“How on earth could he say those things so confidently when he doesn’t have a clue about what’s happening down here? It’s kind of like the American politicians who used to visit Vietnam, look around a bit, talk to the top brass in the military command, review some statistics, and then proclaim that the war was being won and they could see the light at the end of the tunnel. Right!

…

Being present allows you, as a leader, to connect personally with your people, and personal connections help you build your intuitive feel for the business as well as for the people running the business. They also help to personalize the mission you’re asking people to perform.

—Ram Charan and Larry Bossidy: Execution: The Discipline of Getting Things Done

One crucial but often neglected meeting in an organizational leader’s meeting toolkit is the skip 1:1—a one-on-one meeting between a manager and her directs’ directs. In other words, it skips a level in the organization.

Frankly, I haven’t been consistent in my career in conducting them. It’s easy not to do them. They are the kind of meeting that you can get away without holding for quite a while without visible negative consequences. Each individual skip 1:1 may provide a bit of value, but they are an incredibly high-leverage activity in the aggregate. Occasionally, you can uncover a severe and otherwise invisible issue that makes all of your skip 1:1s worth it.

Like 1:1s with directs, they are a purposeful business meeting, not just a chance to chat. The purpose is (1) relationship building, (2) information gathering, and (3) a chance to provide affirmation and praise. More specifically, skip-level 1:1s:

1. Create rapport between you and everyone in your organization. As your team grows, you will have less and less contact with any one individual. Later, as your organization grows, this may be the most substantial conversation you have with an individual that year. Skip 1:1s allow you to build personal connections that can pay dividends later.
2. Give team members time to ask questions or raise concerns. To a first approximation, zero people in your organization will contact you to ask questions or raise concerns. These meetings are the most successful when you give prompts for potential topics and remind the person that the meeting is mainly for their benefit.
3. Give you a finger on the pulse of alignment and communication between you and your managers and how that alignment and communication flow down to ICs. Do people understand what your organization is doing? What is the company doing? Do they understand how their work fits in?
4. Give you a reality check from people on the ground. They can illuminate areas of your organization that you need to pay attention to and lingering issues you may have missed and give you a deeper understanding of the day-to-day work getting done in your organization.
5. Can uncover places where you are being “managed up” to the detriment of those reporting to that manager. In general, you will hear the perspective of the managers reporting to you more frequently and before the perspective of the people reporting to those managers. This is an opportunity for individuals to give feedback about their manager.

Frequency

How frequently you hold these meetings depends on the size of your organization. Two guidelines: I do not recommend holding more than one skip 1:1 per week (your time is too valuable) or meeting with the same individual more than bi-annually (their time is too valuable). The idea is to get insight into your organization, not to build strong individual relationships with every individual throughout your team. As in all things, use your judgment.

Things to watch out for

You don’t want to create a situation where you cut your line managers out of communication loops, send mixed messages about your confidence in them, or issue “accidental orders.”

These are real risks, and you should watch out for them. Skip 1:1s are a great tool, but the primary communication channel should always be IC <-> Manager <-> You. That’s what the organization is for. That’s what gives line managers the autonomy they need to do their jobs and helps push decision-making down to the lowest possible level. Issuing instructions undermines your managers.

In fact, Manager Tools recommends against holding skip-level 1:1s because it can undermine your direct managers. (They have a entire podcast about it!]). They recommend a combination of group skip-level meetings, having your directs conduct 1:1s with their directs, and maintaining an open-door policy. All of these are great! That said, I have found skip 1:1s too valuable of a tool to ignore, even with these risks.

So, when you are conducting a skip 1:1, and someone runs an idea by you, asks for your permission to do something, etc., or even, in some circumstances, complains about something, a key thing to ask is, “Have you talked to your manager about this?” You can recommend this as a first step and ask the individual to follow up with you later. For a truly serious situation, you should, of course, act as you see fit.

Sample meeting invitation template

Here’s an example of a meeting invitation:

A chance for us to meet and chat about what’s working and what’s not on our team.

The goal is to help us all work better together and ensure you’re happy and successful working here.

This is meant to be a conversation. I’ll bring a few questions for you, and if there’s anything you’d like to discuss, we’ll start with that. Ideas for improving your team, observations you think I should know about, and feedback on your manager are all good topics. I’m also happy to answer any questions you have for me.

If this time is not convenient, please don’t hesitate to suggest another.

I look forward to talking with you!

Questions for skip 1:1s

The following are some ideas for questions to ask in skip 1:1s:

Organizational Strategy and Processes:

• What should the organization start doing?
• What should the organization stop doing?
• What should the organization continue doing?
• Are there any process improvements we should consider?
• Are there any opportunities we might be missing?
• Are there any areas of the business strategy you don’t understand?
• What should I know about?

