Here’s The Rub: We Don’t Believe You

Welcome, new leader. We’re glad that you are here. Your arrival fills a critical vacancy in our team, and we can’t wait to see what you can do at this company. We’re going to say that we’re not in a hurry and you should take your time, but we’re in a hurry.

Before you arrive, we’re going to tell you what we think needs to be fixed. You should listen to us, but the issue is that we probably don’t know what is broken. Either we’re too busy to notice, or we’re too close to the source material. We wrote the current script, so we’re required to believe it is good. It’s not. It’s a disaster, and it’s breaking, and we need you to investigate, and then to tell us what’s wrong.

Here’s the rub. We’re not going to believe you when you tell us. If that all feels like a trap, it’s not — it’s just senior leadership.

Hi, Rands here. I’m not typically this prescriptive, as every individual, team, and company has different values and culture. Thing is: everything I include in the checklist is a tactic I’ve used at wildly different companies for the past twenty years. This might say more about me than the teams and companies, but they also work.

Recurring 1:1s with Inner Circle

No surprise here. I’ve been preaching 1:1s for years. Within a few weeks, you should have 1:1s with all of your direct reports and your boss. You should also have a sense of what type of 1:1 works for each of them. There are humans who prefer a wandering, casual conversation, and those who want to know precisely what topics will be discussed beforehand.

The goal for this meeting is to establish a consistent weekly meeting that is a safe place to discuss topics of note. These are issues, questions, or discussions where the two of you can seek understanding. These topics can show up as part of casual conversation, but I like to get in the habit of sharing these beforehand with a bit of context as to the intent. I use a 1:1 Slack channel for this, but any medium works; the content is less important than everyone involved knowing this meeting happens every week, no matter what.

Here’s the rub. Your 1:1 list as a senior leader is bigger than direct reports and immediate leadership; your 1:1 list includes the entire ecosystem of humans who support your team in getting the job done.

Who?

Sorry, the list varies wildly depending on company, culture, and that moment in time, but there is an essential and non-obvious set of other humans who require as much investment as your team and your boss. Most of these humans will be names that you just keep hearing. Sarah this. Sarah that. No one is saying, “You should spend time with Sarah,” but Sarah is clearly in the team’s bloodstream, and it’s your job to figure out why.

My default move in the first three months — and it’s an expensive one — is, “Always schedule 1:1 time.” Possible learnings from this meeting include:

This is a human with some juicy signal about the state of our teams — keep meeting.

This is a human who has a signal that I have already heard — don’t meet again.

This is a human whom I sure like, but who doesn’t really have signal — don’t meet again, have lunch occasionally. You never know.

You’ll know it’s working when you find a mystery. I found one on the second weekend at my third start-up. Ryan wasn’t the first engineering leader to raise the topic, but he did ask the question, “How are we promoting engineers fairly?” We weren’t was the unfortunate eventual answer. Promotion was left up to the engineering manager’s discretion, with a meaningless gut check by senior leadership. They still acted like it was twelve people in temporary space, but there were over one hundred engineers, and we were on track to double in the next year.

Extended Staff Meeting

Of course, you’re doing a Staff meeting. Getting all your directs together for the weekly breaking of the professional bread? A quick metrics review followed by a set of team-supplied discussions with a compelling chase of Gossip, Rumors, and Lies. Unlike 1:1s, I’m not going to regurgitate my thoughts on the necessity of Staff meetings.

Here’s the rub: you need another meeting, the Extended Staff Meeting, which you need to have in place by your second month. Required attendees for your Staff meeting are obvious: your direct reports. Maybe you’ll have special guests who are critical support from across the team, and maybe those folks will be regulars. Go for it. No more than ten 1

Required attendees for your Extended Staff are:

Everyone we just defined for Staff.

Every manager in your organization. (Yes, every single one)

Every leader in your organization — keep reading.

That last bullet is a slippery one, but before I explain how to select these folks, let me explain what is happening in this meeting. Yes, a lot more people than your Staff meeting. Yes, you’ll need to present more than discuss, but this is not your All Hands; this is still a meeting, and discussion is required.

In your 1:1s, you’ve been discovering mysteries, and this venue (and your Staff meeting) is the place to discuss and refine these mysteries. Are we promoting fairly? Do we have a quality issue? Are the robots taking over? The point isn’t to solve the mystery; the point is to explore the mystery. In order for this discussion to be productive, all leaders need to be included.

