Suggestions for first-time managers and the leaders who grow them

Don't jump in to the deep end with rocks in your pockets at 2AM. Go during regular pool hours when the lifeguard is on duty and take the steps.

Jun 30, 2025

My first management experience was awful. I took on way too much way too fast at a time when everything was constantly on fire. There were a few bright spots - my team - but the rest of it just absolutely sucked. I barely slept and was sick more or less non-stop the month I decided to leave. Management is horrible, I concluded, why would anyone make a career out of this?

Then something funny happened a year later at my next company. I had been doing well enough as a senior engineer and generally having lots of IC (Individual Contributor) fun when I realized that my fish bowl was getting tight. At the same time it just so happened that my manager was ready for a new challenge. I had been resisting a return to management for a little while but the team needed a new lead and I didn’t want someone else to do it; I wanted it to be me.

So I asked for the role. I got a trial period while my manager was out on parental leave and we made it permanent when he returned. Management was still hard and I stumbled often. Ultimately, though, I thrived. The next several years saw me take on larger and more complex teams before becoming a senior manager and then a director. I did ultimately burnout again but I had a solid run of continuous growth on the management track leading up to that point.

So what gives? Why was management so much better the second time around? Today I dive in to the big differences between Rounds #1 & #2 before sharing some advice for first-time managers and the leaders who grow them.

Better the second time around

I’ll start by writing up a quick synopsis for each round before digging into the differences:

Round #1

I had been a senior engineer running my own roadmap. I was essentially a lone wolf as was every other engineer on my team. I had some understanding of other folks’ projects just from on-call but we’d never really worked together before. I had minimal interest in documentation believing that it was best for everyone to learn by doing.

When I took on the manager role I inherited half a dozen engineers all at once with the mandate to hire another two. Most were in NYC like me but one was in Toronto and the other in NJ. I continued to own my previous roadmap, cover on-call 24/7 for an always on fire system, and generally fail to delegate until I burned out in epic fashion and peaced out.

Round #2

I had returned to senior engineer life and was enjoying it overall. I clumsily guided an intern through the summer and delivered two solid projects for an exciting product roadmap all while insisting that I was done with management for good.

Later on my manager took parental leave in two parts. I acted as interim TL of our little team while he was out the first time. I realized that I actually liked it and didn’t want someone else leading the team when my manager decided to take on a new challenge in another part of the organization. So I led again when he took the second half of his parental leave and we made it official. I inherited just two direct reports and had a dedicated product manager, something we didn’t have at my previous company. My new manager was a highly experienced director who had been growing first time managers for years.

The key differences

I learned to say ‘not yet’. During Round #1 I just said “yes” to everything when taking on my new role. “Manage all 9 folks all at once?” Yes! So exciting! “Over three locations, one in another country?” That does look very impressive on a resume so yeah! “Continue to do everything you had previously done as an IC?” Well of course, that’s what “ownership” means, right?

I always feel like I’ve jumped into the deep end when I take on something big and new but all of those yeses were like giant rocks in my pockets; I didn’t stand a chance. The second time around I guarded my pockets fiercely and started as small as possible.

I delegated. I completely failed to delegate the important stuff the first time around. My old IC responsibilities, 24/7 on-call and our gory release management process all stuck stubbornly to my plate. The road to effective delegation was a bumpy one but I was at least ready to embark on it the second time.

I got to ramp up slowly and started small. I went from IC’ing to running a big team all at once during Round #1. For Round #2 my manager and I made sure I went slow. It looked like this:

I reduced shield strength. The desire to protect my team from all the non-coding stuff during Round #1 was very strong. We had this uselessly standardized release approval process for the whole bank and it was just horrific. On-call was also an absolute nightmare and at some point, as an IC, I had just kind of taken it all on by default. I didn’t want to give any of it away after becoming a manager because we already had massive retention issues and I wanted to preserve my engineers’ focus the best I could. Luckily my second place didn’t have processes anywhere near this nasty and on-call was manageable by comparison so the decision to shield my team a little less was much easier.

Second time is second. I had done it before which meant that I had already learned many painful lessons like “you can’t not delegate” and “the on-call procedure can’t be ‘call me.’” and “yeah, documentation is very important.” I did not, at least in theory, have to learn them over again.

Most things weren’t on fire. The second team was in good shape when I took it on. My predecessor had gone through significant pains to leave me with the cleanest, tightest team he could. His was an excellent example and a tough act to follow.

