By now, it’s clear to most that 1:1 meetings matter. The pro-tip of setting up a dedicated weekly checkpoint is on virtually every list of best practices for managers these days.

Carving out a corner on your calendar for surfacing issues, nurturing that incredibly important employee-manager relationship, and sharing feedback more consistently is undeniably important. For managers in particular, it’s a chance to maintain a pulse on how your direct reports are doing — and an opportunity to make sure their career ambitions for the years ahead connect back to their more immediate days and weeks.

 on why they matter — and a thicket of meeting templates and agenda tips out there — 1:1s still aren’t easy to get right. Under the pressures and scrambles of early-stage startup life, managers are still juggling several direct reports (although hopefully 

) and wrangling overbooked calendars (but trying to follow that other pro-tip on never canceling these precious 1:1 slots). Then there’s the issue of what to cover. From less-than-chatty direct reports to those who use the time as more of a therapeutic outlet, managers are often unsure whether 1:1s should be freewheeling coaching sessions or highly structured tactical check-ins.

 and running Manager Track (our program for first-time managers at First Round-backed companies), we’ve found there’s still tons of trepidation on how to approach 1:1s. More specifically, there’s a hunger to make sure these meetings are truly 

To that end, we’ve combed through all the pieces we've written that include advice for holding better 1:1s. This collection of six impactful articles rounds up helpful habits from some of the most insightful leaders we've ever interviewed here on the Review, from Michael Lopp to Julie Zhuo to Lenny Rachitsky.

Unsurprisingly, much of their advice centers around thoughtful question asking and careful listening. But that alone is not enough. Their collective wisdom is connected by a 

— an eagerness to avoid turning in a merely perfunctory performance as a manager

That means putting in additional legwork to prevent your 1:1s from becoming rote rituals where you exchange status updates, wade into the waters of small talk and stick to the shores of safe conversation so you can move on with your day. It requires resisting the easy temptation to see them as a line-items on your managerial checklist, or a chunks of time that clog up your calendar every week.

When it comes to holding more impactful 1:1s, asking better questions is key. But so is an ability — and a willingness — to go the extra mile as a manager.

Instead, the very best managers consider the mindset they want to bring to each 1:1 — the thoughtful questions to posit, the dynamic to cultivate with each direct report, and how to tailor these sessions to their unique needs. We hope these tactics challenge you to probe deeper, shake up your meeting structure, follow up more and make things a little awkward. So in that spirit of rededicating yourself to stepping up your manager game and upleveling each of your 1:1s, let’s dive in.

We've built a question bank to pull together all the 1:1 questions suggested in this article (plus a few other gems we've come across) . 

Figure out which category your 1:1 falls into, and keep three topics at the ready to avoid status update territory

 (aka Rands) has led engineering teams at Apple, Slack, Pinterest and Palantir — and he’s been 

 and startup topics for more than a decade. Several years back, he shared his thoughts on 

 here on the Review, which was full of evergreen gems on holding 1:1s.

There were tactical pointers, such as his recommendation to hold 30 minute 1:1s each week, but book 45 minutes so you have room if it runs over. And his bucketing of 1:1 meetings into three different categories was particularly insightful. (We’ve outlined a preview below, but see 

: These are my projects and these are my people and this is how it’s going down. When a 1:1 starts and is clearly an Update, I start listening twice as hard for a nugget of something that we can discuss, investigate, and explore.

: Essentially a therapy session. This most often comes in the form of your report being pissed off about something. You just have to listen, not actually do anything.

: They’re freaking out, they’re going to quit, etc. This is the advanced form of the vent. They don’t want a solution, they want to be heard.

Digging into that first bucket, Lopp gives a helpful pointer: “The goal of an effective 1:1 isn’t for an update from your direct report, or for you to lay down some instructions (this tends to happen a lot). It’s a 

,” he says. “1:1s are a chance to hear about your direct reports’ ideas for your product, their career goals, and potentially their opinion of their performance — it’s 

There are lots of systems for status updates (project management software, bug tracking systems, Google Docs, Wikis) — 1:1s aren’t one of them.

