⚙️ Ops Playbook #33

Gauging trust levels, awkward 1v1's, and feedback with direct reports

Author

Rameel Sheikh
April 18, 2024

Together With

Read Time: 6.4 Minutes

Hi Operators ⚙️

Launching Cornerstone, the private membership for COOs and senior operators, is a ton of work. I figured I needed to hire some help.

So I did! Welcome to the squad, Carlos.

If you’re interested in joining the waitlist for Cornerstone, apply here. (There are only two questions). I’ll reach out if there is a fit. Only 100 people get into the beta. I’ll be raising prices once the full launch happens.

With Carlos getting onboarded, I’ve been reviewing my notes on how to be a great manager. Here are 3 quick tips on how to be a solid (or great!) manager.

Here’s what we got going on today:

  • 2 questions to gauge trust levels → How do you know if your team trusts you?

  • Awkwardness in 1v1’s → 1v1’s are can be awkward if either party doesn’t feel heard

  • Structuring your feedback → 3 steps to make sure feedback is delivered the right way

Let’s jump in.

(P.S Have questions about scaling your business? Reply to this email or email me at [email protected] and I’ll answer them in the next edition)

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5 Operators Library Links

3 Ops Tips

1. Two Questions to Gauge Trust Level

Insight from HBR

When I became a manager for the first time, I didn't worry about my direct reports not understanding the “Why” behind my actions. And as their manager, I thought my direct reports viewed me as their leader.

That's a critical mistake.

Leadership isn't something that comes with a job title. It's a quality you have to earn through your actions and relationships.

And when you're a first-time manager, building that trust with your team is crucial.

To gauge the level of trust in your team, start by asking yourself two critical questions:

  1. Do my reports bring their biggest challenges to me?

  2. And would my reports work for me again?

Now, you might be thinking, "Hey man, this sounds great, but why should I focus on building trust?"

Here are three reasons to do this exercise:

  • Trust is the foundation of high-performing teams. You'll never reach your full potential as a leader or team without it.

  • When your team trusts you, they're more likely to take risks, share ideas, and give honest feedback - all essential ingredients for innovation and growth.

  • Trust is a two-way street. By investing in your relationships with your reports, you're helping them succeed and setting yourself up for long-term success as a leader.

Asking open-ended questions lets you understand what frustrates, motivates, and inspires the team. Don’t waste the opportunity to create deep relationships with them.

Here are some questions to start:

These questions sound basic, but doing the small things right will result in 10x results.

(I didn't follow these when I first started, and it caused me to lose millions in business. That's a story for another time.)

2. Pushing through Awkwardness in 1v1

Insight from Rameel Sheikh

Imagine you're sitting across from your direct report, trying to dive into their challenges, but the conversation feels like pulling teeth.

You ask, "How's everything going?" and they respond with a generic, "Oh, you know, same old same old." They’ve answered the same way the past 3 weeks.

You can feel the awkwardness hanging in the air, and you're tempted to move on to the next topic. But you decide to push yourself to see what happens.

So you take a deep breath and say, "I've noticed you seem a bit disengaged lately. I'm wondering if there's something on your mind that we haven't had a chance to discuss. What's really going on?"

Your report looks surprised for a moment, but then their shoulders relax and they let out a sigh.

"Honestly, I've been feeling like my work isn't being recognized or valued. I pour my heart into these projects, but it feels like no one notices."

Bingo. By embracing the awkwardness and asking a probing question, you've uncovered a real issue that needs to be addressed.

And now that it's out in the open, you can work together to find solutions and rebuild that sense of motivation and purpose.

This is the power of a great 1:1 - it's a chance to dig deep, uncover hidden challenges, and support your team members in a way that moves the needle.

But it doesn't happen by accident.

If you want to improve your leadership skills, you've got to master the art of the 1:1 meeting. Today, I'll explain exactly how to do that.

Step 1: Embrace the Awkward

I know, I know — nobody likes awkward conversations. But here's the thing: the most meaningful and impactful 1:1s often feel a little uncomfortable.

So lean into that awkwardness and use it as a sign that you're diving into the stuff that matters.

  1. Discuss mistakes and missteps openly

  2. Confront tensions and challenges head-on

  3. Create space for vulnerability and honest feedback

Step 2: Ask the Right Questions

As a manager, it's easy to fall into the trap of thinking you need to have all the answers. But the truth is, your team members are the experts on their own problems and priorities.

So instead of jumping in with advice or solutions, focus on asking questions that empower them to find their own way forward.

  1. Identify what's top of mind and where to focus your time

  2. Understand the root of the problem and potential solutions

  3. Support them by asking how you can help them succeed

Step 3: Let Them Lead

1:1s are a chance for your team members to take the driver's seat and steer the conversation where they need it to go.

Your role is to listen, probe deeper when needed, and provide guidance and support along the way.

  1. Resist the urge to dominate the conversation

  2. Encourage them to set the agenda and prioritize topics

  3. Follow their lead and adapt your questions

Now, you might be wondering, "What's in it for me? Why should I bother with all this touchy-feely stuff?"

Here are three big reasons to care:

  1. Stronger relationships: By having meaningful, authentic conversations with your team members, you'll build deeper trust and rapport that will serve you well in the long run.

  2. Better problem-solving: When you empower your team to find their own solutions, you'll be amazed at the creativity and resourcefulness they bring to the table.

  3. Increased engagement: Teams who feel heard, supported, and valued are likelier to go the extra mile and bring their best selves to work daily.

Try it in your next round of 1:1s and watch the magic happen.

3. Structuring your Feedback

Insight from Rameel Sheikh

You're in your weekly 1:1 with your direct report, and you know you need to address a piece of critical feedback.

You've been putting it off for weeks, hoping the issue would resolve itself, but it's only worsened.

You're worried about how they'll react and don't want to damage your relationship. But you also know that giving feedback is an essential responsibility as a leader.

You take a deep breath and dive in:

"I noticed in last week's client meeting that you interrupted the client several times and seemed dismissive of their concerns. I'm concerned that this could damage our relationship with them. Can you help me understand what was going on for you at that moment?"

Your report looks surprised and a little defensive at first.

Giving feedback can feel like navigating a minefield - one wrong step and everything blows up in your face.

But when done skillfully, with care and curiosity, it can be one of the most powerful tools in your leadership toolkit.

Try these 3 steps on giving feedback.

Step 1: Make it Frequent

The first step to giving great feedback is to make it a regular habit. Don't wait for formal reviews or major mistakes to speak up.

Instead, aim to give feedback in real-time, whenever you observe something noteworthy

  1. Set a goal to give feedback at least once a week to each team member

  2. Look for opportunities to give positive feedback and reinforce good habits

  3. Address issues early, before they become bigger problems

Step 2: Make it Specific

Vague feedback like "good job" or "needs improvement" doesn't give your team much to work with.

To be effective, your feedback needs to be specific, focused, and actionable.

  1. Describe the specific behavior or action you observed

  2. Explain the impact it had (positive or negative)

  3. Offer concrete suggestions for how to improve or continue the good work

Step 3: Make it a Dialogue

And if your feedback isn't landing - if you're not seeing the changes you're hoping for - take a step back and examine your approach.

To help your team grow, you should involve them in the conversation and be open to their perspective.

  1. Ask questions to understand their thought process and experience

  2. Listen actively and empathetically to their responses

  3. Collaborate on solutions and next steps together

Mastering the art of feedback takes practice, but it's a skill that will serve you well throughout your leadership journey.

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Rameel from The Bottleneck

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