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In this week’s newsletter, we’ll cover how to give honest feedback to a direct report who might be upset to hear they’re not meeting your expectations:

1. Strategy vs self-expression: Only say what will encourage behavior change.

2. If they already feel remorseful, don’t pour salt in the wound.

3. Take responsibility for your role in not setting the right expectations.

4. Acknowledge that strengths and weaknesses are two sides of the same coin.

5. Cite task-relevant maturity. 

6. Replace “but” with “at the same time” to avoid negating positive feedback.

7. Quote the person back to themselves and get “permission” to be direct.

Read time: 6 minutes

Giving feedback is tricky.

It’s even trickier giving it to a direct report who:

• gave themselves a rating of “4 - exceeds expectations”

• when you gave them a “3 - meets expectations”

• and you actually wanted to give them a “2 - needs improvement”

This happens more often than you think. As a manager, you need to learn how to navigate this uncomfortable conversation so you don’t procrastinate on sharing direct feedback. Often the person is a strong performer, but is now facing challenges because of expanded scope, new responsibilities, or stretch assignments.

One of my coaching clients is a leader at a Series A company backed by Tier 1 investors. They are dealing with this right now:

Q: “I have a few direct reports who may react emotionally to hearing the direct critical feedback they should be getting to perform at the level needed. How honest should I be if it could derail the person—at a time when the company really can’t afford to go off track?”

The stakes feel even higher if your business is in a phase where you can’t afford having folks feel petty, distracted, or resentful. You can’t afford spending 3-6 months to hire a replacement.

Well-compensated senior folks often have bigger egos and are used to seeing themselves as A-players—which makes sharing negative feedback even more of a situation that requires finesse.

If you let them believe they are exceeding expectations, you’re feeding their delusion. They’ll ask for a raise when you’re thinking of parting ways.

But if you’re completely honest, they might freak out.

So what should you do?

1. Strategy vs self-expression: Only say what will encourage behavior change.

If you want the person to stay motivated, this is not the time to give an exhaustive brain dump of everything they need to improve on. There are better times for that.

For now, pare it back to the most critical feedback. What one thing can they work on that will make the biggest improvement? How can you frame why improving in this area will ultimately benefit them?

You’ll likely need to do a bit more selling than you’d normally do. For example, I like reminding folks that improving on X will benefit them immediately in their current role—and in every role thereafter.

I would avoid mentioning things they will want to debate you on. From a practical perspective, this could look like focusing more on what to do differently moving forward—instead of on past infractions.

From my post on strategy, not self-expression:

Strategy means only saying things that get you closer to changing the person’s behavior. You should only say things that you strongly believe will incentivize the other person to change in the right direction. Strategy is probably 10% of what you initially want to say.

Self-expression is venting, having the last word, or trying to teach someone a lesson. It’s trying to prove you are right or wanting the person to feel remorse. Anything that isn’t 100% going to encourage the person to improve goes in the self-expression bucket.

Aim for one goal: behavior change. Sweet, sweet behavior change. Everything else you might want to say? Summon your self-restraint and keep it to yourself.

2. If they already feel remorseful, don’t pour salt in the wound.

If they messed up and disappointed you, why would you downplay this? If the person already feels remorseful, there are diminishing returns to continuing to emphasize how much damage they caused.

(A) It makes them feel worse, which makes them less motivated to improve because they’re too busy self-flagellating and feeling awful for letting you down.

(B) It makes them defensive, which makes them less motivated to improve because they’re too busy debating with you and trying to protect their psyche.

I tend to work with folks who are too hard on themselves. So when they mess up, my goal is to channel their emotions in a more productive direction.

3. Take responsibility for your role in not setting the right expectations.

This requires you to “be the bigger person.” When you take responsibility for your role in a situation, you engender massive amounts of goodwill. Most managers won’t admit that anything is their fault, so if you do this even a little, it makes you seem gracious.

As a leader, I've admitted, “It's on me that I didn’t do X” or “I should have set you up for success by doing Y.” I took ownership for how I could have managed them better.

Humans naturally feel the need to reciprocate. Hearing this usually makes the other person more willing to acknowledge how they contributed to the situation.

Whenever I’ve heard my managers say this, I immediately thought, “No, I can’t let my manager take the blame. This is obviously not on them. This was on me.” It prompts reflection on how I contributed and what I want to do differently.

