Learning by Shipping

Staying connected to your skip level manger and she staying connected to you are valuable for the project, the team, and each of your ongoing development.  Rigorously and consistently making the most of skip-levels, whether as the manager or individual employee, is an important skill to master.  This post looks at one-on-ones from the perspective of the manager with some tips for the employee/individual.

Time pivot, becoming a manager

One day in your career you might come to work and it will be your first day as a new manager. Many things will seem different. All of a sudden you not only feel responsible for code and features, but you’ve taken on a new responsibility for people. For those that you now manage, a new set of demands are placed on your time. One-on-ones are a key tool for you as a new manager.

One-on-ones are the most precious time you can spend with members of the team—your new direct reports. Much has been written about how to “have a good one-on-one” or techniques for making the most of the time (there is a post in our One Strategy book or check out Ben Horowitz’s nice post).  I’m a firm believer that 1:1s are the most important of all scale management tools.

The easiest thing to remember about a 1:1 is that as a manager the meeting is not for you but for the employee. Your opportunity to learn is based on the topics raised and questions asked by the member of the team, only asking questions to draw out the issues if necessary. The first sign of a struggling management chain is when employees on the team start to see one-on-ones as being called to the carpet on a regular basis or when managers view a one-on-one as their time to manage the project or to be the keeper of the agenda.

As a manager, the notion that your time is no longer your own, but is there to serve the folks on your team is significant pivot, and somewhat counter-intuitive. You might have a manager you feel “takes up too much of your time” or you might be thinking “I have real work to do instead of sitting here”. You might be worried about all you need to get done as a team and react by asking more (or too much) of your new direct reports. In other words you’re in for a bit of learning about how you now manage your time, in addition to how you manage your own work and the role of management.  So you aspire to do better when you’re on the other side of the table, and effectively using 1:1s is a key step.

As a first step of this new journey, consider how you can live up to the mantra that your role is to take up as little time as possible from your direct reports. This only benefits the organization as a whole because there will be more time for work, fewer meetings, and overall more time building products. The 1:1 is your request for time, but how you turn that into a benefit for the member of the team makes it valuable and not a manager tax.

A rule of thumb you might follow is don’t ask anyone to do things for you, but ask folks what they could do that helps them get the work done they believe they are supposed to do. In other words, status reports, project reviews, and statistics may all be valuable, but only if the folks on the team decide that on their own.

At the same time, 1:1s are a key tool to get a pulse on the team and on the work of folks on the team. Through an unstructured two-way dialog you can likely learn more about what is going on than you can from status reports or other outputs open to obfuscation, unintentional or not. So spend the energy to make your way over to your direct report’s desk, meet there, and let he/she set the agenda.

When your work is operating from a shared view of the goals and open and honest communication is encouraged, there’s a very good chance challenges and issues will find you rather than you needing to ferret them out. If you’re finding you are surprised by issues, then dig into the root cause before falling back on asking folks to spend more time telling you what might be happening.

When you take on the role of managing managers, presumably you have found this balance for one level of management.  As a new manager of managers, your ability to stay connected to the work is critical but the challenge is much more difficult.  You might react by falling into the traps you worked hard to avoid as a new line manager.  You might feel that your need to stay connected or to drive strategy trumps the need for a skip level manager to be heard, to be listened to, and to be treated just like you would like to be treated.

Skip-level 1:1s

One-on-ones with your direct reports (fellow managers) will not likely feel like enough to get a sense of the project if you’re in the position of managing other managers. A wonderful tool to learn even more about the team is to just continue having 1:1s on the team, but with the direct reports of your direct reports. Personally, I have always found this part of management to be the very best way to learn more about your own team and an incredibly wise investment to make for a number of reasons.

A skip-level 1:1 is exactly like a 1:1 with a direct report in terms of approach. There is no preparation required. The member of the team is not being called to the carpet. The focus is whatever the member of the team wants it to be. Your role as a manager is to listen, perhaps ask a few guiding questions, and to learn by listening.

In fact, the most important part of a skip-level 1:1 is to avoid “making news” or “solving problems”. If something comes up in the meeting that is a surprise, use this as a chance to ask questions and to make sure the member of the team is engaged in addressing the issue through the management in place. A skip-level is not an opportunity for escalation, no more than it is an opportunity to search for decisions you can make or problems you can solve. If someone leaves a 1:1 thinking you decided something or changed course, then that is a good chance to ask yourself if you were stepping on the toes of your direct report.

