A 10-Step Guide To Challenging Your Directs For High-Performance (Without Being An Arrogant Boss Or An Agony Aunt).

Like it or not, challenging your directs for high performance is the most critical factor in getting to your next level.

Engineering managers fall prey to 2 unique behaviors:

1. Abrasive Posturing (“I know I’m right/better, you better catch up”)
2. Empathetic Collapsing (“You’re not incompetent. I don’t mean to hurt you.”)

Why?

Because if you’re an EM, you embody BRILLIANCE and SERVICE. On the one hand, you believe you’re the smartest person in the room. And on the other, you want to help people who believe they’re the smartest person in the room.

Quite an ordeal, if you ask me.

And if you’re aiming for the executive rank someday, you must get good at dealing with the smartest people in the room.

You get ranked high on “develops talent” and “resolves conflicts quickly” only when you can challenge and support your smartest high-performers (who exhibit abrasive posturing or empathetic collapsing themselves).

So, let’s recall the container framework for influencing people fast:

1. What goals are misaligned? Do we need new goals?
2. What agreements are they not holding? Do we need new agreements?
3. What commitments are they breaking? Do we need new commitments?
4. What support do we need for our commitments? Do we need new systems?

We’ll dive into an example of applying this framework to challenging your directs on misalignment.

I want to breakdown:

1. What leads to posturing or collapsing
2. The 1 big invisible sign of misalignment
3. A potential conversation with your direct to resolve misalignment (with powerful empathy)

In 2003, Jeff Bezos said something crazy to one of his reports.

They were trying to explain why they did not meet the objectives. Jeff said, “Which do you think you are exhibiting gross stupidity or sheer incompetence?”

Ouch.

Jeff was no doubt brilliant and successful. Nobody could BS their way through to him. But I bet it’s no fun to work for such bosses (not everyone can and wants to pull that off).

We hear similar stories with Bill Gates, Steve Jobs, and other tough executives.

Unless you want to cut people to bleed like this, you’re looking for a different way to challenge your reports.

Firstly though, why does this happen in the tech corporate leadership?

Abrasive Posturing results from your fear of incompetence.

You see, the same brilliance that got you to be smart, successful, and reliable in the tech industry, becomes a curse.

The horror of incompetence and making mistakes, by yourself or others, becomes projected outwards. You see the world through an “efficient” lens, which is fantastic for getting results but leads to others feeling dumb in your wake.

Being condescending, skeptical, or manipulative become a brilliant person’s defense mechanisms.

The other side of the coin, Empathetic Collapsing, is also a result of your fear of incompetence.

Playing dumb, becoming small, and overgiving (your heart goes out to others who seem to be struggling) become your defense mechanisms.

This is where you either

• Fail to address your underperforming reports
• Have your impostor syndrome take over
• Don’t ask your boss what you want
• Or you procrastinate on high-stakes conversations.

Empathy becomes the safety net to avoid confronting your own or others’ incompetence.

(It is also the reason behind the sh*t sandwich way of giving feedback but, more on that some other time).

In fact, an ability to empathize becomes a measure of brilliance in people.

If you’re thinking, “Oh, I see what you mean. But, don’t worry I never posture or collapse”, think again.

I invite you to consider how you judge your team leads and engineers. Do they appear condescending, skeptical, or playing dumb sometimes? Chances are, you are too, and it’s in your blind spot.

To be clear: you’re not wrong to be so.

It’s the natural consequence of high expectations, a low tolerance for mediocrity and a deep desire to help people. You sense mediocrity from a mile away. And then you either cut it off at its head or try to proactively fix it to your level of brilliance.

Wait, what’s the problem in fighting mediocrity or being empathetic?

Perfectionism, resenting your team, and loneliness — that’s what.

You never make mistakes and never allow others to make mistakes and learn. You never seem to truly get recognition and respect for your smartness. The humans that you judge as mediocre slowly but surely alienate you.

Your strategies and tactics leave you with an experience of “nobody is good enough” or “I’m not good enough”. This results in either pushing yourself hard, or pushing others around you.

And often, you’re stuck proving that you’re right.

This is a problem for your leadership career.

You need to recognize a breakthrough, if you want to

• challenge directly but not cut the person to bleed,
• truly care about the person, not collapse in empathy and resent them,
• expand your capacity to deal with the many different human emotions,
• and support your reports to become leaders.

Only when you see the brilliance in your own ignorance and incompetence can you expand your capacity for leading other ‘smartest people in the room.’

The goal is to hold others with patience and compassion so you can lead them toward bigger results.

The big question is how.

The first step is recognizing your own posturing/collapsing and holding space. Catch your moments of frustration. Because…

Your growing frustration with others is the most crucial sign of misalignment.

When you start to silently judge your report for not meeting your expectations,

• you might be judging yourself for not meeting the expectations of your brilliance
• afraid of being seen as incompetent
• resorting to the safety of complaining instead of taking responsibility.

Take a pause.

Sit with the experience of feeling and being seen as less than brilliant.

Hold your report with compassion for being less than brilliant.

And, instead of waiting for them to bounce back or “hope” that they’ll approach you, initiate a conversation with them.

Think about this conversation as a container to review their commitments. Remember that it’s a partnership to create the results, not you telling them what to do based on your brilliant assessments.

1. What goals are misaligned? Do we need new goals?
2. What agreements are they not holding? Do we need new agreements?
3. What commitments are they breaking? Do we need new commitments?
4. What support do we need for our commitments? Do we need new systems?

Here’s a 10-step conversation guide to support your report with the commitment container:

1. Set up an honest context.

“I sense a disconnect and misalignment. I want to have a conversation about it. Are you open to that?”

2. Help them relax and open up.

“Don’t worry. Nobody is getting fired or getting a bad review. This conversation is only to support you. I want to help you with whatever is going on.”

3. Get specific and curious

Give specific examples of what made you sense that they’re different than before. “I notice…. But based on the past, I would have expected you to…”. “What’s going on?”.

4. Make them feel even safer so they open up

“Even if you’re unable to articulate properly, try to tell me what you’re feeling. It won’t mean that you’re committing to something. We’ll discuss what we both can commit to later.”

5. Reflect without judgment

“So you’re feeling X, Y about Z. Am I hearing that right? Is there anything else I’m not getting?”.

6. Fully understand their context. Bite your tongue from advice.

Your only job is to understand them so much that you feel, “No wonder they’re feeling this way and acting this way. I would’ve done that too”. It’s not the time to give advice. Ask them again, “Do you feel I fully understand you?”

7. Brainstorm options with them

Get them to tell you what they need. “Are you open to brainstorming some options? What do you need at this moment?”

Then tell them what commitment you need from them. This is the most important part of this conversation.

Some options for them:

• More coaching from you learn the new skill
• Contacting a therapist to handle their well-being
• Taking a few weeks off to unwind
• Connecting them to someone in your network to help with other opportunities

8. Get them to commit to one of the options.

Before they leave the conversation and their life takes over again, have them agree and commit to one of the options.

Ask, “Do you agree to this?”

9. Ask if they need more support.

Ask, “What support do you need from me to hold your commitment?”

Then, find out if this conversation supported them and if they would like to talk again soon.

10. Schedule your next follow up

Set your follow-up right in the conversation before both of you get busy and push aside the uncomfortable candor aside.

Note that this is only a sample of what’s possible. To do this consistently and overcome your current default patterns, consider getting the support of a transformational coach.

Now, for the customary GIF, you definitely want to challenge and care more than this: