Hot Take: Not everyone should be a manager
Our cherry-picked takeaways from the book that made Daly a Best Workplace
CHERRY ON TOP 🍒 is our monthly newsletter exploring the ins and outs of everything that modern businesses need to truly shine. We dive into topics that live at the intersection of our two companies – ORCHARD STREET, a venture studio + angel fund & DALY, a comms+ agency – as both help founders get the best ideas out into the world, through outstanding operations, comms, and culture-building.Alex & Ally here! Welcome to Cherry-Picked Books — our new Cherry on Top series where we revisit the books that have shaped how we built our businesses: Daly and Orchard Street.
We’re not here to review them, but to pull out the ideas that actually stuck. Think of it as a business CliffsNotes — but make it juicy.
Each edition, we’ll break down one book through the lens of what we care about most: bite-sized (🍒😉) tidbits on how modern businesses can help themselves truly shine through standout operations, communication, and culture.
xx A&A 💋💋💋
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Ally: Becoming a manager unlocked something for me — professionally, but also personally.
In retrospect, I imagine this happened like in those videos of babies with imperfect vision having glasses slid over their eyes for the first time. They were getting along just fine before, but then—behold! Clarity.
Managing a team felt perfectly suited to my career skills and passions in a way that being a publicist never did, and helped me define what my own brand of leadership looked like.
But just because things clicked into place so seamlessly doesn’t mean the journey has been easy. There’s a lot of imposter syndrome that comes with the process — a concept Julie Zhuo explores quite well in The Making of a Manager, which was the most influential of the many books I devoured back in 2019 as I was first deciding what type of manager I wanted to be.
This passage from the book’s intro resonates with me even more now than it did as a newly-appointed manager 7 years ago:
“I’m by no means a management expert. I’ve learned largely by doing, and despite my best intentions, I’ve made countless mistakes. But this is how anything in life goes: You try something. You figure out what worked and what didn’t. You file away lessons for the future. And then you get better. Rinse, repeat.”
Truer words! Being a good manager is as much a personal journey as anything, which means you’re never going to get it 100% right. But we can certainly help you try. :)
To that end: I recently revisited The Making of a Manager, and pulled out 5 cherry-picked lessons that feel especially relevant for today’s leaders. Whether you’re already a manager or aspire to be one, I hope these takeaways inspire you to reflect on what it means to lead with empathy and integrity.
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Being a good manager involves a healthy dose of daily discomfort
“Time isn’t a substitute for comfort. That new-kid-at-school feeling may linger [...] and new managers often ask, ‘How long will it take to feel like I know what I’m doing?’”
Being a good manager isn’t about keeping everyone happy at all costs; it’s about helping each of your reports feel seen and heard in a way that unlocks their specific potential — for their own sake, and for that of the company.
This doesn’t mean always agreeing with your report, or avoiding giving them critical feedback.
It does mean showing your report you’re personally invested in them by actively listening and advocating for them when needed — and also having the courage to approach them about clear areas for improvement, and then guide them back on track.
Feedback is a big part of why managing can be hard for people pleasers (guilty!) who shy away from perceived confrontation. But thoughtful, specific, timely feedback is a gift, and crucial for a strong manager-report relationship. Avoiding it doesn’t do anyone good, and shying away from tough feedback that will foster growth isn’t kind — it’s lazy!
As a general framework for giving consistent, appropriate feedback:
Task-specific feedback should be given as immediately as possible, and as frequently as needed; a quick Slack note or mention at the end of a call is fine.
Pattern-based or behavioral feedback should be saved for its own dedicated 1:1 conversation, and doled out with an extra layer of thoughtful consideration, as these are often about connecting bigger picture patterns that you’ve observed, and want to make sure your report sees and acknowledges too. “Face to face” or live conversations are usually best here.
360 feedback should be infrequent, thorough, and given a strict framework — and always filtered through your managerial lens (tread carefully!)
Relatedly….
…Your feedback only counts if it makes an impact
“The best way to make sure your feedback is heard is to make the listener feel safe, and show that you’re saying it because you care about them and want them to succeed.”
Don’t pat yourself on the back just for having the hard convo. And don’t waste the effort of a hard convo without making sure it goes somewhere!
If you’re going to spend the time giving feedback, make sure it’s being given in a way that means your message is being heard.