To counteract your reports’ likely tendency to go into status update territory (or reluctance to share any topics they’d like to discuss), Lopp recommends 

keeping a list of three potential topics at the ready for discussion

. “That way when they say, ‘Nope — nothing to discuss’ at the beginning of the meeting you can go right to your list to jumpstart the conversation,” he says. “After a few weeks of doing this, the transition from status to dialog should be well underway.”

Make use of a manager’s best tool to ensure that all your 1:1s are a little awkward

Taking on the role of first-time manager naturally presents several “firsts,” but there’s one that stands out in 

’s mind. She still vividly recalls stepping into a conference room for her first 1:1 as a newly-minted manager, trying to hide her faltering voice and unsteady nerves as she faced her direct report — a former teammate who was now skeptically staring back at her.

Of course, she’s now a practiced hand. Before recently striking out 

, Zhuo spent 14 years at Facebook, building out the product design team, 

, and yes, holding more 1:1s. “The most precious resource you have is your own time and energy, and when you spend it on your team, it goes a long way toward building healthy relationships,” she writes in her book, "

 a handy manual that belongs on every budding leader’s bookshelf.

In this must read, she recommends spending no less than 30 minutes with each report every week, and she also hands out several other tactical tips for making the most of this 1:1 time. But as we noted when we shared a 

preview of her book on the Review last year

, it was another observation of Zhuo’s that caught our eye: “

A coach’s best tool for understanding what’s going on is to 

,” she writes. “Too often, attempts to ‘help’ aren’t actually helpful, even when served with the best of intentions. Your job as a manager isn’t to dole out advice or ‘save the day’ — it’s to empower your report to find the answer herself. She has more context than you on the problems she’s dealing with, so she’s in the best position to uncover the solution. Let her lead the 1:1 while you listen and probe.”

To prepare for that probing, Zhuo makes a habit of scanning her calendar and compiling a list of questions for each person she’s meeting with 1:1. Here are the questions she’s come to rely on to prod the conversation along, organized into three buckets:

 These questions focus on what really matters for your report and what topics are worth spending more time on.

• What’s top of mind for you right now?

• What priorities are you thinking about this week?

• What’s the best use of our time today?

 These get at the root of the problem and what can be done about it.

• What does your ideal outcome look like?

• What’s hard for you in getting to that outcome?

• What do you think is the best course of action?

• What’s the worst-case scenario you’re worried about?

 These questions zero in on how you can be of greatest service to your report.

• What can I do to make you more successful?

• What was the most useful part of our conversation today?

Finally, one more tool from Zhuo’s 1:1 question asking arsenal — but this one’s aimed at you managers, not your direct reports. 

Do all of your 1:1s feel a little awkward?

 Zhuo picked this tidbit up from her friend Mark Rabkin, and she finds it to be a worthwhile goal. 

The ideal 1:1 leaves your report feeling that it was useful for her. If she thinks that the conversation was pleasant but largely unmemorable, you can do better.

“The most important and meaningful conversations have this characteristic. It isn’t easy to discuss mistakes, confront tensions, or talk about deep fears or secret hopes, but no strong relationship can be built on superficial pleasantries alone,” she says. “There’s no wordsmithery that gets around the awkwardness of expressing a sentiment like, ‘

I don’t feel that you recognize when I’m doing a good job,

Last week, when you said X, it made me feel as if you don’t really understand my project.

’ But these things need to be said in order to be addressed, and with a bedrock of trust, the conversations become easier.”

Take a sickness vs. symptoms approach to spot patterns

When people came to him with specific problems or concerns during 1:1s, 

 took a sickness vs. symptoms approach as the founder and CEO of URX (which was 

“It’s easy to see the symptoms of things — that’s what is actually happening on the surface, but it takes more time to truly understand the underlying cause. Having time set aside with people gives me the opportunity to dig deeper and diagnose the root of a problem. Then we have a shot at fixing it,” says Milinovich, who’s currently building 

For instance, if someone mentions in a 1:1 that they're feeling particularly stressed or tense and they don’t know why, he goes granular. “I ask them things like what part of the day these feelings are the strongest. Then we can identify triggers, whether they are meetings, or people, or certain types of work.”

