Struggling to Coach Your Directs? Here's a Crash Course

Hey Reader,

Happy Friday!

One of my clients recently asked me, “But… How do I coach them? How exactly?

If you’re a caring engineering manager, you’re invested personally in the growth of your directs (not just your product/service).

You’ve tried coaching - which you probably define as having them arrive at an answer without you giving it out.

Sorry to burst your bubble- That is just withholding information, not coaching.

In today’s deep dive, I want to walk you through how to get into the coaching mindset and how to develop a coaching cadence that is simple enough. I’m also going to give you a set of questions so you can start coaching deeply right away (without needing hours of training).

But first…

Why Coaching Is So Important

Think of coaching as a “Co-creation” with your employee. Co-creation for what? - for their career and for the next version of themselves.

Co-creation for your product/service/vertical is called brainstorming. And that’s why it doesn’t belong in 1x1s.

When you recognize high-performers for who they are and who they want to be, and actively support them with the growth they want, their investment in your team and you is higher. They Exceed Expectations each time.

So don’t just say… KEEP DOING WHAT YOU’RE DOING.

Seriously, it’s not a compliment. It’s patronizing.

COACH well. Or increase the likelihood of losing them to a different company or losing their investment in your team.

Give them a reason to work hard for you.

Now, there are a LOT of managers who don’t coach much, but get 99 points on the employee happiness index. (And their 1x1s go something like “This happened over the weekend, and I designed this feature this way.”)

But I just don’t think this is a viable strategy if you care enough to develop leaders and want to grow as a leader yourself.

So, the 1x1 is Here. What Do I Do? First, Get into the Coaching Mindset

Before we get into the how-to, knowing some good basic practices turn you from an advice-giver to a coach. I have distilled it down to 4 practices:

  1. Clear you mind before you meet
  2. Setup agreements on your relationship and mutual roles
  3. Champion them deeply
  4. Drop the armor and be vulnerable

Let's dive in!

1. Clear Your Mind Before You Meet

Coaching someone on their goals starts with building your own bandwidth to be a receiver of a wide range of human expression. Of course, the range narrows in a work setting. However, it’s good to prepare yourself for whatever comes up.

I love the metaphor from David Allen (Author of Getting Things Done) -Mind like water.

If our mind is muddled with worries and open loops, we cannot be receivers.

You will be presented with highly aspirational goals, vents, rants, defensiveness, or the passive “I’m cool, everything’s great”. All that is mixed up with substantial coaching opportunities.

One of the biggest mistakes managers make is thinking they need to jump in, ‘fix’ the problems and thereby fix the emotions of their reports (so they don’t have to sit with the discomfort).

But this takes you away from coaching.

So clear your mind and be open to receiving what presents. Keep your judgmental voice out and reserve your advice toward the end of the conversation.

Focus on building trust. That comes with you clearing your mind to accept what is presented.

And to do that, have a 5-minute break between your meetings. Brain dump your worries and the open loops onto a paper. Have a ‘Mind like water’ before you start your 1x1.

2. Setup Agreements on Your Relationship and Mutual Roles

The no. 1 bane of any relationship - personal or professional - is EXPECTATIONS.

We naturally expect people to understand their roles and fulfill their duties without needing any prompts from us. This is the reason for all those fights over who loads the dishwasher and who takes the trash out (ask me how I know 😇).

If you want a relationship based on trust, have clear agreements.

One of the most famous coaches Steve Chandler had this to say about expectations vs. agreements

You have two choices in your relationships with others. You can have relationships based on expectations or relationships based on agreements.
Expectations are cowardly and self-defeating. They are cowardly because by expecting things of others, I place all responsibility outside myself. I expect my co-worker to do his job right, I expect my family member to behave a certain way, and the list goes on. When I am unhappy it’s because of them. Expectations lead to disappointments. It’s a miserable life expecting so much of others and suffering so much disappointment and betrayal.
Agreements are courageous and creative. They honor the other person. They are coauthored between two composers of the agreement. People give their word and keep it.
People honor agreements to a far greater degree than they live up to expectations. They feel stressed when their head is full of expectations of them. They feel pressure and resentment. They rebel. (Ever notice? Do you have children? Employees?) But create a good agreement? Both sides win.

So create agreements on their role and duties. And do this again and again and again.

3. Champion Them Deeply

Did you ever say, “Good job on pushing this out the door today”?

Yeah… you might want to stop saying that.

Remember how I keep saying ‘develop leadership’?

