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CEO Coach

What Jonathan Courtney, Co-Founder of AJ&Smart, Learned From Silicon Valley’s Top CEO Coach On Being a Better Boss

Go to the profile of Jonathan Courtney

Jonathan Courtney: For anyone who doesn’t know, Kim Scott is the co-founder of Radical Candor, LLC, and is a well-known CEO coach in Silicon Valley. She was a member of the faculty of Apple University, where she did a lot of teaching. Before that, she worked at Google where she led AdSense, Youtube, and the DoubleClick teams. Earlier in her career, she was a co-founder and CEO of a software start-up, managed a pediatric clinic in war-torn Kosovo and built a diamond cutting factory in Russia. Kim: you need to chill, you’re making everyone else look bad!

She also wrote this pretty spectacular New York Times bestselling book called Radical Candor: Be A Kickass Without Losing Your Humanity.

Radical Candor

Radical Candor was a book that just came into my life at the best possible time. It was when my agency, AJ&Smart was growing, and I was having a lot of struggles as a boss and CEO. New people were coming into the company and I was really struggling with delivering honest feedback and having hard and uncomfortable discussions that are often necessary when you’re running a company.

Somehow, and I really can’t even remember why or where it came from, I picked up Kim’s book, Radical Candor, How to be a Great Boss Without Losing Your Humanity, and it completely blew me away. It’s honestly the best management book I’ve ever read.

If you are a manager and you have to give feedback to other human beings, buy Radical Candor. I’ll wait.

I’ve got to be honest and say that I was a little bit nervous doing this interview because Kim is a total legend, but she was really, really great interviewee. I could have chatted with her for hours and hours, asking her endless questions about her career and getting her advice on my specific situation, however we only had 30 minutes and I was keen to GO DEEP into some of the stories she shares in the book and have her expand on them.

I wanted to pull out some key points from the conversation for this article, points which I feel that if any manager (or anyone, really) started to bring into their life then their career and working relationships would benefit massively. So here they are…

Management doesn’t come naturally to everyone

Kim Scott: You spend years becoming an engineer or even learning how to sell and yet for one of the most important jobs that any of us ever have, we get very little help.

Often if you’re hardworking and driven you’ll eventually fall into a management position, very often without training. I know for me personally there are a lot of things I wish I knew before I started managing people, and while reading Radical Candor I saw myself in so many of the situations.

It’s funny because I remember going through these things thinking it was only me experiencing this, and that the situation was unique to me and my company, but I got a huge sense of relief when reading Kim’s stories — this happens to the best of us.

One thing that I really got from speaking to Kim is that we should treat being a manager as we would any other career path — you need to train yourself and work on those skills, and it’s always a work in progress.

Care personally, Challenge Directly

One of the key messages in Kim’s book, and one of them that really stuck with me, and that I reference all the time, is the idea of caring personally and challenging directly. In the book, and when we spoke in our interview, Kim shared the story of how her manager at the time (SHERYL SANDBERG!?!) had to deliver very direct and feedback to Kim about her presentation style. The way she did it is something that had a huge impact on the rest of Kim’s career…

Kim: She never she let her concern for our short term feelings get in the way of telling us things that we really needed to know, that we really needed to hear about. It was simple. It was challenge directly and care personally at the same time. That was the essence of good guidance, both praise and criticism.

Kim continues and importantly empathises with the fact that regardless of how ‘harsh’ it may seem, delivering candid, clear feedback is in their best interest, because you care about them and their development…

Kim: Your job as a boss is to make things clear to people and very often we’ll actually say the thing, but we won’t be heard. It’s our job to make ourselves heard. Sometimes the key to making yourself heard is to take a moment and to address the emotions in the room. To reassure someone that the reason you’re telling them this thing is that you care about them and that you care about their professional growth. Very often the job of the boss is to move further out on the challenge directly dimension. Sometimes giving feedback feels like you’re having to pick up a 2” x 4″ and hit somebody over the head to get through to them…It’s unkind not to be clear.

