How to Make Career Conversations with Your Boss Less Stressful and More Successful
My client Susan (not her real name) talked to her boss regularly. They even had a good relationship. But when it came time to have the “career conversation” about her promotion prospects, she found it so stressful that she avoided the topic altogether.
In fact, having such a good relationship with her boss made Susan worried about hurting it by talking about “unpleasant” topics like promotion and compensation.
If you’re reluctant to have career conversations with your boss too, know that you are not alone.
The thing is, having career conversations with your boss is key for your advancement
They give you clarity on where you stand and insight into the steps you can take to improve your position. They’re also a chance to advocate for yourself and get your boss onside.
But these big, important conversations can feel stressful.
Often, they’re once or twice a year events that accompany performance reviews where you and your boss might both feel anxious. And when so much is riding on how well you handle the meeting, it can take on epic proportions.
It’s easy to get it wrong when much depends on that one big conversation
Especially in a virtual environment where you can’t just pop your head into your boss’s office when you can see they’re in a good mood. On top of that, one or both of you might not feel comfortable on a video conference call.
Even when you’re in person, it’s easy to get so worried about getting your points across and focusing on whether you’ll achieve the outcome you want that you aren’t your best self.
Over time and with practice, you can get better at having those more formal conversations.
But wouldn’t it be great if there was something you could do to set yourself up for success along the way instead of waiting for those once- or twice-a-year chances to practice and improve?
There’s one simple thing you can do to improve the outcome of your career conversations
And it’s not about preparing for the conversation itself.
Instead, it’s an overlooked opportunity you have every week, and maybe even every day, that can help you have better outcomes when you do step into those career conversations.
It’s the way you keep your boss updated on a regular basis. These updates play a big role in your career because you can have them on a regular and frequent basis, and they’re something your boss will even appreciate receiving, especially in a virtual environment.
As a former colleague admitted to me, “now that I can’t see my team every day, I have no idea what they’re doing and whether they’re productive.” So whether your updates are in writing or delivered live, they’ll help your boss out by giving her a “visual” in a virtual world.
And it goes beyond the specific content you convey.
The power of your updates lies in the qualitative signals they send about you
In fact, the way you update your boss conveys who you are, how you think, and your ability to operate at a higher level.
For example, each of my six direct reports had their own way of keeping me updated and each gave me a different impression about how they were doing and whether they were ready for the next step up. Ben’s inability to look me in the eye and constant fidgeting made me think he wasn’t ready for more responsibility. On the other hand, Julia’s crisp clear updates gave the impression of calm and control.
And beyond the impression and reputation aspects, your updates are an opportunity to influence your boss’s thinking and plant seeds for the future. When Nick included data on revenues per team member in his update, it showed me that his team was producing at a very high level and perhaps we should be investing more resources in his region.
Your updates also show the kind of mindset and approach you’re taking to the business
Sven’s updates showed me that he was thinking like an owner who balanced the long-term and short-term opportunities in his region.
And the team members who updated me consistently built trust while those who left me “in the dark” destroyed trust.
Far from being boring obligations, your updates can play a huge role in the outcomes of your career conversations when you ultimately have them. Done well, your updates can even pre-sell your boss on supporting you in what you’re asking for in your career.
So embrace updates as a way to set yourself up for better career conversations
They’re a simple yet powerful tool for paving the way for those key conversations with your boss.
To make the most of your updates, remember that it’s not just what you tell your boss. It’s also how you frame it that creates their perceptions.
It’s time to stop taking those updates for granted and recognize them for the golden opportunities that they are.
If you want to know how to keep your boss updated and do it well, then be sure to check out the workshop below to master this essential skill.
Keeping your boss updated and doing it well is one of your career secret weapons because it’s a great opportunity to be more visible with the people who matter in your career. Especially when working from home.
In this exclusive workshop, you’ll discover:
- Common mistakes to avoid in your updates
- Key elements for updating your boss well
- Strategies for updating different kinds of bosses