Challenging Situations: Delivering Bad News

We all have times when we have to deliver bad news to our teams. Maybe the company is having layoffs. Maybe the team is being disbanded in order to give more support to other projects, and everyone is being scattered onto other teams. Perhaps there’s a policy change that you know will be unpopular. Those roadmap changes we just talked about sometimes fall into this category as well. You, the manager, have to be the messenger and deliver this news, but you know the team isn’t going to be happy.

What do you do in this situation? Well, communication is key. As a person in senior leadership, you’ll need to excel at communicating sensitive information to large groups. Here are a few dos and don’ts:

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. Your team deserves to hear the message coming from your mouth directly, and without you to guide the message, you can expect some misunderstandings and bubbling animosity. That being said, 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. You may think that trying to communicate bad news to everyone at once is the best way to keep it from spreading before everyone has heard it, but the result is still impersonal. It’s hard to see everyone’s reaction, and one or two deeply unhappy members can quickly rile up the whole team before the message has had the chance to sink in.
Do talk to individuals as much as possible. Instead of impersonal or group-based communication, try your best to talk to people individually about the news. Think about the people who are going to have the strongest reaction, and try to tailor the news to them. Give them space one-on-one to react, to ask questions, to get it straight from you. 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. In a case where you need to get the message out to your whole organization, talk to your managers first, give them talking points, and then let them share with their teams before bringing the whole group together.
Don’t force yourself to deliver a message you can’t stand behind. You may have a hard time delivering this news because you don’t like it yourself. Maybe you violently disagree with the policy change. Maybe you hate the fact that the team is being split up. If 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. Perhaps you ask another executive to step in, or maybe someone from HR. Depending on the size of your team, you can deliver the information to a trusted lieutenant and have that person help to share 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.
Do be honest about the likely outcomes. The more you can commit to the direction specified by the news yourself, the easier this will be. If there are layoffs, acknowledge that this process is not fun but that everyone needs the company to survive. If a team is being disbanded, feel free to point out both the accomplishments of the team up to this point and the changes that make this the right path forward, and emphasize that there are many new opportunities now for learning and growth. Being forthright with people will help them trust you more and make them more likely to tolerate the unhappy news well.
Do think about how you would like to be told. One piece of news that you may have to deliver someday is the news of your leaving. In fact, you’ve probably had the experience of resigning from a job already, or moving from one team to another. How did you communicate that news? Did you send a memo? Well, maybe to HR, but to the rest of the team you probably pulled people aside to tell them face-to-face if you thought they would want to know before it was public. You may have had a going-away party, written a farewell letter, or given a final lecture to the team about what you learned in your time at the company. It’s OK in some circumstances to celebrate these sad changes, so long as you can do it with grace. All of these lessons apply to delivering hard news to your team.

Ask the CTO: I Have a Nontechnical Boss

This is the first time I’ve ever had a boss who was nontechnical, and it’s turning out to be really hard. How do I effectively manage this relationship?

The first time I ever experienced a fully nontechnical manager was when I started reporting to the CEO at Rent the Runway. Reporting to a nontechnical manager can be a total culture clash. Fortunately, a few best practices will help you manage this relationship:

Don’t hide information behind jargon, and be careful with details. Your new boss is probably very smart, but he may not have the patience for technical jargon, and it is very unlikely that he wants to hear a ton of details about nuanced technical decisions. Part of this process is learning to distinguish the type of information that is valuable to communicate from the type that is not.
Expect that you will need to run your 1-1s with your new boss, so come prepared with a list of topics. Busy executives can be frustratingly hard to pin down; even getting 1-1 time is a challenge, so don’t waste the time you have. Up until now you may have expected both parties to bring some specific topics to the meeting, but that won’t necessarily be the case now, so always come prepared. 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. In the case that you have a CEO who doesn’t want to hear too much about problems, respect that you’re not going to get much coaching from him on the management side of things, and find another person to get that from. With that said, don’t shy away from delivering bad news.
Ask for advice. It sounds contrary to my advice to bring solutions, but nothing shows respect like asking for someone’s advice. Your boss may not want to be stuck solving your problems, but you can bet that she’ll be happy to provide feedback if you phrase it as needing advice.
Don’t be afraid to repeat yourself. If you’ve brought up an important issue that seems to have been forgotten, bring it up again if it’s really important. You may have to do this a few times before you get any traction. Three times is often the magic number.
Be supportive. Always ask if there is more you can be doing to help. As much as you can, show that you are there to support your boss and the company.
Actively look for coaching and skill development in other places. You no longer have a manager; you have a boss. You probably still need to work on some skill development the first time you work in a senior leadership position, so get a coach, ask for training, and create a peer group outside of the company to support you through this brave new world.