You might find it helpful to be systematic with skip level 1:1s and work to meet each of your skip level folks once-per month/quarter/year depending on the size of your organization. If you manage a team of 100, it should be possible to have a skip level with every member of the whole team yearly. More than that and you will probably want to structure your skip-levels to include only your directs of directs, perhaps every six months.  It can help to have skip-level meetings take place during specific times in the project when they might make most sense (just before or after a milestone for example). As a suggestion, don’t define “skip level 1:1 days (weeks)” as the assembly line can be a bit off-putting to some, especially if scheduled back to back. You might consider a “head’s up” mail with a skip level invitation just so folks don’t panic :-)

It is important to be consistent in the implementation. In other words, it is important to meet with the same frequency and duration with each of the folks. Don’t short change employees that might be further away, in slightly different projects, or just on areas you might find less in need. The more senior you are the more important this consistency becomes as the team looks for signals of your priorities based on who you spend time with.

My own view is that skip levels are so important that I would routinely spend 15% of scheduled meetings in a year in skip level 1:1s. Some find this a surprising use of time given how much might be going on. The reality is that a consistent approach to meeting with people across a team you manage can offer a unique lens on what is going on. It also affords an opportunity for you to reinforce the work you might have been doing with respect to accountability, decision making, and rhythm of the team.

Some topics

For a skip level 1:1, just as with a regular 1:1, the topics are driven by the attendee and not you. Just as with direct reports, some folks will show up with a long list of topics (or questions). Others will show up assuming you have an agenda. And probably everything in between is possible. Regardless, your role is to facilitate the member of team opening up, to reduce the potential stress of the situation, and to reassure the member of the team that this meeting is not a career moment.  This starts with you showing up in the office of the employee, not summoning, the employee to your office.

This latter point is critical. A skip level 1:1 is not a meeting to pass judgment or to evaluate performance, just as it is not a time for “new business”. Folks should know this. While one of you might believe that the meeting should be “confidential”, you should be cautious with that sort of dynamic, not just for skip-levels but in general. Confidentiality is important for matters of personnel but is usually counter-productive when managing a project. If someone requests confidentiality for a personnel issue, it should be handled in the appropriate manner.

If a person shows up with a long list, sometimes it is fine to allow them to work through it. It might also be a good idea to “pace” the dialog and start off by asking “what’s on your mind?” or “how are things going?” In a first 1:1, if you don’t have a history with the member of the team, why not use the time to learn more about each other’s background (as appropriate) and to reciprocate?

There’s likely going to be some interest in hearing answers “from your perspective” – “how are things going”, “did you hear about…”, “what do you think…”? That is interest in topics that are perceived to be talked about at some higher level on the team. It is great to spend some time on those, though it is worth considering how you can put those topics in the context of the project rather than just gossip.

For a larger organization, there’s a benefit to spending time in skip-level dialogs on the efficacy of the work environment. Asking questions about the velocity of code, collaboration, getting things done, and so on. In any organization of size, a manager of managers is where action can (and should) be taken to avoid the perils of a stagnating organization.

Similarly, topics that will surely come up will be related to processes that are corporate wide (compensation, recruiting, and so on). It is probably a good idea to be extra careful about “making news” in how you discuss these—that is different than being guarded and evasive—by focusing on the information previously discussed broadly with the team. You might learn something wasn’t clear, in which case there’s a chance to clear things up for the whole set of folks in a consistent manner.

During different phases of the project, it is great to enable a discussion about that—feedback on pre-release, design challenges, ramping up, and so on.

If you’re the individual

A skip-level 1:1 is a great time to offer your perspectives on what is going well and not.  There’s a fine line between offering up all the potentially bad news and sounding like you’re setting expectations, and polishing up all the potentially good news and sounding like you’re showing off.  You have to be the judge.  A few other potential tips/topics:

• Use right level of detail.  Speak the truth and what you know, but match the level of detail that your skip level manager will find valuable.  Keep in mind no matter how hands on the manager is, you have a lot more detail in your head :-)
• Ask clarifying questions.  Managers often have a tough time with “what is that” or “no I don’t understand” so don’t be afraid to ask questions clarifying if you were clear.  Feel free to volunteer to expand acronyms or code names, rather than assume a deep knowledge (without sounding too pedantic).
• Discuss cross-group, collaboration, partnerships.  There’s a good chance your skip level manager is pretty tuned in and curious as to how things you are working on contribute to cross-team initiatives.  Consider focusing on those topics and if you do, just speak the truth as if your partner is sitting right there with you.
• Limit strategy.  There’s a time and place for strategy.  While you might be tempted to use the time for big strategy topics, this might not further your goals much and might not be the best use of time. Spend the time thinking about how you could help your contribution to the project with insights and information.
• Don’t make news.  It is probably not a good idea to “make news” in this discussion–news about the project, you, or feedback about team/people.  You might want to resist the urge to share something for the very first time in this forum and certainly not something you would not share with your manager as if she was sitting right there.  If you have candid feedback on your manager, then be clear about what you’re doing and don’t conflate that with the rest of the meeting topics.

Above all, make the most of the time to make sure your skip-level manager is familiar with you and your work in a neutral and constructive way.

When used consistently and effectively, skip-level 1:1s are a great, two-way tool for both of you and the team.

–Steven

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