Being nice isn’t always nice: Create an environment that evokes praise AND criticism

If you’ve read Radical Candor then you’ll be familiar with the Bob story. The heartbreaking tale of a loveable employee and teammate, who everyone has a soft spot for, but who just isn’t performing. To cut a long story short, at the risk of hurting Bob’s feelings and/or looking like a jerk in front of the rest of her team, Kim Scott avoided giving Bob honest feedback, but as time went on she realised that if she didn’t let Bob go, she’d lose some of her best performers who had become disgruntled by picking up Bob’s slack, so she fired him only to realise that he would have loved, and appreciated, to have heard this earlier so he could have changed.

Kim: I didn’t solicit guidance, praise and criticism, most importantly criticism, from Bob. I also failed to give him praise that was meaningful. The kind of praise I gave him was really just a head fake or an ego self. I failed to tell Bob when his work wasn’t nearly good enough. I failed to give Bob criticism. Probably worst of all I failed to create the kind of environment in which everyone would give Bob the kind of praise and the kind of criticism he needed to be successful in which everyone would tell Bob what was genuinely good about his work and also working with him but also would tell Bob when he was going off the rails. Because I had failed in all these different very important ways I’m now having to fire Bob because of it.

For me personally, being liked as a manager was always something I’d prioritise over most other things. Regardless of whether or not the person was underperforming, I’d prefer that they liked me rather than addressing the issue, which of course isn’t the best thing for them, the company, or their teammates.

Kim: It’s the most natural thing in the world to want to be liked. Don’t worry so much about whether or not people like you, but focus on whether or not you’re doing the kind thing for those other people. Are you putting their interests ahead of your own interests? That makes it much easier to do the things you need to do to be an effective leader because I think that very often we have this notion that we have to choose between being a total jerk and being really effective. That’s a false choice, we don’t have to make that choice.

Keep your star performers top of mind.

Something that very often happens at companies is that the managers spend most of their time dealing with troublemakers and underperformers, assuming that the stars in the company are fine to get on with things on their own. This makes sense, I get this rationale and have experienced this myself, but Kim makes a great point about why it’s important for the individual, and the company, that you don’t do this…

Kim: If you really focus on putting your time into helping the people who are doing the very best work, continue to improve on being a really good thought partner for those people, you will help not only those people, but the whole team. If you think about your time, pretend that it’s money, would it be fair to give equal bonuses to everybody regardless of performance? No, obviously, that wouldn’t be fair. The same thing is true of your time. Your time is really a valuable currency and you should invest it where you and the team are going to get the biggest returns.

Kim continues with a KILLER metaphor that I think nails this mindset perfectly…

Kim: Some people even will say, my approach to management is to hire right, and then give them full autonomy and basically ignore them. That’s like saying, the best way to have a good marriage is to marry the very right person, and then refuse to spend another moment with that person.

When I read this in Radical Candor it completely resonated with me. It inspires me a lot more as a manager to move something that is great to something who is stunningly great, rather than something that is bad to mediocre.

Kim: Management is not Marxism. You don’t need to give all your time to the people who are neediest.

Let your reports set the agenda for your 1-to-1s

A very practical (and super easily applicable) learning for me is having regular 1-to-1s with my direct reports, and letting them set the agenda for these meetings. I really like Kim’s thoughts on this…

Kim: I would remind people that anything was fair game, from strategy to furniture to stuff going on in your personal life. The one-on-one was the time I set aside for each direct report to talk to me about what was on their mind.

It’s easy as a busy manager to want to reduce meeting time and free-up space in your calendar, especially when you think the 1-to-1 might not be needed because the person is doing great, however I’m realising the importance of keeping these things going, because it’s a space where brainstorming and problem solving happens. A suggestion from Kim that I regularly use in my 1-to-1’s…

Kim: It shouldn’t feel like calendar clutter, or something like that. That’s why it’s useful to do it over lunch, or over a coffee or taking a walk or in some way that the human connection is more likely to be front and center, than the updates or the agenda or anything like that.

Remember to praise.