Team Dynamics and Collaboration:

• How do you feel about the communication in your team and the broader organization?
• Is this team working poorly with any other team?
• What do you need from your peers?
• Who on your team has been doing well recently?

Individual Performance and Satisfaction:

• Do you feel you get appropriate recognition when you do a great job?
• Do you have the training & resources to improve?
• What are the biggest time wasters for you each week?
• What’s keeping you from doing your best work right now? Are there resources or tools you need that you’re currently not getting?
• How happy (or not) are you working at the company?
• Do you see yourself working at our company in three years?
• What do you like best/worst about the project you are working on?

Managerial Relationship and Feedback:

• If you were the team leader, what would you focus on (or do more of) and why?
• Do you have any feedback about your manager—what’s going well and what isn’t?
• Is your manager giving you enough feedback?
• How often does your manager cancel 1:1s?

Open-Ended Questions:

What’s on your mind? What questions haven’t I asked that you wish I would?

References

• What are Skip Level Meetings? (+8 Skip Level Meeting Tips)k
• Getting the most out of skip-level 1:1s | by Michael Boufford | Medium
• 4 Pitfalls of Skip-Level Meetings | by marc davis | Medium

Giving feedback is a core responsibility of any leader. But it can be surprisingly easy to convince yourself not to do it—especially if you are empathetic and caring. (Both great qualities!) Every leader has shied away from saying the necessary thing at times. It can be incredibly uncomfortable!

Genuinely caring about your people and their success, and using that care to build a relationship on a foundation of mutual trust, is the hallmark of a great manager. Giving difficult feedback is not only 100% compatible with achieving that—it’s required.

Here’s what we tell ourselves to let ourselves off the hook:

1. Feedback is a confrontation

Feedback that works is anchored in humility and a desire to help. Effective leaders rely on feedback to help team members better understand their strengths and areas for improvement—approach feedback with the mindset that you offer a valuable perspective to aid your colleague’s growth. Great feedback opens up discussion rather than closing it down.

On the other hand, if you are angry, don’t give feedback. Then it will be a confrontation. And it won’t work.

2. Feedback is criticism or blame

Great feedback doesn’t litigate the past—it creates a better future. It builds conditions for improved performance by encouraging effective behavior. When you withhold difficult feedback, you deny your team member an opportunity to learn.

3. Feedback is uncaring

Managers often equate negative feedback with not caring, but giving negative feedback demonstrates that you care enough about your people to help them improve. When you give feedback, show that you genuinely care about the person as an individual while challenging them to improve. Be direct yet compassionate. Feedback is an essential tool to help your people grow, achieve their potential, and advance professionally in their careers. Withholding it is apathy.

4. Feedback makes the other person feel bad

It might, in the short run! But ultimately, helpful feedback is kindness. Feedback delivered with genuine good intent helps your team members understand how they can do better—which can positively impact their career.

Be willing to put your team members into mild, temporary discomfort to extend their reach beyond their grasp. There is supposed to be some stress associated with urgency and working to achieve difficult things. Your job is to challenge your people and lead them through discomfort into deep, long-lasting pride of accomplishment.

Put another way: Your job is not to make your people happy. It’s not possible. You can create an environment of kindness, respect, psychological safety, and achievement. But happiness is ultimately up to them.

5. Feedback creates resentment

Real resentment comes from not receiving helpful feedback that could have helped the individual improve and succeed. But by providing constructive feedback, you can prevent future issues and frustrations—and open up new opportunities.

6. Feedback damages your relationships

Managers often worry that giving difficult feedback will damage their relationships. But if you’ve invested the time in building solid relationships and genuinely care, the opposite is true. Honest feedback builds trust. People appreciate and respect leaders who are transparent about areas for improvement. Not giving clear and direct feedback can lead to misunderstandings that turn minor issues into larger ones.

7. Feedback demotivates

It’s true that poorly delivered feedback can demotivate. But for your best people, well-structured and thoughtfully conveyed feedback is a positive challenge to improvement.

8. I might be wrong

No leader has all the answers, and no one expects you to. Giving feedback isn’t about being infallible but sharing your perspective based on observations and experiences. Speak with humility but be confident in your convictions. Your company has entrusted you to lead people for a reason.

We had an internal culture of counting the passage of time from Day 0, the day (in California) we started working on the project. We made the first calls and published our first vaccine availability on Day 1. I instituted this little meme mostly to keep up the perception of urgency among everyone.

We repeated a mantra: Every day matters. Every dose matters.

Where other orgs would say, ‘Yeah I think we can have a meeting about that this coming Monday,’ I would say, ‘It is Day 4. On what day do you expect this to ship?’ and if told you would have your first meeting on Day 8, would ask, ‘Is there a reason that meeting could not be on Day 4 so that this could ship no later than Day 5?’

