He Asked How to Meet Expectations. His Boss Said 'Keep Going.'

About a month into his first job ever, a junior engineer on my team asked me something during a one-on-one that I've been thinking about since the call ended.

We were wrapping up. Twelve minutes of easy conversation - how he was settling in, what he was working on, what goals he had for the next year. Good stuff. Then, right near the end, he said something like: "In which way should I walk to follow the expectation?"

That's the question. Word for word. A guy with no professional reference point, no prior job to compare this to, asking his founder-manager directly: tell me what success looks like here. Tell me what direction to walk.

I said something like: I'm feeling pretty good about the team, we're grinding, there are a lot of moving pieces, just keep going. My door's always open.

And then we ended the call.

I've been in this game long enough to know when I dropped the ball. That was a drop. And I want to break down exactly why - because if you're managing anyone right now, whether it's one person or fifty, you are probably doing the same thing. Not because you're a bad manager. Because warmth feels like an answer when it isn't one.

The Disguised Closed Door

When someone asks you directly how to meet your expectations, and you respond with positivity instead of information, you haven't reassured them. You've taught them that asking is pointless.

That's the part that stings. Because my intentions were fine. I wasn't blowing him off. I genuinely like this guy, I think he's doing solid work, and I wanted him to feel good about that. The warmth was real. But the warmth wasn't what he needed.

He needed criteria. He needed to know: here are the two or three things I'm watching, here's what it looks like when those things are going well, here's when we'll check in and compare notes. Instead, he got encouragement dressed up as direction.

There's a specific danger when this happens with someone in their first job. A senior hire who asks that question and gets a non-answer will probably push back. They've had enough managers to know that "keep going" is a dodge. They'll ask again, more specifically, or they'll triangulate from other signals.

A first-job employee doesn't have that calibration. When you say "I'm feeling good about the team," he doesn't know whether that means he specifically is crushing it, or whether you're just a positive person, or whether you actually have concerns but you're being polite. He has no baseline. So he files away the exchange, resolves to keep doing what he's doing, and stops asking - because the last time he asked, he didn't get an answer.

That's what I mean by the disguised closed door. You said your door was open. But the experience of the conversation taught him the door is closed. He just can't see it yet.

Why Vague Encouragement Feels Like Enough In the Moment

I'm not going to pretend this is a simple failure to fix. There are real reasons founders and managers default to this.

First, if things are going reasonably well, you genuinely don't have a detailed critique ready. You haven't sat down and written out what "good" looks like for this person's role. You haven't defined the two or three metrics that actually matter. So when someone asks, you reach for the thing that's true and available: I feel good about the team.

Second, the question itself is a little hard to answer in real time. "How should I walk to meet your expectations" is broad. It could mean technical work quality. It could mean communication habits. It could mean growth trajectory. It could mean all three. The easy move is to respond at the same level of generality: things are going great, keep it up.

Third - and this is the one nobody says out loud - specificity feels riskier. If you name actual criteria, you're now accountable to them. If you tell someone "the thing I'm watching is whether you can own a module end-to-end by month three," you've made a commitment. The employee will remember that. So vague positivity protects you from that accountability while still feeling like a supportive response.

I'm not saying this is conscious. Most of the time it isn't. But the incentive structure rewards the dodge, and the cost doesn't show up until later - when the person is quietly disengaged, or when they come back in six months confused about why they didn't get the raise or the promotion they thought they were on track for.

What an Honest Answer Actually Requires

So what should I have said? What does a real answer to "how do I meet your expectations" look like?

It requires three things. Not a performance review. Not an HR process. Three specific things you can do in about two minutes.

1. State Your Actual Priorities

Not the job description. Not the company values. The two or three things that actually matter to you for this person's role right now.

In this case, I know what I care about. We're building out the front end of a product that needs to match the architecture of an existing codebase. Speed matters. Cleanliness of integration matters. Not having to redo things in six months matters. Those are my priorities. I didn't say any of them.

A real answer starts with: "Here's what I'm actually watching." And then you name it. Specifically. Not "I want to see you grow technically" - that's a non-answer wearing the costume of an answer. More like: "I want to see you be able to own a front-end module from brief to deployment without me in the loop. That's the benchmark I'm tracking."

Now he knows something. Now he can orient toward it.

2. Give Him a Measurable Signal of Success

Priorities are necessary but not sufficient. You also need to tell him what it looks like when he's hitting them.

This is where most managers stop short. They'll say something like "I want clean code" but they won't describe what clean code means in practice on their specific codebase. Or they'll say "I want proactive communication" but won't clarify whether that means a daily Slack message, a weekly summary, or just raising blockers when they appear.

The employee is left to guess. And they will guess wrong at least some of the time, not because they're not trying, but because they're working from incomplete information.

A measurable signal doesn't have to be a KPI. It can be as simple as: "The thing that tells me you're hitting this is when I stop having to check in on a task and the output just shows up done, correctly, on time." That's observable. He can self-assess against it. He knows where the bar is.

