Managing Up is Hard: A Survival Guide for Mid-Level and Senior Leaders

Hey ,

The Revenue Reimagined team met this week for our quarterly business planning session. We spent two days together, but could have used another two days to keep working heads down. Reflecting on where we have been over the last quarter and where we need to go for the rest of the year was eye-opening.

The challenges that many companies are experiencing with their GTM are:

• Increasing the number of leads that convert to opportunities

• Closing at a higher rate

• Expanding current opportunities

• Figuring out how to incorporate AI into their

We are working on several exciting projects to grow our business and help even more founders, CEOs, and revenue leaders tackle their biggest GTM challenges. One of these will be a workshop and dinner in Park City on August 27th with our partners, Growth Elevated. We will conduct a hands-on AI workshop (more details coming soon).

Estimated reading time is 4 minutes—feel free to hit reply and share your takeaways or questions.

On Deck:

• Managing Up is Hard: A Survival Guide for Mid-Level and Senior Leaders

• Marketing Tip of the Week - Powered by Decoded Strategies

• Episode #97 You’re Solving the Wrong Problem — Here’s What’s Actually Broken with CEO Hannah Ajikawo

Managing Up is Hard: A Survival Guide for Mid-Level and Senior Leaders

If you're a mid-level or senior manager reporting to the C-suite, you've likely discovered an uncomfortable truth: managing up is often more complex than managing down. While you've mastered the art of leading teams, motivating direct reports, and driving results, navigating the complex dynamics with your executive leadership can feel like walking a tightrope, where the stakes are higher, the visibility is intense, and the margin for error is razor-thin. Have you ever felt this way?

The challenge isn't just about impressing your boss. It's about building a strategic partnership that enables both of you to succeed while maintaining authenticity and sanity. Let's explore why managing up is so challenging and, more importantly, what you can do about it starting tomorrow. Hint: Set expectations early and visit the expectations often!

Why Managing Up Feels Like Mission Impossible

First, let's acknowledge the elephant in the “boardroom”. C-suite executives operate differently and think differently than the rest of us. They're juggling board pressures, investor expectations, and strategic decisions that can make or break the company. Their time is scarce, their patience is limited, and their expectations are high.

Add to this the power dynamic. Unlike with your direct reports, where you hold positional authority, managing up requires influence without power. You're trying to guide someone with the authority to determine your career trajectory while maintaining professional boundaries and delivering exceptional results.

The communication gap doesn't help either. While deep in the operational weeds, your C-suite leader thinks in quarters and fiscal years. Bridging this gap requires constant translation between tactical execution and strategic vision, a skill nobody teaches in business school.

Five Actionable Strategies You Can Implement This Week

1. Master the Art of Executive Briefing

Starting with your next interaction, adopt the "BLUF" principle: Bottom Line Up Front. C-suite executives don't have time for lengthy preambles or buried leads. Structure every communication, email, presentation, or hallway conversation with the key message first, followed by supporting details.

Try this template for your next executive update:

• Lead with the headline (what happened or what you need)

• State the business impact (why it matters)

• Provide 2-3 bullet points of context

• Close with a clear recommendation or next step

2. Become a Strategic Translator

This week, start reframing your team's work through a strategic lens. Instead of reporting that "the marketing team launched three campaigns," explain how "we've accelerated customer acquisition by 15% through targeted campaigns, directly supporting our Q3 revenue goals."

Create a simple translation guide that connects your departmental activities to company-wide OKRs. Keep this visible during every executive interaction to ensure you're speaking their language.

3. Proactively Manage Information Flow

Implement a "no surprises" policy starting immediately. Set up a simple system to flag potential issues before they escalate. This could be as simple as a weekly email with three categories:

• Green lights (on track)

• Yellow flags (watching closely)

• Red alerts (need intervention)

The key is consistency. Even when everything is green, send the update. Your executive will appreciate the predictability and transparency.

4. Build Strategic Capital Through Small Wins

Instead of waiting for the perfect moment to showcase significant victories, start accumulating strategic capital through consistent small wins. Identify three "quick wins" that align with your executive's priorities this week. Document these wins and their impact, then share them in your regular one-on-ones. Drive your 1:1’s with an agenda and send to your boss the day before so they can be prepared.

Remember: executives value leaders who can execute consistently more than those who promise moonshots.

