Self-Awareness for Executive Job Transitions: Understanding Your Strengths and Weaknesses

Self-Awareness for Executive Job Transitions: Understanding Your Strengths and Weaknesses was originally published on Ivy Exec.

To be a successful leader, it’s important to be able to evaluate yourself accurately.

You are likely called on to assess what your team members do well and what they need to tweak, but oftentimes, you may not have anyone who gauges your strength and weaknesses. 

This is why developing a capacity for self-assessment is so important for leaders, especially those with executive-level aspirations. 

“Self-awareness is about developing your capacity to sense how you’re coming across – to have undistorted visibility into your own strengths and weaknesses – and to be able to gauge the emotions you’re personally experiencing. If you’re going to mobilize others to get things done, you can’t let your own emotions get in the way,” says Harvard Business School Professor Joshua Margolis.

While self-evaluation is critical to improvement and promotion, it isn’t as easy as we might think to be honest about ourselves. Only about 10 to 15 percent of people can accurately self-assess themselves. 

Scott Baldwin, the co-founder of, a leadership platform for board directors, talks about why it’s so important to develop your self-evaluation skills. 

“Research shows that those of us with self-awareness have more integrity, make sounder decisions, and form stronger relationships,” he suggests. He also mentions improved collaboration skills, better emotional regulation (which improves trust), an increased alignment between values and behavior, and boosted motivation. 

Clearly, there are significant reasons to be able to accurately self-assess your strengths and weaknesses. So, how can you see yourself more clearly? 


✅ Make a list of your strengths and weaknesses as a leader.

One of the mistakes some leaders make is listing their strengths and weaknesses from other contexts as part of their leadership skills assessment. For instance, if you’re good at “making people like you,” that may not actually be a strength if you’re seeking an executive-level transition. 

A much more effective exercise, on the other hand, is considering the strengths and weaknesses that serve or hurt you as a leader. 

“According to researchers, strengths and weaknesses are highly contextual and dependent on the mix of our values, goals, interests, and situational factors,” suggests High-Performance Consultant Dr. Malachi Thompson.

You likely also want to know the qualities that strong leaders in your organization possess. In other words, what skills does an executive at your firm have? In turn, which of those qualities do you already have, and which do you need to develop?


✅ Consider moving beyond “strengths and weaknesses” to consider what motivates you and what wears you out.

The idea of making a list of your strengths and weaknesses can in itself encourage a less-than-accurate self-evaluation.

Instead, consider listing what energizes you and what wears you out. If you can pinpoint these activities, you’ll have both a neutral observation of how you can excel long-term as well as how you should be developing your career. 

“What you find energizing [sic] and motivating is also crucial in determining your strengths. At college, it’s possible to do well in a subject you don’t find energizing, but it’s hard to keep this up for 10+ years. What doesn’t feel like work (but is)?” wrote Benjamin Todd for 80,000 Hours.

Specifically, Todd suggests looking for the tasks that you find “naturally absorbing” but that others may find tedious or uninteresting. He mentions that when you’re connected only with people who do the same things you do, you might not realize that your energizing tasks are unusual

Similarly, Thompson mentions swapping out “strengths and weaknesses” for other differentiators like:

  • “easiest to hardest.”
  • “effortless to effortful.”
  • “ineffective to highly effective.”
  • “completely unfamiliar to familiar.”


✅ Use questionnaires and personality tests that give you a stronger sense of yourself.

You should also consider taking assessments that let you move outside of yourself for assessment.

While you may not agree with every aspect of your assessment results, they give you a jumping-off point for self-evaluation. 

“[You] receive a report commenting on your personality type or your character traits which points to possible areas for attention and development. In addition to telling you about yourself, such tests can help you make sense of how you approach certain situations, providing welcome ‘aha’ moments,” said Ivy Exec Career Coach Alexandra Sleator.

One well-respected is Gallup’s CliftonStrengths assessment.


Identifying Your Strengths and Weaknesses


Self-assessment is imperative in increasing your chances of an executive job transition.

Your goal in this type of evaluation is to be as removed and unemotional as possible when critiquing yourself. You may even want to collect less loaded self-observations, like tracking what energizes and depletes you and external personality assessments. 

At the same time, while it’s important to be honest with yourself, it’s also important to seek out honest critiques from your colleagues, team members, and impartial observers of your strengths and weaknesses. For instance, Sleator suggests asking those you supervise to provide honest and anonymous feedback about what they like and dislike about your leadership style. 

What’s more, it’s always a smart idea to meet with a job coach who can offer you a truly neutral assessment of your strengths and weaknesses as a leader.

An Ivy Exec Career Coach can provide you with this type of evaluation, as well as support you through the coursework and training that might be necessary to develop the skills you’re missing.

By Ivy Exec
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