Your boss needs you as much as you need them

Getting the Boss on Your Good Side

Healthy side effects include collaborative career and skill development.

In today’s work environment, everyone is expected to work more, achieve more, and strategize more—in less time.

But, that same fast-paced environment limits us from envisioning a clear path towards professional growth, getting promoted, and generally onto bigger and better things. Many positions in tech, social media, startups, and small businesses exist in an ecosystem that defies the traditional rules of moving up the ladder. In many cases, there is not a defined next step to take. So, when that drive to grow professionally kicks in, what do you do?

Research shows that less than 50 percent of employees see viable career advancement opportunities with their current employers. This leads to “job-jumping” to move up the ladder. It’s a challenge that both employers and employees face. But, if you want to plan a viable future for yourself at your company, you better take the situations into your own hands. That means coming up with a strategic plan and sitting down to have “the talk” with your manager. When you do, here are a few tips to help you make it happen.

1. Come Prepared

It’s your career. No one is more invested in it than you. Think about your most substantial assets and how that can help you be successful in your next role. Come prepared with accomplishments and reflect on the actions you’ve taken to help the organization. Think about the meeting with your boss as a strategic business meeting – because it is.

2. Approach at the Right Time

Assess the situation. If your boss is trying to put down a fire, they won’t be in the mood to entertain your career advancement plans. Focus on choosing the right moment to talk about your plans. For example, my company has regular team meetups to discuss issues and ideas related to our workplace and success. In my case, that’s the perfect time to bring up career advancements. Think about the best moment for you.

Start with your purpose:

Boss, I’d like to talk about what the next steps in my career look like. I’ve been here x years, and I’ve proven my ability to grow y and z. It’s been a tremendous experience for me. I’d like to get your feedback and work together on a professional development plan.

Pause, and wait for feedback to assess if your boss is aligned on your performance. If they’re an advocate, then you can move on to the next steps.

3. Show Your Vision

Share with your boss how you see yourself in the future. You don’t need to come up with specific job titles to have an understanding of where you’re headed. Consider the skills you’d like to develop, the type of experiences you’d wish to obtain, and how these things can help the company in the future. Demonstrating an awareness of how your contributions and skill development will impact the company’s bottom line can be crucial.

4. Explain Your Plan, and Be Willing to Flex

Don’t come in empty-handed. You have to explain your plan to make these things happen. Your boss already has their plate full with obligations, and adding more to that won’t help your cause. Keep in mind, you’ll need to maintain a flexibility that accounts for your employer’s shifting priorities. Maintain an open mind, and don’t expect huge promises. But instead of leaving the conversation open-ended, do make sure you ask for clarity on expectations and deliverables.

Boss, based on our conversation, what should my next steps be? Can we check in again later this month?

This lets them know that you’re serious about executing, and ready to get started on the next steps. It also shows determination, and dedication to your professional growth.

5. Develop Your Strategy

Lastly, develop a strategy that explains precisely how you’re planning to grow professionally with their help. Look for things that will help the department or the company at a larger scale. Your boss needs to know that this is not just a selfish request, and that you’re trying to help the company grow as well.

For example, as a content writer, I was looking for ways to improve my creating writing skills. My ask? To help our team develop a collaborative skill that will improve our writing across the board. My plan? Let the team task each other with out-of-the-ordinary copy subjects, then critique each other once a month.

My boss’s answer: Love it! You’re in charge of finding the topic ideas, assigning each writer with their topics, and setting up the meeting for revisions.

This is what I said during our meeting:

Team, I think we’re excellent copywriters when it comes to keyword research and writing for SEO. However, I believe we can all use some polishing of our creative writing skills. To this end, I propose we task each other with non-client related topics that ignite our creative juices and expand our horizons.

By doing this, I gained buy-in from my boss on our team’s professional development, received the opportunity to prove my supervisory skills, and learned a thing or two along the way.


Skill Development Opportunities—Free Vs. Paid

Now, let’s talk about skill development that’s free, versus skill development that costs you or your company money. Hopefully, you work at a company that has a budget allocated to help employees improve their professional skills. Be sure to take advantage of any opportunities for free online courses, certifications, or reimbursement for educational programs. But if your company doesn’t offer these, ask your boss or HR team if they plan to in the future.

Free opportunities, like my copywriting idea, are easy to implement, and are most likely to earn an immediate response. Paid programs, however, such as a webinar, conference, or certification, may need more proof of return on investment for the company. In this case, you can still use the above steps to help you win your case. Here are some additional guidelines to keep in mind.

Finding the Right Words

If you’re confident that these opportunities will help with your professional development, think strategically about how to win over your employer. Make sure the skill you’re pursuing is not something you’re already too familiar with. Otherwise, you risk the chances of getting your idea pushed back.

Be careful. You don’t want it to appear as if you don’t excel at the things you were mostly hired to do. The idea is to set the ground for an opportunity to help you learn another set of skills that can help you and the company move on to the next level.

Here are some email templates you can use as a starting point for your conversations.

If They Have a Budget:

Hi Boss,
I came across this [event, course, or certification]. Based on the description, I think it would be an excellent learning opportunity, and I’m confident I can come back with [skill you’re hoping to gain from attending]. I believe this can be a great booster for my professional growth, and will help the department by [how it will benefit the company].

Please, let me know if there’s a budget available. If we can’t cover all the expenses, but I can be reimbursed for part of it, I will consider that as well.

Thank you in advance.

If They Don’t Have a Budget:

Hi Boss,
I’ve been enjoying the free software tools we use. I do, however, think that I could better my skill set and work faster if I took [course, certification, or conference]. I looked up a few options and here’s what I found best: [link to the opportunity you’re interested in pursuing.]

We’ve never discussed if there’s team budget for these opportunities. I don’t want to go ahead of myself, but, if there’s a way for me to enroll in the course and potentially be reimbursed for the professional development, I would love that. I’d be more than eager to share my learning with my department.

I understand if we don’t have the resources at this time. Will you please let me know if this is viable?

Thank you for your consideration.

What’s Next?

The task is yours. It’s possible that your boss has too many priorities on their plate to proactively brainstorm with you on ways to improve your skill set. So if you want their support in your professional growth, you’ll need to own it and take matters into your own hands. Hopefully, these tips will give you the confidence you need, and the planfulness to follow through. Good luck!

🤝 Navigating power structures

Ask yourself:

Do you dread meeting with your boss, or do you see it as an opportunity?

-Chris Cantino, Supermaker Co-founder