I started every meeting and status report to the team by reminding them what Day it was. Our internal stats dashboard had a counter of what Day it was. I had a whiteboard in my apartment showing what Day it was. I wrote that every morning as soon as I woke up, and updated the other two numbers right before I went to sleep. Those were: the number of locations we had published to Californians where they could currently get the vaccine, and the number we knew about elsewhere across the United States with the vaccine.

The latter was zero at this point, of course. I brushed my teeth, wrote my emails, ate my meals, did media interviews, called my family, negotiated with funders, and said my prayers with the zero where I could see it.

From The story of VaccinateCA.

A lot of people think of Twitter as a public utility, a public trust, “the town square,” a company with an important social mission that many of its users and employees and Elon Musk care about deeply. And its CEO and board of directors essentially can’t bring themselves to talk about it. When employees asked him about what was best for the company, Agrawal could talk only about the shareholders. Elon Musk is not at all embarrassed to say that Twitter has an important public mission, which is why he’s buying it. But its current management can’t say that, which is why they’re selling it.

I want to be clear here that I am not saying that it was a bad decision, for Twitter’s product or users, to sell to Elon Musk. I have no idea; that’s not the point. The point is that the board seems to have put almost no weight on these questions. … I have written this before, but the basic problem with Twitter’s management and board of directors seems to be that they do not care about Twitter, as a company or as a product, so they are left to care about shareholders. This seems bad for everyone, including shareholders.

There are a lot of tech companies whose CEOs do not think this way. They are not all companies with “other legal mechanics,” as Agrawal said: Tesla Inc. and Amazon.com Inc. do not have dual-class stocks, and Elon Musk and Jeff Bezos have exactly the same duties to their shareholders as Agrawal has to his. But what Tesla and Amazon have are executives and boards who believe in what they are doing, and shareholders who trust them to pursue a long-term vision. If you ask Elon Musk about his decision-making, he would never say “Tesla is a public company owned by shareholders and I just try to maximize their profits.” He would talk about his master plan to decarbonize the world, he would talk about self-driving cars and rockets and tunnels. He cares about the product, not the shareholders. That’s why Musk’s shareholders are rich, and why Bezos’s are, and why Twitter’s are selling at $54.20.

From Matt Levine, Twitter’s Board Gave Up.

As an engineering leader, it’s important to remind your team that moving fast doesn’t mean working harder, or longer, or on the weekends. And it definitely doesn’t mean releasing a perfect product from day one. It requires cutting scope, iterating over time, and being more at ease with putting out a feature that’s not fully baked in order to learn what customers want.

You’re not going to get everything right from the outset, and that’s okay. The goal is to learn as you go: formulate a hypothesis, establish metrics, derisk, gather feedback, iterate, rinse, and repeat. Once you embrace the uncertainty, working on finding product-market fit isn’t just a challenge, but a thrill.

From Planning in the Dark: Planning for Product-Market Fit - Increment.

The already classic scene in which Paul wrenches the chorus to Get Back out of himself shows us, not just a moment of inspiration, but how the group pick up on what is not an obviously promising fragment and begin the process of turning it into a song. In the days to follow, they keep going at it, day after day, run-through after run-through, chipping away, laboriously sculpting the song into something that seems, in its final form, perfectly effortless. As viewers, we get bored of seeing them rehearse it and we see only some of it: on January 23rd alone they ran it through 43 times. The Beatles don’t know, during this long process, what we know - that they’re creating a song that millions of people will sing and move to for decades to come. For all they know, it might be Shit Takes all the way down. But they keep going, changing the lyrics, making small decision after small decision - when the chorus comes in, where to put the guitar solos, when to syncopate the beat, how to play the intro - in the blind faith that somewhere, hundreds of decisions down the line, a Beatles song worthy of the name will emerge.

A good song or album - or novel or painting - seems authoritative and inevitable, as if it just had to be that way, but it rarely feels like that to the people making it. Art involves a kind of conjuring trick in which the artist conceals her false starts, her procrastination, her self-doubts, her confusion, behind the finished article. The Beatles did so well at effacing their efforts that we are suspicious they actually had to make any, which is why the words “magic” and “genius” get used so much around them. A work of genius inspires awe in a lesser artist, but it’s not necessarily inspiring. In Get Back, we are allowed into The Beatles’ process. We see the mess; we live the boredom. We watch them struggle, and somehow it doesn’t diminish the magic at all.

From The Banality of Genius: Notes on Peter Jackson’s Get Back.

A recurring bug in many leaders’ operating systems—including mine—is overlooking just how much useful context a leader can have than folks on their team.

