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April 17 - May 2, 2021
People who are good at managing a single team, or even a couple of related teams, fall apart when asked to manage managers, or teams that are outside of their skill set.
I’ve discussed getting uncomfortable before, but this is a place where you need to find your discomfort, chase it down, and sit with it unblinking for a while.
It’s so easy to take this position and assume that it’s just more of what you were doing before, but that’s a mistake. This position is the first level in a much bigger game, the entrée into senior leadership and upper management, and that will require a large number of new skills.
There exists an idea that if you make yourself accessible, hold office hours where anyone can meet with you, and tell the team that you are always available, people will naturally bring their problems to your office.
Except this basically never happens.
you must make the time to proactively hold skip-level meetings with the people who report to your direct reports.
What is a skip-level meeting? Put briefly, it is a meeting with people who report to people who report to you.
One form of skip-level meeting is a short 1-1 meeting, held perhaps once a quarter, between the head of an organization and each person in that organization. This tactic accomplishes a couple of things. It creates at least a surface-level personal relationship between you and everyone in your organization, which keeps you from viewing them as “resources” instead of human beings (something that is a risk in managing large organizations).
Whether you have experienced managers or first-timers reporting to you, there is one universal goal for these relationships: they should make your life easier. Your managers should allow you to spend more time on the bigger picture, and less time on the details of any one team.
By trying to make everyone happy, people pleasers often burn themselves out.
You might think people pleasers create teams that feel safe to be vulnerable and fail, but in fact the opposite is true.
Use skip-level meetings to help you detect areas where you need to support your new manager fully, and let her know that you’ll be holding skip-levels frequently as you help to guide her most effectively.
Keep an eye on your new managers. You may need to provide not only coaching but strong corrective feedback in the first six months.
Experienced managers will have different ideas about management than you do, and you’ll have to work out the differences. Working out these differences, however, is different than letting the manager do whatever he thinks is best.
Hiring for managers is a multipart exercise, and those parts are actually very similar to those of a good engineering interview process. First, make sure that the person has the skills you need. Second, make sure that she’s a culture match for your organization.
The biggest difference between a management interview and an engineering interview is that managers can, theoretically, bullshit you more easily.
Boring meetings are a sign. They may be a sign of inefficient planning on the part of the organizers.
If people are afraid to disagree or bring up issues for fear of dealing with conflict, or if managers always shut down conflict without letting disagreements air, this is a sign of an unhealthy team culture.
In almost every model of motivation, people need to feel an understanding and connection with the purpose of their work.
Sometimes patiently reminding the other person that things are going as fast as they can and everything is on schedule is the only solution.
Finally, don’t be afraid to work with your managers, tech leads, and the business to cut scope toward the ends of projects in order to make important deadlines. As the senior manager, you may need to play tiebreaker and make decisions about which features are worth cutting, and which features are essential to the project’s success.
Changes in strategy are where being stuck in “middle management” feels the most unpleasant. You may have very little ability to push back on the changes to strategy coming from above, and even when you’ve promised your team that certain projects will happen, you sometimes have to pull back on that promise because of unexpected changes. This makes the team unhappy, and they complain to you. Because you have no ability to do much about it, you can feel like it exposes you as powerless, and your team might feel that they’re being treated not as humans, but as cogs in the corporate machine.
Dedicate 20% of your team’s schedule to “sustaining engineering.”
The calmer you can be in the face of these changes, and the better you can show (or fake) enthusiasm for the new direction, the easier the transition will be for your whole team.
Foster a network of technical people outside of your company. The best stories are the ones that come from people you trust. Keeping up a network of peers in engineering and engineering management gives you people to ask for opinions on new trends.
You’re capable of making hard decisions without perfect information and willing to face the consequences of those decisions.
as anyone who has spent a lot of time managing can tell you, making decisions is one of the most draining and stressful parts of the job.
The VP is usually at the top of the management career ladder for engineers. This generally means that the VP is expected to be an experienced manager of people, projects, teams, and departments.
The people I know who excel in this role are capable engineers who care deeply about their teams and prefer to stay out of the spotlight in favor of creating high-performing organizations.
My advice for aspiring CTOs is to remember that it’s a business strategy job first and foremost. It’s also a management job. If you don’t care about the business your company is running — if you’re not willing to take ultimate responsibility for having a large team of people effectively attacking that business — then CTO is not the job for you.
People generally don’t enjoy being pulled off of what they’re working on for a new executive whim, especially if they believe their current work is important.
The more senior the management and leadership position you take in a company, the more the job becomes making sure that the organization moves in the direction it needs to move in, and that includes changing direction when needed.
Finally, never underestimate how many times and how many ways something needs to be said before it sinks in. Communication in a large organization is hard. In my experience, most people need to hear something at least three times before it really sinks in.
When you want your boss to act on something, expect that you’ll need to tell him the same thing three times before he actually listens.
It’s not uncommon for company boards to read through the slide deck before a meeting, so that the meetings can be focused more on details than on presentations. I didn’t understand this at the time, so I wasted a lot of energy trying to make something that wasn’t informative on paper.
Don’t blast an impersonal message to a large group. The worst way to communicate bad news is via impersonal mediums like email and chat, especially mediums with commenting abilities.
the second-worst way to deliver this message, especially to a large group that you know won’t be happy, is with them all in a room at once.
Instead of impersonal or group-based communication, try your best to talk to people individually about the news.
And as necessary, make it clear that these are the marching orders and that you need your people to be on board with the changes, even if they don’t love them.
Don’t force yourself to deliver a message you can’t stand behind.
you absolutely can’t deliver the news in a way that won’t betray your strong disagreement, you might need to have someone else help you deliver it.
As someone in senior leadership, you have to learn how to maturely handle decisions you don’t agree with, but that doesn’t mean you have to go it alone.
If you’re having trouble getting your 1-1 time honored, send the agenda in advance to remind your boss that you need her attention — and it never hurts to be on good terms with the executive assistant who manages her calendar!
Try to bring solutions, not problems to be solved. CEOs generally do not want to hear about how things are failing, nor do they want to hear about your disagreements with your peers or your troubles managing.
Senior leaders, more than any other group in a company, must actively practice first-team focus
They are dedicated first and foremost to the business and its success, and secondly to the success of their departments as a way of contributing to the overall business success.
A very common clash occurs between people who are extremely analytically driven and those who are more creatively or intuitively focused.
You have to figure out how to understand and trust everyone’s styles across the spectrum.
It can’t be said strongly enough: your peers who are not analytically driven are not stupid.
Once a decision is made, we commit to that decision and put on a united front in front of our engineering teams and anyone else in the company.