3. Name a Timeline for Revisiting

The third piece is a date. Not a vague "let's check in," not "my door is always open" - an actual moment where you both agree to compare notes against the criteria you just stated.

This does a few things. It makes the criteria feel real rather than aspirational. It gives the employee something to work toward with a concrete horizon. And it protects you from the scenario where feedback piles up silently for months and then lands as a surprise performance conversation.

Monthly is usually enough if you're already running sprint reviews or team calls. Quarterly is probably too long for someone in their first job who doesn't have a baseline yet. The frequency matters less than the commitment. Just name the moment: "Let's revisit these specifically in our call next month."

Three things. Stated priorities, measurable signal, named timeline. Two minutes. That's the difference between a closed door and an actual open one.

The Sprint Review Trap

There's a related thing I mentioned on the call that's worth pulling out separately, because it's a different version of the same problem.

We talked about the presentations the team does at the beginning and end of each sprint - the check-in structure. I said we were thinking about making those less of a feedback call and more of a celebration of work completed.

I still think that's the right move for morale. But let me be clear about the distinction: celebrating completed work is not the same as communicating expectations. You need both. If your sprint reviews become pure celebration with no directional signal, you end up with a team that feels appreciated but doesn't know where they're going.

The celebration should acknowledge what got done. The directional signal should answer: here's what we're optimizing toward next, here's what I'm watching, here's how I'll know it went well. If you only do one, you're missing half the job.

The pattern I see with a lot of founders - myself included - is that we're so conscious of not wanting to be micromanagers that we overcorrect into ambient positivity. We don't want to feel like the boss who's always critiquing, so we swing to the boss who's always encouraging. Both extremes fail the team. People don't need you to be easy on them. They need you to be clear.

First-Job Employees Deserve Explicit Scaffolding

I want to flag something specific about the context of this conversation, because it changes the stakes.

This was his first job. He said so on the call. He doesn't have a prior employer to benchmark against. He doesn't know if what he's experiencing - the amount of feedback he's getting, the way check-ins are structured, the pace of expectations - is normal or not. He's building his entire mental model of professional work from this one experience.

That's a significant responsibility. And it means that when he asks "how do I walk to meet your expectation," the right answer is more specific, not less, than what you'd give a senior hire. A senior hire has context. He doesn't. He's working with only what you give him.

When I think about the teams I've built over the years - across agencies, SaaS companies, the various ventures I've run - the people who performed best weren't always the most talented. They were the ones who knew exactly what winning looked like. You tell someone the target clearly and specifically, and most people will find a way to hit it. You leave them guessing, and even talented people will drift.

The same logic applies to cold email, by the way. I've helped thousands of agencies and entrepreneurs build outbound systems, and the single most common failure mode isn't a bad list or a weak subject line. It's that nobody defined what success looks like before the campaign launched. They send emails, get some responses, and have no framework for deciding whether the campaign is working or needs to change. Same problem, different context: doing work without clear criteria for what done looks like.

What I'll Do Differently

This isn't a post about being a perfect manager. I'm not one. This is a post about a specific thing I did wrong in a specific conversation, and what I'll change going forward.

Next time someone on my team asks me - in any form - how to meet my expectations, I'm going to stop and actually answer it. Not with warmth. With information.

I'm going to say: here are the two things I'm watching for your role right now. Here's what it looks like when those are going well. Here's when we're going to revisit this conversation and compare notes.

If I don't have that answer ready, that's on me, not them. And the right move when you don't have it ready is to say exactly that: "That's a fair question and I want to give you a real answer, not a generic one. Let me think about it and get back to you by Friday." Then actually get back to them by Friday.

What's not acceptable is reaching for the warmth because it's easier. Warmth feels like support. Sometimes it is. But when someone asks you a specific directional question and you return a feeling instead of a framework, you've told them something about whether their question was worth asking. And they will not forget that answer.

The Actual Management Job

I've said this in a few different contexts, but the job of a manager isn't to make people feel good about work - it's to make sure they know what work to do and why it matters. The feeling-good part is a byproduct of clarity, not a substitute for it.

If you want your team to perform, you need to be willing to say specific things. Specific goals. Specific signals. Specific timelines. The more concrete you get, the less room there is for misalignment to accumulate quietly until it becomes a real problem.

This applies whether you're managing an engineering team, a sales team, or a one-person operation where the only person you manage is yourself. Ambiguity is always more comfortable in the short run. It costs you later.

The call ended with this engineer telling me he was looking forward to seeing me in person if I made it back to India. Good guy. Working hard. First job. Asking exactly the right question.

I gave him warmth when he needed a map. I won't do that again.

If you're managing people and you want a real framework for how to structure these conversations - not just the one-on-ones but the whole outbound performance system - the 7-Figure Agency Blueprint covers a lot of the operational scaffolding I use. And if the sales-side of your business is where the directional clarity is missing, start with the Discovery Call Framework - knowing what you're trying to learn before a conversation starts is the same skill whether you're running a sales call or a one-on-one.