Being a first-line manager is an in-between state - you are not yet ‘middle-management’, but not an IC anymore. Your people see you as part of ‘management’, but the senior leadership sees you as part of the dev team.
Becoming known and respected in ‘higher circles’ is not easy, and might require changing a couple of behaviors.
In today’s article, I’m going to cover my 6 top lessons from Wes Kao's Newsletter - each about a mistake I was making:
Not having finesse
Having insecure vibes
Delivering bad news poorly
Not being explicit enough with your team
Using inaccurate and misleading language
Giving senior leaders feedback the wrong way
In each one, I’ll share:
The concept in a nutshell
A real example where I messed it up
Relevant resources for becoming better at it
is one of my top 3 Substack authors. She’s the co-founder of Maven (Andreessen Horowitz, First Round), and co-founder of altMBA (with Seth Godin), and she writes a newsletter for senior operators and leaders.
Thanks Wes for her help in writing this article!
1. Not having finesse
In a nutshell
Finesse can be defined in different ways, but Wes defines it as:
In short - don’t be a bull in a china shop, otherwise senior leadership won’t take you seriously.
How I messed it up
We had a severe technical problem that affected only our Brazilian customers. We found out about it in hindsight, and the result was incorrect data presented to customers for 2 months.
The team from Brazil asked me on Slack what does the problem mean for them. Like most engineers, I prefer the straightforward approach, so I answered:
“Well, everything we presented in the last 2 months was a lie”.
A few minutes later, our COO sent me a message. He said I can’t just send messages like that, as it’s very demoralizing. He told me he was going to take it from here, and asked to not interfere.
I remember being very angry, as I felt he was hiding the truth! I believe that inside the organization we should be ‘100% transparent’.
Now, 3 years later, I still think we should be honest - but HOW we present the information has a huge impact. That’s exactly what finesse is about.
I behaved like a kid in a grown-up world, and I’m sure it affects how the COO perceives me to this day.
How to become better at it
Wes wrote 3 great articles on the topic, with many practical examples:
2. Having insecure vibes
In a nutshell
Here’s how Wes defines “insecure vibes”:
Insecure vibes are subconscious clues and signals we emit when we really want something to work out, but aren’t sure if it will. If you want to become a senior leader, you need to get rid of those.
How I messed it up
I was 26 when I was promoted to a manager’s role, which was quite young in my company. Everyone else on the R&D management team was in their 40s and 50s.
2 years later, I was promoted to director, and I became a manager of people 2 decades older than me.
In both cases, I was overly conscious of the age difference and cared too much about it. I kept mentioning it with stupid jokes, making fun of other’s ages or of my own. I didn’t speak my mind with my direct reports, afraid they’d think “What does he know? I have 20+ more years of experience!”.
When I finally let it go, it turned out nobody cares. :)
Age differences are not an issue. There are enough young founders/managers. I was promoted for a reason, and I should have just focused on my strengths.
I shared my full experience in ‘The 3 top mistakes of managers under 30’
How to become better at it
"Insecure vibes" are a self-fulfilling prophecy
3. Delivering bad news poorly
In a nutshell
Wes believes this topic is especially important because:
We often associate negative feelings with people who tell us bad news.
Work is hard enough as is. You don’t need that negativity associated with you, especially if a situation is out of your control.
Common mistakes are:
Bad news are part of work. You don’t want to be associated with the news you bring.
How I messed it up
One of our biggest customers requested an urgent change, which required the team to work throughout a holiday weekend. The customer insisted they mentioned that deadline a few months back, but nobody on our side knew it.
Somebody messed up, but the bottom line was an urgent phone call from the CEO, who mentioned how critical it is (a very big contract hinged on that).
When breaking the news to the team, I made all the mistakes above. A very long preface about the importance of that customer, multiple negative words, and lots of details.
How to become better at it
How to deliver bad news when it's not your fault
4. Not being explicit enough with your team
In a nutshell
In Wes’ article on this topic, she wrote:
Managing juniors can be a blessing - they are eager and aren’t burdened by bad habits they learned from other organizations. But one of the biggest downsides? You often have to spell things out for them - they might not know what “normal” expectations are for someone in their role.
A common mistake is ‘throwing them into the deep water’ and feeling resentful that they don’t rise to the opportunity.
The first step of being promoted is to have a high-performing team, which doesn’t depend on you. For that, you need to learn how to be explicit.
A practical example
Think about situations like
Code reviews
On-call responsibilities
Writing documentation
Creating a design for a new feature
For a senior engineer, all of them are obvious and not challenging at all. But here’s the thing - we often forget what it’s like to be in the shoes of someone doing it for the first time.
Think back: do you remember the stress of your first on-call shift, constantly worried you’d miss something critical? Or the uncertainty of requesting your first code review in a giant, unfamiliar codebase? Or the sheer terror of presenting your design to a room full of much more senior engineers?
