option by allowing it to be unvoiced.

Once options are on the table, the good leader should establish buy-in and act decisively, never losing sight of the mission.

Every time an obstacle is overcome, these four steps start again, just like in the book. We overcome the obstacle, reaffirm the mission, add our experience with prior obstacles to our confidence bank, and prepare for the next obstacle.

One last thought. Good leaders understand sunk-cost fallacy, which is the reluctance to abandon a course of action because they’ve invested heavily in it, even if abandonment would be more beneficial.

The parent in this book is not a good leader. After the river, wind storm, and snow storm, it was probably a better idea to quit and avoid hypothermia (not to mention potential mauling). If abandonment is the best option for your vision, continuing to invest in your course of action is more likely to move you away from your vision. Sometimes stopping is okay, and the best leaders have the humility to know that and explain it to their team.


  • A good leader clearly defines the mission of the team.
  • A good leader authentically develops confidence throughout the team by being transparent.
  • A good leader proactively prepares for obstacles.
  • A good leader collaboratively identifies options and takes action. 
  • The best leaders are humble enough to know when to abandon a course of action.


By Matt Murphy, MBA - VP of Mission Support, Stadia

Matt is married to Becky and together they have two kids and a dog named Ravenclaw. He enjoys going on adventures with his family, which do not include going on bear hunts.