One single skill that distinguishes you from the rest is how you provide updates to your boss.
This skill is too often underestimated in its importance of building your credibility, authority and ownership in your role. It's not just about conveying information, but more so about strategically positioning yourself in how you handle, manage and lead your projects to success.
It also serves as key moments to reinforce your value, impact and strengths, while building a win-win rapport with your boss that actually drives your growth faster.
Whether providing project updates, raising risks, highlighting opportunity areas or seeking alignment and approvals, how you approach this conversation with your boss can easily build the trust they put into you and the autonomy you gain in moving the business forward.
Ultimately, you must transform the mundane task of 'updating' into a strategic advantage that contributes to your development goals, and leverage every interaction as an opportunity to shine.
Here's how.
Mistakes when updating your boss
There are subtle but critical errors that can turn a potential opportunity for advancement into a misstep, undermining your credibility and the perception of your competence towards your boss.
With that in mind, here's 5 mistakes to avoid:
→ Lack of preparation: Stepping into a meeting without a clear agenda or key points will easily lead the conversation to get overtaken by your boss and lead you to lose control. Remember, this is your moment to manage your time with your boss, not the other way around. Be clear on what you plan to cover, how long each topic will take to discuss and what outcome you're looking for in presenting each topic to your boss.
→ Overloading information: Less is more. Your job is to bring forward the right details and information to your boss so you can guide your target outcome forward. If you share too much, this will likely distract and dilute your messages without you receiving the support you need in that moment.
→ Neglecting the 'big picture': Focusing solely on the minutiae without connecting it to the larger company goals is a missed opportunity to demonstrate your strategic thinking. It can also come off as though you're unaware of the internal climate or top priorities. Without proper recognition of the 'big picture' in your updates, getting your boss' full attention and commitment will be challenging.
→ Ignoring feedback: Communication is a two-way street. Disregarding your boss' feedback or failing to incorporate it into your work is a major no-no. It also runs the risk of creating a strained relationship where your boss does not believe you're adaptable, slowing your progression in the company as a result.
→ Lacking confidence: Confidence in delivery reflects confidence in content. Hesitancy or uncertainty in your updates can undermine your authority. This will lead you to get challenged, questioned and likely not receive the alignment you need to move forward on your projects. It will also play against your perceived readiness for your next step in the company because you will have not demonstrated what they needed to see in you to make that an easy yes decision.
3 strategies to update your boss with confidence
1/ Tailor your communication to their needs
Go beyond simply knowing their preferences for email or face-to-face meetings. Instead, grasp their goals, challenges, and the pressures they face.
For instance, if you notice your boss is particularly focused on cost-saving measures, you can align your updates to highlight how your projects are staying under budget or factoring in cost considerations.
Tailoring your communication means tuning into these nuances and ensuring that your updates resonate with what matters most to your boss.
Remain focused on key facts that have the biggest impact on your projects or progress. Your updates should not be a laundry list of tasks but a curated selection of the most pertinent points that highlight your ability to plan, be strategic, and show up with intention, just like my client Lara did with her boss.
Here's 4 action steps to help you implement this:
→ Observe and adapt: Pay close attention to your boss' communication style and priorities. Note what types of information they focus on during meetings and what they tend to skim over. Adapt your updates to match this style.
→ Focus on relevance: Before updating your boss, ask yourself, "Is this information directly relevant to their goals or concerns?". If not, consider omitting it or framing it in a way that ties it back to their priorities.
→ Use clear and concise language: Avoid jargon and overly technical terms unless they are familiar to your boss. Aim for clarity and brevity to make your updates more digestible and impactful. Pro tip: Whatever you're thinking to say can almost always be cut in half and maintain the same essence. Challenge yourself to do that exercise repeatedly to have more succinct, impactful messages.
→ Solicit and incorporate feedback: Actively seek feedback on your communication style and the content of your updates. Use this feedback to refine future communications. You'd rather be on the same page with your boss with this rather than turn a blind eye to improvement areas.
2/ Build the right narrative to support your target outcomes
Your ability to build constant narratives around your work and impact is invaluable.
For example, if you're a sales manager, instead of merely reporting quarterly sales figures, your narrative can walk through your exact sales strategies that grew your market this quarter, contributing to the company's broader goal of closing the gap versus your #1 competitor.
Storytelling transforms mundane updates into compelling narratives that highlight your role in driving meaningful outcomes. Your narrative should bridge the gap between your daily activities and the larger, strategic objectives of your company.
