The Nature of Leadership and Career

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The Nature of Leadership and Career is a weekly newsletter where I provide 1 illustration and ~3 ideas to help you connect to your career, leadership, or work journey more naturally.

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Today at a glance

• Illustration of the week

  - Career Storyline

• The Nature of Leadership + Career

  - The fear of making the wrong career decision

  - A common dilemma between career choices

  - 5 Steps to improve your odds of not making “the wrong” career choice

Illustration of the week

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The Nature of Leadership + Career

“I don’t want to make the wrong decision.”

This is the number one thought that runs through our minds and bodies when we are making a career choice.

Why?

Based on one or more fears, such as:

• What if I lose the stability or certainty I currently have?

• What if I am not =good enough to achieve my most desired career option?

• What if I get stuck in a mediocre boring job?

• What if the option I choose doesn’t meet my expectations?

• If I make the wrong choice it will take a lot of effort to make another change

• Recruiters and hiring managers will have questions if I decide I don’t like the job and need to change jobs soon after.

• What will people on Linkedin think when they see I’ve changed jobs again?

These thought loops increase our levels of anxiety.

If we consider Anxiety = fear + uncertainty, as Dr. Judson Brewer suggests in his book Unwinding Anxiety…

Then I would suggest that a lot of the uncertainty and fear during career choices is driven by thinking in possibilities i.e. the “What ifs” and the “ What coulds”.

What is the alternative?

Thinking in probabilities. “What is the likelihood that”

What does this mean and how do we do it?

Let’s first draw inspiration from narrative structure.

One of my favorite story structures is from author John Gardener:

Immediately this made me think of our career journeys and career choices as a cascade of wins, draws, and losses.

Which leads us to the question:

• How can we quantify the likelihood of a win, draw, and loss?

• Then how do we increase the odds of the win and the draw?

• How to minimize the rejection sensitivity to the loss?

A common dilemma between career choices

To answer the questions above, let’s explore a relatable scenario between different career options;

Option A: A role in a different company with a higher salary, a better job title, and the growth opportunities you desire in the next phase of your career. In this role, you would lead a global team and handle a larger PnL. However, you're not particularly passionate about the product the company deals with, and you would be the only woman on the team. Nevertheless, the team is enthusiastic about increasing diversity and welcomes your presence.

Option B:  Move to a company that presents an enticing opportunity for you to take on a new and exciting role in a different department. This move aligns with your contemplation of making a career change. Although this transition may initially result in a slight reduction in your compensation and job title, the hiring manager appears to be an excellent leader, and they have assured you of promising career advancement prospects in the long run.

Option C: Stay in your current company, where you have been promised a promotion and salary increase. However, this path doesn’t provide you many opportunities for you to acquire new skills you desire, such as leading a team or managing a larger PnL. You find yourself increasingly frustrated by the company's lack of recognition and its stagnant approach to fostering diversity, equity, and inclusion. You don’t see many people like you at the top.

5 Steps to improve your odds of not making “the wrong” career choice

1. Ask yourself what the key fears you have in each of the career options

E.g. Will I be intellectually challenged enough in the role? Is the culture going to be progressive and inclusive enough? Will I have a narcissistic boss? Will there be progression opportunities? Will I be passionate enough about the product to want to keep working at the company?

Translate these fears into your career criteria which I call “career mandatories”, and list your top 1 - 3 mandatories.

Examples:

• Being challenged in the role

• Having a progressive inclusive environment

• Having a supportive boss that gives you autonomy

2. For each career criterion write down what a win, draw and loss would like

E.g. Having a progressive and inclusive environment

✅ Win: There is already a high percentage (50%+) of diverse leaders in all departments (diversity of demography and thinking).

🟰 Draw: There is some (10%) of representation of diverse leaders in various departments, and the company has a strategy to increase this e.g. talent acquisition quotas, and succession planning.

❌ Loss: The company has diversity washing on its website and in its annual report and you join the company and realize that all the “diversity” is at junior levels and due to a lack of inclusion talent keeps leaving.

3. Quantify in percentages of the wins, loss, and draw for each career mandatory for Options A, B, and C.

This step will let you know whether you have enough information, or whether you can turn down the volume of your fears by doing some additional research.

Generally, this step involves having more information:

• This is a mix of desktop research and more importantly networking and personal outreach.

• The personal outreach part means getting in touch with various individuals who work at the companies you're interested in.

• A warm approach includes reavcching out to friends, former colleagues, or friends of friends who may have experience with the company or the Hiring Manager.

• If you can't find warm leads, muster up your courage and networking skills to connect with people on LinkedIn who might be open to discussing the company's culture and work practices.

  **Note that the percentages you assign are relative sizing for comparison purposes based on your information.

  ⚠️ A word of caution: While websites like Glassdoor can provide a general perspective, it's essential to approach comments with a pinch of salt. Keep in mind that reviews, whether positive or negative, are often written by individuals who are either extremely disgruntled or prompted by their companies to leave good reviews to improve the company’s overall rating. Use these review insights as discussion points during your conversations.

4. Ask yourself the steps you need to take to increase the odds of wins and draws and decrease the chance of loss.

This often looks like:

• Getting clearer on your career mandatories and ranking them as Must Haves, Should Haves, Could Haves, and Won’t haves (for this particular period of your career).

• Coming up with pointed questions in your interviews with recruiters and hiring managers.

• Knowing when to walk away from a career option that doesn’t add up.

• Mastering your negotiation strategy.

5. Learning to reduce our sensitivity to loss

Finally, we can sometimes do all the steps and land in a position that is a loss. Whether it’s not landing a career role, or landing a role and it not being what we expected.

Our fear of losing often puts us in a scarcity mindset and impacts our decision-making process.

Or because we have lost once before and do not like the pain, it stops us from taking future calculated risks that may be in our best interest.

Finding ways to reduce our sensitivity to rejection or loss is crucial.

Career navigation is tough.

We often try to navigate career choices with logic and biased decision-making processes such as pros and cons list.

We often try to ignore the emotional drive behind career choices.

The key is acknowledging the emotions and using them as signals as you think in probabilities rather than possibilities.

In this issue of The Nature of Leadership and Career, we have focussed on how to compare.

The question that remains, once I have compared …. how do I decide?

…. Until the next issue!

If you are going through a career or leadership transition and would like to discuss coaching support in navigating options:

Find out more about me here.

Catch up on recent issues of The Nature of Leadership + Career

• Can a little self doubt be useful?

• Part 1: Why we don’t like going backwards in our careers

• Part 2: Backwards or Backloop - Why we don’t like going backwards in our careers

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