Kim: If you think about praise and criticism, praise helps people see what to do more of and criticism helps them see what to do less of.

Being totally honest, praise is something I’ve struggled with. We’ve tried a few different approaches at AJ&Smart, like bonus programmes where you can reward colleagues for doing something great, and I still haven’t found something that’s really stuck, because for me praise shouldn’t just be about making someone feel good — it should instead be about really directing people in the right direction and rewarding positive action. Kim’s advice really drove home to me the importance of praise and its impact…

Kim: Your job as a leader is to fundamentally show people what success looks like. Praise is a much more powerful tool for showing people what success looks like than criticism. Criticism just shows them what it doesn’t look like.

So to summarize…

  1. Management doesn’t always come naturally to everyone. It’s your job as a manager to continually better yourself and seek out growth opportunities.
  2. Care personally, challenge directly: it’s unkind not to be clear.
  3. Being nice isn’t always nice: create an environment that evokes praise AND criticism.
  4. Keep your star performers top of mind: focus on bringing things from great to amazing, rather than bad to mediocre.
  5. Let your reports set the agenda for your 1-to-1s: anything is fair-game.
  6. Remember to praise: show people what success looks like.

Managing people is hard, no doubt about it, and I think any managers reading this (if they’re honest) will admit that they too have fallen short at times and can relate with Kim’s stories, however by following guidance from seasoned pros like Kim and even implementing just 1 or 2 of the suggestions, you’ll be WAY further ahead than most, and your team will notice (and appreciate) your efforts.

Full interview on the Product Breakfast Club

A version of this story was published on Medium by Jonathan Courtney.

Don't Compete Work Martyr

To Compete With a Work Martyr, Don’t Play the Game

compete work martyr It’s frustrating to work with somebody who expects to be rewarded for being more miserable than you are, who’s constantly trying to engage in a contest about who can work longer hours, who has masochism confused with commitment. These people are known as work martyrs. And if your boss is too blind to see what’s going on, it’s even harder. I used to try to compete with work martyrs.

But, truth be told, work martyrs aren’t always as bad as you think. I once worked with a group who worked all the time: 90-hour weeks were common. At first, I thought of them as work martyrs and that made me feel resentful. Over time though, I realized they just wanted to live differently than I did. For them, work was the safest, happiest place on earth. They actually liked being at the office all the time.

Rather than trying to compete with these people, continue striving to do your best. And when you feel like you’re getting sucked into work martyrdom, keep these tips in mind.

Do’s and Don’ts When You’re Tempted to Compete With Work Martyrs

Do prioritize your work. Identify all the things you’re doing that aren’t necessary and just quit doing them. Extra time in the office, for example, is rarely imperative. If you still have too much work to do, make sure you understand your team’s top priorities, and put low priority work on a “do not do” list. (One note: seek explicit agreement from your boss that you’ve gotten the priorities correct, and that it’s OK not to do the less important stuff so you can focus on what really matters.)

Don’t enter competitions you don’t want to win. That means not attempting to put in more hours than the people around you. You’ll probably lose if you try, and if you win, you lose in the end when you find yourself burned out and resentful.

compete work martyrDo set your own boundaries, and let others work the way that works for them. When I was in a similar position and relayed to my team how much I was realistically willing to work, they were absolutely fine with it. They didn’t care if I was there 40 hours or 70.

But they didn’t want to be kept to a maximum either. I knew not to insist they work less if they were genuinely eager to be there. So be clear with your colleagues where your boundaries are — and respect that theirs may be different.

Don’t become promotion-obsessed. We live in a culture fixated on external rather than internal validation. At work, this often plays out in an over-emphasis on promotions, title changes, and expanded responsibilities instead of the often more meaningful professional growth and stability.

Do focus on what’s most important to you, and to getting it. Working fewer hours does not have to translate to lower ambition. It does have to mean really clear thinking, greater efficiency, and more ruthless prioritization.

