The importance of self-awareness in your search

Don’t chase roles you clearly aren’t a fit for

• It wastes your time

• It makes it less likely your network will help you when you are asking for help with your ideal role

We see many executives apply to roles at hot companies where they lack the background or credibility to compete.  

“Hot brands are magnets for applicants. That also means they can afford to be picky and over-index on exact-match experience. Chasing them without fit doesn’t just fail — it burns mindshare with recruiters you may want later.”  Top Recruiter

At Whispered, we evaluate potential Pro members for self-awareness and maturity in their role targeting. If they don’t show it, we often decline to work with them — they’re hard to introduce to senior recruiters and talent teams.

Clarity is the foundation for self-awareness

If you don’t have clarity in your search, see our playbooks on clarity and use our Focus Statement template to guide yourself through articulating where you are focused.

Some areas we have seen executives lack discipline in their search include:

• Scope:  Understand the team sizes you have led and use them as a guide.  For example, if the biggest team you have led is 5 people, the company you are interviewing with will have a tough time believing that you can fit for a VP role leading a 40 person team.  

• Level:  It can be hard to step up a level while changing jobs (particularly if the market is tough)

• Geography:  Don’t chase roles in locations you aren’t in unless you have a great reason to move.

• Your Superpower:  There are many flavors of marketing, revops, sales and CS.  Two VP of X roles are not the same.  Understand what superpower they are seeking and prioritize those

• Company Stage:  If you have only been at smaller companies and don’t know how to deal with complex politics, think again about targeting late stage.  And vice versa moving from enterprise to startup requires a total mindset shift.

• Industry:  This is probably the easiest to stretch on.  Many companies over–index on industry but you can overcome this with research and preparation in many cases.

In addition to where you are focused, we’ve found it effective to build (over time - you don’t have to have this at the beginning of your search) a list of categories of roles that don’t fit for you.  For example:

• “I’m ruling out roles that require relocation unless the company is in my top 3”

• “I’m avoiding pre-seed companies unless they’ve raised >$5M”

When you stretch, be thoughtful about why and how

You don’t have to stay in your lane — but stretching in too many areas lowers your chances.  Each “new” factor in a role you are seeking  makes success harder. Stretch in 1–2 areas max.

• More than that, and it signals a lack of self-awareness.

• No stretch at all, and you risk stagnation. 

• Be intentional. Know where you're stretching — and why.

“When someone tries to stretch too much, it demonstrates a lack of self awareness.  If people see those things about you that you don’t see yourself, they are less likely to want to help you as it will reflect poorly on them.”   Whispered exec

When you pass on roles, do it strategically

Even if a role isn’t in your strike zone, don’t just pass on it.  Be thoughtful about how you pass on a role and think of ways to leverage it to:

• Learn about what top companies are hiring for

• Engage recruiters they love trading insights

• Show maturity by acknowledging what’s not a fit - that earns respect

“Opportunities are like at-bats — waste too many on wild swings and you’re on the bench when the right pitch comes.”