Your manager is already investing in you
Don’t romanticize what it means to be mentored and coached. You might already be getting the support you've been looking for.
👋 Hey, it’s Wes. Welcome to my bi-weekly newsletter on managing up, leading teams, and standing out as a high performer.
To level up faster, check out my intensive course on Executive Communication & Influence. You’ll learn alongside mid-career operators from Netflix, Stripe, Meta, Figma, Anthropic, etc. → Join the May 2026 cohort
⛑️ If you’re looking for 1:1 coaching to dramatically improve your communication and leadership, learn more about my coaching approach.
Read time: 6 minutes
In my early twenties, I wished I had a manager who would “coach” and “mentor” me. I wanted this so badly.
One day, I realized, my manager taking the time to rip my work into shreds AND patiently share actionable feedback…
This WAS coaching me.
This WAS mentoring me.
This WAS investing in me.
I was too busy whining to realize, in fact, I was getting what I wanted all along.
Don’t romanticize being coached and mentored
You may have an idealized version of the perfect manager in your mind, but your manager won’t able to live up to that ideal.
“Coaching” and “mentoring” and “investing in your growth” don’t only show up in formal career conversations, or look a certain way.
If your manager cares enough to say, “Hey, this kinda sucks, but here’s how to make it better,” they are investing in you.
Who would you rather have?
A manager who talks about your career during performance reviews, but doesn’t give you detailed feedback on a weekly basis.
A manager who talks about your career path when you initiate, but gives you consistent, actionable, detailed feedback regularly.
Of course, you’d want both.
But if I were to choose, I’d say the latter is more important.
You might be thinking, “Alright Wes, my manager is already giving me some feedback. But how do I get more coaching from them?”
Read on, my friend.
1. Show your manager that giving you feedback is worth their time
Yes, it’s part of your manager’s job to give you feedback. No, this doesn’t mean they feel obliged to do it, mainly because giving good feedback takes effort and your manager is probably swamped.
You’re more likely to get feedback if you sell them on the upside of doing so. For example:
If your manager were to engage with you on this topic, how will it save money or make money for the company?
How will it allow you to add more value?
How will feedback now improve everything that comes after?
If your response is, “Getting an answer to my question doesn’t really impact my ability to add value to the business,” your question might not be worth the time to discuss.
Most senior leaders are ruthlessly focused on driving value for the firm. If addressing your question doesn’t contribute to that, it makes sense why they’d deprioritize it.
2. Become someone your manager wants to invest in
At the end of the day, managers invest in people they believe are worth investing in. It’s a bit circular, but it’s worth saying because there are a few implications.
Generally, you want to behave like someone who learns quickly, is going places, and is a strong performer. You want to act like an owner and do what’s best for the business. When you have a history of good judgment and continuous improvement, this makes your manager want to give you more feedback.
Try to react positively when managers give you any type of coaching. This matters because many managers have learned the hard way that they need to carefully phrase their feedback using words that will be more acceptable for their direct reports.
Otherwise, they risk being seen as an insensitive asshole.
If you’re a direct report, you do not want your manager to feel the need to “translate” too much because it reduces the chances they’ll give you feedback at all.
You benefit when your manager can speak freely with you. For example, you can say,
“Feel free to be super direct. If this sucks, tell me and share why/how I can improve because I want to learn. Feel free to rip it apart.”
3. If you’re not getting what you need, switch things up
It’s usually much easier for your manager to react to something specific, soon after it happened, than it is to ask about vague ways you can improve.
🚫 “What can I do get to the next level?”
✅ “What do you think I did well in the presentation to our SVP just now? What could I have done differently to be more effective?”
In the “before,” questions like this are hard for your manager to answer. They require your manager to think about everything you do, don’t do, where you fit in the org…then create a curriculum to teach you.
In the “after,” this is a much more manageable question that feels less loaded. Your manager can give you feedback about the meeting you were both in just now, which you can apply to future presentations.
Another example:
🚫 “Can you teach me about strategy?”
This is hard. Your manager has to think of how to teach you this intimidating, complex, large topic of strategy.
✅ “I drafted a strategy doc. Could you tear this apart? What are you skeptical about? No need to hold back. I want to make a strong argument and address any potential risks.”
Here we go. This ask minimizes cognitive load and is less intimidating to tackle, so it invites your manager to teach you about strategy on the job.
Other questions you can ask:
“What would you do differently? What’s missing?”
“What grade would you give this? What would make this an A+ in your eyes?”
“What is the most interesting 20% of this? Most boring 20%?”
“Could you mark which parts of this memo are confusing?”
“What would you do if you were in this situation?”
“Do you see any risks or logical gaps that I missed?”
Notice how these questions are designed to draw out insights from your manager.
When your manager is actively giving you their insights on how you can improve, this is coaching. This is mentorship. Don’t let it go to waste.
Further reading
If you’re a manager (or want to be one), here’s how to coach your direct reports:
Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.
Wes
✨ Next week: Free workshop for product managers
I rarely do free workshops, so if you’ve been curious about my course or if you found my Lenny podcast episode valuable, this is for you…
I’m excited to be featured in Lenny Rachitsky’s “The AI-Native Product Manager” series. As part of this series, I’ll be teaching a free workshop on the topic “How to Get Executive Buy-in as a PM.”
Product managers are one of the biggest groups represented in each cohort, and about 1/3 of my private coaching clients are product leaders. I believe the bar for product is getting higher each quarter, so if you are a self-aware and thoughtful product person, I want to help you stand out.
In this session, I’ll cover how to:
Present to impatient executives: Be prepared to move fast, speak directly, etc.
Manage up to senior leaders: Most PMs suck at managing up. We'll cover principles that will serve you now and throughout your career.
Anticipate questions and prevent skepticism: How to anticipate questions to avoid endless back-and-forth.
You will be able to apply these principles to stakeholders upwards, downwards, and laterally.
The free workshop will be on Friday, March 13 at 12:00 - 12:30pm ET.
There are already 4,584 people signed up, which is pretty nuts.
If you’re interested, click here to RSVP.
Connect with Wes
Is this your first time here? Subscribe (it’s free)
Follow me on LinkedIn for more insights
Learn more about 1:1 coaching to sharpen your executive presence
✨ Course: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in a 2-day workshop. Over 1,500 tech operators have taken this course, and every cohort so far has sold out. → Save your spot in the May 2026 cohort
I'm very used to saying when asking for feedback: Please be rude with my work if you need to, I'm not going to take it as a personal attack, and it also helps me to do better next time.
Looking back, I wasted so many investments from so many managers. Now as a manager myself, I don't mind when my reports ignore my input. A lot of time I'm just happy to have planted some seeds.