Don’t concede defeat if you do want to move up but you simply can’t put in the hours because of demands from your personal life. If you prioritize wisely, and don’t waste time at work, you’ll be amazed how much you can get done. When I asked Susan Wojcicki, the CEO of YouTube, about balancing work and parenthood, she had a simple formula: “You work less.”

And there you go, a few guiding tips for when you’re worried about competing with people who are putting in more hours. Remember: Success isn’t measured by the hours you spent sitting in front of your computer. Success is measured by your results, and how fulfilled you feel achieving those results.

A version of this story was originally published on Ask a Candid Boss on The Muse.

Growth Stability Career

A Happy Marriage of Growth and Stability

I recently learned that my great-grandfather Taylor Malone started a company with my husband’s great-great uncle, Joe Hyde, in Memphis, Tenn., my hometown. Oddly, it took us 11 years of marriage to learn this. We just found out thanks to a visit to a cemetery in Connecticut, but we’re happy to know now. It’s a great story about how we all need a balance of growth and stability to build great teams, to have successful careers, and to live the lives we imagine.

Listening helps achieve growth or stability for your life and career.

The whole story nicely illustrates something I learned about building cohesive teams from an executive at Apple. If I’d just been listening around the dinner table, maybe I could have learned it much sooner.

For much of my career, I tended to focus on hiring only the most hyper-ambitious people. I assumed that was the only way to succeed. Then a leader at Apple pointed out to me that all teams need stability as well as growth to function properly; nothing works well if everyone is gunning for the next promotion.

She called the people on her team who got exceptional results but who were on a more gradual growth trajectory “rock stars” because they were like the Rock of Gibraltar of her team.

These people loved their work and were world-class at it, but they didn’t want her job or her boss’s job or to be Steve Jobs. They were happy where they were.

The people who were on a steeper growth trajectory—the ones who’d go crazy if they were still doing the same job in a year—she called “superstars.” They were the source of growth on any team. She was explicit about needing a balance of both.

This was a revelation. Apple was big but still growing like crazy. And yet Apple made room for people with all sorts of different ambitions. You had to be great at what you did and you had to love your work, but you did not have to be promotion-obsessed to have a fulfilling career at Apple.growth career stability

For most of my career I’d systematically undervalued the so-called “rock stars.” This mistake had caused a lot of unhappiness for people who contributed significantly.  (To learn more about balancing superstar mode and rock star mode, read chapters three and seven of Radical Candor.)

Taylor Malone was the ultimate rock star, a man focused on stability. He started Malone and Hyde to support his family, not because he had a passion for business. His passion was fishing. He worked hard, and the company did well. He fished on the weekends.

Joe Hyde was the ultimate superstar, an ambitious man focused on growth. His passion was to build a big business. The company did well, and he wanted to take on debt to grow faster.

Taylor Malone was worried about what the stress of debt and growth would do to his fishing weekends. He decided he’d rather give control to Joe Hyde, let him build on the foundation they’d dug together, forego much of the financial upside, and spend the time taking his grandkids, including my father, fishing.

Lest we leave our female forebears out of the story: My great-grandmother was so loved by her children and grandchildren that nobody could talk about her after she died without bursting into tears. So all I know about her is that she was much loved. But that’s enough to know…growth and stability for your career

Both Joe Hyde and Taylor Malone got what they wanted. My great-grandfather now fished three times a week, and Andy’s great-great uncle built their little store into Malone and Hyde, one of the largest food distributors in the country.

Both Joe Hyde and Taylor Malone’s decisions have contributed to our family’s psychological freedom to do what we want. They also remind us of the courage and clarity it takes to figure out what we really want.

Joe Hyde reminds us we can take risks and build something big when that’s what we want. Taylor Malone reminds us that may not be what we want, and we can live life at a slower pace and still be productive .

If you can build a team that balances growth and stability, that allows everyone to take a step in direction of their dreams, the benefits to you, your business can be surprising and delightful for generations to come.

Being A Manager Feels Like A Lonely One-way Street

What’s the Ideal Manager-Employee Relationship?

