How to Go in Deep to Avoid Making a Dilbert Career Move


I have a client, let's call her “Lucy,” who was hired to lead a new division of a venerable company, but was re-routed almost immediately to lesser role and function due to politics and an unbreakable boy's club.

She was miserable. She was bored and ignored. Her true strengths and skills were being under-utilized and despite all her efforts to build relationships and influence outcomes, she just couldn’t seem to re-route things back to the original reason she was hired. She was in a kind of bait-and-switch Dilbert cartoon nightmare.

Luckily, Lucy had some outside opportunities. A former colleague gave her a lead to a role in their company, and recruiters routinely grabbed her attention on LinkedIn.

Lots of shiny new objects appeared on her horizon and in her boredom and frustration, she put those opportunities in action. She applied. She interviewed. She landed a new role as a senior director. She was in the cross-hairs of a decision and she was scared.

Despite how exciting the new role looked, Lucy's recent experience caused her to have doubts about all the unknowns. Could she measure up to her own promises? How long will it take to ramp up and make an impact? What if all the company culture hype is just hype?

That's where I entered Lucy's story.


For you, the solution to avoiding a Lucy dilemma is hitting the pause button long enough to do an inventory on your core career values before you engage in a new job search. In order to avoid your past showing up in your future, you need to do some career planning and ask yourself:

  1. What’s important to me?

  2. What makes me happy?

  3. What pisses me off?

  4. What strengths must be put to use for me to feel whole and complete?

  5. What skills do I love using all day long?

  6. What skills do I want to get good at?

  7. Waving my magic wand, what would I need to accomplish to say, “I’ve had a great career” at the end of my days?

  8. What am I willing to give up to get what I want?

  9. What’s really in my way?


Tackling those questions will unearth juicy core career value words like freedom, autonomy, challenge, change, stability, recognition, contribution, adventure, beauty, and joy.

But that’s just scratching the surface, so after answering each question, ask a follow-on question or two: WHY? and SO THAT...? This part of the exercise gets you to “chunk up” to the big deal reasons why you get up in the morning and do what you do.

Now you have the raw material or the guideposts for your job search, and knowing your values and priorities will also inform the questions you ask during interviews. And when it comes to negotiating your compensation, how succinctly your values and priorities are being met will act as a litmus for identifying deal or no deal.


Lucy's core career values were freedom, recognition, achievement, creativity, and change. Her goal was to reach VP level in five years, and her priorities included: remote/flexwork culture, women in leadership roles, an expressed commitment to collaboration, a clear path to promotion, and the word "fun" in the company's mission.

For Lucy, some of those priorities were present, and some were not. Since Lucy had already accepted the role, we had to do a little backpedaling. Here are a couple of examples of what Lucy's chunking up exercise revealed:

Remote/flexwork culture:

  • WHY: To go at my speed without interruption.

  • SO THAT: I can implement creative solutions to projects with alacrity.

  • And another SO THAT: I grow my reputation, activate my values of recognition and achievement, and achieve VP in five years.

Women in leadership roles:

  • WHY: Any company I work with has to value women's strengths and contributions to the bottom line, and be conscious of inclusion in a transparent and quantifiable way.

  • SO THAT: I can rise up and so can any woman I work with or hire.

  • And another SO THAT: I'm living the change I want to see in the world.


All of this work on values discovery, setting aspirational goals, and defining job satisfaction priorities is key to engaging in the interview process with your eyes wide open and your ears functioning like tuning forks, prepared to ask essential questions that help you avoid making a Dilbert move.

You have some homework to do…