The Ask – Rands in Repose Skip to content Archives About Books Slack Speaking Podcast Guides Feed Management Someone here needs something The Ask Coffee in hand, I sit down in the Cave. Any Tuesday during the work week, a sip, and I parse the calendar. 1:1 — he’s fine. Status meeting — listen. Staff meeting — read the notes from last week. Exec review — figure out the biggest fire, have a defensible opinion. Wait — Mark Team Review? Who is Mark? And what are we reviewing? Double-click on the meeting — unfamiliar names. No agenda. AND IT’S AN HOUR? I message my Chief of Staff, who is familiar with this morning meeting vetting process. Carolyn responds immediately, “No clue. They run one of the infrastructure teams. We’ve never worked with them.” AN HOUR. And I have no idea what is happening during this time. My finger hovers over the Decline button when I remember that part of my job involves infrequent but important meetings. In your regular 1:1s, you’ve sorted out how to communicate. He’s an introvert, and I must pull him out of his shell. She’s operationally focused — which is great — but we must move to strategy and stop crossing things off lists. Your approach is well-known and expected. This is a good 1:1. It’s high-signal, predictable, and a worthy investment. In the infrequent but important meeting, you have no such contract. But you still go. Three Assumptions, Three Meetings, Three Asks Let’s start with three assumptions as you sit down and get comfortable: There is a good reason that this meeting exists. There is a good reason that you are in this meeting. You are not a meeting accessory. You are expected to do something because of your attendance. In senior leadership circles, we call this “The Ask.” Someone in this room has an ask specifically for you. This meeting has a human capable of making sure this ask is delivered. Heads up: this might be you. Stay tuned. The Promotion Conversation Let’s start with an easy one. An individual on your team you never meet with schedules thirty minutes. If trust is high, someone (probably their manager) has already given you context (“She’s new and wants to get to know the team”), but let’s assume you have no heads-up. Just thirty minutes and a name. It’s not the point of this chapter, but the arrival of this mystery is always good news. I mean, they might be quitting, but the fact that you are involved in that possible disaster is good news — you’ll have a chance to react. These meetings are infrequent and vitally important. Ok, not quitting, but nervous. They keep saying, “I know you’re busy,” and you keep saying, “My job is the team, and that’s you.” Nice job, slick, but what is the good reason? What’s the ask? And who is going to make this happen? For this meeting, you are the person who needs to get to the ask. No one told you what’s coming, so even though they proactively got time on your calendar and they’ve been chit-chatting for ten minutes trying to connect, what’s the ask? It’s a simple question, and I’ve used it thousands of times: “How can I help?” “I’m wondering how you got started as a manager and…” The Ask: I want to become a manager. “I’ve been working really hard and…” The Ask: I want more compensation. “Well, I heard it’s important as part of the promotion process to get visibility with your Director…” The Ask: I want someone to finally explain how the promotion process works. Those are three. There are many more, but the initial point is not the ask; the point is to be the human who wants to help. Leadership, especially senior leadership, gives off this air of otherness, of being busy, of having access to information that others do not. While some of this might be true, in this meeting, you are simply there to help. The We-Need-You-(Your Team)-For-Something-Only-You-Can-Do-(And We’re Not Quite Sure How This All Works)-Meeting Harder now. Again, it’d be super if someone took the time to tell you what was going down in this meeting, but as we’ll discover shortly, this miss is part of a larger problem. Larger meeting, more people. The other privilege (curse) of senior leadership is that teams meeting you for the first time spend a lot of time fretting about how to present to you. They ask your managers, “How does she like to be presented to? What questions is she going to ask?” The end result for this meeting is a lot of formality — they want to set the table… just so. Hour meeting, and we’re twenty minutes in, and it’s all still preamble. It’s an unfamiliar team, and you’ve never worked with them before, so much of this is irrelevant, but a senior leader’s job is the constant gathering of intelligence, so, yeah, you know who many of the folks are and what they build. You knew a lot of this before you met, right? The core issue in this meeting is one of culture. This team doesn’t know how your team works, builds, or plans, so they are laying it thick. They have an ask, but the issue isn’t figuring out what they want to build; it’s explaining how you can build with them. It would’ve been great if a program manager, project manager, or other operationally minded human had intercepted this meeting, but they didn’t, so it’s you. You need to explain: How your team builds plans, where you are in the current planning cycle, and when the next planning cycle kicks off. How you and your leadership allocate your precious humans during this cycle — how the hard decisions about what is built are made. How you have historically worked with new teams. What’s worked and what has not. If this information feels remedial, just imagine how this team feels. You