You may have seen me featured as “The Candid Boss” for The Muse, an online career resource destination. One of the questions I am often asked is, can managers and employees be friends at work?

An even more essential question to ask is, what does an ideal manager-employee relationship look like? How is it different from a friendship?

The “boss-employee” relationship is relatively new. For most of human history, we accomplished our great collaborative feats through terrible brutality forced labor.

During the Industrial Revolution, we replaced brutality with bureaucracy; a giant step in the right direction, but hardly inspiring. In today’s economy, companies like Google have shown there’s a more productive, more human way to work than command and control.  

And at the center of a manager’s ability to fulfill their core responsibilities is a good relationship.manager employee relationship


The relationship a manager has with an employee is definitely not a friendship, which may be described as a two-way street. As such, being a manager often feels like a lonely, one-way, pay-it-forward street. 

While it’s not a friendship, you need to care personally about your employee. This doesn’t mean you need to go out to drinks with them every night (or know the exact date of their Golden Retriever’s birthday).

It does mean you need to give a damn about them, and understand what’s important to them (hiking with their Golden Retriever). 

Being a manager feels like a lonely one-way street

An important part of your job as a manager is to provide your employee with frequent guidance as well as with the necessary challenges and opportunities to support their ongoing growth.

Caring personally means it’s your job to listen to people’s stories, to get to know them well enough to understand what motivates them, to encourage them to take a step in the direction of their dreams, and to help them do the best work of their lives.

Caring personally means you are willing to find time for real conversations.

This takes a lot of emotional energy. It requires a commitment to your team member’s ongoing success and a desire to help them grow in the way they want to grow in their careers.

If you don’t genuinely care about the people who work for you, you’re going to struggle with this.

manager employee conversations

If you’ve ever had a great boss, you know it’s also one of the most deeply personal and meaningful relationships life can offer.

The manager-employee relationship is not a friendship. But it is a deeply human relationship, and when it works, it unlocks human potential.

Learn more about the manager-employee relationship, and check out the rest of my Ask a Candid Boss Q&As.

Radical Candor Intern

The Star Intern: A Mentor’s Radical Candor Journey


Radical Candor Intern

We recently heard from Dimitar Simeonov, who shared his story about reading Radical Candor while managing an intern when he was working at Twitter as a senior data scientist. While Dimitar’s no longer at Twitter, at the time he had been there for four years and was responsible for the intern’s technical mentorship. Thanks for sharing the learning and the love, Dimitar!


Two weeks in as an intern mentor, I had a dilemma. My intern was performing with the cadence and quality of a full-time engineer. I felt I needed to challenge him and help him learn further. I felt like he hadn’t reached his potential and I needed to help his growth. I thought if I didn’t do it, he might get bored and start underperforming, not get a return offer, or not be interested in a return offer. Most important, the internship wouldn’t have been worth his time.

Dimitar Simeonov

This was the first time I was a mentor, and I was quite anxious, feeling unease about providing personal criticism from a point of authority. I was happy with the progress, but also worried, because it made the task of giving critical feedback harder for me.

I didn’t feel like criticizing him at all. There weren’t many things to criticize. I was afraid that if I spent too much time on minor issues, I might come off as complaining too much. That he might feel discouraged, and we’d have a harder time building camaraderie.

To contrast personal and technical feedback, I am very happy to go into a technical argument, but very rarely, or never would go and criticize the approach of others. I was providing technical feedback to my intern all the time, on the code reviews, without having to wait until the next 1:1.

So technical feedback was not an issue for me — I could go into a technical argument with other engineers, focused entirely on technical merit, and emerge without me or them feeling personally insulted. The code is the code, but people are hard for me.

Having recently read Radical Candor, I knew that if I didn’t point things out, complacency could sneak in, and he’ll have a “meh” experience. I would have failed as a mentor to do my job.

I used two techniques for overcoming my dilemma.

The first technique I learned from the Radical Candor book, that if I am more receptive to feedback, and listening earnestly, then he in turn would be more receptive, because he’ll see that I care personally through my actions. During our one-on-one meetings I was trying to extract things I could have done better, asking the same questions every time, and providing enough pause so he could answer.