The good-job compliments do not do that. They’re, in fact, patronizing for high-performers.

When we’re told we’re doing a good job, two things can happen -

  • We subconsciously try to avoid what could be a bad job and try to live up to seeking the ‘good job’ compliment again.
  • We think, “I didn’t do much. It was natural.🤷”

Either of these responses takes people away from their leadership. Instead, it gives you a person who seeks your validation.

So should we refrain from giving any appreciation at all?

NO. In fact, I’m telling you to give deep appreciation. And give a lot of it.

‘Good job’ is quite limiting. Instead, champion people for who they showed up to be and talk about the impact of that.

Hey, I noticed you stepped up and asked Eva if she had any inputs. I want to acknowledge you for considering the team spirit and including her in the conversation. This will ensure we don’t miss any fresh ideas. And it aligns with my ideals of having an inclusive team.”

There’s an excellent HBR article on how to give more profound compliments. I’ll link it below for further reading.

4. Drop the Armor. Be Vulnerable.

Vulnerability is quite loosely thrown around in the self-help industry in the context of leadership. It’s one of those things which is easy to give advice on (“hey, be yourself!”) but extremely difficult to model.

Vulnerability comes from choosing responsibility instead of blame.

My definition is this - WHATEVER may be the situation, think of your part of the responsibility and come out clean.

Vulnerability is not about over-sharing. Nor is it about self-blame.

It about -

  • Shedding your armor
  • Cleaning up your messes
  • Committing to creating a new behavior

In the context of coaching conversations, there will be many moments of awkward pauses, defensive triggers, or discomfort from sharing too much. Take a breather, accept these moments and state them out loud.

I am not sure where to go from here. We have 15 mins, where do you want to go?

That’s it! You’re already being vulnerable and stepping out from being the expert.

Now, For The How-To

Here is the step-by-step guide for a simple coaching conversation. You can directly lift these questions and ask them one after another in your next 1x1.

The goal here is to

  • Start knowing your direct report a little more.
  • Build more connection with them, so they open up with you.
  • Tune their thinking (and yours) to your roles being a transient step in a bigger mission.

Step1: Start by Drawing Out Their Vision for Themselves.

🙋 Why? Opens them up to coaching from you. Gets you an understanding of how they think.

1. Where do you see yourself 3 years from now?
2. What role/title do you want to have by then?
3. How do this team and company fall into the vision?

Do not judge or comment negatively on what your report says. They may as well say my only goal is to make money right now or jump to BigTech Company X in 2 years. If they did, congrats! You did the job of creating such a safe space that they’re so honest with you.

Step 2: Find Out the Impact They Want to Have.

🙋 Why? Starts expanding their thinking towards a mission and inspires them to work for you.

4. What impact do you want to have on people around you?
5. What impact do you want to have on the tech industry?

Step 3: Find Out About the Impact on Their Life

🙋 Why? Uncovers the intrinsic motivation.

6. How’s your life changing because of the work you are doing in this team?

Step 4: Get an Idea for Their Strengths and Goals

🙋Why? Gets you an idea about the work they would be interested in.

7. What strengths (or superpowers) do you want to build in the next 6months - 1year?

Step 5: Set up Your Future Conversations

🙋Why? Sets up the agreement that you would be coaching and leading them towards their goals.

8. What are some areas you would love coaching on in the coming months so you can reach your goals?

When you start coaching along these lines, you will naturally fall into a deep conversation. More ideas are going to jump into the space.

That is the point of these questions - to get you started in having deeper conversations that actually build their leadership.

And once you start coaching them consistently, you’ll build the resilience and trust for fast feedback in your relationship.

So take these questions and get going!

One Final Thought

To coach well, you need to know your own answers to these questions.

Go through the questions, ANSWER THEM for yourself today, and remember your role as an executor should (and probably will) change to a leader as you coach more. The more you coach, the more you step back as an executor or the project manager, the more you’ll understand the ‘people’ part of the people manager.

To do this well, have coaching modelled to you.

  • Ask your manager to coach you more in your 1x1s
  • Hire a leadership coach (shameless plug 🙋)

That’s it for today’s deep dive! Hope this was helpful.

Here's the HBR article on deep championing.

Who else would love this? Forward this email to a fellow engineering manager.

If you’re struggling with coaching your directs, hit reply and tell me the challenges you’re facing. I’ll help you out.



Mounica Veggalam

Hey, there! I talk about non-linear growth strategies and leadership development for tech leaders. Get mindset deep dives to break through into senior leadership roles.

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