The Comprehensive Guide For First-Time Managers

Lifelong Lessons From Seasoned Leaders

Table of Contents

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On Learnings From First Management Role

Clear the way so others can be successful

“My first managerial role came when I was promoted to a service supervisor from a waiter at Sizzler, and my job was to manage the other waiters during our shift. During this time, I realized that I could no longer argue to have the best section of the restaurant assigned to me, but rather as the manager, I had to provide the best section to the other waiters working that shift. The biggest lesson I learned, that I have carried with me throughout my career, is that being a leader isn’t about getting your way — it’s about clearing the way so others can be successful.” - Jeetu Patel, Chief Product Officer at Box

Leadership isn’t about the boxes and lines on an org chart

“I started my career as a software engineer at Amazon, where I worked on “third party payments” (3PP), the system that moved money between buyers and sellers on their marketplace. About three years in, I took on a project management role within the team. Even though no one reported to me on paper, I was in a position to lead the broader team to a successful outcome. That was the first time it really clicked that leadership isn’t about the boxes and lines on an org chart, but about following people that you trust and respect.” - Isaac Oates, Founder & CEO at Justworks

Manage expectations, build trust, and be humble

“My first management role was in consulting before I started working in tech & startups. It was a people and project manager role. I learned a ton about working with people — both those I was managing and also the clients we were working for. From that first role, I learned how to manage expectations, how to align the work we were doing with the strengths of individuals on the team, how to build trust, and how to be humble.” - Justin Gallagher, Head of Product Management at Trello

The importance of setting the tone for team

“I first started managing while working in Uganda in 2007. The organization I was with was based in the northern part of the country, which had experienced decades of civil unrest. This made for an intense environment that lacked basic infrastructure for getting programs off the ground.

People management is very different from content leadership

“The first person I managed was a product management intern, and I remember how surprised I was by the amount of time I ended up having to spend with him. The biggest learning I had from that experience is that people management is very, very different from content leadership. Being a seasoned product person can easily translate into being a good product content lead, but good people management doesn’t necessarily come inherently and requires very different skills and training. Today, any time someone on my team expresses the desire to dabble in management, I make sure they understand that this is a very different function from what they’ve been doing, the switch doesn’t always work out for everyone, and it’s not the only path forward to growth — just to make sure they’re really ready for it.” - Sara Wajnberg, SVP of Product at Oscar

Leadership doesn’t come from an org chart

“I was a technical leader (Chief Architect and then CTO) with no direct reports at an online file storage company called Driveway during the last tech bubble (1998–2001). Then I moved to Boston to found a crypto/security company where I eventually managed a small team.

The distinction between a technical “leader” versus a “manager” is very important.

Successful companies now intentionally construct parallel paths for technical leaders to progress as organizational managers or technical leads. These non-managerial leaders should provide significant impact through design, mentorship, and cross-functional coordination. Companies should recognize these leaders with comparable pay, titles, and informal status. My staff meetings include both managing Directors as well as non-managing Principal leads”. - Dave Engberg, CTO at Livongo

On Great Manager Qualities


“My favorite managers were the ones that gave me autonomy and provided direct feedback. This way, I always knew where I stood and what I needed to work on. Additionally, high integrity has always been a very important character trait to me — it was important to me that I knew that my manager had my back.” - Jeetu Patel, Chief Product Officer at Box


“I’ve been very lucky to always have managers who cared a lot about the people working for them. I had friends who didn’t have the same experiences. Talking with them, I really grew to appreciate managers who always put their people first.” - Justin Gallagher, Head of Product Management at Trello

Being Human

“The managers that I’ve most respected and have learned the most from have always been the ones who didn’t pretend they were perfect. They admitted to not knowing answers, apologized for mistakes, and in doing so, invited others to be their partners in the work. There’s nothing more powerful than saying to someone, “I don’t know the answer, but let’s work together to find it.


“The managers I most appreciated were the ones I felt had my back and would go to bat for me — help me out when I needed something to be more effective at my job (e.g., access to production data!) or had a conflict that I couldn’t resolve on my own. Lack of action for me bred mistrust and disillusionment, so those managers that took my frustrations and concerns seriously and actually did something about them were the ones I most wanted to work for.” - Sara Wajnberg, SVP of Product at Oscar

Relatability & Reliability

“My first manager at Amazon, Phil Wilson, really cared about me as a person. I was 22, fresh out of school and had just started as an engineer on the payments team. Phil would talk with me about his own career experiences and help me think through the challenges I was facing. I think the big lesson was that he could lead by asking questions rather than telling you what to do. He was really good at letting you draw your own conclusions but also getting you where he wanted. This is something I wish I was better at. It requires a lot of patience. He was much more like a coach or older brother in the support he gave and we’re still in touch to this day.” - Isaac Oates, Founder & CEO at Justworks

Servant Leadership

“I’ve always been drawn to the “servant leader” model of management, and a big part of that is demonstrating that you’re never “too important” for anything the team needs.

