A higher-up is someone higher up than you in a company. They could range from a (senior) vice-president, program manager, managing director, or a c-suite executive (CEO, CIO, CTO, etc.)
Even your direct manager is a higher-up, but for this blog, think >2 levels up.
Why > two levels up?
Because when you start your career, depending on your goals, you'll want to climb the ladder at some point to see how far you can go. If you hear of promotions, this is such.
To ascend the ladder, you'll want to find people who are where you want to be, most of whom are higher-ups. They've done the work, they're making bank, and it's now your chance to learn from them.
Why do you like reaching out to higher-ups?
#1 - Higher-ups make for good mentors
Many people at the upper echelons of their careers acknowledge that they had support from their network and mentors, creating a repetitive cycle of paying it forward. Thus, it would make spiritual sense to pay it forward to someone in need and eager to learn.
Even if they don't mentor you per se' because of what's on their plate, they're happy to occasionally catch up to check in with you and ensure you're doing okay.
One of the superiors at my company said something I like:
"Titus, thanks for stopping by; it's always great getting to know you. Now my schedule is all mixed up and my calendar is crazy these days, but if you find me at a hallway and have something burning to say, just ask for a quick five-minutes to listen through. Or you can have my secretary throw something on my calendar for next month."
They care and are happy to see you grow.
Best case you make it in life - they'll be glad to have been part of your journey.
#2 - They see opportunities you don't
Depending on how well the senior knows you, they can keep you in mind for fitting opportunities that come their way. The more you converse with them, the more they'll know your interests, strengths, and capabilities.
If that opportunity comes up by happenstance and you fit it, they'll let you know. Similarly, if you're looking for something that's not within their parameters, they can then refer you to their network.
Part of it has some self-interest, of course (since everyone wants the best talent on their team). Still, it becomes a trifecta win-win situation - the higher-up gets a capable person under them, the team has yet another competent member, and you get a better opportunity.
#3 - They have a plethora of experience you can borrow
Some of the higher-ups I've talked to have been in their jobs for over a decade; others have had theirs for 26+ years, and they like it. Some are industrial experts in their game; others are highly sought-after speakers during conferences.
By scheduling 30 minutes with them, I can condense 20+ years of experience into half an hour.
Sure. They can't tell you everything in that span, but they'll give you the highlights to consider in accelerating your career. All the better reason to approach these meetings with carefully drafted questions that you'd like answers to, else they'll see it as a waste of time. Plus no guarantees that you'll get another chance with them.
Once you establish camaraderie with them, you can then meet them during other times (e.g., outside work, during events) to continuously learn from them.
Since I like talking to people who are where I want to be, chatting with them is a good precursor for what "up there" feels like. And since they won't tell me everything, I'll have to figure out the rest of the dirty work myself.
They have varied perspectives
They think differently. They've experienced a lot.
I like to see how they think because that provides insight into what they do, what they've been through, what's at stake, and how that's evolved over the years. How Peter, some VP, thinks now is vastly different from how he did 20 years ago as an associate.
By knowing how they think, I can also position myself on how to interact with similar people with that mindset. This is more like prep work for tolerating divergent schools of thought and perspectives at work.
How do you approach your higher-ups?
With courtesy, genuineness, and curiosity.
Courtesy - Being humble and acknowledging that you're in front of someone who has achieved a lot in the firm is akin to knowing your place. That should put things into perspective.
Genuineness - Being real and authentically yourself, hiding no ulterior motives (e.g., looking for a promotion and such.)
Curiosity - There is much to learn from someone who has achieved a lot career-wise. Grab a pen, paper, and an open mind to soak it in.
A mentor recently told me, "Complement and ask," so I'll twist it to "Complement genuinely and ask."
So if I meet a higher-up, it would look something like this:
"Hi Sir/Ma'am, I genuinely appreciate your leadership and the results you've brought to the engineering team this quarter. I was wondering if I could schedule 30 minutes with you next month to learn more from you."
Many of them are happy to meet with juniors and disseminate their wisdom. Sometimes, during their busy schedule, you conversing with them is a breather in between projects.
You don't know if you don't ask, so shoot your shot. The worst case is they could say no because they don't have the time.
What are some good questions to ask?
Depends on what you're looking for, but for purposes of career growth, I like to ask the following questions:
What are some ways I can contribute to the company?
Seniors have different perspectives on how employees can increase their value to the company and themselves, so asking this question to different execs can give you a scope of where the company is and the direction it will take.
By asking different superiors this question, you can connect the dots from the answers you get and follow up with similar insights you heard from them.
"Thanks for mentioning this. I was talking to manager Y who suggested this, and I thought both of your insights make sense because they touch on this. What do you think?"
From what I've seen, you impress these higher-ups with your initiative and networking ability, so not only will they share more, but they could also recommend you to other colleagues within their network to learn from. Before you know it, you know four higher-ups at the price of two.
If you could talk to your 23-year-old self today, what would you tell them?
This is probably the most interesting question I could ask anybody - it presents some of the most interesting answers I've ever heard.
The people I could talk to lie between ages 35-68; the older they get, the deeper the answer. By asking this question, I get profound one-liners that, at times, help me rethink life.
I asked this question to an ex-CEO and a major general, both retired and in their early and late sixties, respectively.
"Don't take yourself so seriously." The CEO said.
"I would mortgage a duplex, triplex, or quadruplex, live in one room, and rent the others. That would pay my mortgage and build home equity." Said the army general (pretty much househacking.)
If it were a peer mentor a few steps ahead of me (3-5 years), I'd ask them a variation of the question.
"What would you tell yourself if you could go back five years now?"
"Knowing what you know now, what would you do differently in your senior year of college?"
They haven't lived it out yet, but that's a good enough timeframe to provide some critical answers. Neats out a good perspective in mind.
Asking the good questions - works like a charm. 😉
Did you ever imagine being where you currently are today?
Another good one.
Most of them will say no - they did not. Those who did probably worked their lights off to get it.
For those who did not, they certainly had a mid-career realization that they could make it big in a different industry elsewhere - think of a career pivot like from construction to tech or nonprofits to consulting. So they probably sought an advanced degree (usually an MBA) and worked up the ranks in a few companies that gave them a chance before settling on where they are today.
Many higher-ups barely imagined themselves being at their current point today, so they have a mix of hard work, lessons, realizations, grit, determination, and circumstances that all propelled them to their current situation. This question should also elicit unique answers.
Do you have mentors you look up to?
Another good question.
As previously mentioned, your higher-ups most likely have a dependable support system from inside and outside the company, plus influences from their personal lives. They share their stories with them, some of the best advice ever received, and perhaps connect you with them...if you want.
Conclusion
Go for it. Shoot your shot - you may be surprised.
They may or may not remember you, but if you authentically maintain the relationship with them and demonstrate your enthusiasm towards keeping it, they'll remember you for a minute and appreciate your audacity.
Education is eternal, and to learn it from career veterans can propel your career a hundredfold in half the time. And best of all, one day, you'll be at that point where someone looks up to you - then you'll know.
Peace,
.
.
.
~T.K.K
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