Practically speaking…what are the right questions?

One Problem for transitioning veterans is that we completely lack a frame of reference around what the day-to-day responsibilities and activities of a job might entail as a civilian.

When I advise service members, a topic that has come up recently has been exploring functional focus areas. Unfortunately,

• Very few roles in the military have direct equivalents in the civilian world
• It’s really hard to know what you’re going to enjoy doing as a civilian
• Veterans usually have no trouble cold-calling/reaching out to other people to get on phone calls/meetings
• Veterans aren’t very good at asking questions that are specific enough to get any meaningful learning.
• I think it’s valuable for veterans to learn about the day-to-day pace and activities of various roles in order to help gauge a good “fit” for their personalities and aptitudes.

So here’s a collection of questions that I think are useful when you do informational phone calls, e-mails, and actual interviews when you consider different careers as a civilian. There are an infinite number of questions you could ask someone when learning about roles, but here’s a few that I think will be the most useful. If nothing else, you shouldn’t ever be stumped when someone says “do you have any questions for me?”:

• How will my performance be measured in this role? What does success look like for me in terms of metrics? What does success look like for the team/company?

Probably the most important question. If nobody at the company can answer this immediately, this should be a big red flag. Companies that can’t turn their mission into specific metrics are mediocre, in my opinion.

• Is this a new role, or will I be replacing someone who has recently been promoted/departed?

Good to know if there’s already an expectation of what you’ll do day-to-day

• What are the backgrounds of the other people that I will be working with day-to-day?

Familiarize yourself with the aptitudes of your teammates. Does your gut tell you that you’d enjoy working with these people every day? Are they going to challenge you and push you to be better, or not?

• What are the key relationships for someone in this role? What people will this role report to on a day-to-day basis?

Are you going to be working just within your team, or will you get exposure to other parts of the organization?

• What’s the rhythm of work like in this role? Does the tempo pick up in a particular time of the year/quarter/month, and why?

As companies start to mature, they should be able to answer this. If you go to a young company, this question may be less relevant. Having a predictable cadence can be good/bad, depending on what you’re looking for.

• How many projects will I be managing at any given time? Will I manage one project at a time, or be expected to handle several at one time?

Sometimes your job isn’t about “projects”, however, and may be more about continuous improvement/day-to-day operations.

• What’s the daily/weekly cadence for formal meetings in this role?

I can’t stand doing meetings more than 1–2 times a week. Some people enjoy them more than others, so you should ask this up front.

• What do people in this team do after they settle in? Has anyone in this role moved to another part of the organization? What’s a logical “next step” for this role?

Do people tend to stay in this team or do they move around the organization? Are you going to grow within this company or will you need to keep a close pulse on your industry to keep an eye out for future career moves?

• What’s considered a “win” for this team/role? What is celebrated?

What’s really important for this team?

• What are some traditions or cultural norms that this company has that you like?

It’s important to understand the things that are reinforced and prioritized from a cultural perspective. For me, any kind of norms that promote transparency/cross-functional understanding is a big win.

• How often will I get to talk to our clients/customers?

Some people prefer to maintain relationships within the company alone. Some people prefer to talk to clients/customers.

• Are there any technical skills/software/aptitudes that I absolutely need to know before starting in this role?

This can help you determine if there’s a specific set of skills that you need to pick up before applying for this role/similar roles.