I never worked at Disney, but I love their policy that “no one is too good to pick up trash when they see it.”

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On 1-on-1's

Clear hurdles, bring an agenda, and discuss bad news first

“I’ve made it clear to anyone who schedules 1-on-1 meetings with me that this is their time and it is up to them to set the agenda. My job is to clear any hurdles and make their life easier. And I tell them to bring me the bad news first.”- Jeetu Patel, Chief Product Officer at Box

Keep it casual, build relationships, and focus on listening

“I keep my 1-on-1s pretty casual and conversational. Our team is majority remote, so for me, these meetings are as much about building relationships as they are about checking in on projects, performance, and career aspirations.

Stay organized and discuss substantial content

“To keep things organized, I have a private Slack channel with each of my direct reports where we can both post agenda items to discuss in 1-on-1 meetings. Sometimes something can be solved more quickly in that channel, otherwise, we collate all the topics posted each week for in-person discussions.

Prioritize real-time, get out of the office, talk career goals

“My approach to 1-on-1's is pretty personal, starting from the amount of time and cadence — I try to let my reports figure out what amount of time they want from me and how often we should meet, and adjust as needed as time goes on. For frequency, it varies: Sometimes it’s twice a week for 30 minutes each time (one tactical, one career-oriented ), sometimes it’s once a week for a 30-minutes, and sometimes it’s once a week for an hour, etc.

Don’t overdo it

“I like to review the goals that we’ve set together, discuss if any changes are appropriate, and then exchange feedback. I have 30 minutes per month with each of my direct reports, so most of our substantive discussion happens in group meetings rather than 1:1. That’s intentional — I think group meetings are helpful in building shared consciousness and minimizing politics.”- Isaac Oates, Founder & CEO at Justworks

Focus on advancing employee development

“I’m of the school of thought that these meetings should be primarily the time for the employee to express their needs and advance their development. My main job as a manager should be to make my team successful in their current tasks and overall careers. So the agenda is mostly owned by them, with explicit instructions that this shouldn’t just be a status update or summary of work. Those are better handled through separate meetings like standups.

My main job as a manager should be to make my team successful in their current tasks and overall careers.

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On Giving Effective Feedback

Early, often, and lead with details

“Giving feedback early and often is one of the most important things you can do as a manager, including both positive feedback about the things someone is doing well, and constructive feedback about areas where someone can improve. However, I often see first-time managers shy away from giving direct feedback out of a fear of not being liked or a concern over hurting someone’s feelings. Avoiding hard conversations ultimately harms the relationships between a manager and their direct reports, so I encourage first-time managers to master *how* to give feedback, as the way in which it is delivered has the biggest impact on how it will be received.

Give it time

“Giving effective feedback is difficult but it gets easier with time. I think this is probably the #1 management challenge for many people, including very senior and experienced leaders. Just keep working on it.” - Isaac Oates, Founder & CEO at Justworks


“I’ve been trained on a few different frameworks, such as SMART (Specific, Measurable, Attainable, Relevant, Time-based). I think it’s worth the time to learn one of these and do a couple practice runs.

If you’re only giving feedback once a year when compensation changes are due, you’ve failed.

Of all of those letters, I think the ‘T’ is the one that first-time managers may find the hardest. If you’re only giving feedback once a year when compensation changes are due, you’ve failed. You should force yourself to schedule frequent incremental feedback where you can point to specific recent examples rather than batching it up over a span of months to drop on someone like a pile of bricks.”- Dave Engberg, CTO at Livongo

On Important Habits To Form

Use your org chart as a mental touch base

“One thing I have found invaluable is to regularly pull up my org chart and go through every individual in my mind to make sure they’re getting what they need from me/my reports, that I know where they stand and what we’re working on to develop them, and that I have a good read on how they’re feeling. That continuous mental touch base often allows me to get ahead of things before they start burning.” - Sara Wajnberg, SVP of Product at Oscar

Communicate your preferred communication method

“I am terrible at responding to email and learned early on that people get frustrated if they can’t get a hold of you. But, I realized that text messages work much better for me and am always responsive on text — so, people who really need me can always get a hold of me this way.

