Avoiding The Awkward: Tips on communicating with your boss


Picture this: It’s your first day on the new job, congrats! You’ve been applying to different positions for weeks, made it through several rounds of interviews, negotiated a job offer – and now you’re finally starting. You met your manager before and seemed to click – everything seemed great. Gingerly, you arrive at your desk and notice a frustrated looking manager – did you already do something wrong on your first day? Fear not, there was probably just something lost in communication. *Phew*

Communication with your boss is arguably one of the most important aspects of work; it allows you to showcase your work and develop a relationship with the person who is responsible for evaluating and hopefully developing you. It’s safe to assume that different people have different management styles, each with a unique communication preference. Here are our top 4 suggestions on how to effectively communicate with your new boss!

1. Observe

First and foremost, observe your colleagues. How are they interacting with your manager? What are other direct reports doing? Are they simply walking up to his/her desk to ask questions, or do they book a meeting? This may be reflective of a workplace culture as well – many open concept offices encourage open communication with no offices in sight. For example, in an open office, you could likely have upper leadership sitting across from you! Some places may encourage you to just walk up to their desk and ask questions whenever they arose (though careful – some may not!). Other offices may have closed office doors that have a bit more formality surrounding them. In your first few days on the job, scope out what others are doing and what the general norms are.

2. Ask communication preferences

There’s nothing wrong with asking your leaders and direct managers how they prefer to be communicated with. Do they prefer emails? Scheduled meetings? In-person communication, phone calls  or maybe even quick text messages? The best time to ask this question is in your first week, especially if you have a touch base with them already set up. Even better if they are the one training you. This ensures that there is nothing lost in translation and you can communicate with them in the best way possible, that works for both parties. It’s an important skill to be able to adapt to different communication styles and your manager will appreciate that you’re making the effort to ask the source directly.

Tip: Write an email or make a note to confirm any details you went over in a meeting with your leaders – even just as a recap of a quick verbal meeting with something important mentioned. It is always a good idea to have a backup of important information in writing that way neither you nor your boss forgets what was said! 

3. Set up meetings

The first few days in a job can be chaotic; learning new things, meeting new people, getting familiar with a new environment, can all be very overwhelming. Your colleagues and managers are there to help, so don’t be afraid to set up some introductory meetings to understand how the team works and what is expected of you. Remember on your first few weeks you’re learning how to be the absolute best you can be in your role. In your meetings make sure you ask things like the approval process for your work, how to utilize communication tools in the office (virtual meetings, teleconference systems), the hours you are expected to work etc. It’s best to clear these up ahead of time so there is no confusion later.

4. Ask colleagues for advice

If you notice that a colleague has a great relationship with your manager, take them out for a coffee one day and get their advice! You can ask them what they have found to be the best way to communicate with your manager and what’s worked for them so far at the organization. You’ll not only build a better bond with your co-worker, but you may also receive some great advice.  

Every leader has a different preference for communicating, and that’s ok! In your new role make sure you take some time to establish what these are so you can hit the ground running from day one. Don’t be afraid to ask questions and seek help when you need it! 

About the author

Shaan Ali Jessa is a recent marketing grad from the BBA program at the Schulich School of Business-York University. Most recently he completed internships focusing on customer experience and marketing at Bell and L'Oreal. Outside of work he's passionate about social media and blogging about careers and food. Follow him on Twitter (https://twitter.com/sjessa18) or connect with him on LinkedIn (https://www.linkedin.com/in/shaanjessa/).