and your team are accountable for an important bit of software or infrastructure that is required by this other team. The problem is, for reasons that should be addressed, you and your team are a black box, so now you’re in this meeting. Five minutes to go, and heads are nodding, and there is a path forward. My hard-earned advice: You might not get to The Ask. That’s ok. There needs to be another meeting. If you get to The Ask, never say yes. All those good feelings and nodding mean the room is communicating; they don’t mean their Ask is good or aligns with your strategy. That’s the next meeting. The Shared Fate Meeting This one is non-obvious, and to understand it, I need to tell you a story. Back at the fruit company, my boss told me, “And don’t forget to meet with Rachel. You’re going to be building with her at some point. Good person to know.” Of course. First ninety days? Meeting with everyone is my jam, so I meet with Rachel. Smart, a culture carrier, a great conversation. Let’s meet again. We do. And then again. However, after three meetings, my assessment is that we aren’t going to be building anything for years. I moved my Rachel meetings to my dangerous bucket of nice-to-haves, which means they are the first thing to drop when work gets spicy. Which is always. My impression is Rachel received the same guidance about the necessity of meeting me, so when I started to reschedule frequently, she Slacked me and gave me a gentle reminder, “Shouldn’t we be meeting?” Of course. Looking forward to it. We don’t. Almost two years later, during my performance review, my boss informs me that Rachel’s boss is disappointed that we stopped meeting… because we did. We weren’t building anything together, and I was busy with the work ahead of me. My boss, this is a career-limiting move. A senior leader’s job isn’t just the constant gathering of intelligence; it’s playing the long game. I resume my fortnightly 1:1 with Rachel. Still a good human, culture carrier, and, again, every conversation was valuable. A year after our regular meetings resumed, we randomly discovered two planned programs happening on opposite sides of the company that were about to collide head-on. After a few more meetings, we compared notes and built a joint proposal, making the other proposals irrelevant (those teams did not want to do the work anyway) by asking our teams to work together on the effort. My boss, after reviewing the proposal, commented, “See?” See what? Three years ago, two SVPs had a feeling that Team Rands and Team Rachel would accidentally stumble upon a possible huge waste of work performed by unwilling teams who would prefer we didn’t do it? That’s ridiculous. It’s Not Ridiculous I am going to write something, and if you’re a full-time engineer who has never worked as a leader of people, you’re going to be mad. Much of the work of senior leadership is feeling and instinct. You were right to be suspicious. What was The Ask for the Rachel meeting? It wasn’t the eventual joint proposal. The Ask was “Our feeling is these teams need to work closely together — please figure out why.” My working life would be much easier if the decisions were all well defined and supported by a rich set of verifiable data, but more than I want to admit: I’m staring at a random 1:1 and sitting in a meeting with no agenda, and I’m listening to my gut: What is really going on here? I’m attempting to solve what appears to be a vast, impossible problem and intuit, “You know, Parker and David… they’ll know how to tackle this.” I can’t really explain why. Sitting on my bike, riding to work, the idea will just pop into my head, “Monday. First thing. You’re going to say this ridiculous thing to this person because that’s going to force them to see the situation differently.” But it’s not guessing. Those feelings came from experiences I’ve had over and over. That instinct has been built by endless trial and error. That meeting? The one with a bad title, but those two attendees I keep hearing about? I should probably go and figure out The Ask. # May 25, 2026 Leave a Reply Cancel replyYour email address will not be published. Required fields are marked *Comment * Name * Email * Website Δ See also... Barely Treading Water Sometimes Your Job is to Get in the Way The Slide The Complicators, The Drama Aggregators, and The Avoiders Three Bad Managers NextBarely Treading Water BOOKS Managing Humans: Tales of leadership from the Silicon Valley. The Software Developer's Career Handbook: Chaos is an Opportunity. Small Things, Done Well: Practice becoming a better leader. Daily. Merch Rands Schwag: Leadership leading with the letter R. Don't Skip This Thank you for scrolling to the bottom. If this is your first visit, I recommend starting by reading don't skip this. Categories Apple Biking Buzz Design Excerpt Fake Notebook Guides Hollywood Management Media Photo Plugs Product Rands Surf SXSW Tech Life The Important Thing Tools Vegas Writing The Leadership Newsletter New writing and links on leadership, technology, and the things in between. Delivered weekly. PRESENCE. The last 10% of anything is the most important part. 912 posts since 2002 Writing about leaders & builders since 2002 ReadBarely Treading Water Still debugging the humans (and robots) HONK. Belief is hard to earn, easy to lose. 39,520 words written in the last year Rands in Repose · est. Los Gatos, California The discipline isn't picking a stance — it's knowing which moment you're in. 3 books on engineering leadership ReadShields Down AWARE. © 2002-2026  · Rands in Repose Crafted by Alex King