I reported to the new manager whisperer. Both of my managers for Rounds #1 and #2 were highly experienced, empathetic and supportive leaders. I am a huge fan of both. The manager I had for Round #2, though, was basically the new-manager whisperer. He knew exactly how to grow me into that role. I also had hands on support from his manager and his manager. On top of that it helped that my manager for Round #2 was local; we were in the same office whereas my Round #1 manager and I had a 5 hour timezone difference. I swear I got much of the same advice from my Round #2 manager as I did from my Round #1 manager but it was more effective coming from the Round #2 manager simply because we were sitting on the same couch.

The trainings were top-notch. I did receive some new manager training at my first place but it didn’t compare, quality wise, to the training I received during Round #2.

I had regular access to my peers and they wanted me to succeed. The environment for Round #2 was highly collaborative compared to what I had at for Round #1. Weekly syncs with other TLs and EMs and a bunch of Slack channels did wonders for communication, growth, and camaraderie.

I enjoyed a healthy engineering culture. My second company just had a much healthier engineering culture overall compared to that of the first. Toxic work environments and non-stop turnover make first-time management roles next to impossible to pull off well.

Supporting your shiny new manager as a senior leader

So, noting these differences, how can leaders set first-time managers up for success?

Insist on high quality training, even if it’s just informally with you
Start new managers small - small teams, small roadmaps - before growing their breadth.
Consider phasing but do it intelligently. Let your first time manager take on two people on the team and then move the rest over in a few months. If they manage someone, though, then they own the full vertical. Don’t, for example, have your first time manager handle the day-to-day but then take on the end of year performance reviews yourself. Certainly don’t offer to do things like deliver critical feedback or make hard decisions on their behalf. You don’t do them or the team any favors by shielding a new manager from their responsibilities.
Provide lots of focused support in 1:1’s and transition fully into coaching mode. Your junior manager is moving into a bigger role with more ambiguity. They are going to need more help from you as they take on new challenges but they will also need more space to figure things out. It is now less about giving them cut-and-dried answers (eg “re-use this utility class, don’t recreate it elsewhere”) and more about making sure they consider the right questions (eg “who do you think is best suited to that project given their abilities, their desired growth areas, and the project deadline?”). There will still be times when you just tell them what to do but open ended questions are now the default.
Invest in your culture. You should always do this anyway but it’s impossible to lead a team that turns over every 6 months.
Give your first time manager meaningful access to their peers. You can’t teach your new manager everything they need to know. Peers are the key for broader learning, problem solving, and camaraderie.
It takes a village to grow a new manager! Every leader in the org should feel invested in their success.

Wait, but what if you are the shiny new manager?

What if you are the new manager who is struggling just to keep their head above water and your leadership has not magically provided you with all of the wonderful things above?

If I had a time machine, these are the frying pans I would hit myself over the head with as a first time manager:

You must delegate. Not tomorrow, not next week; right now.
You must write documentation and have your team write documentation, too
You must have a functioning on-call rotation
You must have more than one person familiar with each thing your team owns
You must control your roadmap. That requires saying ‘no’, ‘not yet’, and ‘yes, but.’
You must ask for and accept help from other leaders who you trust.
You must have a functional onboarding setup
You must maintain regular 1:1’s with each of your folks that don’t just devolve into status updates.
You must have access to people who can guide you. Ideally that is your own manager, your peers, and senior leaders at your company. If you don’t have that, though, then you must look for it elsewhere.

Closing thoughts

I’d like to close by saying that management was still hard the second time around. There is a big difference, though, between “hard” and “impossible.”

So, to new managers: your first management experience might suck. It could be truly awful. It’s easy to mistake discomfort for unsuitability, though. You might not know which one it is until you try management once, possibly twice. Ask for the support you need and find it externally if it’s not available internally.

For senior leaders: you can’t possibly create the perfect environment for your new manager. That would defeat the point; you need them in that role to handle hard things that you don’t have the bandwidth to handle yourself. If that weren’t the case then you probably wouldn’t bother putting someone into the role to begin with. That being said, your first time manager will be far more likely to fail if you throw them into the deep end with rocks in their pockets. Look through this article for ideas and see what you can do to help them keep their head above water while they learn to swim. Remember that you get to take the steps and put one foot in front of the other, too: