The Survival Guide for
Your First Time Managing People

Nobody trains founders to manage people — you’re just suddenly responsible for someone else’s growth, performance, and wellbeing. Here’s what actually matters in the first 90 days of managing someone for the first time.

The Shift Nobody Tells You About

The transition from doing the work to managing someone doing the work is one of the hardest transitions in a career — and almost nobody prepares for it explicitly.

As an individual contributor, your success was measured by your own output. As a manager, your success is measured by someone else’s output — which means your job changes from “do the work well” to “create the conditions for someone else to do the work well.” These require almost entirely different skills, and the skills that made you good at the first job don’t automatically transfer to the second.

The most common failure mode: continuing to do the work yourself because it’s faster and more comfortable, while also trying to manage — resulting in being bad at both.

Setting Expectations From Day One

The single highest-leverage thing you can do as a new manager is be explicit about expectations — because most management problems are actually misalignment problems that were never surfaced.

In the first week, have an explicit conversation covering: what does success look like in this role over the next 30/60/90 days, how do you prefer to communicate — and how does the team member prefer to communicate, what’s the right level of independence vs check-in for this person’s current experience level, and what does each of you need from the other to do your best work.

This conversation feels awkward the first time. It prevents months of frustration on both sides that comes from unstated assumptions.

The Most Common New-Manager Mistakes

Micromanaging out of anxiety. When you’re new to managing, the uncertainty of not knowing exactly what someone is doing is uncomfortable. The instinct is to ask for frequent updates. This often comes across as a lack of trust — even when that’s not the intention.

Avoiding difficult conversations. New managers often delay addressing performance issues, hoping they’ll resolve themselves. They rarely do — and the delay makes the eventual conversation harder, not easier.

Trying to be friends first, manager second. Especially when managing former peers, there’s a pull toward keeping things comfortable. But avoiding the manager role doesn’t make it go away — it just means the team member doesn’t get the support, feedback, or advocacy a manager should provide.

Taking on too much of their work. When someone is struggling, the instinct is often to step in and do the hard parts yourself “just this once.” This can become a pattern that prevents the person from developing the skill — and increases your own workload indefinitely.

How Much to Delegate, and When

Delegation isn’t binary — it’s a spectrum, and the right level depends on the task and the person’s experience with it.

For a new task or someone new to a role: “do exactly this, the way I’ll show you” — high direction, low autonomy. As they demonstrate competence: “here’s the outcome I need, you decide how” — outcomes defined, approach is theirs. For someone experienced: “here’s the broad goal, keep me posted on anything significant” — high autonomy, light touch.

The mistake in both directions: giving high autonomy to someone who needs more direction (they flounder, and you don’t find out until something goes wrong), or maintaining high direction with someone ready for more autonomy (they feel micromanaged and disengage).

Having the Conversation When Something Isn’t Working

Every new manager will eventually face a situation where someone’s performance, behaviour, or fit isn’t meeting expectations. The instinct is often to wait — for more evidence, for the problem to resolve itself, for a “better time.”

The conversation gets easier the earlier you have it, and harder the longer you wait. A small issue addressed early is a quick conversation. The same issue addressed three months later, after it’s become a pattern affecting other people, is a much harder conversation — and one that often comes as a surprise to the person, because nobody told them earlier.

Use the feedback framework: specific observation, impact, question, request (see our feedback playbook for the full framework). The goal of this conversation isn’t to assign blame — it’s to give the person clear information and a real chance to course-correct.

Managing Someone Who Used to Be Your Peer

In early-stage startups, it’s common to find yourself managing someone you used to work alongside as an equal — sometimes someone who’s been at the company longer than you, or who you’re personally close with.

This requires an explicit acknowledgment of the change. Pretending nothing is different — continuing exactly as before, just with a new title — usually creates confusion. A direct conversation: “Our relationship is changing in this one specific way — I’m now responsible for your growth and performance here. I want to be upfront about that, and I also want our relationship outside of that to stay the same.”

The discomfort of this conversation is much smaller than the discomfort of an unaddressed dynamic that surfaces months later in a difficult moment.

Using AI to Think Through Management Situations

New managers often don’t have a manager of their own to ask “is this normal? How would you handle this?” AI can be a useful sounding board — not a replacement for human mentorship, but a way to think through situations before they happen.

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