How to tell your boss anything

Do you tend to hold your workplace frustrations, needs, dreams, and uncertainties inside until they eventually bubble up? Maybe these thoughts and feelings even explode outward in a way that may feel good in the moment, but ultimately don't get you the support or results you're looking for? Lingering resentment or unspoken drama, anyone?

This one's for you.

Every day in May, I explained how to start a single sticky conversation with your manager. My goal was to provide realistic talk tracks for #howtotellyourboss common concerns, needs, and issues to advocate for yourself in the workplace...without sounding like a passive aggressive corporate robot.

But the conversation opener is just the beginning! What happens before and after you start the discussion is just as, if not more, important.

With that said, this week in #makeworksuckless, let's break down how to tell your boss what's on your mind and get the support you need in your career.

First, what makes these talks so spicy?

Let's say you're unhappy at work. You know you're not being paid equal to your counterparts and you want to know there's a clear growth path for you at the company. There are two main reasons why this conversation with your manager can go sideways.

One: It's about you. Like, the deeply personal YOU. Your future, your opportunities, your fears--they aren't just chitchats. You're personally invested in the outcome. And, rightfully so. Because it feels like there's an element of risk (for example, risk to your livelihood), we can get knocked into the defense zone, turning the conversation into a heated standoff and derailing it pretty quickly.

Two: There's a knowledge gap on both sides. Perhaps you've never had to advocate for yourself in this way. And perhaps, your manager doesn't have the experience to navigate an empathic and support responsive within the bounds of company policy. Being able to have a conversation like this is a skill you build with practice.

Don't let bottled emotions or inexperience get in the way of your goals!

Come prepared

If you're looking for your manager to help you drive your career forward in a productive way, you're going to need to do some ground work before broaching the subject with them. Leaders appreciate it when you walk in a plan.

• Bring a specific ask. Bring a proposed solution for your boss to react and respond to. For example you want work to pay for you to attend a conference. Bring details: when, where, cost for travel, etc.
• Do some research. Before coming to your manager, do your own digging. They don't have all the answers but they'll likely be more willing to partner with you to find a resolution if they can see the effort you put in. For example, if you're asking about a maternity leave of absence, try to find and understand your company's policies.
• Prepare examples. If you want to talk about a difficult coworker or situation, bring examples of when it's been most challenging. If you want to talk about feeling not cut out for a role, bring examples of situations in which you've felt most and least confident.
• Bring data and artifacts. If you need help particularly with your current role, for example needing to adjust your work load or identify areas you'd like to lean into more, bring your current job description, a list of your projects, your priorities and goals (as you understand them). Bring wins, losses, key metrics--anything that will help you make your case for what you need.

Conversation opener

Not every one-on-one with your boss needs a script. And some do. Instead of rage-screaming the first thing that comes to mind (again, this feels great in the moment but is not so productive), prepare how you want start the discussion. Set the tone. If you want your manager in your corner, start with vulnerability. Here are some general tips to keep in mind going into any conversation:

1. Honesty without accusation. Be open and honest about your concerns without throwing blame on anyone else.
2. Growth mindset. Express your willingness to learn, grow, and contribute to the team. A good leader recognizes that your personal growth ultimately leads to positive outcomes for the organization. Help draw that line.
3. Take responsibility. You ultimately own your career, but that doesn't mean you need to do it alone. Ask for guidance and take responsibility for your own development.
4. Respect their time. Respect your manager's expertise and time while advocating for your needs. Book a separate meeting or bring the topic to your next one-on-one.
5. Be open to learn. Be willing to act on some of their suggestions, even if it's the approach you would have chosen for yourself. If you demonstrate flexibility in trying new things, they're more likely to help you out next time.
6. Gratitude. Say thanks for the insights, resources, and support they give. Again, leaders are not all-knowing super-beings, so what they have to say may not pan out in the end. But appreciate the effort and know you've got a partner willing to figure it out with you.

Follow-up

You've done all prep work. You have a banger of an opener. You also should anticipate follow-up questions your boss will have for you, and additional answers you'll need from them to get true clarity on your next steps.

Let's say imposter syndrome is kicking your butt right now. You're really unsure of the value you bring to the table, like your peers are questioning why you were even hired in the first place, and like you can do nothing right. (It's not true, FYI.)

You reflect on your strengths and areas of opportunity, are prepared to be open to constructive feedback, and tell your boss, "I can’t shake this doubt in my own capabilities. Can we talk about where you think I bring the most value so I can lean into that more?" Hopefully they have amazing insight to share about you contribute to the team like the total rockstar you are, and how they can support you in share areas where your confidence seems shaky. A couple follow-up questions if they are less insightful than we'd like:

• Are there specific examples of where you see my strengths?
• What specific areas do you think I can improve in?

Mom always said...

My mom always said I could tell her anything at all, I just needed to mind how I said it. Infuriating for a teenager who just wants to shout into the void. Now it makes sense. If you want your boss in your corner... and you should expect them to be... approach potentially spicy conversations with vulnerability, collaboration, and respect.

So what do you need to tell your boss? Comment below!

I'll share my guide the breaks down how to prepare for, initiate, and follow up with 20 different conversations with your manager. Whether you need help with the work, managing relationships, finding balance, getting more, or preparing for a career transition -- advocate for your personal and professional needs (like a boss).