Lesson #12: How to manage surprises from above

May 11, 2023

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I’m glad you’re here!

First off, some news!

I’m launching a course on Engineering Management! You can sign up for the waitlist here. I’m preparing the curriculum for this course now.

How to manage surprises from above

Since I started this newsletter, I’ve mostly focused on communicating with your direct reports and peers. For the next 2-3 newsletters, I’ll be discussing how to communicate up to senior leadership. I feel like this is an area that is often overlooked and under-practiced.

Let’s start with a hypothetical situation (that surely has never ever ever happened at your company):

You’re midway through a quarter and things are going great. You’re working well with your PM counterpart, your engineers are crushing their bi-weekly sprint tickets, and your customers are super happy.
Then comes the wrinkle. (There’s always a wrinkle, right?)
You have a new directive coming down from senior leadership that is going to require your team to completely shift priorities for the remainder of the quarter. Some originally planned items aren’t going to get done, or perhaps will stop mid-work stream. And you, my friend, are the one who will be communicating this to your team. You know they’re not going to like it. Hell, you don’t like it either.

What do you do?

Senior leadership at times needs to make decisions that affect an entire organization, such as a reorganization or a change in product direction. If you disagree with this decision, or you know your team won’t be happy (or maybe both), the first thing to remember is that decisions are often made with more information than you currently have. You likely don’t have the full window into the “why” of a request - which means your first directive is to ask for more context.

Next, speak up. Communicating effectively with senior leadership (or anyone above you in any direction) requires a healthy debate and being able to clearly state your case. Leading in from my first point, it's essential not to go on the attack—gain understanding first and start off this conversation stating that you have some concerns about the decision being made. Make it a conversation rather than an argument, and gain as much business context as you can. This will hopefully guide you to better defining the “why” so you can form a more educated opinion on the matter. You may not still like the decision being made, but you at least have context you can share with your team.

Here’s the most important part: as a leader, you will sometimes have to make the most out of situations even if you don’t fully agree. The reason for this is two-fold: your team needs to see that you’re bought in (as much as you can be) on the decision at hand, and you are setting an example for your team to follow. It can be a challenging position to be in, but it's essential to be a strong advocate for your organization as well as the company’s overarching direction and ensure that everyone is on the same page. Your team is watching and learning how you’re reacting, and you will have an impact on the overall morale of your team.

I’ll be honest—this sort of conversation is never easy as an early leader, and it something I see even in mid- or later-stage managers where they struggle with this type of communication. It’s equal parts careful confrontation, debate, deliverer of (sometimes bad) news, and cheerleader. It’s also one of the key skills that can really build you into becoming a great leader.

What I’m reading

I’m… still reading High Output Management. My husband is quietly scolding me for getting past the “boring part” (breakfast factory) and then putting it down before reaching the fun part (whatever else comes after the breakfast factory, which I will hopefully discover soon).

Check out the full book list for recommendations and an ever-growing reading list.

Note: Links to books in this section are affiliate links to help support the purchase of the rest of my books :)

What I’m working on

I made it through performance review season, I have fewer people reporting to me now, and I have (whispering because I don’t want to disturb it) a lot more free time on my calendar, which is mostly being spent buried in the depths of Salesforce as I look ahead for the next 6-12 months.

I’m also hiring a lot! I’ll be back in Poland next month so if you’re in the Warsaw area, I’d love to meet up for a coffee :)

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