4. Acknowledge that strengths and weaknesses are two sides of the same coin.

These two statements are pretty universally accepted:

1. Each person has traits and skills: When applied appropriately, it’s a strength, and when applied too much/too little/in the wrong contexts, it’s a weakness.

2. Most people are better at some things, and worse at other things.

I like to share the above as a premise because it creates solid ground for the rest of the feedback conversation.

When I've framed things this way, the person accepts the message more readily because the logic makes sense. Your recipient is likely to agree with the statements above—they are neutral, non-controversial assumptions.

For example, let’s say your direct report could have better managed the quantitative side of their business unit. You could say:

“Creativity, big picture thinking, and storytelling are your strengths, which makes you so great at X. The shadow side of this is I’ve noticed you’re more likely to be very light on quantitative analysis and subconsciously avoid data. This totally makes sense, but the impact is [negative impact]. Going forward, I need to be on top of the weekly metrics so we can...”

The reason this is so effective is because of the underlying logic:

Before: “You’re bad at X for no reason.” ← This is hard to swallow.

After: “You’re bad at X because you're good at Y, but we still need to admit that you’re bad at X and address that so it won't limit your ability to contribute.”

In my experience, this framing makes the person more open to hearing you. You’re not triggering their ego to say, “But hey, I’m good at a lot of other things! Why don’t you ever focus on that?”

I’ve used this framing with my team, and have had my managers say this to me in the past. And on both sides, it feels fair and reasonable.

5. Cite task-relevant maturity. 

I love this concept from Andy Grove, co-founder and CEO of Intel. Citing task-relevant maturity makes feedback sound more objective and less personal.

You’re NOT commenting on whether your team member is intelligent and capable. You’re simply mentioning this person’s experience, and therefore judgment, with a certain topic.

It's very reasonable for you to say:

“I thought you had more task-relevant maturity in this area than I realized. I was surprised by XYZ. That's on me. Going forward, it might make sense for us to be more closely aligned as you ramp up on this. What that looks like is... And when X happens, let’s have you do...”

For example, if the person had a stretch role but failed to step up in the way you expected, you need to be clear that they didn’t meet expectations. At the same time, through the lens of task-relevant maturity, it’s kind of reasonable that they missed the mark.

It doesn’t excuse their shortcomings, but it removes some shame around the conversation. You’re both wanting to find out the best way to increase their impact.

6. Replace “but” with “at the same time” to avoid negating positive feedback.

I was reading through a draft of my clients’ feedback to their team and realized how negative it was to see a glaring “but.”

But isn’t great in the context of feedback because it negates all the nice things you said before. Your recipient will only hear what comes after but, i.e. all the negative stuff.

There’s common advice about replacing “but” with “and,” which I partially agree with. On the one hand, this was meant to address how people only hear what comes after “but.” On the other hand, it’s confusing because “but” and “and” legitimately have different meanings—it’s weird to use them interchangeably.

This is why I like “at the same time.” At the same time is the best of both worlds: It signals a difference like “but” does without the negativity. It’s like “and” in that it shows a continuation, as opposed to a severe break or negation.

Before: “I really like how you X. But when you Y, it has this negative impact.”

After: “I really like how you X. At the same time, when you Y, it has this negative impact.”

7. Quote the person back to themselves and get their "permission" to be direct. 

This is one of the most effective persuasion tactics. It works on people who are notoriously hard to persuade. The idea is to leverage cognitive dissonance and the principle of consistency.

People want to be consistent with what they said and who they think they are. 

So you could say something like,

“You’ve mentioned you always want me to give you direct feedback and push you to be better. This is one of those times. I’m saying this to you because I know this wasn’t your best work, and I know you this doesn't reflect your abilities.”

I take liberties with generously recapping what someone might have said re: wanting me to challenge them to be better. If your direct report chose to work at a startup and sees themselves as a high-performer, chances are they are eager to hear feedback.

And if you put this list into practice, your team will especially appreciate honest input from a leader who shares feedback thoughtfully and cares about their’s team morale—all of which ultimately allows you to set high standards and push people to achieve those standards.

One of my favorite parts of this newsletter is hearing from you. If you’ve applied what I write about and would like to share a story/example, hit reply or share in the comments. I’d love to hear about it.

Thanks for being here, and I’ll see you next Wednesday at 8am ET.

Wes

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