I know that you will not always have major updates or huge progress in each update conversation with your boss. And that's okay.
That said, you can still focus on the evolution of where you're at now versus where you were when you last discussed this topic. This approach will allow your boss to see the journey, not just the endpoints of your projects, and also understand the cumulative impact of your work.
Finally, be explicit in your asks. If there's something you need your boss to support you on, say it and say it clearly. Do not put the ownership on your boss to figure this out for you.
Communication template example:
"I wanted to share an update on my latest report for X project. It has been progressing well in [A, B and C] areas. That said, I've hit a roadblock on this particular part because of X. I've already tried doing Y and Z and although it helped to some degree, it's not where it needs to be. I'd like to brainstorm some other options with you that could work instead, this way I can keep moving forward and respect the deadline we agreed upon. Would this work for you?"
Additionally, here's a few considerations when building your narrative:
→ Identify key themes: Reflect on your work and identify themes or priorities that align with your company's goals. These themes will form the backbone of your narrative.
→ Create a story arc: Structure your updates like a story, with a beginning that sets the stage, a middle that outlines the actions taken, and an end that highlights the outcomes and lessons learned.
→ Use data to support your story: Integrate relevant data and metrics into your narrative to quantify your impact and lend credibility to your story. For example, integrating a statistic that further supports your recommendation can go a long way. It's hard to deny facts.
→ Highlight challenges and solutions: Include challenges you have encountered and how you overcame them. This adds depth to your narrative and highlights your resourcefulness.
[Check out my LinkedIn Learning course Storytelling to Influence Leadership and Decision Makers]
3/ Demonstrate your leadership qualities
When updating your boss, showcasing proactive problem-solving and initiative are essential. Peak performers understand the importance of anticipating challenges and taking intentional steps to address them before they escalate.
For example, if you're a team lead in tech who noticed potential delays in your project due to resource constraints, you can update your boss by highlighting both the issue and present a well-thought-out plan involving resource reallocation and timeline adjustments.
This proactive approach not only solves the problem but also showcases your foresight and ability to take charge, all key qualities of effective leadership.
When you update your boss, integrate how your work contributes to the company's future. The skill of future-pacing is a great way to get further support from your boss on your projects, while demonstrating a strategic, forward-thinking mindset.
Additionally, when updating your boss, make it a point to highlight the collective efforts of your team while also distinguishing the results that have specifically come from your efforts. Pro tip: Ask yourself "what wouldn't have happened if I wasn't there?" to clarify this distinction for yourself.
Here's 4 quick tips to reinforce your leadership qualities when updating your boss:
→ Bring solutions, not just problems: Whenever you bring up a challenge in your updates, accompany it with a proposed solution or steps you've already taken, showing your problem-solving skills.
→ Connect your work to the bigger picture: In your updates, draw connections between your tasks and the company’s long-term goals, showing that you understand and contribute to their broader vision.
→ Share success stories: Include examples of how you or your team overcame obstacles or achieved significant milestones, highlighting your ability to lead and inspire your team, despite challenging and difficult moments.
→ Show continuous improvement: Regularly update your boss on how you're developing your skills and those of your team, aligning with leadership and personal development goals. This will show a growth-oriented mindset both for you and the business needs.
[Check out my recent newsletter on How to build your leadership skills]
How will you choose to update your boss?
The way in which you update your boss has the potential to be a major career catalyst. By avoiding common mistakes and embracing strategies like tailored communication, building a compelling narrative, and demonstrating your leadership qualities, you position yourself not just as a diligent employee, but as a strategic thinker and leader.
You've got this!
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This week's mission is aimed at helping you to update your boss most effectively tied to your project updates. The below reflections are designed to elevate your communication and get the buy-in you require.
1/ Tailor your communication approach:
- For the next few days, observe your boss’ communication style and preferences. Note the types of information they prioritize and how they process information best.
- Using your observations, draft an update on your current project or tasks. Ensure it aligns with your boss' preferred style and highlights information pertinent to their current focuses.
2/ Build the right narrative:
- Reflect on your current projects and identify a key theme or storyline that aligns with your company’s objectives. Think about how your work contributes to these larger goals.
- Craft a brief narrative around this theme for your next update. Include not just what you did, but why it matters - the impact, the challenges overcome, and the future implications.
3/ Elevate your leadership skills:
- Identify a challenge you're currently facing or foresee in your work. Develop a potential solution or a plan to address this proactively and share it with your boss without them needing to ask.
- In your next update, include a brief mention of a recent team achievement or how a team member’s contribution positively impacted a project.
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