Assessing Your Own Readiness: Be Bold, Realistic, and Courageous

In my last post, I offered some guidelines for distinguishing genuine leadership opportunities from mere temptations. Today I respond to another pressing issue for those considering a new leadership role: how to assess your own readiness for that next position.

This can be especially challenging for women and others who have been historically excluded from leadership positions. We tend to focus on our deficiencies and to believe–sometimes rightly–that we have to be twice as accomplished to get half of the credit and a third of the opportunities. We are also vulnerable to imposter syndrome, imagining that because we don’t look like the leaders who have preceded us, we are somehow less legitimate. These external and internal factors make it hard to objectively determine one’s own readiness. But an objective self-assessment–one grounded in self-compassion and self-care–is an important part of building your career.

I always recommend you start with an assessment of your strengths. Make a “for your eyes only” list of your accomplishments in both your personal and professional life–not just the ones that earned public accolades, but the ones that truly made you proud of yourself. What do they have in common? From which aspects of your deepest self did you draw? Where do you see the overlap between your joy and your talent? What have you sacrificed and what have you held as sacred? The answers to these questions reveal your deepest leadership qualities and the special transferable skills and traits you bring to your work. If you have a trusted friend or companion with whom you can talk these questions over, you may arrive at additional insights.

Now take that very personal list and map it onto the title, roles, and projects you have undertaken. Think about how you have demonstrated your special combination of leadership traits within the context of your current resume and about how they will transfer to the work you would be doing in this next hoped for job. Ideally, this exercise gives you confidence. But it should also lay the groundwork for a rewriting of your CV to highlight these strengths and for a draft of an application letter that maps your experience and skills onto the requirements of the position.

At this point, you should pause and take a hard look at the gaps. Where would you need to grow and learn if you were to take on this new role? Are they areas that interest you and are aligned with your current skills? Or are they radically new ones? Is it a matter of scale (e.g., I would need to become comfortable with asking for bigger gifts and managing more people) or a matter of scope (e.g., I have never had much to do with athletics and now athletics would be reporting to me)? This analysis should give you a pretty good feel for whether you could be a strong candidate or not. If the gaps, are mostly ones of scale and small ones at that, then this is likely a lateral move and you might want to reconsider whether it is a real opportunity. If the gaps are multiple, more scope than scale, and way beyond your comfort zone, then you may need to get additional experience before you are ready to apply for this kind of new position.

My most successful job moves have been the ones when the gaps–a combination of both scope and scale–have felt big enough to be exciting but narrow enough to give me confidence that I could handle them. That is likely your sweet spot too. Be bold as you claim your talents, realistic as you assess areas for growth, and courageous as you prepare yourself to step into the unknown of a new opportunity.