I asked for things I could do or stop doing to make it easier for him. I asked for feedback from him. I also repeatedly asked him about the direction of his career, whether he’d prefer to learn more about code patterns and how to write great quality code, or whether he’d be more interested in product development. 

I saw these kinds of career questions in Radical Candor, and I thought it would be a good way to break the ice and show that I care. After several weeks of bringing up these questions, my intern started answering them. He chose to focus more on the product aspects and I assigned him more product-related tasks. He provided feedback to me that having a written plan for the work we were doing together helped him understand more easily the scope and importance of the various tasks.

I heeded his comment. I made sure to always have a written up-to-date plan, which helped us collaborate more closely as his internship progressed. This written plan evolved into a wiki page containing all the current, past and future work on the project, broken up with milestones and tickets’ statuses. Having learned this from my intern, I used the same format for my other projects.

The second technique was to create a dedicated space for suggestions for improvement during our 1:1. I structured the meeting in a way that we talked about feedback and career prospects for him before discussing any kind of “status updates” or technical issues.

After the first few weeks, I told him, ‘Hey, let’s try the following approach. Every week, during 1:1, I will talk about one thing that you could have done better during the last week.’ This provided me a cover to discuss seemingly minor things without being petty. What’s more, focusing on a single thing per week provided more clarity to him about what I thought was important.

Instead of saying three things and noticing that the next week he has improved on two of them, but not the most important one, we would instead focus on the most important thing first.

One of the weeks he did a great job on his project, and I didn’t really have much critical feedback — he even made a presentation to the team that he delivered well. That week I gave him feedback that he did great and the only improvement that I see is that he used the word “study” incorrectly, instead of “experiment” during the presentation. This showed that I still paid attention to his work through the week and valued it, and still helped him make a minor adjustment.

At the end of the internship, he did a presentation about his work and there was a slide in it that made me happy. The slide was about what he learned during the summer. He started mentioning things that would appear as bullet points on the slide.

But when the space on the screen was full he kept on going … new bullet points appeared all over the place, overlapping at angles with the pre-existing ones, faster and faster.  It was a pour of learnings. He said, “I learned so much.” Everyone laughed and clapped.

I cannot claim credit for all the learnings, but as his mentor I’d like to think that my behavior and feedback during the 1:1 meetings helped, and that Radical Candor helped me challenge directly and care personally.


You can continue following Dimitar’s journey on his blog and on Twitter. And let us know how you are bringing Radical Candor to your team, too!

Rolling Out Radical Candor: Part One

We love working closely with teams rolling out Radical Candor, and offer coaching, training and customized workshops. We can help teach you to:

  • share the ideas with your team and learn how to tell your feedback stories;
  • practice key skills like soliciting feedback, offering meaningful praise, and giving helpful criticism; and
  • create a culture of guidance so that all the burden of feedback doesn’t fall on your shoulders.

We also work with leaders to help you build more cohesive teams and to achieve results collaboratively. Let us know how we can support you.

We love doing this work so much and care so deeply about these ideas that we would do it for free if we could. Alas, we need to keep body and soul together. However, to help organizations that don’t have budget for Candor Coaches, we are offering a free “roll-your-own-Radical Candor-rollout.”

Here is our recommended Order of Operations (part 1 of 2-part series):

Step 1. Share your stories.

Explain Radical Candor to your team so they understand what you’re up to. You can also ask them to read the book, show them videos from the Radical Candor website, or from the series we created with Amazon, Day One: Insights for Entrepreneurs.

But it’s best if you explain it in your own words. What is your version of the “um” story or the “Bob” story? Tell your stories to your team. Show some vulnerability. Your personal stories will explain, better than any management theory, what you really mean and show why you really mean it. That’s why I told all those personal stories in this book. Your stories will mean a lot more to your team than mine do, because they mean something to you.  

Step 2. Solicit feedback: Prove you can take it before you start dishing it out.

