By Kevin Haas – July 9, 2018

“I just don’t want to make the same mistake again.” Those were the words coming through the phone from my good friend and client of many years.

About a year ago, Steve had suddenly found himself on the outside looking in at his previous company. Unexpectedly let go, he landed a new job in a town that was going to require him to move and commute until his family could join him at the start of the new school year.

The money was okay, but not great. A lucrative long-term comp plan was supposedly in the works. The job itself was fine, but he found the work to be what he had done before. In the recruiting “pitch” there were assurances about growth strategies and new lines of businesses that Steve was going to launch.

A year later, the world was very different.

Operational hiccups were obscuring the ability for launching the strategic initiative, the long-term comp plan had not materialized and the family had let him know that they were not going to be relocating, fueled in part by Steve’s ambivalence about the job.

So, like the familiar song’s lyrics above, Steve now finds himself struggling with a “high stakes” decision: should I stay or should I go? This time around the decision is even more complicated as he is concerned about repeating the same mistakes in his decision process that has led him to be in a job that is not quite “fitting” him well. He knows something went wrong before, but is not sure what happened or why.

In working with executives, “high stakes” decisions are the norm.

The types of decision can be quite different. Some examples of “high stakes decisions” are:

  • Is it time to seek a new job at a different company?
  • Should I pursue the promotion?
  • Do we need to abandon this line of business?
  • Should we go ahead with this strategic initiative?
  • I am not happy in my job, marriage, life, etc. and I think I need to do something. Now what?

High stakes decisions have a couple of common elements.

First, they are important. The decision we make will impact our life and the lives of those around us in a substantial manner. Second, by nature they are “difficult” decisions. The answers are not obvious and clear. Generally, most leaders are well equipped to handle daily decision making as we have honed those skills over the years. High stakes decisions require a different set of decision making “muscles” that we typically do not exercise enough. As a result, we struggle with the decision process itself.

Here are a set of questions you can ask yourself to allow more clarity and understanding of the situation, and the impact:

1. Assume your feelings are important. There is a reason you feel the way you do about a high stakes decision. The dissatisfaction with your current job, your excitement about another prospect, the dread of confronting a difficult challenge that is keeping you “stuck” are all examples of our feelings providing feedback to us. Deeper than day-to-day emotions, our inner feelings will consistently reveal our internal perspective on what is really important to us. In short, assume there is a reason why you feel the way you do.

2. Understand why you feel the way you do: This is perhaps the most important part of the process. Get as specific as you can about why. Many times, our minds will unconsciously create a story about how this decision will make you happier. The story is not nearly as important as the reason why the story is important. For example, if you want to be CEO, then ask yourself why do you want to be CEO? What is it about that job that appeals to you? Is it the perception of autonomy? Is it the intellectual challenge? Is it the impact you can have on others to build a culture? The “job” of CEO represents something internal. It is far more important to understand the “internal” feelings underneath what that job is representing. Also, be sure to understand the whys of your current situation. What do you love and what do you dislike? Once we understand these “whys,” we can then use our clarity to move in a direction that aligns with our true internal feelings.

3. Revisit Options: Now, look at the different opportunities or directions you have with “fresh eyes.” In our example above, if autonomy is important, consider why autonomy is important and explore if there are options in your high stakes decision process that would allow you to create greater levels of autonomy. Perhaps it is something that can be negotiated with your boss, or developed over time with some changes to your current portfolio? Sometimes, we discover hidden possibilities that were laying at our doorstep that we never recognized. You may be able to incorporate many aspects of your whys in your current situation. And, if not, your new-found clarity will allow you to identify and even negotiate what really matters to you as you consider other alternatives.

4. Confirming the path forward: Take the the time to “test” your thesis! With each step forward you take in your new direction, check to see how you feel. Do you feel your movement is moving you closer to what is truly important to you? Do you feel excitement? Calmness? Clarity? Alternatively, are the internal feelings uneasy? Do you feel like you are “pushing” too hard, or, are things in flow? Use your experience in the first steps as feedback to tune your approach. It can be equally effective to use your imagination to visualize how your high stakes decision is playing out and notice how you feel. Be very careful and attentive to what you are perceiving. Again, there is a reason for these feelings — they are showing you the attunement of your direction to your internal compass. If it does not feel right, there is a reason. Stop and repeat the process until you are sure you are aligning.

In Steve’s example, he realizes now that he actually knew at the time, deep down, that he was making a mistake by accepting that job a year ago. The warning signs were there, but he didn’t pay attention to them internally.

Now, by using the process described above, Steve is feeling less fear of making the same “high stakes mistake”.

With the benefit of experience, and a little bit of hindsight, Steve is clarifying exactly what kind of job is going to be the best “fit” for him.

He is using that understanding to open conversations with his boss about re-negotiating his current position, and he knows he can use his new found clarity for a new career decision, if required.

Ready to try it yourself?

Find clarity through a decision-making process that works for you. Using a few simple steps can help you gain more clarity and understanding when making difficult decisions.

Looking for a personalized approach? We understand that every situation and decision has complexities. Reach out and open the conversation to get one on one answers.