Working from home

The 5 questions to ask your new boss (when you’re in the same job)

Office meeting between 2 women - questions to ask your new boss
Photo by Amy Hirschi on Unsplash

New boss, same job? It’s always unsettling to get a new manager, but even more so if you are staying in the same job and work from home now. You won’t have the same opportunities as the old days to get to know them face-to-face.

There are plenty of smart questions to ask your new boss if you’re actually in the same job, but keen to impress and build a solid relationship. You can adjust to this change if you engage and show keenness.

I’ve had 3 managers in the last 18 months of working from home (thanks to so many changes and restructures) and I always feel a little anxious about it. If you feel the same, here are the questions to ask your new boss and start on the right foot.

1. What is your preferred way to communicate?

If you are working from home then you have an array of options: Teams, Skype, Zoom, email or old-school phone calls. The list goes on these days, so check what is their preference or find something that works for you both.

If you also have office time then you may prefer to use that opportunity for face-to-face meetings. Hybrid workers can make the most of their time in the office to get to know their new boss and even enjoy team lunches.

If you are mostly going to be meeting and talking online then make sure you are punctual and respond to any messages in a timely fashion. It’s important to show that responsive in the early days when they will be making an opinion on you.

Remember to show courtesy and respect and let them know your whereabouts and schedule if you work from home, by sharing your calendar or showing up as ‘available’ online.

2. How often should we meet for a 121?

Decide the frequency that will work best for your regular meetings: monthly, fortnightly or weekly. Of course, it depends on how things work at your organisation, your style of work, and between you as individuals.

I’ve found new managers often like regular meetings at the start at least, as they want to know what I’m working on and how much I have on my plate. Use the opportunity to let them know exactly what you do and any challenges you face.

Once the trust is built and they see I’m capable and responsible, I can then ask for less frequent 121s as that’s my preference. You may prefer more or less frequent meetings, depending on how you work and the demands of your job.

Remember to be punctual and dress respectfully, even if you work from home. You have no excuse not to be on time when there’s no commute! And you might not have to dress up like you did for the office, but still, no slobby clothes on camera please.

Women in meeting - Questions to ask your new boss

3. What is your background and experience?

This question should be framed in a friendly and interested manner so it doesn’t sound aggressive or as if you’re checking they’re qualified for the job! You should explain you are keen to hear how they ended up coming into this role, and how you might benefit from their experience.

Be warm in your approach with this question, so they feel comfortable opening up and showing off their skills and experience. Ask more questions to show you are genuinely interested and impressed.

You may find you have shared experiences and interests which could further cement your relationship and mutual goals. Or perhaps you have previous colleagues in common which could help break the ice.

4. What are your goals and plans for the team and wider organisation?

This is a great way to gauge your new manager’s plans. You don’t know how honest they will be but you should still be able to read between the lines e.g. where they might want to invest in or drop certain priorities or processes.

If you’ve gone through a restructure or period of uncertainty, you are well within your right to ask this. A good boss will understand your concerns and share their plans or strategy when they are able. They should be keen to assure you that things will be more settled now.

5. How can we support each other to achieve our goals?

This is the question to ask to build trust and show your commitment to the role and organisation, while also asking for mutual respect. It shows enthusiasm and willingness toward your new boss.

You can also ask for their advice on how to grow in your role and show you are keen to act up or help out in any way. You could ask about ways to improve your learning and development through trainings or courses.

If you’ve been demotivated lately, read make positive changes at work and see what ideas you can bring to your boss to revitalise your role. If you want more flexible working, then read how to ask to work from home. Your new boss may surprise you and be supportive of your requests.

Final thoughts on questions to ask your new boss

Remember that this is an ongoing relationship and more questions will arise as you get to know each other and learn his or her expectations. Be patient and allow time for this.

It’s also important to stay open to change and be flexible. Change can be hard at work. Perhaps your manager wants to change a process or way of working, but give it time before feeding back, as you might find it makes sense.

It can be difficult when you’ve done your job for a while and then have to adjust to a new manager. But you can show your job commitment by using the above questions to ask your new boss, staying enthusiastic and interested.

Sometimes you can be very pleasantly surprised by a new boss. They may end up being more supportive than the last one and champion you in your career. They could be keen to hear and apply your ideas.

If you work from home, make sure you are visible online and communicating with colleagues as well as your manager, via Teams or other software. It’s easy to hide away when you work from home but you want to give a good impression with a new boss so make sure you’re seen!

For more work-related posts, check out how to face your first day back after holiday and tips for a successful zoom interview.

Share your thoughts on questions to ask your new boss when you’re staying in the same job. What has worked well for you?

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The questions to ask your new boss


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