Here's how you can effectively manage up and keep your boss informed in the digital learning field.

Upon hire, request at least to provide a weekly update to your boss in the manner they would like to receive it: face to face, email, automatic digital report (succinct format) or dashboard update. Adhere to the schedule of reporting and periodically ask your boss for feedback on the reporting mechanism and feedback on your progress/work. Be open to any and all feedback because it allows you to constantly improve.

Create a project tracker and share it with your manager. The key is to update the document or application regularly with detailed notes about what project tasks are completed, which are in progress, and which remain to do in the future. Log time estimates for how long you think the work may take to complete. Track how long each task actually took. Now when your boss needs an update, they can simply access your tracker without pulling you in. Now when you need to share your accomplishments or want to gather data around your project completion rate, how fast each task takes, etc. you have a solid idea. A win for you and for the boss.

One great way to communicate effectively with your manager is to use your scorecard and issues during L10 meetings if you are an EOS company. The L10 meeting is a weekly meeting during which the team discusses headlines, weekly scorecard items (KPIs), status of to do items, solves issues, and discusses quarterly goals. What I love about this approach is that you have a set time to review how the team is doing via the scorecard. Additionally, if issues occur during the week, they are recorded, and then discussed and solved during the meeting. This prevents constant interruptions, and ensures that everyone on the team has visibility into the issues and solutions.

Define goals upfront, communicate progress regularly, and be proactive in addressing potential issues. This clarity ensures everyone is on the same page and enhances trust and efficiency in your projects.

Set up a shared file or workspace to track and publish progress to allow your manager to check at their convenience. This gives them real-time access and you don't have to take the time to manually create, or send, updates (win-win!). It also makes you look really organized if you can set it up so there is automatic notification of changes or includes KPIs and charts (visuals) for quick assessment.

Alignment helps, I have found this particularly useful at the beginning of a new mgt relationship, discussing the problems and opportunities can really build that all important trust

Schedule a meeting. Prepare a proposal. Seek input. Clarify expectations. Align with organizational goals. Agree on metrics. Document agreement.

When your manager comprehends the reasoning behind your actions, they are more inclined to support your decisions and value your strategic approach. Engage in an open dialogue about these goals to ensure you’re both on the same wavelength, which will streamline your work and make progress reporting more straightforward.

Asking questions is not a weakness. Don’t be transactional in your questions. Visualize yourself as your boss. Research what you feel necessary to understand the overall institutional mission. THEN identify the decisions you believe are most important to your boss. Only then can you have meaningful dialogue with your boss about their intent. This will unlock the ability to take initiative on behalf of your boss and “lead-up”

Using regular updates, socialising different perspectives can help influence your leaders thinking, then when the potentially difficult conversation happens they are already halfway on board. I find this is more effective than 20 powerpoint slides. Asking questions, seeking clarity, paraphrase and using similar language can all support cultural fit adjustments

Clarify expectations, seek feedback and ensure alignment with your boss's vision. This proactive approach prevents misunderstandings and demonstrates your commitment to delivering results that meet or exceed expectations.

Don't wait until you encounter problems; ask questions early to clarify expectations and understand the bigger picture. Please pose questions that show your eagerness to contribute and learn rather than simply seeking answers. If something is unclear, don't hesitate to ask for clarification on priorities, goals, or company vision. Please listen carefully to the responses you receive and ask follow-up questions if needed to ensure you understand.

Behind this topic is the presumption that you'll learn to mesh with how your boss communicates. Some managers want to be more involved in the 'day-to-day', others are more focused on seeing the results. Knowing your boss's style, and respecting it helps both of you be better performance partners. Ask questions, observe your boss, listen and understand. These are important skills not only in the workplace, but in life.

When challenges arise, don't just highlight problems—propose actionable strategies. This approach showcases your problem-solving skills, eases your boss's burden, and aligns your work with the broader organizational goals. It’s a proactive way to demonstrate leadership and drive project success.

Houston we have a generation problem!! Some older executives are overwhelmed with digital communication, while some embrace it. My aunt was an early adapter and she was outstanding with digital communication. My grandsons (8 and 6) are extraordinary with electronic devices. Now to the best approach. It starts with questions. Explore the preferred communication method for your boss. This includes sending and receiving communications. If they are uncomfortable with digital communication, ask them if they would like appropriate training. Adapting new communication methods can be threatening. Be patient and remember the goal. I have been in both roles, teacher and student. Software up grades can be frustrating.

When encountering obstacles in your digital learning projects, it's beneficial to approach your boss with potential solutions rather than merely presenting problems. This proactive stance not only lightens their workload but also positions you as a problem-solver within the team. By taking the initiative to think through challenges and propose actionable solutions, you demonstrate leadership qualities and a strong commitment to the success of your digital learning initiatives.

A critical thinker, proactive, and solution-oriented employee is valued higher. It doesn’t only benefit the team but also a healthy approach for personal growth.

Managers are busy people; when you vent and complain, without any ideas to resolve, you put the burden on them to solve it for you. Work your network and peers for ideas, if you need, then as others have said, bring those suggestions to your manager for discussion and vetting. They will appreciate your leg work and you learn a lot by collaborating on options with peers and co-workers.

Utilize project management tools like Trello, GANNT for transparent updates and streamlined workflows. Regularly sync through video calls and detailed emails to keep your boss informed. This tech savvy approach ensures clarity, enhances communication and demonstrates your commitment to efficiency and accountability.

Creating check-ins with your leader to give and get feedback is imperative to the success of any project. Three simple check-in questions are: What is go well? Where are you struggling? and What will you do different? You can answer each of these questions and it will give your leader great information. Also, as you receive feedback, remember all feedback is a gift, even if it is hard to hear.

If you can not become comfortable with feedback, you’re limiting yourself. Asking your Manager what is working well? What they see as needing improvement? And what they see as needing to just disappear altogether on the project.. will help you streamline. Feedback is a positive thing not a negative. It’s really all about how you look at it - if you want to grow - you need feedback.

Effectively managing up in digital learning involves proactive communication with your boss. Regularly update them on project progress, challenges, and milestones using concise reports or brief meetings. Use data and insights to highlight achievements and demonstrate how your work aligns with organizational goals and enhances digital learning initiatives.

Remember, effective communication and consistent updates are key to managing up and keeping your boss informed in the digital learning field. By demonstrating your expertise, proactive approach, and commitment to delivering results, you can build a strong working relationship with your boss.

Most importantly, understand your Boss’s goals, and align your strategies to support your Boss's and the Orgaization's Objectives. To effectively manage up and be in sync with your Boss, regular practise of proactive communication, strategic alignment with your Boss and other Leaders, and leveraging digital tools to ensure transparency and collaboration on every progress, milestones, and potential roadblocks is very important. Proactively identify challenges and propose solutions and strategies by demonstrating a commitment to continuous improvement is the key.

Managing up in the digital learning field requires clear communication and proactive updates. Start with regular check-ins to discuss progress and challenges. Use concise, data-driven reports to highlight key achievements and metrics. Utilize project management tools for transparency and shared access to timelines and milestones. Anticipate your boss's needs by understanding their priorities and aligning your work accordingly. Offer solutions to potential issues before they escalate. Seek feedback and be open to adjusting your approach. Demonstrating initiative and a forward-thinking mindset will build trust and keep your boss well-informed and confident in your contributions.