This also works on the organizational level, particularly if, like Milinovich, you’re wearing the CEO’s cap. “I get the chance to aggregate all of this information from all of these meetings, and then patterns start to emerge,” he says. “I’ll start hearing the same thing from more than one person. For example, back at URX, three separate people asked me about how we were going to message a product, and I realized that I was repeating myself. It occurred to me that this was something that needed to be broadly communicated to the entire company. Just because only three people asked doesn’t mean they’re the only ones who didn’t know the answer.”

To surface these patterns and make a diagnosis, transparent 1:1 conversations are critical. “A lot of times people just don’t know how to get over a certain hump or out of a rut. If that’s the case, we want them to tell us with zero reservation what’s going on so we can help,” says Milinovich.

To jump start those conversations, he relies on one trusty question at the top of every 1:1 meeting: 

“You’d be surprised by the range and depth of responses you’ll get from this simple question,” says Milinovich. “Sometimes people want to dive very specifically into what they’ve been working on. Sometimes they’ve had all this angst bottled up about not doing as good of a job recently because of something going on in their lives or with their relationships or health, and we give them a chance to talk about that and be honest.’”

Another way to get people to open up is to model the behavior yourself, Milinovich says. He’s made a point of being extremely open and honest about his own life, problems he’s facing, and concerns he has about the business, no matter where someone ranks in the organization. “One of the first lessons I learned when URX was at about nine or 10 people was that the entire organization tended to reflect my emotions,” he says. “If I was stressed out, people would come up to me and say how they were just as stressed. I get reminded often that how I’m feeling influences everyone else.”

The smallest gestures, ticks or even tone of voice from the founders can cause anxiety, insecurity and turmoil within a fledgling startup. Milinovich views 1:1s as a chance to speak candidly about this, and make sure his words and actions come across clearly. “This is especially important if I don’t have a lot of confidence in something we’re doing,” he says. “It gives me a chance to explain things in a more nuanced way, and to reiterate how excited I am to be here working with everyone on these problems.”

Stay specific (yet open-ended) — and don’t forget to bring the empathy

’s content team from scratch (first as a news editor and now as VP of Content), managing a large and critical team of writers and editors. In this capacity, and across her career as a veteran reporter, editor and executive, Leung’s seen her fair share of sticky situations. And there’s one simple habit that’s helped her survive, learn and grow through adversity: asking questions. Not just any questions, though. Over the years, she’s crafted specific lists of inquiries, designed to put herself in other people's shoes, see all dimensions of a problem, and arrive at the best approach or strategy.

 on the Review a few years ago, giving insight into how to handle a wide range of tough situations (such as managing sideways, handling conflict and letting an employee go). But of course, for our purposes here, we are most interested in the ones she leans on to power up her 1:1s. Here are those lines of questioning, front and center:

Get past the small talk with specific, yet open-ended questions.

“I have a one on one meeting with everybody on my team on a rotation. Often the conversation starts out with superficial responses. ‘How are things going?’ is followed by ‘I'm fine,’ or ‘Things are going well,’” says Leung. “You let them direct the conversation for a bit and see whether they get to the heart of things. If not, then you nudge them.”

You want to get to the heart of things as quickly as reasonable. With the typical range of 30 to 45 minutes per meeting, that means you need to ask the right kind of questions to get past small talk more quickly. To that end, your questions should be specific but open-ended, says Leung. Here are several examples of that blue sky specificity:

 “It helps you identify patterns when you talk to various people. It helps you smell smoke early. That question could apply to many situations, jobs and companies. And it isn’t judgmental,” she says. As a manager, it’s important to surface issues in a blameless way. The goal is to normalize these human moments — not veer into accusation. “If you say, ‘Hey, are you stressed?’ that attempts to force a confession in an awkward way,” says Leung. “Instead, you could say: ‘I know that you're juggling a lot of work right now. I know you're doing X and Y. If I were in your position, I might be a little stressed.’ Or, ‘I’m not sure how you’re feeling about this, but if I had to guess, I’d say. …’ It’s OK to be wrong or off, as long as you give the person a chance to set you straight, to be direct with you.”

Is there anything you'd like to ask or highlight?

