It can be an uphill battle to get personalized advice about your job performance and your career progress. Earlier this week a friend and I texted about the challenge of extracting good feedback from management in our modern litigation-averse corporate America.
He noted that in his job he hasn’t been getting the feedback he’s been asking for:
“I like the idea of knowing how I’m actually doing. I credit honest feedback at every stage of my life where I claim to have grown.”
I replied:
“Hard to get that from an employer. Good to try to cultivate a mentor wherever you go—someone senior but not in your org chart—but even then I’ve never been able to get the kind of constructive criticism that I’d like from anyone other than same-level colleagues.”
So the trick is to find those mentors. I appreciate constructive criticism from anybody willing to lob it my way, but I especially appreciate getting it from successful entrepreneurial types (S.E.T.) who are living their dream.
Along those lines I recently had a great discussion with another S.E.T. acquaintance about my career goals, plans, and aspirations. I described how my long-term goal has been to found and lead my own company (preferably successfully, that second time around). I explained that as a step in that direction, my current dream job would have me being an entrepreneurial engineer. I noted that I’ve been seeking out jobs where I am able to come up with ideas, pursue the good ones, and (if they fail) come up with more ideas and pursue them—jobs where I can:
- have a product vision unique in the industry,
- execute independently on my vision by applying my (and my colleagues’) unique and most prominent skills, and my interesting background, toward realizing the vision, and
- increase my employer’s profits by the boatload (not all ideas are big wins, but all big wins come from ideas).
Unfortunately, such jobs are few and far between. While there are some great aspects of my current job (it’s challenging, fast-paced, exposing me to new-to-me parts of the business, and immersing me in new technologies), I’m not in a role in which I am expected to—or in which I or my peers have largely been able to—have a broad degree of product, business, and technical influence. So I asked my S.E.T. friend: How do I sell myself and my capability, to advance into more senior roles—what do I need to convey about myself, and to whom?
The answer was to talk with a career coach.
Great idea! One I’d never considered before. And via a friend I came across a good coach willing to squeeze me in for one session. (Protip: If your prospective coach suggests that you meet over a slice of pizza and a glass of beer, you know you’ve found a good one.)
Here were my takeaways from my chat with a career coach:
Do I need more experience in startups to do another startup?
He suggests not. If I have an idea and can grab people and start pursuing it, the sink-or-swim-myself model is apparently just as good as watching someone else sink or swim.
He was definitely big on the idea of me going to startup(s) though. He noted that if I feel that my career has stalled that’s because it has stalled, and at mid-sized companies filled with relatively young people there just aren’t going to be opportunities that open up for me for vertical movement.
He was also very cautionary to do my due diligence before going to a startup. Know the founders, know whether they’re in good shape technically—are they hiring me to grow or to survive?
How do I market myself to land the opportunities I crave?
Change my resume from a laundry list of things I’ve done to an expression of who I want to be. De-technicalize it, replacing the jargon with evidence of leadership—in general, present myself in my capacity to lead. Clarify through the top-of-page-1 material that I’m looking to be considered for executive leadership, and that (separately) I have the credentials of coming from a solid technical background.
As an example, if I’m being evaluated for a CTO role then a CEO is going to look at whether I led a team through something instead of just the individual things I’ve done. Don’t make the reader search for it, put it clearly and up front. If you want to be an executive you need to tell the reader that you’re an executive.
Simultaneously update LinkedIn profile to be a resume supplement, focusing on brief powerful statements in the “summary” section at the top as an attention-grabber. Also create an AngelList profile.
What might I get out of business school? (The coach works frequently with current and former business school students, so it seemed apropos to ask.)
If I want to inject speed into an executive career path—moving through a career at a faster pace than I could expect by simply working through promotions—business school can provide that. But don’t look at school as all you need or as the last piece of the puzzle; you’re being taught in the classroom a lot of what you’ll have learned in the workplace.
There are too many B-school graduates already and they’re mostly in their mid-20s. It’s less of a unique credential/ticket than it used to be.
He espouses a go-big-or-go-home philosophy: If you’re gonna go to business school, and if you can afford it, go full time so that you get an intense, immersive, fast-paced experience.
What are my next steps?
Make an effort to land that next job that gets you on the right track to find the position you want. Look for director or VP roles. Don’t move horizontally.
Always be job hunting; never settle down. Submit your resume early and often. Write your CV and cover letter in such a way that you can recycle them in 5 minutes for any new opportunity you see.
(When asked about whether I should try to find a longer-term coach to work with.) Don’t worry about finding a regular coach for now. He doesn’t know anyone who does coaching on the side (except coaching for C-level executives) but in any event he feels that being in the game (circulating, getting interviews under my belt) would be more useful for me than being on the sideline (talking to a coach).
Overall a great conversation. The main takeaway matches something I’ve heard before (though it’s hard to do): Market yourself by presenting your past in the context of the job you want, not necessarily by conveying the minutiae of the job you had. Describe your previous work by highlighting the things you did that you did well, that you got something out of, that you enjoyed, and that are most relevant to the position you seek.