Moving From Hope To Action: Having An Honest Career Conversation With Your Boss

You do a good job, perform up to expectations, have good relationships at work and assume you’ll naturally be promoted, and given raises. If only life worked that way. What if expectations don’t meet reality? What if you’re working below your skill level? Should you speak to your boss, or would you be seen as complaining? Or, what if you’re feeling that your current work is over your head, and you lack the skills to do a great job. Can you ask for additional training and resources to help you succeed? Maybe you made a mistake that could expose the team or company to risk. How should you bring this up to your supervisor? Directing your career requires more than just doing what’s expected and avoiding missteps. Today, you need to advocate for yourself, understand your reputational assets, be accountable for your professional growth and deliver value to all stakeholders to stay in the game, and advance. In the same way that you’ll need to speak up if something is amiss, your boss will expect you to advocate for yourself when things are going well, and you want more. Follow the advice offered in my LinkedIn Learning course, “Having an honest career conversation with your boss," which includes: 1. Take charge over your career. You have a lot of power over how your career unfolds. When you proactively manage your career, you can see the big picture of your goals, and create the steps needed to achieve them. Be clear about what you want and need, and advocate for yourself. There are no guarantees your requests will be granted, but simply crossing your fingers and hoping you'll be recognized and rewarded, gives away your power. 2. Know where you stand. It's important to know what you're walking into when you sit down to have this conversation with your boss. How do they perceive you? Do they feel you're a valuable member of the team? Or could they secretly be hoping you're leaving the company? To understand your reputation and credibility, reflect on past assessments, performance reviews and evaluations and see what praise and feedback you’ve received. Look for examples where your boss praised your work and contribution and how they perceive your value in the company. If there are areas you’ve been asked to grow and improve, consider doing this before you ask for a promotion or pay increase. 3. Be prepared. You only get one chance to make a first impression, but you only get about 90 seconds to set the right tone for an honest conversation with your boss. The more you know, the more empowered you’ll be in the conversation: For example, does your boss have the information they need to help you decide on your request? Gather and bring supporting data to back up your request. When my client, Tim, was preparing to ask for a raise, he scanned several online salary websites to get an idea of common salaries in his industry and his community. He outlined the original responsibilities he had when he first took the job and all the additional responsibilities which had been added to his job over the past 18 months. Tim also learned that his employer was leading competitors in sales and market share. All of this helped him make a case for why he should be paid more and why the company could afford to pay his increase. 4. Ask for what you want. Rarely are we surprised with a promotion or raise out of the blue. More typically, you’ll need to advocate for additional rewards for the work you’re producing and the results you create. To have this conversation, inventory your performance and the direct benefits to the company you’ve produced. Speak to others about the process so you know what to expect and what’s reasonable for your boss to consider. Your goal is to ensure the best possible conversation, and a lot of that is up to you and how you conduct yourself. Remember, there’s nothing shameful or inappropriate about speaking to your boss about a request you have as long as you do so with respect and preparedness. Get past the feelings of discomfort. Asking for a promotion can bring up feelings that we’re asking our boss to validate that we're worthy or special or important. We might feel vulnerable to rejection, as if we're looking for approval in addition to a new title or a raise in our salary. Be genuine, but don’t oversell it. Like you, your boss also has emotional needs. They might want to feel empowered or respected, valued or admired by you. If you miss meeting those needs and keep the conversation strictly focused on the facts of the conversation, you miss the opportunity to enlist compassion and empathy from them towards your cause. 5. Set clear expectations. As you approach your boss for the discussion, put your goal and request upfront. Do you need a decision now, tomorrow, next week? Are you looking for coaching or input? Let them know why your request has a timeliness to it and be sure you’re realistic. Just because you’re impatient and want an answer today doesn’t mean that’s feasible for your boss. Who else needs to be involved? If you made a mistake that needs fixing, for example, your boss might need to discuss what happened with other colleagues or departments (such as legal, HR, etc.) before they can fully advise you. Think this through to ensure your conversation is the most successful. What happens after you have the honest career conversation also matters. If your request is granted, resist gloating around others, as they may have a different experience. If your conversation doesn’t produce a positive outcome, also refrain from being negative.