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.