How I Learned to Talk to My Boss

Enough years have passed for me to make this somewhat embarrassing confession:

When I joined Google 9 years ago, I thought it was wrong to prepare an agenda for 1-on-1 meetings with my manager.

So for the first few months at Google? I would show up to my 1:1 meetings with my manager... and essentially wing it.

Why? Because here's what I (rather naively) believed at the time:

• If I know I'm working on the right stuff, shouldn't the convo just flow organically? Wouldn't we naturally cover what's top-of-mind anyway?
• If I have to prep for every 1:1 with my manager, wouldn't that imply a rather artificial or even forced relationship?
• Given my manager is more senior, isn't it natural that I let her dictate what she wants to talk about with me?

Of course, as time went on, I would eventually learn the errors of my ways (the hard way, unfortunately).

Thankfully, I would also get better at having 1:1 meetings – not just with my manager, but also with business partners and cross-functional stakeholders.

So in today's issue, we'll talk about my top 5 learnings over the years:

1. Success starts way before the meeting.
2. There's no one-size-fits-all format.
3. The first 2 minutes are critical.
4. The 1:1 serves you – not the other way around.
5. Simple hygiene can work wonders.

1️⃣ Success starts way before the meeting.

A successful 1:1 meeting doesn't occur only when the meeting starts.

Instead, it gets decided by how much prep was done leading up to it.

And here's the thing: the prep work need not be onerous. No one is expecting an hour's worth of prep for a 30-minute 1:1 meeting.

Instead, it can be as simple as practicing the discipline of:

• Jotting down topics as they emerge throughout the week (so you aren't fumbling on the spot)
• Sending pre-read materials if necessary (and explaining how it will enable the live discussion)
• Pinging the other person ahead of time (if you want their view on something)

The last point is worth elaborating on further.

Becaue way too often, people simply drop loaded questions in 1:1 meetings ("Can you give me some constructive feedback on my performance this past quarter?") and expect thoughtful answers.

The result? The other person is forced to improvise on the spot. You won't get a thoughtful response – and your interlocutor probably feels caught off guard.

This is a lose-lose situation. And the meeting will have felt like a waste of time for you both.

A better approach instead? Give the other person a quick heads-up beforehand.

For instance:

"For our 1:1 on Thursday, I'd love to get your thoughts on what I could've done better on the last project. No action needed – just wanted to give you a heads-up!"

When you do this, you do both yourself and the other person a favor. They'll have enough time beforehand to brood on your question, and you'll get a much more measured response come the actual meeting.

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2️⃣ There's no one-size-fits-all format.

Not every 1:1 meeting has to be run the same way. The format and flow should be highly flexible based on your needs.

For instance, if you have to triage several small but time-sensitive topics? Then run a "lightning round" type of meeting. List out all the items on the docket up front, and ask for a bias towards decision-making.

What if instead you have a topic that requires deep discussion? Then make sure it's the first (if not only) item on the agenda, and explicitly ask for it to be prioritized.

This principle applies as well when it comes to the nature of your discussion.

In other words, not every meeting needs to be highly intellectual or strategic. Sometimes you have to talk about very tactical decisions. Sometimes you need to cover operational updates.

And that's okay.

As long as you are highly intentional about what kind of 1:1 meeting you want – so you can then shape it accordingly.

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3️⃣ The first 2 minutes are critical.

I learned this lesson the hard way. Because early on in my career, I would jump into 1:1 meetings and just start talking.

The problem with this? The other person didn't know if I planned to spend 2 minutes or 20 minutes on it.

They didn't know if it was the only topic I had in mind, or 1 out of 5 that I wanted to cover.

As a result, I would mislead the other person into going deeper than needed on certain topics. It would also come at the expense of more pressing topics from the other person.

The key to avoiding this mistake?

Practice the discpline of "talking about what you want to talk about" in the first 2 minutes.

Because when you do this, you get a full view of all the topics on the table. And this is beneficial for a couple reasons:

1. You now get to reprioritize the agenda, allowing you to start with either the most important (or the quickest) topics.
2. You now have a sense of how deep to go for each topic, and when to move on to the next one

I've been in meetings where people asked questions that were only meant as icebreakers, yet took up half the meeting.

The reason? Neither side stated upfront what they wanted to discuss. And both sides were too polite to disrupt the existing flow.

As a result, half of the meeting time was essentially wasted.

So sure, the convo may have flowed organically — but also terribly ineffectively.

4️⃣ The 1:1 serves you – not the other way around.

Most 1:1 meetings tend to be recurring (e.g. weekly or bi-weekly). It's a permanent fixture on our calendars.

The mistake people tend to make? Treating the cadence as sacrosanct, and assuming they have no say over it.

But this is misguided: you are always in control. The structure is in place to serve your needs – not the other way around.

You are empowered to do things like:

• Cancel the 1:1 if you don't need it (instead of showing up and awkwardly trying to fill up the time)
• Extend the meeting time (if you anticipate a hairy topic to be discussed)
• Propose longer but less frequent meetings (or the other way around)
• Reschedule it to before or after another meeting (if the sequencing helps)

On that last point, here's an example: imagine that you're expected to discuss project updates with your manager in your weekly 1:1 meeting.

A smart thing to do? Schedule your project-related discussions prior to that 1:1, so your manager gets the freshest updates.

Similarly, what if you expect to cascade information from that 1:1 meeting to other people?

Then you'd probably want to make sure those touchpoints occur after your 1:1, so as to create the most natural information flow.

The key is this: you can't simply show up to a 1:1 meeting and expect it to work perfectly.

Instead, you are empowered (and expected) to continuously tweak the setup – until it actually works for you.

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5️⃣ Simple hygiene can work wonders.

Sometimes, the effectiveness of 1:1 meetings boils down to very simple things.

For instance:

• Maintaining a shared agenda doc, where both sides can add topics (and prevents things from falling off the plate)
• Tracking action items in a shared document (thereby instilling accountability for both sides and allowing for prioritization)
• Periodically reviewing past meeting notes to identify patterns (e.g. Do you always run out of time? Do you focus too much on tactical topics?)

Remember when I said that early on in my career, I worried about instilling too much structure into 1:1 meetings, for fear of making the relationship too formal, or making the discussion appear too forced?

Ironically, it was only when I practiced better meeting hygiene, that I actually started being taken seriously by my manager and business partners.

Why? Because...

• ...I was no longer improvising on the spot (which made me come off as unprepared and unorganized)
• ...I stopped showing up to meetings waiting to be spoon-fed (and instead demonstrated that I could proactively identify business priorities)
• ...I reduced a lot of mental anxiety for my managers (as they now found predictability in how I operated)

Takeaways

• A good 1:1 meeting requires intentional prep. Much of this starts before (and even after) the meeting.
• Not all 1:1 meetings are created equal. Your job is to customize the setup as needed.
• Ineffective 1:1 meetings are often due to a lack of hygiene. But simple things like aligning the agenda upfront or capturing action items diligently can do wonders.