Normal Job Transition Questions You May Be Too Embarrassed to Ask

April 4th, 2019

Fifty-eight times. That’s how often I refreshed the Gmail app on my phone that Friday.

Why was I obsessively sitting there, checking my phone? What does this have to do with job transitions? These are good question.

I’d taken what felt like a career-defining leap and submitted a pitch for a short presentation at an industry conference I was heading to.

While the talk would last for just over 10 minutes, it would be on the main stage… and it would solidify my ongoing transition from a conversion copywriter to a conversion copywriter and strategic consultant.

The results were going to be announced that Friday…

… So while I knew that my time would be better spent focusing on the work at hand, I couldn’t help but check my phone… Over. And over.

When the email finally came through (I was in!) my first thought wasn’t anything to do with the slide deck, or the content or what this could mean for my career. Nope.

It was: What am I going to wear so I don’t look stupid on stage!?

A bit of context. 

I’m not usually someone who puts a lot of thought into clothes. As long as I’m clean and mostly professional looking, I feel good to go. So the force of my own question surprised me. I was moving into brand new territory - talking in front of people - and even though I’d been in the industry for a while, suddenly I didn’t know what the rules were.

This kind of sudden confusion - even though you are a smart, capable pro - is normal whenever you’re faced with something new. Change brings up conflicting emotions because suddenly, and often subtly, the rules of engagement you were familiar with have shifted.

Learning the new rules

When you change roles - whether you’re moving laterally, changing career paths completely or moving to a new company or industry - you’re faced with a brand new and yet strangely familiar environment.

And while you know the answers to most of the big questions - like what your salary would be, what you’ll be expected to do in your day to day and how to actually do your job - the little questions are often left unanswered.

These split into two camps: navigating the last days of your old role and settling into your new one. Let’s take a look at each one in turn.

Letting go of your old role

Leaving is often… confusing. I don’t know about you, but my transitions tend to follow a similar pattern. I get incredibly excited about the new opportunity. And yet as the time nears, things start feeling less clear cut…

The old role begins to feel safe. Familiar. Any positive aspects blur out the challenges and reasons that made you decide to move in the first place. And then the questions come.

1. Am I making the right move?

It’s normal to experience a bit of emotional turmoil when you change jobs. One of the culprits is a cognitive bias known as loss aversion. Our brains feel potential loss with a lot more intensity than potential gains.

So as you prepare to take the leap into the relative unknown, your brain is going through all the things that it may lose during the shift. Things like safety, security, comfort, friends, the feeling of belonging… These are all momentary losses that you’ll face as you shift into your new role and they do affect the way we feel.

So if you find yourself second-guessing the move, don’t worry about it too much. Most people go through the same thing. Go through the reasons you decided to make the change in the first place and focus on how it's helping your career growth.

2. How can I have the smoothest transition possible?

Depending on your role in your team and department, your move can affect a number of other people. Try to make the move as easy on yourself and everyone in your team by following a structured hand-off process.

1. Find out who will take over your old role and help smooth the way

Is the company hiring a replacement? Are the tasks getting split up into different roles? Speak to your manager and find out how you can help make the transition as easy as possible. This will help retain (and even strengthen) the relationships you cultivated during your time on this team.

2. Check the company’s off-boarding process and schedule any activities in advance

There’s no standard exit process so speak to your manager and HR team to find out what you need to do. Book any exit interviews and admin work in advance and make sure you get the information on any 401Ks, pension plans and health insurance policies before you leave.

3. Archive any data from company emails you need

If there are any emails and information you need to save, now’s the time. Just make sure that you have legal permission to do so! Some companies have very strict policies so before saving anything, check you aren’t breaking any rules.

3. What happens to my healthcare and retirement savings?

A lot of companies offer 401k plans and health insurance to employees. Find out how they’ll be affected, what forms you may need to fill out and gather all the information you may need before you leave.

4. What’s the best way to professionally keep in touch with everyone?

If you spent a lot of time at your old role, leaving it (and everyone you worked with) may feel particularly difficult. You invested a lot of time in honing and developing those relationships.

There may even be a little guilt lurking under there, even though you know you’re making the right move for you.

LinkedIn is a great way to keep in touch with everyone. It’s a little more passive than email but it provides a fantastic way to follow everyone’s career progression.

Settling into your new role

Your first day is finally here and it brings up a few questions… I’m not going to go into the work-specific questions like how to get to know your team and on-board properly here. Instead, we’re going to take a quick look at the stuff you may not know who to ask.

1. What should I wear to work?

Dress codes vary across companies, industries, regions and countries. What’s perfectly acceptable (even fancy) on the West Coast in the US may be too casual for Casual Friday on the East Coast. Then there are things like personal preference and comfort to consider… And it doesn’t help that business casual means different things to different people.

What you wear to work is a reflection of the company- and the way it wants to be seen. As an extension, it also reflects on the way you’re seen during those first few weeks. So when picking out your wardrobe, think back to your interview- what did your interview panel wear? What about the other people in the building? Take your initial guidance from your co-workers and build from there.

2. How much time can I really take for lunch and coffee?

A lot of companies have a lunch hour- some get lunch delivered, others expect their employees to either bring in lunch or go out to get it.

But what about the implied expectations? Do people generally take that lunch break? Do they go out? Do they eat at their desks?

The way we say things are doesn’t always reflect the way things actually are. The best way to find out the reality? Watch what your co-workers do and take your initial cues from them until you get the lay of the land.

3. What time are you really expected to start and finish work?

The reality of work isn’t always the same as the image you got during the hiring process. So how do you know when to start and finish?

As with the other questions, for the first few weeks, watch what your colleagues are doing. As you get familiar with the place, start paying attention specifically to what your most successful colleges are doing.

Give yourself time

Transitioning into a new role is hard. It comes with all sorts of things you may or may not have thought about.

In your first few weeks, give yourself the opportunity to get to know your co-workers and find people you can connect with- people you can ask questions. Then just go out and rock it at your new role.

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