Peak Performers by Tiffany Uman

How to update your boss like a pro

January 29, 2024

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As you strive towards peak performance, one single skill that will distinguish you from the rest is the art of effectively updating your boss.

That said, this skill is often underestimated in its importance of building your credibility, authority and ownership in your role.

It is not just about conveying information. Rather, it is about strategically positioning yourself in how you handle, manage and lead your projects to success.

It is also a great opportunity to reinforce your unique value and strengths, while building a win-win rapport with your boss that will catapult your career to new heights.

Updating your boss transcends routine reporting and becomes a powerful narrative of your contributions, aligning your personal achievements with the company's priorities and goals.

Whether providing project updates, raising risks, highlighting opportunity areas or seeking alignment and approvals, how you approach this conversation with your boss can easily reinforce the trust they put into you and the autonomy you gain in driving the business forward.

It is also critical to go beyond just words.

Peak performers know the importance of listening to understand, not listening to respond.

"The most important thing in communication is hearing what isn't said." - Peter Drucker

Practicing active listening will help you to understand the nuances, unspoken expectations, and power of perception that occurs in these conversations with your boss.

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.

The manner in which you update your boss, keep them informed and highlight your impact will either positively contribute to your development or lead to miscommunications and frustration.

You must avoid making mistakes that significantly hinder your ability to effectively communicate and diminish the impact of your efforts towards your boss.

Here are 5 mistakes to watch out for:

→ 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. Preparation is the bedrock of effectiveness. 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 are looking for in presenting each topic to your boss.

→ Overloading information: Bombarding your boss with excessive details can be overwhelming. Less is more. Your job is to bring forward the right details and information to guide your target outcome forward. If you share too much, this will likely distract and dilute your messages without you receiving the support you needed 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 are unaware of the internal organizational climate or where certain focuses may be right now. 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's feedback or failing to incorporate it into your work can be detrimental to your growth. It also runs the risk of creating a strained relationship where your boss does not believe you are adaptable or coachable, and this will hurt your progression goals in the company.

→ 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 needed to move forward on your projects.

3 strategies to update your boss like a pro

1/ Tailor your communication to their needs

In order to update your boss effectively, you must go beyond simply knowing their preferences for email or face-to-face meetings; it is about grasping 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.

Tailoring your communication means tuning into these nuances and ensuring that your updates resonate with what matters most to your boss.

Once you understand your boss's preferences and priorities, the next step is delivering information strategically. This means being selective about what you communicate.

For example, instead of bombarding your boss with every detail possible, remain focused on key facts that have the most significant 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 underscore your strategic value.

Effective communication is dynamic, evolving with feedback and changing needs.

After receiving feedback, you can frame your updates to incorporate what was shared and demonstrate your adaptability to follow-through on that. This will improve your two-way communication while providing updates, and also showcase your ability to respond to feedback positively.

Being receptive to feedback and adjusting your communication style accordingly is key to maintaining effective and relevant updates with your boss.

Here are 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.

→ Solicit and incorporate feedback: Actively seek feedback on your communication style and the content of your updates. Use this feedback to refine future communications.

2/ Build the right narrative to support your target outcomes

The ability to build a narrative around your work is an invaluable skill. It involves weaving your tasks, projects, and results into a story that showcases your contributions and impact.

For example, if you are a sales manager, instead of merely reporting quarterly sales figures, your narrative can walk through your innovative sales strategies that opened new market segments, contributing to the company's broader goal of market expansion.

This storytelling approach transforms mundane updates into compelling narratives that highlight your role in driving meaningful outcomes.

A key aspect of building the right narrative is ensuring that it aligns with the overarching goals of your organization. Chances are, the work you are doing is directly playing into a broader focus area of the company.

For example, if you are a digital marketer in a startup, you could connect your efforts in increasing social media engagement with the company's focus on building brand awareness. This would clearly demonstrate not just the effectiveness of the work but also how it played a critical role in the overall growth strategy.

In other words, your narrative should bridge the gap between your daily activities and the larger strategic objectives of the organization.

An effective narrative also illustrates progress and impact over time. You will not always have major updates or huge progress in each update conversation with your boss.

That said, you can certainly still focus on the evolution of where you are 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 is 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. Here is an example template you can follow:

"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 have hit a roadblock on this particular part because of X. I have already tried doing Y and Z and although it helped to some degree, it is not where it needs to be. I'd like to brainstorm with you now on other options 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 are 4 considerations to keep in mind in building your narrative:

→ Identify key themes: Reflect on your work and identify key themes that align with your organization'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.

→ Highlight challenges and solutions: Include challenges you have encountered and how you overcame them. This adds depth to your narrative and highlights your resourcefulness.

3/ Demonstrate your leadership qualities

When updating your boss, showcasing proactive problem-solving and initiative is essential.

Peak performers understand the importance of anticipating challenges and taking intentional steps to address them before they escalate.

For example, if you are a team lead in a tech company 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.

Leadership is also about having a visionary perspective and communicating it effectively.

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. This approach brings attention to the impact you create, while also shining a light on your capability to foster a productive and effective team environment.

Here are 4 quick tips to reinforce your leadership qualities when updating your boss:

→ Highlight solutions, not just problems: Whenever you bring up a challenge in your updates, accompany it with a proposed solution or steps you have already taken, showcasing your problem-solving skills.

→ Connect your work to the bigger picture: In your updates, regularly draw connections between your tasks and the company’s long-term goals, showing that you understand and are contributing to the 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 are 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.

How will you choose to update your boss?

The way in which you update your boss is a pivotal skill that can significantly influence your professional trajectory. By avoiding common mistakes and embracing strategies like tailored communication, building a compelling narrative, and demonstrating leadership qualities, you position yourself not just as a diligent employee, but as a strategic thinker and leader.

Remember, every update you share is an opportunity to reinforce your value and strengths, showcase your achievements, and align yourself with the company's vision.

You've got this!

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 for you to elevate your communication and get the buy-in you require as you have these conversations in your day-to-day environment.

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.
After delivering your update, ask for feedback on its format and content. Use this feedback to refine your approach for future updates.

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 are currently facing or foresee in your work. Develop a potential solution or a plan to address this proactively.
In your next update, include a brief mention of a recent team achievement or how a team member’s contribution positively impacted a project. This showcases your role in team success and your leadership skills.
Share a recent instance where you learned something new or improved a skill, emphasizing your commitment to continuous growth and development.

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