How to prepare for a conversation with someone much higher up?

Question

I am in my mid 30s and currently work at a senior technical position (software architect) in a Fortune 500 company. My current boss (a director), who brought me into my current company from my previous job (where she was also my boss) is getting more and more visibility in the company and is about to be promoted to a VP position. Due to the matrix organizational structure, I believe my boss will be reporting to her current boss's boss's boss (Enterprise Vice President, two levels below the company's CEO).

I was invited to fly to the headquarters soon. Also, in an email exchange, my current boss introduced me to this EVP and mentioned some work I've been doing that is very relevant to the entire company. I am quite confident that my current boss wants to bring me along with her to her new role - it makes a lot of sense since she's the one who brought me in in the first place. After the email, I was then invited for a 1 on 1 meeting with this EVP when I'm at headquarters.

Now I am trying to find ways to prepare myself for this 30 minute conversation. I think there may be some sort of lateral promotion in the mix, higher responsibilities, or at the very least the chance of a lifetime to present myself and showcase my work.

I am technically competent and I would expect to climb up the corporate ladder one day, but never thought I'd be having a 1:1 so early with someone so high up. How does one prepare for this? I would love recommendations (literature welcome!) on business etiquette, attire, small talk, how to handle a potential conversation about a promotion, how to present my (technical) work to a high level executive (who obviously doesn't have time for detailed explanations), and overall the best way to use the 30 minutes I have.

Answer 1

How does one prepare for this?

Perhaps the most important thing is to keep calm and be yourself and don't pretend/boast. I also suggest you ask your boss if there is anything you should prepare or do before the trip and meeting.

Regarding attire, you should most definitely suit up, specially when going to important meetings like this.

Now, I must say a few warnings regarding your post. I can sense from the way you wrote it that you are very excited about the meeting, so again be careful not to over-think or stress out about this.

First warning is that you seem to be assuming that a promotion will likely happen. I know you are talented, but this meeting is more likely for this VP to get to know you. It's not that very likely that someone you have never met before (and who is several tiers higher than you) offers you a promotion on a 30 minute meeting, on a trip your boss asked you to come along.

I'm not saying that it's impossible that you will be promoted, but don't be too eager about it. This could even backfire on you if this VP perceives that you are acting with only that goal in mind.

Second, you say you want to prepare for small talk and for showcasing the work you've done. Regarding small talk, I doubt there will be any, specially in a 30 min meeting with the VP of a Fortune 500 company ;)

Regarding showcasing your work, you don't even know if this VP wants to talk about this, or what topics does he want to talk at all. In meetings like this I suggest you listen and try to move along with the things and topics the VP comes up with. Again, you trying to steer the conversation towards your work and promotion could backfire if done too evidently.

Now, this doesn't mean you won't have chance to showcase your work, or to ask the VP questions. You are already proficient and good in the work you do, so I think you will have no problem in efficiently communicating the work you do, as long as you keep calm and try not to go too deep into details unless asked.

For this I also suggest you ask your boss if you have to prepare anything for showing the VP.

Answer 2

The other answer is great, but my comments were too long for a comment.

The first thing to understand is that an EVP / SVP has the same goals any 2nd or 3rd line and above manager has -- the effective and profitable operation of the business. The higher up the ladder the more abstract the objectives become, but the goal is generally the same -- the effective operation of the business, and making as much money as possible.

In my conversations with EVPs, VPs and C-suite people at previous employers, most were interested in the workplace environment where I was, the challenges and opportunities (heh) we faced, and things we could be doing better or doing less of. I interacted with a number of EVPs, including one of the "corporate diversity" EVPs and in his case, he wanted to make sure the workplace was "safe and inclusive". Knowing what the EVP in question does is important.

You mentioned that your boss is apparently up for a promotion and you have reason to believe she wants to bring you with her. That's a question you need to ask her, and that's a conversation for you and her to have together. I would suggest that if your current boss does indicate she wants to take you with her, the two of you need to discuss how you "sell" that promotion -- why are you the most appropriate candidate for whatever role she has in mind for you -- to whomever you speak with in the future. But again, that's a discussion the two of you have to have, not you and the EVP at this point.

One last comment -- the further up the food chain / career ladder you get the more "professionalism" and "concern for the needs of the business" increases. The other answer says to "suit up" -- yes. If you don't own a nice professional suit, get one. It's moderately okay to "let your freak flag fly" in most companies, but the higher you get, the more they will want conservative (in the sense of rational, predictable, sensible) behavior.

Answer 3

Developer here. Since I've actually talked to executives a fair amount of times, and my step-mom worked for CEOs of an F500 corporation, and I've visited their offices, I think I can help.

I would love recommendations (literature welcome!) on business etiquette, attire, small talk, how to handle a potential conversation about a promotion, how to present my (technical) work to a high level executive (who obviously doesn't have time for detailed explanations),

1. RELAX! The Execs are people too. They can get tired and grumpy or just have a bad day, that does not mean it's your fault. They can also have a pretty wicked sense of humor, but keep your humor clean.
2. Wear business attire, like a suit and tie, even if your department attire is business casual. You want to make a good impression.
3. When you meet them shake hands and say "Nice to meet you." Smile.
4. If they don't start the small talk, you can start something. Did you notice something in their office? Like a trophy? Ask them how they got the trophy. Do you see an award? Ask them about their award. I'd focus on professional things in the office.
5. If there is a lull in the conversation, ask them if you can show them the work you've done. As far as your technical work, avoid the details, they don't understand them, as it's not their job to understand them. Give a high-level view of what you did.
6. Pictures tell a thousand words. Prepare at least a few high-level pictures about how the system works, list how it benefits people, and list how much money it helps them save or how it helps their customers. Execs tend to like dollar figures.
7. Give one or two examples of how your work saved money or made a customer really happy. Link actual results to your work. This is called "marketing yourself".
8. You should talk to your boss about promotions, I don't know why you'd talk to another exec about this.

Answer 4

The more you learn about how senior leaders think, the more you learn the concepts and language that connect most effectively with them. This will need to be a bit of a crash course, since you only have a week, but you can learn a bit. Find some of the stuff out there on the 'Net on management (Manager Tools is my favorite; you could also read some articles by notables like Drucker)1 and read or listen just get a sense of the way senior people approach strategy.

In short, you need to be very strategic about getting to the "So what?" of what you do.

• The EVP probably doesn't care about details of some cool algorithm you deployed.
• They might care about some of your architectural decisions as examples of your effectiveness.
• They definitely care how your decisions advance the broader business goals of your group.

And get to that "So what?" fast. Practice a bit. Summarize each of your best accomplishments in 60 seconds, come up for air, and go for another 2-3 minutes if you sense deeper interest via body language.

Try to learn a bit about their background. Are they a techie who worked their way up to a CIO-like role? That's much different for your conversation than someone with, say, a finance or operations background.

Finally, learn as much as you can about interviewing, especially internal interviewing. Another MT link: Internal Interviews.