Working in a fast-moving team with piles of tasks and projects means you’re inevitably going to be working with and / or directly managing other people.

That means, at some point, you’re going to have to tackle one of the hardest parts of management and leadership: giving critical feedback to your team.

In this post, I’m going to cover:

  • “Ruinous empathy” – the death of all feedback
  • How to give critical feedback to your team
  • Embodying “Radical Candor”
  • Applying the feedback and radical candor to your workflows

“Ruinous empathy”

I was riding the subway to the office while listening to the book “Radical Candor” by Kim Scott and I had a moment.

For those of you who may not know, Kim Scott led AdSense, YouTube, and Doubleclick Online Sales and Operations at Google and then joined Apple to develop and teach a leadership seminar. Additionally, Kim has been a CEO coach at Dropbox, Qualtrics, Twitter, and several other tech companies.

So when she wrote “Radical Candor,” she was coming from an authentic place of leadership and management legend.

She opens with a story that carries through the entire book about how she had to fire a member of her team because she felt deeply uncomfortable with providing feedback to him.

That lack of feedback led to major compensations on behalf of herself and the rest of the team, and ultimately led to her having to let him go — a direct result of her own discomfort.

We all know the value in giving critical feedback to our team members — whether they are freelancers, contractors, clients, direct reports, or executives.

And yet, many of us still struggle with it.

According to Kim, that places us in the category of “Ruinous Empathy.”

Ruinous empathy is when you care so deeply about the person and the situation that you fail to challenge the person directly and provide the all-too critical feedback–the feedback that person needs to take away to do a better job, make a clear decision, or just function in general.

If this sounds familiar, and you’re feeling like you fall into the ruinous empathy category, then definitely keep reading.

How to give critical feedback to your team

Whether you’re a manager of a team, a project manager, an account executive, or the CEO, you need to be able to deliver the feedback your team needs to move forward.

Here’s some helpful ways to do that:

1. Don’t sandwich your criticism

How many times have we been told to wrap our criticism in compliments? Start with a compliment to soften the blow, deliver the criticism, and then end on a compliment to, again, soften the blow.

By the time the feedback reaches the recipient, it’s been softened with so many pillows and cushions that the recipient isn’t sure which aspect of work they actually need to focus on (or if they need to at all).

Worse, the compliment-sandwich diminishes the effect of the praise, too.

In the end, it’s a lose-lose situation. You’ve neither delivered effective feedback nor made the person feel the praise was sincere.

Our brains are wired to detect sincerity, and compliment-sandwiches send off every alarm in our mind that what we just heard was #fakenews.

Instead, give praise where praise is due — not when it’s wrapped in criticism. Give criticism where criticism is due.

2. Care personally while challenging directly

The radical candor framework depends on two core actions:

  1. Care personally
  2. Challenge directly

Failing to do both or one immediately puts you out of radical candor.

If you’re a manager of a team, there’s a good chance you already care a lot about the individuals on your team. But sometimes, “caring” means wanting the individual to become even better at their craft, and the only way to get there is through consistent improvement (and therefore feedback).

If you work primarily with freelancers or contractors, caring personally means helping them understand exactly what you’re looking for and taking the time to communicate your needs while also learning more about them and their strengths.

As for challenging directly?

That’s easy — it can just be communicating the specific details of why the work produced fell short.

3. Just get the words out

You ever find yourself wanting to give positive feedback but end up a little tongue-tied? Maybe your palms get a little sweaty or your heart starts pounding. There’s feedback you want to give, but something about it gives you anxiety.

You, my friend, need to just get the words out. Whatever it is you want to say, take a deep breath and just say it.

Because most of us are naturally conflict-averse, we try to talk around the criticism without ever actually saying the words the other person ultimately needs to hear to do a good job.

We need to be careful, however, that we’re always respectful and we don’t blurt out anything that ultimately could offend the other person.

4. Make it about the work, not the person

“This code is sh*t.”

It was the phrase that became the stuff of legends in the office. I worked with a development architect named Martin at an IT consulting firm on a project for a client, and one of our favorite things he said was, “This code is sh*t”.

To top it off, his thick South African accent somehow made it even more poignant.

It might sound harsh to say to someone, but we loved it.

Every developer in the office knew that when Martin said his code word, that there was going to be a huge learning opportunity and a massive overhaul of whatever was just built.

The crazy thing? No one ever took offense to it.

This is partly because the culture of development and engineering permits (and even encourages) that kind of bluntness.

Martin did something that naturally softens the blow: he made it about the work, not the developer who produced the code.

If you need to deliver feedback about someone’s work and it makes you feel clammy, try rephrasing in the context of the work itself.

What is it missing? Why or why not does it miss the mark? What could be improved upon? What would make it better?

Thinking and talking about it in this way will also help you truly identify what the real reason is that you’re giving the feedback.

It could be about the person’s strategy or approach in solving a problem, it could be because they missed certain inputs, or it could be that you just didn’t communicate well enough what you were looking for.

5. Take it offline

Going digital does something weird to people. Seeing text on a screen means we get to interpret the message however we want — and that includes with or without any emotional baggage.

Most of us aren’t exactly the best at reading comprehension either. We’re humans, and most of us can’t help but read with “tone.” A simple message that we think is direct, to the point, and helpful can come off as mean, passive-aggressive, or manipulative to someone else.

You might learn that you are just be downright terrible at explaining your point-of-view and letting your teammates in on your thinking process (which is a fail in and of itself).

So how can the rest of your team pick up on where your mind’s at if communication is already a struggle?

You get my point.

That said, if you feel compelled as a manager or leader to deliver critical feedback through an email or a Slack message, here’s some advice: DON’T.

While most of us would rather not have to look someone in the eye and tell them in-person the feedback they need to hear, the reality is that giving feedback through text is a lot like sending a text-message break-up.

Even if it’s totally needed and justified, it’s probably one of the most disrespectful things you can do.

If it’s truly critical feedback, it’s always best to deliver it in person — not through an email or a Slack message. And never in a million years through a text message.

That’s showing someone the respect they deserve.

When in doubt, take it offline.

Applying “radical candor” to your workflows

You can tell when a company or team values each other and values each other’s feedback.

It’s like they’re able to summit just about any challenge or project that’s thrown their way. Even if there are bumps, they always seem to come out on top.

It’s also clear they’re able to handle and deliver feedback to each other, especially from the manager or project leader.

In a workflow, radical candor looks a lot like using comments and collaboration to provide feedback to each other on deliverables and overall status of a task or larger project.

You might also discuss and provide feedback in your communication platform of choice, whether it be Slack or Skype, to make sure the details and feedback are hashed out before continuing the work. From there, the task or project is updated with new information and a new direction.

The first key ingredient to embodying radical candor?

Trust.

Giving and implementing feedback shouldn’t be something that your team shies away from. If they don’t feel comfortable giving feedback to each other, you can bet that there’s something missing from the trust factor.

Is something more toxic happening in the team? What fears are preventing them from giving each other or even valuing each other’s feedback?

These are all questions you might want to consider and investigate for yourself.

Be honest with yourself, and if you find there’s some serious underlying issues, you might want to bring it to your own manager for guidance.

Every work culture is different, but when the trust is there, you’ll be able to move mountains together. ✨