The core premise of the text explores the often-unspoken dynamics and implicit expectations within senior leadership meetings and one-on-one interactions, arguing that understanding these interactions is crucial for effective navigation of organizational strategy. The author introduces the concept of "The Ask," suggesting that these meetings, especially those lacking a clear agenda, are opportunities for an individual to uncover what the attendees truly seek from them, rather than passively receiving information. This principle is applied to various high-stakes scenarios, such as scheduled meetings, promotion conversations, and team introductions.

When faced with unplanned or ambiguous meetings, the author advises shifting focus from simply participating to becoming the human who seeks to understand the underlying purpose. In situations where an individual is expected to attend meetings, the key is to ascertain the underlying motivation—the specific request or goal that necessitates their presence. For instance, in a promotion conversation, the focus should be on identifying the "Ask," whether it is a request for more compensation or a clearer understanding of the promotion process, rather than just reacting to the conversation. The author asserts that the appropriate response in these contexts is to adopt a helpful stance, positing that the leader’s role is to be the person who helps facilitate the delivery of the request, perhaps by asking questions like "How can I help?"

The text further delves into the challenges inherent in senior leadership, particularly when interacting with unfamiliar teams. Senior leaders often function as a "black box," holding information others do not possess. When teams meet leadership for the first time, they frequently focus on presentation and formality rather than substantive work. The author argues that the real issue is not just explaining what the team is building, but establishing the context for collaboration by explaining how the team operates, its planning cycles, resource allocation, and historical working patterns. This requires the leader to provide critical operational intelligence to bridge the gap between the team’s execution and the broader organizational goals.

A deeper strategic layer is introduced through the concept of the "Shared Fate Meeting," which addresses long-term relationship building versus immediate demands. The author recounts an experience where a focus on frequent one-on-one meetings with a valuable contact ultimately yielded no immediate tangible results, leading to a perceived disappointment from senior management. This experience highlights that a senior leader’s role extends beyond mere intelligence gathering to playing the "long game," which involves nurturing relationships and allowing time for emergent strategic opportunities to materialize. The ultimate ask in such relational interactions may not be an immediate outcome but the mutual development of a shared understanding and a framework for future collaboration.

Ultimately, the text advocates for trusting instinct and experience over relying solely on perfectly delineated data when dealing with complex interpersonal and organizational problems. The author contends that the intuition developed through repeated experience and trial and error—the ability to sense what is truly happening—is a valuable tool in navigating leadership complexities. This instinct, built through experience, guides the leader toward determining the authentic request and pursuing the necessary actions to solve the perceived, though often frustratingly nebulous, problems arising from organizational dynamics.