” It’s their time to surface things, says Leung. “Sometimes they need to hear that explicitly from us as managers. It’s our job to care. That’s how we help people do their best work and grow. That makes them more valuable to our company and in the job market. That’s a fair trade.” This won’t happen overnight; building trust rarely does. “

,” says Leung. “If people see consistently that things aren’t punitive or judgey, that you don’t hold things against them or look for the ‘right’ answer, that it’s OK to trust, your interactions will become increasingly open and productive.”

Check your empathy before discussing performance.

Whatever a manager says in a 1:1 meeting can leave a lasting impact. You want to add value, not create cognitive drag that slows productivity. That’s where something that Leung calls “dynamic empathy” comes in. It involves empathizing with and sussing out how your direct report feels — and then figure out how to 

 on it in a swiftly changing startup environment.

As with any other learned skill, you can make considering other people’s motivations an automatic habit if you do it enough. “When I understand and can articulate what someone needs from me, that makes it easier to say, ‘Makes sense. This is what I need from you.’ Then it’s a fair exchange rather than ‘I’m just demanding things from you,’” Leung says.

It’s not about just understanding what’s going on with someone else, but actually doing or saying something about it. It’s about moving things forward.

To walk the tightrope of providing continuous 

, Leung recommends reflecting on these types of questions in advance of 1:1 meetings that touch on performance to put yourself in your report's shoes.

• Does the person you're managing feel invested in your company or team goals? Why should he/she be? Have you clearly explained the vision or goals, and his/her part in achieving them?

• Does he/she feel as if you've got his/her back?

• In every relationship, both parties must get something out of it. What are you offering vs. what you're expecting? Is what you're offering good enough, or can your employee do better elsewhere?

• Does your direct report understand what he/she is supposed to do? How to do it?

• Does he/she have the right training, right scope, right authority, right resources and enough time to do as you need?

• Does he/she know how important your ask is?

• What does he/she need from you or other colleagues?

• Is he/she encountering bottlenecks? Are those localized or systemic? If they’re systemic, do you need to address this bigger picture?

Make performance reviews more impactful by keeping careful notes and actually following up in special 1:1s

Let’s continue pulling on this thread that connects performance reviews and 1:1s.

 has quickly established himself as one of the sharpest voices on startup topics. Case in point: Last year on the Review, this former Airbnb product lead shared the 

 he developed and honed over the years, unpacking why most reviews “suck” and offering up a collection of templates and real-world examples managers can use to take these critically important conversations to the next level.

There’s one story in particular that sticks out. Early on in his tenure as a manager, Rachitsky had a direct report who was underperforming. After hours of preparation for their performance review conversation, he felt that he’d made a real impact and was excited for the progress ahead. But when Rachitsky checked in a month later, things still weren’t trending in the right direction. “My direct report had vague memories of a few points I had mentioned, and a clear desire to improve, but 95% of the message was lost,” he says. 

“At that moment I learned two lessons. One, it’s my fault as a manager if my report doesn't remember what development areas to be focusing on. Two, 

I was treating the performance conversation as the end, when it’s really only the beginning of the performance development process.”

We want to believe our carefully-chosen words of wisdom are interpreted correctly and seared into the minds of our reports. It’s safer to assume they aren’t.

In other words, failing to formulate a follow-up plan after performace disucssions is one of the biggest mistakes you can make as a manager. And if that initial conversation is only the beginning, the rest of the process should play out over the course of the year in the ongoing, regular touchpoints you have with your direct report.

Here are two targeted tactics from Rachitsky on how managers can use 1:1s as a venue for that important follow-through work:

Keep tabs and take (specific) notes in your 1:1s throughout the year.

When it comes time to fill out evaluations of your direct reports, you want the specifics in the accomplishments and development areas sections to be significant and meaty. “Your reports are hungry for feedback. They’re looking at every morsel of information you share with them to figure where they should spend their time. Don’t waste this opportunity,” says Rachitsky. To ensure you have enough substantive material to draw from, use your 1:1s as an opportunity to keep closer tabs and put in the leg work.

“Keep track of instances where your report did well, didn’t do well, or generally did something noteworthy. Share these things with your report in weekly 1:1s and save them in a running file so you can refer to them come performance season. For example, ‘July 10th - Ran an excellent meeting with senior execs,’ or ‘Sept 3 - Put together a very strong strategy for Q3,’ or even feedback from others such as ‘Jan 4th - Spike shared with me how impressed he is with Jane’s ability to run a meeting,’” says Rachitsky. “I keep a separate Google Doc for each of my reports for this purpose. In addition to Google Docs, there are neat feedback and performance management tools like 

 that can help you keep tabs on performance throughout the year.”