A regular practice I’ve adopted is sending a brief, five-minute weekly video communication to my team. The weekly comms, in fact, has been a long tradition in my org predating me that I have continued. Having been on both the receiving and sending end of the regular weekly comms, I’ve come to believe that this is a critical leadership activity on a growing team.

Information dissemination is a core responsibility of a leader. Leaders have access to a huge amount of information that most individuals on the team do not. Why is Sales hiring so much? Why did we decide to work on X instead of Y? What exactly is Marketing working on? By communicating habitually with my entire team, I can tell them what is going on, why it is going on, and critically, reinforce core cultural values.

The format

My weekly comms consist of an informal 5-8 minute video and transcript, published internally and announced on our internal all-company listserv. I record a video for a few reasons:

1. There are people willing to watch a video but not read an email.
2. It feels more personal and creates a bit of face-to-face connection on a distributed team.
3. It is easier.

The last bit is surprising. It surprised me, at first, and would not have been true a year ago. But now I am practiced at talking to a camera and have a good video setup that I use every day. Another factor is some excellent software called Descript that makes it simple to edit video and create transcripts. It feels like a magical advance in video editing.

I’m someone who obsesses over word choice, so I’ve found it easier to bang out a video script because I don’t worry as much about polishing it to the same extent as a stand-alone document. In the past, I tried to write a weekly email in the same format, but I was never consistent. It always felt like too much work. Recording a video is more sustainable.

I record in one take.

In practice, about one-third of the team watches the video, and one-third read the transcript, for about 2/3 total penetration.

What I talk about

• Welcoming new team members.
• Acknowledging major, company-impacting accomplishments.
• Acknowledging significant accomplishments that can fly under the radar of the business. Things like open source contributions, technical debt paid off, continuing iterative improvements after a big-bang launch.
• Announcing new policies.
• Connecting revenue numbers with project initiatives, site traffic, major closed deals, etc.
• Project team spin ups and spin downs.

A regular weekly comms is a great way to get a consistent message out to the entire team at once.

The habit

The key to making this work is forming a habit. If I wait until Friday morning to sit down in front of an empty text editor, I create lots of head-scratching and not much writing.

So on Monday, I create an empty document for the week that will serve as a script and transcript of the recording. I leave it open all week. On the side, I keep a running document of possible, non-time-sensitive topics to cover or topics that didn’t make it into the previous week.

Throughout the week, as I learn things from leaders on the team or hear of any information that needs to be flowed down, I capture that in the script as a quick bullet point.

On Friday morning, I write a quick draft and often send it to a few people for a quick review. Their feedback is critical—it’s a quick check to make sure I’m communicating what I mean. It is especially important to ensure I acknowledge the right people for accomplishments and don’t leave anyone out.

Then I record, almost always in one take. My assistant edits the video, exports, and then I Slack and email it to the team.

I dedicate 1.5 hours to my weekly video. Is this a lot of work? Yes. Is it worth it? Also yes. It is a chance to acknowledge efforts that could go unnoticed. It is a direct conduit to people on my team. It also makes me a better listener. Consistently creating a weekly comms puts me in a mindset of asking questions like “Is this important?” “Is it important for the team to know?” And critically, “what culture values can I communicate and reinforce?” It gets me out of my own head. It makes me a better, more informed leader.

What you talk about is what gets thought about

The weekly comms is a nudge. Done well, it can consistently and subtly shift the conversation in a positive direction. The weekly comms is an opportunity to create a story around the team and give it purpose.

References and further reading

• Week in Review Leadership Comms | Lara Hogan
• Sending weekly 5-15 updates. | Irrational Exuberance

Groups of technically oriented people often want to optimize the work process to those activities needed for the technically oriented output, and overlook those that are focused on the needs of humans and groups of humans working together. Yes, you can have a standup and not get any value from it. You can also not have a standup and avoid providing a convenient mechanism for taking advantage of the differences in observation, interpretation, and significance made by the entire team.

If you’ve got a really good team facilitator, they’ll likely notice this and help bring it out. If they’re really excellent, they’ll convince the team to work in a fashion where it can more easily come out without them acting as a middleman to make it happen. They might use a simple technique such as a daily standup to create such an opportunity.

From George Dinwiddie’s blog » Daily Stand-Up Meetings. Reflects my background suspicion of the efficacy of Slack “standups.”

… most decisions should probably be made with somewhere around 70% of the information you wish you had. If you wait for 90%, in most cases, you’re probably being slow. Plus, either way, you need to be good at quickly recognizing and correcting bad decisions. If you’re good at course correcting, being wrong may be less costly than you think, whereas being slow is going to be expensive for sure.

Yes, I’m quoting Jeff Bezos’ 2016 Letter to Amazon Shareholders again. This quote is referenced in Working Backwards, which I’ve added to my recommended reading for engineering managers.

Pair with Making the decision right.