Being the Bearer of Bad News

Last night we had another monthly Engineering Leadership Roundtable, where the topic was “Communicating Bad News Upwards and Downwards”. As usual, we brainstormed a full board of topics based on challenges we were currently facing or had recently solved. Once we had enough, we voted on our favorites and started the discussion!

Here are a few bits of wisdom and inspiration that we uncovered:

Topic: Setting up culture so your team can deliver bad news to you

Our discussion centered on ways to create a culture of learning, where talking about failure is normalized and people aren’t punished for voicing issues.

Some signals that things are going badly:

• If a leader feels like their team cannot make decisions on their own, the leader is probably punishing people for making the wrong decision, instead of helping them grow.
• Bad team relationships can come from a bad interaction early on. For example, if a new engineer gets a code review that is mean and personal, they might not trust their teammate going forward.

A few ideas that have worked in the past:

• “Celebrate failure” — when something goes wrong, reinforce the value of bringing it up and discussing it in detail to learn from it.
• Leaders need to admit their mistakes and be vulnerable on a regular basis. A leader who deflects blame will create a team that does the same.
• Bad news should always come with a solution. One suggestion is to ask for “3 suggestions and a recommendation” whenever a problem is raised.
• Leaders need to project calm when things go badly, to help team members keep a level head while finding solutions.

Sometimes your team raises bad news that doesn’t have a workable solution

• Gather as much information as possible. Prepare to represent your team to the rest of the org.
• A structured process for bad news helps. Documenting conversations lets you synthesize information across time, and structuring followups makes sure things don’t fester.
• Having a separate place and time for bad news (e.g. spring planning, retrospectives) lets people get into the right headspace and encourages speaking up.

A few caveats came up as well:

• Celebrate failure, but don’t ignore the consequences. Teams should understand the importance of getting things right.
• Encourage “controlled failure”, where people learn from their mistakes, address issues, and get better over time. “Uncontrolled failure” needs to be addressed directly.
• Sometimes bad news just needs to be direct. On the bright side if you spend most of your time focusing on solutions and projecting optimism, then that makes direct criticism hit harder.

Topic: How to communicate a deadline that is impossible (to your team) or a deadline that will be missed (to the organization)

We started the second topic with a focus on an unreasonable incoming deadline from “on-high”, but also got into discussions about how to push back, or to communicate that an existing deadline won’t be reached.

The conversation started with some real-talk at a high level:

• At the end of the day, you need to toe the line, and to some degree, speak out of both sides of your mouth.
• This is one of the core parts of the job as a manager, and as a result, you’ll need to be a punching bag in one or both directions at various points.

We covered ways to set the tone:

• Take lessons from parenting: go in with confidence, optimism and clarity.
• Building credibility beforehand can be really helpful. Your team needs to believe that you did everything you could to push back, and showing that you’re capable of pushing back helps.
• Go in with humility, asking rather than telling. Let the team know that “you’re allowed to doubt this, but I’m asking you to support it”.
• Don’t try to hide the truth. Saying “the worst thing that could happen is we all get fired” is the sort of levity and clarity that puts things into perspective.
• The worst thing you can do is to degrade team trust. Don’t complain, don’t make people feel bad about the situation, don’t start to play favorites when some people feel frustrated or unhappy.

We also covered a few tactics to deal with getting projects back on track:

• There can be varying levels of “done”: see what’s really shippable. Converting requirements to fast-follows can be crucial.
• Communicate in probabilities: as a project starts to go off track, describing an outcome of “70% chance of completing” can clarify things upwards.
• Go in with a story. Educate the team about the organization’s perspective, data on the company, or anecdotes from customers that illustrate why the deadline is what it is.

We also went into depth about when the executives need to hear that a plan is unreasonable.

Unlike with your team, you can’t just absorb responsibility. You need to negotiate:

• Lay out the downsides of the current plan and scope in detail. Make sure senior management is comfortable with the sacrifices that will need to be made.
• Don’t ignore the effect on culture. Even if it is technically possible to deliver, it may come at the cost of the team members themselves.
• Communicate risks in addition to timelines. If a feature is delivered, but has a high probability of failing, it may not be the right choice.
• Again, if possible, speak probabilistically to give people an idea of the range of possible outcomes

We had a great conversation, and at the end of the day, it was nice to all agree that clear communication is the most important thing. If you’re an engineering leader, I hope you’ll join our group and attend our next event!