This means:
Be clear, direct, and kind. No rambling!
Reduce or eliminate preamble; get to your point quickly
No compliment sandwiches (padding your true feedback with softer points is distracting)
Be specific vs general and overarching
Be prepared to give clear examples
Don’t bring up anything tangential that might distract from your core point
Good management is multiplicative, not additive
“Your role as a manager is not to do the work yourself, even if you are the best at it, because that will only take you so far. Your role is to improve the purpose, people, and process of your team to get as high a multiplier effect on your collective outcome as possible.”
If you’re a manager who is often doing everything yourself and avoiding critical delegation, I’ve got a wake up call for you: you’re acting as an individual contributor (IC) and not doing your core job of optimizing the full potential of your team!
Training, coaching, and giving consistent, thoughtful feedback all leads to multiplicative success, in which your team is able to achieve in ways that are far greater than the sum of its parts.
As Zhuo writes, “your job as a manager is to get better outcomes from a group of people working together” — and thus your success as a manager is judged by your team’s reputation for excellent outcomes and success. You’re not going to achieve this by doing everything yourself and then bemoaning the fact that no one’s chipping in.
Don’t be a hero. Teach your team to fish!
You have the freedom to create your own managerial template
“Your team’s culture is like its personality. It exists whether or not you think about it. If you’re not satisfied with how your team works together [...] it’s worth examining why this might be, and what you can do about it.”
Maybe you’ve had great, life-changing managers in the past. Maybe you’ve had terrible managers who have been absent at best, or left you with workplace PTSD at worst. Both scenarios offer crucial foundations from which you can learn and decide what kind of manager you want to be (or not be)!
Your own managerial track can be entirely your own, rooted in your unique skills and those of your team. Good managers are ones that meet their specific reports where they’re at, not who follow some templatized rulebook based on what came before.
Structure meetings in a way that works for your specific team or reports. Find out how each of your reports prefers to communicate and tap into that. The more you throw the playbook out the window and create your own based on your personality and the needs of your team, the easier it’ll be to get into “multiplicative” territory (see: Lesson #3).
A good manager leads with authentic vulnerability (accept that you’ll never have all the answers!)
“Strive to be human, not a boss [...] When we are going through tough times, the thing that’s often the most helpful isn’t advice or answers, but empathy.”
Think of the last great manager or mentor you had. Were they great because they helped you solve every problem and always had all the answers? Maybe (if so, lucky you!) ... but that’s probably not why you remember them.
The managers that make the greatest impact on their reports are the ones who establish a foundational two-way street of trust, mutual respect, and connection. And the foundations of trust must always begin top-down with the Manager — it’s your job to set the tone of trust for the relationship, not your report’s! Be the manager you always wished you’d had!
This includes:
Establishing a personalized connection with each report. Show them you understand their personality, needs, skills, and goals. But make sure to maintain a balance, and avoid becoming overly friendly to the point where it’s uncomfortable when you inevitably need to switch to giving tough feedback that helps them grow!
Owning your company’s leadership decisions as your own. Resist the urge to scapegoat as a middle manager! It may seem like the easy way out to play the good cop, but it’s ultimately better for employees if their manager and leadership are aligned on a clear vision for them to understand and work towards.
Being honest and open to pivoting in tough times: managing in ‘survival mode’ looks different than managing in a time of security, abundance, and growth. You will need to put on different managerial hats in each case — adaptability is key! Things you wouldn’t let fly in a time of success may need to come into play in a time of strife.
Zhuo’s in great company with her reflections on this — topics of authentic vulnerability also come up with other workplace visionaries like Glennon Doyle, Kim Scott, and Brené Brown (if you’re looking to add additional powerhouse women to your TBR list!)
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The Cherry on Top: My hot take has long been: becoming a manager should not be a prerequisite to one’s career growth.
Many people’s skillsets are better suited to remaining forever-ICs, and companies that are structured to force their top-performing ICs into manager positions as a necessary stepping stone to higher titles and more money are hamstringing their employees’ success, and thus their company’s, too.
You won’t be able to unlock the true potential of your company’s org chart until it becomes more of an established practice to separate Manager and IC growth tracks — and make sure that everyone in a Manager role is actually suited to be there!