Create a two-sided action plan after a performance review — and turn one of your 1:1s into a monthly career coaching chat

At the end of your performance review conversation, ask your report to list five to seven concrete actions they want to work on over the next six months and add them into a 

. It’s important to check in regularly on this plan between performance conversations — but don’t use your regular 1:1 time. In Rachitsky's view, 1:1s are for talking about how a project is going, upcoming deadlines, or blockers. An additional, special session is needed monthly to check in on the performance review action plan and broader career discussions.

“The focus of these meetings is to step back from the day-to-day and focus on career and performance development. Remind your report ahead of each meeting to update their spreadsheet with a status and any new discussion items they’d like to make time for,” says Rachitsky. “The meeting should be mostly you listening, asking questions, and (when really necessary) offering suggestions.” 

When your direct report asks for advice, Rachitsky recommends turning it around and asking “

’s writing have taught me a lot about how to be a better manager by asking good questions,” he says.

Add more than a splash of structure to make sure you’re delivering on what you owe your reports

As the Head of Customer Success and Sales Strategy at 

 sees is that while managers sink tons of time into 1:1s, more often than not they don’t make the best use of it. While the debate over who should “own” the 1:1 meeting is a long-running one, Rhorer is firmly in the camp that managers are on the hook for making this time useful.

“Managers say that they want to loosen the reins because they want the report to take ownership of the meeting. 

But how can you expect your report to maximize their 1:1 if you don’t set them up for success?

” she says. Here’s how she divvies up responsibility: “You prep and set the agenda. Your reports fill in part of the content.”

Unstructured meetings are a waste of time. Remember, time is your most precious resource as a manager — and wasted time harms yourself and your team.

While her advice is tailored for sales leaders, we think managers of all stripes stand to learn from Rhorer’s highly structured and data-driven approach to 1:1s. Here’s a look at two more specific strategies she uses to bake that structure into every meeting:

Remember what you owe your direct reports.

“Leading a sales team is about more than just checking whether reps hit their numbers. Set fair expectations — and make sure reps have a clear pathway to hitting those goals,” says Rhorer.

To do just that, she finds it helpful to view every 1:1 as an opportunity to deliver on the three things she believes that all managers owe to their teams:

: “Frequent feedback, grounded in data, helps strong performers prepare for success in their next role; it gives those who are struggling an opportunity to improve.”

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1:1s aren't just line-items on every manager's to-do list—it's critical to make sure these weekly meetings are as impactful and effective as possible. Here's a collection of tactical tips from the Review archives to help you take meetings with your direct reports to the next level.

Managers, Take Your 1:1s to the Next Level with These 6 Must Reads

 as an intern over a decade ago. Since then, she’s risen through the ranks to become VP of Product Design at the company, leading a team of hundreds that’s charged with designing the app billions of users see every day. But reflecting on her career, it was the moment when she first put on the manager’s cap that stands out most.

“I was 25-years-old and all that I knew of management could be neatly summarized into two words: 

. It was the equivalent of Harry Potter getting a visit from Hagrid on a dark and stormy night, the first step in an adventurous and fulfilling career,” Zhuo says. “But I was completely unprepared for just how much this new role would stretch me. In those early months and, frankly, years, I was riddled with fear, doubt, and ‘Am I crazy?’ kind of feelings. Everything felt new and uncomfortable, and in contrast, the other managers around me made it look so easy.”

Whether it’s the memories of getting through her first 1:1 with a direct report, trying to hide her shaking hands in her first interview with a candidate, or making the hard choice to let someone go for the first time, Zhuo’s first brush with management came with a heavy dose of trial-by-fire milestones that, at the time, loomed large and seemingly threatened to drag her under.

Now, with more than 10 years as a manager under her belt, Zhuo has the perspective to recognize that virtually all new managers feel the same way. And after sharing her hard-won design and leadership insights in many articles on her 

as well), she was prodded by her readers to write a book — not at the twilight of her career as a C-suite executive, but now, while the imprint left by her first experience as a manager hadn’t yet faded.