Identify an actionable next step for every to-do item

“To make sure I’m prepared for the day ahead, I spend a few minutes every morning on the train going through the items in my “Today” list to make sure they all have an actionable next step. This helps me keep up the momentum so I don’t get bogged down by big, overwhelming projects. For meetings and 1:1s, this exercise ensures that I go into every conversation with at least some forethought and preparation so I can make the most out of that time.” - Justin Gallagher, Head of Product Management at Trello

Sort tasks into groups to increase your operating tempo

“Whether it’s on paper, on a spreadsheet, or in my inbox, sorting tasks into different groups and then attacking them together head-on has helped me be more productive. Recently, for example, I set up some filters in my email account that separate messages that demand a response from everything else. That might seem small, but it’s changes in habit like this that have helped me be much more responsive to the people I work with. It’s made a surprisingly large difference in our operating tempo. I also take time on Sundays to draft emails to send out on Monday morning. It helps me catch up on my inbox without also dumping work on my team over the weekend.” - Isaac Oates, Founder & CEO at Justworks

Aim for Inbox Zero

“When you choose to go into technical management (instead of leadership as a staff/principal contributor), you need to give up on having any deep blocks of focus during working hours. You need to be interruptible and responsive so that your team can afford to flow.

On Changing Team Members’ Behavior

Ask lots of questions

“I have a well-earned reputation for asking a ton of questions. Sometimes this makes people who aren’t used to working with me feel as though I’m questioning how prepared they are or whether they’ve thought through something fully, but I am usually just genuinely curious and feel as though I can’t really weigh in on something if I don’t adequately understand it. Asking lots of questions often reveals that someone has made assumptions they still need to validate, or that they don’t have the answer to something that probably will be asked of them. My goal in doing this, beyond improving my own understanding, is to help people learn how to get the full picture of a problem before forming an opinion or designing a solution, and I do think that this style of interaction helps train people to do that more naturally. I apply the same methods when talking about less tactical things like cultural concerns or questions about career pathing; asking lots of questions allows someone to sort through and better understand their own thinking, as well as consider other perspectives.” - Sara Wajnberg, SVP of Product at Oscar

On Top Advice From Coaches & Mentors

Be deliberate about your words & actions to avoid confusion

Be cognizant of insecurities that can block your career progress

“I haven’t worked with a formal professional coach, but we do have a function at Oscar called People Strategy (similar to the role of a traditional HR business partner, but even more expansive), and I am paired with someone that is essentially a coach who has had a huge impact on my thinking and on my career development. The biggest lesson I have learned from working with her is that I have subconscious mental blocks and insecurities that prevent me from proactively stepping up to take on broader roles and responsibilities. Each time I’ve progressed roles and become more senior it’s taken months to build up my confidence and get myself into the right mindset, but it’s definitely getting easier the more I’ve internalized and recognized that this is a gap that I have to work extra hard to overcome and that I usually do just fine after I’ve gotten over the mental hump!”- Sara Wajnberg, SVP of Product at Oscar

How to communicate with executive peers

“I’ve done a bit of coaching, with some mixed results. The most actionable thing I picked up in my last attempt was around communication with executive peers. It’s very easy/common for the technical leader to be stuck in the role of the naysayer since they’re usually on the hook for the actual delivery of their peers’ desires.

Always start responses with explicit enthusiasm first, dramatic pause, and then give my input.

My last coach gave me some feedback about always starting my responses with explicit enthusiasm first, dramatic pause, and then give my input. E.g. ‘Wow, this sounds like a great opportunity. I’d love to help figure out what it might take to get it done. [Deep breath…] Here are two questions I’d want to start with…’”

On Delegation

“I’ve been fortunate to hire and work with some extremely talented people at Justworks, who are much better at most things than I am. That makes it easy to delegate. That said, if I’m still getting comfortable with their work style or it’s a high-risk project then I ask to stay involved as it progresses. Some things I’ll always stay closely involved in, for example, activities that impact or send messages about our culture like promotions to leadership roles and company-wide events.” - Isaac Oates, Founder & CEO at Justworks

On What They’re Working On Now

Workplace Diversity

“Diversity in the workplace is an area I feel passionately about, especially working on getting more women in technology, across all functions. I truly believe that teams perform better in an environment where there is a diversity of backgrounds, beliefs, and where employees feel like they belong.” - Jeetu Patel, Chief Product Officer at Box

Communication at Scale

“When an organization scales, a leader has to transition from doing the work to getting things done. This isn’t an easy switch for many leaders or their teams, however. Leaders have so much more context about the work given the information they have access to, and they also have opinions on how the work happens and what quality and craftsmanship in execution look like (or at least I do!).

Long-Term Vision vs. Short-Term Action

“One thing I’m working on now is helping the team achieve a better balance between long-term vision brainstorming and articulation vs. day-to-day execution against our nearer term objectives. We are doing a lot, and sometimes it feels as though there isn’t enough time to think far ahead. We’ve already put some mechanisms in place to help get us in the right mindset (such as healthcare tech strategy sessions every few weeks, regular strategy offsites, newsletters we all subscribe to, etc.) but we still have a lot of work to do to achieve a healthier balance between the now and the future.”- Sara Wajnberg, SVP of Product at Oscar



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