April 6, 2026
Every time you speak, your boss places you into one of two buckets: Order taker or future leader.
If you walk in and you say, “Hey, I have a problem. What should I do?”
Well, they’ve already put you into the order taker bucket.
But to land in the future leader bucket, you have to radically change how you speak.
And it comes down to these five simple communication habits.
Imagine every problem at work is a small, noisy monkey sitting on your shoulder.
Now imagine walking into your boss’s office and saying, “I have a problem with this project. What should I do?”
Well, that monkey just jumped from your shoulder onto your boss’s shoulder. Now they are carrying the burden. They have to think. They have to decide. They have to act.
If you do that a few times a day, well, your boss ends up covered in monkeys. It’s a zoo in his office. And your boss hates this.
They don’t promote people who give them more monkeys. They promote people who make their own monkeys disappear.
So don’t ask for a solution, propose one. But let me show you the difference.
The Order Taker
“The shipment is delayed. How do you want to handle the customer?”
The Future Leader
“Well, the shipment is delayed, but I’ve already called the warehouse and they can get it done by Tuesday. I recommend that we send the customer a $20 voucher today for the trouble. Does that work for you?”
Or if the situation is more complex, give them options.
Don’t say:
“Well, we’re a bit over budget on the event. What should we cut?”
Say:
“We’re $2,000 over budget on the event, but I found two ways to fix it. Option A is cutting the gift bags, which saves us $2,500 instantly. Option B is switching to a cheaper catering menu. But I recommend option A so we don’t sacrifice food quality. Which one of the two do you prefer?”
Notice what happened here.
You did 90% of the work and they just have to sign off. And knowing that you can solve those problems proactively, well, that makes them trust you so much more.
So, the next time you’re about to ask for help, ask yourself, “Am I trying to hand over my monkey?” If the answer is yes, wait until you have a recommendation ready.
Have you ever been on a date that went well, but then nothing? You’re sitting there staring at your phone, but she doesn’t text you back.
That is exactly how your boss feels when you don’t give them updates.
In moments, you stay silent. Your boss might be thinking, “Did they forget? Is the project falling? Am I going to look like an idiot in that next board meeting?”
And bosses don’t promote people who make them feel anxious. They promote people who make them feel certain.
How do you fix this?
Send them a brief update before they have a chance to worry.
It could sound as simple as,
“Hey, here’s a quick 30-second update so you can keep this off your mind. The report is 80% done. I’m just waiting on one final number from finance, but we are on track for Friday. No response required.”
Those three words, no response required, are super powerful. You’re giving your boss the gift of information without having to reply.
Now, how often should you do this?
Well, it depends a little bit on your boss’s anxiety level. If you have a more of a micromanager, well, they need that hit of certainty every day. So, for that, just send them a message daily.
If you have a more hands-off executive, well, they just need to know that the plane is landing on time. And so, for them, a weekly message should be okay.
In my first year as a consultant at Bain & Company, I walked into a meeting room to give an update to the senior partner, and I was proud, right? I had 20 slides of data, charts, and deep analysis.
So, I started at the very beginning. I explained the methodology and all the background information. But about 5 minutes in, the partner on the team literally slammed his hand on the table and said, “What is the point?”
At first, I felt so embarrassed. But then I realized he was right. I was talking all the way bottom up. I was giving him all the ingredients when he just wanted to know whether the cake was baked.
Most people think that more information equals more value. But to an executive, more information just feels like noise.
If you want to be promoted, you have to flip the pyramid. Instead of starting with data, then the hypothesis, then the recommendation, flip the script. Do the opposite.
Let me show you what that looks like.
The Order Taker
“So we looked at the Q3 numbers and we noticed the marketing team had a delay and we talked to the warehouse and so basically we missed our target.”
The Future Leader
“We missed our Q3 target by 5%. The main reason was a delay in marketing but I’ve already scheduled a meeting for Monday to fix the workflow. Do you want to see the data points behind that?”
Notice how the leader started with the recommendation first and then went into the hypothesis.
Also, notice the last sentence. I ask if they want to see the data points. That way, I’m not hiding it. I’m offering it as an option.
It tells my boss, “Hey, I know all the details, but I respect your time.”
Imagine it’s Thursday afternoon. You’ve been grinding all week, finally cleared your to-do list, and you’re so much looking forward to the weekend.
But then your boss walks over and drops this 20page document on your table and says, “Hey, I need this done by tomorrow.”
Now, in that moment, most people do one of two things.
They either say yes and stay late feeling resentful and burned out, or they say no and look like they aren’t a team player.
If you want to be promoted, you have to realize your boss isn’t trying to drown you. They’ve just forgotten everything else that is on your plate.
To be a leader, you have help them prioritize and talk them through the trade-offs.
Here’s the difference:
The Order Taker
“Okay, I’ll try to get this done. I guess I’ll stay late tonight.”
The Future Leader
“I can definitely take that on. Just to make sure I give this the focus it needs, I’d have to move the client report or the budget review to next week. What do you prefer?”
Why does this work?
You aren’t saying no. You’re saying, “Hey, I care about the quality of my work.”
Now, the next time you feel overwhelmed, don’t complain about being busy. Show your boss your list and ask them what’s urgent right now.
The person who knows what not to do is the person who gets trusted with the big decisions.
In my last job at Uber, I walked into my end-of-year review. By then, I had worked super hard. I hit all my numbers and was 100% sure that this was my year.
Quickly after I sat down, my manager said,
“Philipp, you’ve done a great job. We really value you here. But just to be clear, we can’t move you up this year.”
Immediately, my brain went, “What the hell?” I had worked so freaking hard for this. I was furious.
I rushed out of the room with all these toxic thoughts. “They don’t value me here. This place is a joke. I should quit.”
But once I calmed down, I realized the mistake was mine. I had been acting like an order taker, waiting to be noticed instead of taking ownership.
I had spent the whole year hoping that they would notice me. I had treated my promotion like a surprise birthday party.
If you want to move up, you have to stop waiting and clarify the requirements months in advance. So, don’t wait for the yearly review.
At the start of the cycle, say this, “I’m curious, what are the two to three specific milestones I need to hit in the next six months to make the senior role an absolute no-brainer?”
Now, that works because it does something brilliant. It turns your promotion into a contract.
When your boss says,
“Well, for that, you need to lead a project and hit X revenue.”
You can respond,
“Great, if I hit those two things by December, can we agree that the promotion is the next step?”
Now you aren’t guessing, you aren’t hoping, you are executing a plan that they helped create.
Don’t wait until the end of the year to check in—every 3 months, show them the roadmap and ask, “Hey, are we still on track?”
The person who manages their own growth is the person your boss trusts to manage the growth of others.
If you start these five habits, your boss will start seeing you as a leader rather than just support staff.
But there’s another strategy we didn’t cover today: how to make your message stick.
That is exactly what we’re going to cover in the next article on how to speak 10 times more engaging.
See you there.
P.S. Want to become a stronger communicator?
Here are two ways I can support you:
👉 Want to tell more engaging stories? Join our next Storytelling Workshop.
👉 Want to speak with confidence and clarity? Check out our Communication Skills Training.
Both are fun, practical, and designed to help you grow fast.
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