5. Develop Your Executive Presence

Starting tomorrow, implement the "two-minute rule" for executive interactions. Before any meeting or communication with your C-suite leader, spend two minutes:

• Reviewing their current priorities (check their recent all-hands communications)

• Anticipating their likely questions

• Preparing concise, data-backed responses

This small investment will dramatically improve your executive presence and credibility.

The Path Forward

Managing up isn't about manipulation or playing politics; it's about building a productive partnership that drives organizational success. The strategies above aren't just theoretical; they're practical tools that successful senior leaders use daily to navigate the complexities of executive relationships.

Remember, your C-suite leader needs you to succeed as much as you need their support. By mastering the art of managing up, you'll advance your career and become the strategic partner your organization needs to thrive in an increasingly complex business environment.

Start with one strategy this week. Build the habit. Then add another. Within a month, you'll find that managing up, while still challenging, has become a navigable part of your leadership toolkit rather than an insurmountable obstacle.

Your executive relationship doesn't have to be a source of stress. With the right approach, it can become one of your most significant professional assets.

We have created a worksheet for you here if you are interest in putting the above into action TODAY: Executive Alignment Worksheet

Thanks ZoomInfo for Keeping This Newsletter Free!

ZoomInfo is the Go-To-Market intelligence platform that empowers businesses to grow faster with AI-ready insights, trusted data, and advanced automation. Our solutions provide a complete view of your customers, making every seller your best seller.

Marketing Tip of the Week - Powered by Decoded Strategies

This week's tip is all about deeply understanding your audience by actively listening to where they talk, not just where you ask them to. Move beyond surveys and formal feedback for a moment.

Here's how to do it:

• Dive into Online Communities: Identify the Reddit subreddits, Facebook groups, forums, or even specific influencer comment sections where your target audience hangs out. Don't just broadcast your message there – lurk and listen. What are their pain points? What language do they use? What products or solutions are they already raving about (or complaining about)?

• Monitor Social Mentions (Beyond Your Own): Use social listening tools (many have free versions or trials) to track keywords related to your industry, your competitors, and the problems your product/service solves. What are the candid conversations happening?

• Analyze Review Sites (Yours and Competitors'): Go beyond your star rating. Read the actual words customers use in reviews for your business and, just as importantly, for your competitors. What features do they love? What are their biggest frustrations? What unmet needs are being expressed?

• Engage with Sales & Customer Service Teams: These teams are on the front lines. Schedule regular check-ins to ask them: What are the most common questions you're getting? What are the recurring objections? What feedback are you hearing consistently?

Episode #97 You’re Solving the Wrong Problem — Here’s What’s Actually Broken with CEO Hannah Ajikawo

This week on Bridge the Gap, powered by Revenue Reimagined, we’re joined by the award-winning go-to-market strategist Hannie Ajakaiye. As the founder of RevenueFunnel, a LinkedIn Top Voice, and one of the “100 Most Powerful Women in Sales,” Hannie has spent over 17 years helping B2B scale-ups design, align, and optimize their revenue engines for the modern buying journey. She’s a Salesforce and HubSpot insider who doesn’t just talk strategy—she lives it, globally

5 Key Takeaways

1. Define the Right Problem First

• Most GTM chaos stems from solving the wrong problem.

• Leaders often default to “fix marketing” or “train sales” without a clear diagnosis.

• Finding your catalyst starts by slowing down to assess before taking action.

2. Alignment Isn’t Just a Buzzword

• Lack of internal clarity leads to wasted effort and mixed results.

• Cross-functional teams must align on objectives and ownership.

• Transparent communication is a catalyst for high-impact collaboration.

3. Enablement Must Be Literal

• Sales teams fail when expectations are vague or inconsistent.

• “Call 20 people” only works when reps know who, why, and how.

• Your catalyst could be creating step-by-step clarity in onboarding and training.

4. Trust the Process, Not the Panic

• GTM strategies need time and data to prove success.

• Leaders often pull the plug too early, chasing false urgency.

• Patience and iteration are critical catalysts for long-term success.

5.  AI Is No Longer Optional

• Leaders must adopt and understand AI tools, especially agentic AI.

• Ignoring AI puts you behind competitors who are scaling smarter, not harder.

• Your catalyst may be learning to lead with AI, not fear it.

Ready for some real talk about what it takes to build a multi-million dollar company?

Agree? Disagree? Have Questions?

We love engaging with our community—reply to this email with your thoughts, and let’s chat!

Talk soon,

Adam, Dale, & Jake
Helping companies bridge the GTM Gap™.