In her article, Wes shared 6 simple techniques that will help you do it better:
Sharing the bigger goal
Signposting
Using an analogy
Explaining your thought process
Being more specific than you think you have to be
Reinforcing that they are the project owners
Let’s take a design review as an example. You have a junior engineer who is tasked with designing a new feature and presenting it in a design review meeting.
Here’s what you can say to help them:
“Don’t worry if it feels huge, I’ve been there too. Let’s break it down together.
A useful way to think about this is that you’re the conductor and your colleagues are the orchestra. You will be creating the melody (the design), and the meeting is like the final rehearsal to ensure everyone’s aligned and ready to play their part.
It’s your job to ensure all the prep is done beforehand so the meeting runs smoothly - it isn’t the time to rewrite the music.
Here’s what I’d recommend:
Share early and often: Instead of creating the design in isolation and only asking for feedback once it’s finished, share a rough skeleton early on and involve others to refine it. You might have to completely redo it - it’s ok!
I’m here to help: Share drafts with me as soon as you need feedback - I’ll make sure to respond quickly and support you throughout the process.
Pre-align with stakeholders: Everyone attending the meeting should already be familiar with the design. Sending them a link is not enough, use 1:1s if you need to walk them through it beforehand. Hear their thoughts, and address concerns early.
Iterate as needed: For me, it typically took 2-3 iterations to refine a design. Plan for this upfront to avoid last-minute rushing.
Schedule a dry run: Please schedule a dry run with me at least a day before the design review. We’ll walk through the design together, simulate the meeting, and ensure you’re fully prepared.
Guide the meeting: You’re responsible for leading the discussion during the meeting. There should be no surprises. Walk everyone through the design, clarify trade-offs, and align on the next steps.
These are just a few tips off the top of my head, but there might be other aspects to consider based on the situation.”
Give your team a chance by being upfront and concrete with what you want from them.
How to become better at it
Managers, be explicit about what you need from your team
5. Using inaccurate and misleading language
In a nutshell
Wes mentions 2 common mistakes here:
When you speak accurately, senior leaders will learn to trust what you’re saying, and can rely on you.
How I messed it up
Until a few years ago, I didn’t even know my overconfidence annoyed people.
Then one day we were waiting for a bus with a coworker. 2 buses arrived, numbers 40 and 240. He said “Let’s get number 40, that’s my usual one”, but I insisted: “240 will get us there faster”.
He listened to me. Turns out 240 was not even in the right direction...
I laughed about it, but he said seriously: “You know Anton, you do that A LOT. You are very sure about everything. Most of the time you are right, but in the 10% you are wrong, it’s very annoying. If you had given me even a little clue you are not 100% sure, I would have insisted on my opinion”.
Since then I have tried hard to re-evaluate my confidence in things before I speak, and put in proper caveats.
How to become better at it
Tone and words: Use accurate language
6. Giving senior leaders feedback the wrong way
In a nutshell
You see a senior leader making life harder for themselves and their team. Wes wrote:
If you don’t speak up, you’re robbing your organization of your good insights. If you do speak up, you might put your employment and well-being at risk.
Traditionally, the more powerful person gives feedback to the less powerful person.
So if you want to give feedback to a more senior person, it’s an inversion of norms. This causes a moment of potential chaos, which is why you want to control the energy and channel it in a positive direction.
Feeling nervous about giving your senior leader feedback is a good thing. It means you have survival instincts that help with self-preservation.
How I messed it up
2 of my developers complained that the VP of Product is ignoring good ideas if they come from engineers. I raised one of those ideas myself in a design review meeting, but still nothing happened.
I got angry, and complained to my manager. When nothing happened, I wrote an angry email to the CEO (we are a small startup), citing that ‘innovation’ is a company value and how this approach stifles good ideas.
We had some back and forth, but in the end he just told me to figure it out with the VP Product myself (what a surprise).
I reached out in Slack, we scheduled a meeting, and it worked much better than any previous try.
How to become better at it
Wes’s article could have a lot in that case. She mentions 4 powerful techniques:
Deploy the “even more” technique
Use yourself as an example
Adopt a diplomatic, curiosity-forward language
Bring data and examples to support your point
Thanks Wes Kao for the super practical and valuable articles!
If you’d like to go deeper on improving your soft skills, Wes has a 2-day intensive course on Executive Communication and Influence for Senior ICs and Managers (not sponsored, but highly recommended!). The upcoming February cohort is sold out, but the course is currently enrolling for April 2025. Engineers from Meta, Salesforce, Pinterest, GitHub, Adobe, Equifax, Grammarly, Workday, Block, Shopify, eBay, Google, Airbnb, and more have taken the course. Check out the details and save your spot.
What I enjoyed reading this week
Two Shticks by
Managing Remote Teams Can Make You a Better Leader by from . Rafa recently doubled down on his newsletter, and I believe he’s going to rock it in 2025. Highly recommended!
