Embrace the Pit of Success

 Yesterday, Amy West was a fantastic manager of five talented individuals. Without warning, Amy’s comfortable employment was turned upside down when she was catapulted into a job far beyond her experience! She now manages a division with 300 people in 4 different countries.

Overnight, Amy went from giving pat answers for familiar situations to deliberately considering (and reconsidering) every request. Though she once felt competent—an expert at her previous job—Amy now hesitates and feels insecure of her decisions.

If you met Amy, you would say she looks confident, capable, and fully qualified to lead her division. In meetings, there is no doubt she is the leader. Yet, in contrast to her self-assured appearance, Amy admits that inside she vacillates between total excitement and a gnawing sense of self-doubt. In highly reflective moments, she admits to feeling stressed, completely overwhelmed, and, yes, maybe even scared to death.

Amy has been thrown into the leadership pit. Whether it is “a pit of despair” or “a pit of success” is yet to be decided.

Amy’s seemingly dramatic situation exists in a very real way in most every workplace today. Shrinking budgets, expanded demands, and reduced development cycles throw managers into their own leadership pits.

In these demanding times, how can leaders be and feel successful at something beyond their experience? How can they cross the pit, maximize their own careers, and save their companies? Here are four strategies for accelerating your career when you are thrown beyond your experience.

Embrace the air: You are flying between your comfort zone and your future capability level. Accept the fact that you don’t know all the answers. No leader does. You are no different. You don’t have to be a superhero to be a leader.

Give yourself permission to not know. That’s right! Give yourself permission to be mortal. Much of the pressure you face as a leader is what you tell yourself, not what is actually going on. Eliminate destructive “shoulds” from your self-talk—I should be smarter, I should be faster, I should be better. Yes, you need to aggressively learn new things. But, no, you shouldn’t be smarter, faster, better! You have not been granted a reprieve from laws of learning just because of your position.

Your demands, doubts, and mistakes are trying to teach you something about yourself and leadership. Embrace that sometimes you have no clue about what you should do. Embrace that you are in this position to find answers, not know answers. Embrace that each challenge has a lesson for you to learn. Know that when you embrace the air you are free to spend your time on the real issues.

Accept your real job: You don’t want to lead based on the assumptions of your last job (or last year). The rules, challenges, and players have changed.

You need to rethink what you real job is. What value must you provide to your customers? What stakeholders’ needs must you fulfill? What expectations do you need to renegotiate and quit delivering on? Who do you need to build relationships with? Who do you need to reduce your time with? What does success really look like? What is the real purpose for your job?

Write up the real job description for your job (not the one they gave you when you took the job). Get buy-in from your boss and stakeholders about your definition of the job. Post the description on your desk and ask yourself each day if you have fully accepted this job. Don’t get lost in the million daily tasks of your job. You will gain freedom by doing the real job.

Initiate game-changing conversations: You need to get out and talk to the key stakeholders. Don’t make the mistake of sitting in your office waiting for a grand inspiring thought. After all, an office is a terrible place to try and lead from. You can change the game and grow your influence by changing who you talk to and what you talk about.

You can talk with people who are familiar and convenient or you can talk with people who are strategic and influential. Don’t let your comfort level lull you into doing what is easy. This doesn’t mean you abandon all past relationships. But, it does mean that you need to be more intentional about building new key relationships.

When you meet, reduce your discussions about the daily tasks and focus more on issues, assumptions, purposes, and strategy. Get out and discover key concerns and obstacles. Find out where the passion and energy are trying to go.

Bring people together who don’t usually talk to each other. Your challenge is to find a way to bring out the pink elephants (problems) that no is willing to talk about. As you become the catalyst for these conversations, you create the power to find solutions.

Listen to your stakeholders like their lives depended on you understanding: Causal listening will never provide you the insights you need to transform your organization or yourself.

Stakeholders want to share key information but they are rarely given the space to fully share. Provide stakeholders with both emotional and physical space for ideas to come out. Avoid trite phrases like “I know how you feel” or “I have been there.” Even if you have been in similar situations, you don’t know their situation. Try to discover the story behind the story. Encourage people to share their thoughts, insights, assumptions, intuition, opinions, and recommendations.

And, when it is time to receive feedback about yourself, open your ears extra wide. Rarely would stakeholders risk giving you feedback unless they thought it could really make a difference. Feedback is usually a sign of someone caring deeply. Don’t miss their message by minimizing them or acting self-righteous.

Remember, listening is never convenient. That’s why it is so valued. Create the greatest value by listening until you understand and the person feels understood.

You and Amy can turn your challenges into a “pit of success” as you apply these principles. And, the great news is that these skills are total scalable. You can use them your entire career. So, get ready to fly.

About the Author
Dave Jennings accelerates meaningful change. He has worked with leaders from 20 of the Fortune 500 and spoken in 23 countries. His articles and commentary have been featured in The Washington Post, Forbes, and thestreet.com. He is author of Catapulted: How Great Leaders Succeed Beyond their Experience. Contact Dave at dave@davejennings.com.
  1. Danny Lunt Reply

    This particular concept has helped me in my work (software development) as well as with the challenges of everyday life.

    Thanks for the insight Dave – this is a keeper!

  2. John Montgomery Reply

    This Pit of Success concept is so true. Have to admit that I was skeptical at first, but after discussing with my team, it was like a light bulb went on for everyone. It’s done wonders.

  3. Bob Spiel Reply

    As a friend said once, there is no growth in the comfort zone..and no comfort in the growth zone. Great pointers Dave. Thanks.

  4. Camron Wright Reply

    Interesting analysis that applies equally to our personal lives and relationships.

  5. Benoit Leclair Reply

    This concept is useful to everyone, even if you do not occupy a leadership position. Your ability to survive the pit of success is a demonstration of your ability to deal with challenging “stretch” assignments. That’s something upper management takes notice of.

  6. Thomas Walker Reply

    The ‘Pit of Success’ is where growth happens. It’s exciting, adventurous and at times a bit scary! The key is to embrace the uncertainty with boldness, confidence, and a heavy dose of humility and willingness to learn. This concept has helped me approach significant change in my career with a positive mindset and belief that success lies on the other side of the Pit if I am willing to leave my comfort zone.

  7. Don Negri Reply

    A little humility provides a safe opening for stakeholders to provide useful input.
    As an aside, I once went to a workshop on a book that the presenter later admitted he had not read. He put the audience into groups with specific questions about the book that would help the groups draw meaning and insight from the reading. The smaller groups then reported back to the larger group. At the end of the workshop after effusive praise for the value of the book and the workshop leader he admitted that he had not read the text. It is a lesson I will not forget and I apply it to other contexts.

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