You can’t have every single person in the Extended Staff (that’s All Hands); you need to draw the line somewhere, but in my experience, a pure manager meeting can turn into a manager-echo-chamber where everyone starts agreeing with each other because of the chain of command. You need someone who is going to say the hard thing, which is why you need a selection of senior leaders from the team. Your most senior engineers? Sure. Longest tenured humans? Maybe. Some easy-to-define and explain slice of leaders who don’t have the management title.

You’ll know it’s working when someone in Extended Staff points out something terrible about one of your mysteries. It’s hard to make these up, but it’s easy to imagine when they show because it’s like getting punched in the face. You are instantly and forever changed by the comment, and, again, it usually shows up from an unexpected someone who many think should not be in the room.

But they are there. And they say it. And what was a mystery is now a critical problem. And it’s your job to fix it.

All Hands

It’s your third month. You have a reliable set of recurring inner circle 1:1s. Your Staff meeting is a weekly event. You’ve had two or three Extended Staff meetings at this point, and now you’re ready for the Main Event, which isn’t actually the Main Event.

Your All Hands includes your entire team, and the agenda for this first one is straightforward:

Hi, this is who I am.

This is who I’ve spoken with, and this is what I’ve discovered: both good and bad. It’s very enticing to focus on the bad because that is where you need to invest, but highlighting the good gives you credibility points — He has a full awareness of what’s up — which you are going to need later when you start tearing stuff down.

And, most importantly, this is what I’m going to do about the bad stuff.

I’m not going to say a lot more about the All Hands because there’s a chapter in the new book. If you already followed my advice on 1:1s, Staff, and Extended Staff, then this meeting is more performance than content. You’ve already clearly identified the critical mysteries, and it’s not the point of this article to define how you might address the issues. This article is about building communication structures, and your All Hands is mostly a one-way report to the team. Be sure to:

Give them a reason to show up — donuts are a surprisingly cheap way to improve attendance. Also, delicious.

Keep the presentation tight — practice a lot, practice in front of people who will give you feedback, practice some more.

When you declare what you’re going to do about it, clearly define when you (or your team) will be following up with status.

Here’s The Rub

Third start-up. I’d been hired as the VP of Engineering. The prior fellow had a rough go at it. Deeply technical, but unable to communicate his vision to his peers and his team. My read was that it ended poorly, and when I arrived, everyone was rattled by his exit.

First VP gig. Prior occupant — it didn’t go well. My instinct. Learn everything, and until you know everything, lie low. When someone asks, “What’s your vision?” tell them, “I’m still learning.”

Month two. The co-founder, who I was sure was the reason I was hired in the first place, pulled me aside, ashen-faced, and told me, “You gotta start talking.”

Me: “Why? I’m still figuring this place out.”

Him: “We’re wondering if we made the right move with you.”

Six. Weeks. The company had been around for seven years at this point. There were 110 engineers and a wildly successful product with a commensurate amount of absolute chaos. I could see potential brokenness, but I was still gathering signal.

I scrambled. The good news is that I had already done everything I described above. Mysteries had turned into heinous problems, and I had vetted solutions with people I was beginning to trust. Got the All Hands on the books, practiced, practiced some more, and then show time. Laughs at the right time. Claps, too. Appropriate solemn silence when I described what was fundamentally broken. A success.

How did I know? Because the CEO walked up to me after the All Hands, grimacing. Uh oh

Him — synthesized: “A good assessment, but I don’t see the problems you describe. I see the problems I can see. You should focus on the problems I can see.”

A front-line manager’s job is to take the time to understand and adapt to the current situation. For a new senior leader, you are the situation. Chances are, your boss and your senior peers are in the middle of it. They are smack dab in the center of the chaos, and while their perspective is relevant, it’s blurred by history and chaos. One of your immense fading advantages as the new senior leader at the table is that you have no history in this current chaos, yet. You have fresh perspective that has not been beaten into submission by the chaos.

It’s no one else’s job but yours to fix what ails your team. No one is going to give you permission.

And you’ll know it’s working when they don’t believe you.

More than ten? Time for a reorganization, sorry.