The Making of a Manager: What to Do When Everyone Looks to You

, in which she offers practical advice, relatable anecdotes and tested tactics for the newly minted manager. She covers the full-range of the first-timer’s experience, diving deep into the weeds of everything from dealing with the anxieties of imposter syndrome to navigating the awkwardness of managing former peers and doling out more direct feedback, all with the goal to pen the manager’s manual she wishes she had at the start of her own journey.

After leafing through an advance copy, we were struck most by a single, powerful observation from Zhuo. Deep within a section on 1:1s in the third chapter, this sentence stands out as the invisible throughline that connects her managerial wisdom: 

As Zhuo writes, most of our attempts to “help” aren’t actually helpful, even when they’re offered with the best of intentions. The best way to understand what’s going on or how to get better is to pose probing questions to the people you manage, and above all, to yourself. Pausing to infuse intention into every move at the outset, take a step back at key points along the way, or stop for a tune-up if you’re already further along the road is critical to leveling up as a leader — and questions are the keys that unlock the door to development.

 hot off the press, we’re pleased to present a selection of the questions in Zhuo’s toolkit that helped her become a better manager. We’ve excerpted several different sections from her book to weave together a collection of the essential questions new managers should ask themselves as they look to build trust, improve 1:1s and make sure feedback is heard.

Read on for a preview of Zhuo’s detailed advice for new managers seeking to earn their leadership sea legs and swim more comfortably in the deep end.

THE QUESTIONS NEW MANAGERS NEED TO ASK TO BUILD TRUST

When I first started my job, I considered 

 to be synonyms. Over time I’ve come to learn that leadership is a quality rather than a job. While the role of a manager can be given to someone (or taken away), leadership is not something that can be bestowed. It must be earned. People must want to follow you.

First-time managers need to nail the essentials of leading a small team. Only when you have built trust with your reports will you have the credibility to help them achieve more together.

That trust means your reports feel that they can be honest with you. You’ll know you’ve accomplished this when you can answer these two questions:

Do my reports regularly bring their biggest challenges to my attention?

One of my teammates shared with me a simple litmus test for assessing the health of her relationships: 

If she asks her report how things are going and the answer for multiple weeks is “Everything is fine,” she takes it as a sign to prod further

. It’s much more likely that the report is shy about getting into the gory details than that everything is consistently rainbows and butterflies.

Would my reports gladly work for me again?

When you see a manager taking on a new role and members of his former team also make the leap with him, that says a lot about his leadership.

In anonymous surveys to track team health, some companies explicitly ask the question, “Would you work for your manager again?” If your organization doesn’t do this, simply reflecting on the question can be useful. For each report, can you say with confidence that he or she would want to be on your team again? 

You can also get an approximate reading by asking your report, “

What are the qualities of a perfect manager for you?

” and evaluating how you compare to the description you get back.

Can you say with confidence that each report would want to be on your team again? If you aren’t sure that the answer is yes, it’s probably no — much like how if you have to ask, “Am I in love?” you’re probably not.

THE QUESTIONS NEW MANAGERS NEED TO ASK TO HAVE STELLAR 1:1S

As a manager, the most precious resource you have is your own time and energy, and when you spend it on your team, it goes a long way toward building healthy relationships. This is why 1:1 meetings are such an important part of management.

The ideal 1:1 leaves your report feeling that it was useful for her. If she thinks that the conversation was pleasant but largely unmemorable, then you can do better. Here’s how:

Ask yourself: Do all of my 1:1s feel a little awkward?

My friend Mark Rabkin shared a tip with me that I love: 

strive for all your 1:1 meetings to feel a little awkward

. Why? Because the most important and meaningful conversations have that characteristic. It isn’t easy to discuss mistakes, confront tensions, or talk about deep fears or secret hopes, but no strong relationship can be built on superficial pleasantries alone.

There’s no wordsmithery that gets around the awkwardness of expressing a sentiment like, “I don’t feel that you recognize when I’m doing a good job” or “Last week, when you said X, it made me feel as if you don’t really understand my project.” But these things need to be said in order to be addressed, and with a bedrock of trust, the conversations become easier.

