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Women at Work

Managing Up, One Conversation at a Time

37 min episode · 2 min read
·
Melody Wilding

Episode

37 min

Read time

2 min

Topics

Career Growth, Productivity, Leadership

AI-Generated Summary

Key Takeaways

  • Alignment conversation timing: Initiate alignment discussions at natural transition points like quarter starts, new projects, or team changes by saying "I've been thinking about how my team makes the biggest impact this quarter and realized it would be helpful to take a step back." Frame it as a refresh benefiting both parties, not addressing a problem.
  • Strategic metrics question: Ask your manager "What are the metrics you discuss with your own manager?" or "What metrics are being discussed at board meetings?" This reveals how your boss will be evaluated and helps interpret their direction, feedback, and priorities. Understanding their success measures clarifies what they truly care about beyond stated goals.
  • Binary choice technique: When working with vague managers, present constrained options rather than open-ended questions. Say "When you say improve financial strategy, do you mean more like this or more like that?" This removes cognitive load from busy leaders while demonstrating your analytical thinking and making it easier for them to provide clear direction.
  • Promotion conversation timeline: Discuss advancement months before performance reviews, not during them. State your goal explicitly: "By year end, I want to move from senior manager to director. What do you need to see to be comfortable putting me up for promotion?" Contract around specific milestones and check progress regularly to avoid last-minute disappointments.
  • FYI update strategy: For managers who dislike weekly dumps but want visibility, send brief outcome-based milestone updates labeled "FYI, no response needed." This creates visibility without appearing dependent. When seeking input, present your analysis first: "I've weighed these variables and narrowed to option A or B. Which path do you recommend?" This demonstrates competence while getting guidance.

What It Covers

Executive coach Melody Wilding presents a framework for managing up through ten essential conversations with your boss. The episode focuses on two foundational conversations: alignment (clarifying expectations and success metrics) and styles (understanding communication preferences using four personality types: commander, controller, cheerleader, and caretaker). Real listener dilemmas demonstrate practical application.

Key Questions Answered

  • Alignment conversation timing: Initiate alignment discussions at natural transition points like quarter starts, new projects, or team changes by saying "I've been thinking about how my team makes the biggest impact this quarter and realized it would be helpful to take a step back." Frame it as a refresh benefiting both parties, not addressing a problem.
  • Strategic metrics question: Ask your manager "What are the metrics you discuss with your own manager?" or "What metrics are being discussed at board meetings?" This reveals how your boss will be evaluated and helps interpret their direction, feedback, and priorities. Understanding their success measures clarifies what they truly care about beyond stated goals.
  • Binary choice technique: When working with vague managers, present constrained options rather than open-ended questions. Say "When you say improve financial strategy, do you mean more like this or more like that?" This removes cognitive load from busy leaders while demonstrating your analytical thinking and making it easier for them to provide clear direction.
  • Promotion conversation timeline: Discuss advancement months before performance reviews, not during them. State your goal explicitly: "By year end, I want to move from senior manager to director. What do you need to see to be comfortable putting me up for promotion?" Contract around specific milestones and check progress regularly to avoid last-minute disappointments.
  • FYI update strategy: For managers who dislike weekly dumps but want visibility, send brief outcome-based milestone updates labeled "FYI, no response needed." This creates visibility without appearing dependent. When seeking input, present your analysis first: "I've weighed these variables and narrowed to option A or B. Which path do you recommend?" This demonstrates competence while getting guidance.

Notable Moment

One listener's boss accused her of having her own agenda and lacking emotional maturity after she shared strategic thoughts with the CEO. Wilding advises this crosses from difficult to damaging behavior, recommending the gray rock technique: limit personal details, use silence to avoid escalation, and focus on self-preservation rather than relationship building with emotionally volatile leaders.

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Episode Transcript

You're listening to Women at Work from Harvard Business Review. I'm Amy Gallo. Everyone reports to someone, and managing up is how we proactively build a productive, mutually beneficial relationship with our boss, whether that person is a VP or the CFO. It's the effort we put into understanding their priorities. It's the way we tailor updates and feedback. It's balancing their needs with ours. It's a mix of skills you keep honing because managing up isn't something you ever really finish. Thankfully, in executive coach Melody Wilding's new book, she breaks the work of navigating your relationship with your boss into 10 conversations. Her book's called Managing Up, How to Get What You Need from the People in Charge. In it, she prepares us for conversations about boundaries, about visibility, about advancement, about money. Before those, though, she strongly recommends having two foundational conversations, one about alignment and one about styles. Very simply put, the alignment conversation is creating clear expectations, getting on the same page with your manager about what success looks like. If the alignment conversation is about what we're accomplishing, what's most important to be spending time and energy on, then the styles conversation is how do we accomplish it together knowing that we may have different personalities, approaches, preferences. Melody's here to help us rethink managing up as a career long practice. And she and I will give examples of what to say so that these critical conversations are easier to get started and lead to more impact. Melody, first of all, thank you for joining me. It's always lovely to be chatting with you. Good to see you. You structure the book around 10 different conversations, and I wanna dive deep into two of them. The first is the alignment conversation. And you say, this is one, if not the first conversation you should have with your boss, whether you have a new boss or you're just getting to know them or your team is working on a new project. What if you've been working with your manager for a while and you realize, oh, we actually never had this conversation, and I've been making assumptions about what success looks like, and maybe we're not as aligned as I thought we might be. How do you bring it up? And is it ever too late to bring it up? It is never too late. And so if if you have a manager where you haven't had this explicit discussion, very easy. Tie it to some sort of natural segue. Maybe it's the beginning of the quarter, a new month, a new year, a new project, an industry change. Mhmm. Frame it as something that is a refresh or a reset that benefits both of you, not addressing a problem. So Yeah. For example, you might say, I've been thinking about how my team makes the biggest impact this quarter, and I realized it would be helpful for us to take a step back, make …

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