Use these questions to get the conversation moving:

Managers shouldn’t dole out advice or “save the day.” Instead, empower your report to find the answer herself. She has more context than you on the problems, so she’s in the best position to uncover the solution. Let her lead the 1:1 while you listen and probe.

To aid in that probing, every morning, I’ve gotten into the habit of scanning my calendar and compiling a list of questions for each person I’m meeting with. Here are the questions I rely on to prod the conversation along:

: These questions focus on what really matters for your report and what topics are worth spending more time on:

•What’s top of mind for you right now?

•What priorities are you thinking about this week?

•What’s the best use of our time today?

: These get at the root of the problem and what can be done about it.

•What does your ideal outcome look like?

•What’s hard for you in getting to that outcome?

•What do you think is the best course of action?

•What’s the worst-case scenario you’re worried about?

: These questions zero in on how you can be of greatest service to your report.

•What can I do to make you more successful?

•What was the most useful part of our conversation today?

THE QUESTIONS NEW MANAGERS NEED TO ASK TO GIVE FEEDBACK THAT LANDS

For a leader, giving feedback — both when things are going well and when they aren’t — is one of the most fundamental aspects of the job. 

But your feedback only counts if it makes things better

I might feel accomplished in pointing out the problem, but that’s not effective if it doesn’t actually help. The mark of a great coach is that others improve under your guidance. 

Giving feedback knocks down two of the biggest barriers preventing your reports from doing great work — unclear expectations and inadequate skills — so that they know exactly where to aim and how to hit the target.

The question that should always be in the back of your mind is: 

Does my feedback lead to the change I’m hoping for?

 Broken down one level further, consider how you’re doing with the two following questions:

I’ve read thousands of reviews written by reports about their managers, and the most common response to the question “How could your manager better support you?” is simply “Give me more feedback.”

Before getting deep into the nitty-gritty of the how, the first step is simply to give feedback more often and remind yourself that you’re probably not doing it enough. Every time you see one of your reports in action — delivering a project, interacting with a customer, negotiating a sale, speaking up in a meeting — see if there’s something useful you can tell her. Strive for at least 50 percent positive feedback so she knows what she’s doing well — “You made a particularly keen observation” or “You showed a lot of empathy in that interaction.” If you hear something positive from a colleague, pass it along. Or, if you have a suggestion for improvement, even if it’s small, tell her that as well — “You said a lot in that meeting, which made it hard for others to get in a word.”

watch out for only ever giving task-specific feedback

. The second most common ask from reports is: “Give me more feedback related to my skills and my career trajectory.”

I knew a manager who was a designer’s designer and a top-notch creative director. He could casually glance at a mock-up and tell you if the spacing between the icons was two pixels off. His team always knew where he stood on their work. However, in their upward reviews, I would read comments like, “I want to understand my manager’s opinion on how I’m progressing” or “I want to have conversations about my career goals and how to achieve them.” His team longed for additional attention about them as people, not just on their output.

If you’ve ever played a game of telephone as a kid, you know this to be true: What you intend to say and what the listener hears are not always the same. 

You might think you’re being clear when in fact you’re saying too much, or too little, or sending a different message through your body language. (I’ve been told, for example, that I’m prone to rambling, which can make it hard to understand my main point, and that my friendliness can mask the seriousness of a tough message.) Add to that the listener’s confirmation bias — our tendency to recall things that confirm preexisting beliefs — and it’s no wonder that messages get muddled in translation.

The best way to make your feedback heard is to make the listener feel safe, and to show that you’re saying it because you care about her and want her to succeed. If you come off with even a whiff of an ulterior motive — you want to be right, you’re judging her, you’re annoyed or impatient — the message won’t get through. When you do have critical feedback to share, approach it with a sense of curiosity and an honest desire to understand your report’s perspective.

One simple trick is to state your point directly and then follow up with another question: “

Does this feedback resonate with you? Why or why not?

If the answer is yes, now the person has both acknowledged and reflected on the feedback, so it’s more likely to stick. If the answer is no, that’s fine as well — now we can discuss why that is, and what would make the feedback more useful. To make doubly sure you’ve been heard at the end of a conversation ask: “

Okay, let’s make sure we’re on the same page — what are your takeaways and next steps?

If you're seeking to improve as a manager:

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