Start asking your team to criticize you. Review “soliciting impromptu guidance” in Chapter Six. And remember, don’t let people off the hook when they don’t say much—because they won’t, at first. Embrace the discomfort to move past it. Pay close attention if you aren’t getting any criticism.

If you want, you can copy the Radical Candor framework in Chapter Two and track who’s saying what to you there. Just because people aren’t criticizing you doesn’t mean they think you’re perfect. If you realize that you’re not getting any criticism, try Michael Dearing’s “Orange Box” technique (see “orange box” in Radical Candor, Chapter Six).

Soliciting guidance, especially criticism, is not something you do once and check off your list — this will now be something you do daily. But it’ll happen in little one- to two-minute conversations, not in meetings you have to add to your calendar. It’s something to be conscious of, not something to schedule. It will feel strange at first, but once you get in the habit, it’ll feel weird not to do it. You won’t ever “move on” from getting guidance any more than you’ll ever move on from having to drink water or brush your teeth. But don’t stop there.

Step 3. Growth Management: Career Conversations.

In order to build a great team, you need to understand what motivates each team member, and how each person’s job fits into their life goals. A leader at Apple had a good way to think about different types of ambition: rock stars are solid as a rock, and a force for stability at work (think Rock of Gibraltar, not Bruce Springsteen), while superstars are highly-ambitious change agents, constantly seeking new opportunities.

The most important thing you can do for your team collectively is to understand what growth trajectory each team member wants to be on at a given time, and whether that matches the needs and opportunities of the overall team. Learn more about our Growth Management philosophy in First Round Capital’s Warning: This is Not Your Grandfather’s Talent Planning.

To be successful at growth management, we recommend a series of three Career Conversations you’ll have with each team member. Begin with people you’ve been working with the longest. (Review “Career Conversations” in Chapter Seven and The Problem with Career Conversations Today for more background.)

When done well, these conversations should connect a person’s past – gaining a detailed understanding of who they are and what motivates them at work through their life story – with their future – the wildest dreams they have for themselves at the pinnacle of their career.

Conversation 1: Learn what motivates your team member, what they value, the things that drive them; their Life Story.

Conversation 2: Understand where someone wants to be at the pinnacle of their career; their Dreams.

Conversation 3: Plan for the present with a Career Action Plan.

“We have to understand the past and the future in order to know what to do in the present, what to do right now.”

Like getting criticism from your team, Career Conversations are not something you do once and check off the list. Remember, people change, their growth trajectory changes, and you need to change with them! That’s why it’s a good idea to do one round of Career Conversations a year with each of your direct reports during your 1:1 time.

Step 4 / Ongoing: Perfect your 1:1 conversations.

In parallel — because it will take you at least three to six weeks to get through these three Career Conversations with everyone on your team, since you want to leave a week or two between each of the three conversations — make sure you are having meaningful 1:1 conversations with your direct reports.

First, make sure you actually have the meetings! We have to start at the beginning here, because it’s simply not the case that all managers are holding regular 1:1s. 1:1s are quiet, focused collaboration time for employees and bosses to connect. It’s also the most important chance for you to hear from your employee, and it’s their time, not yours. (Review 1:1 conversations in Chapter Eight and How to Have Effective 1:1s.)

It’s equally important for you to figure out how to enjoy the conversations. If you feel like they are “calendar clutter,” your approach is not going to work. Quit thinking of them as meetings and began treating them as if you are having lunch or coffee with somebody you are genuinely eager to get to know better.

If scheduling them over a meal helps, make them periodic lunches. If you and your direct report like to walk and there’s a good place to take a walk near the office, make them walking meetings.

If you are a morning person, schedule them in the morning. If you are a person who has an energy dip at 2 P.M., don’t schedule them at 2 P.M. You have a lot of meetings, so you can optimize the 1:1 time and location for your energy. Just don’t be a jerk about it. You may like to wake up at 5 A.M. and go to the gym. Don’t expect the people who work for you to meet you there.

After you have explained Radical Candor, asked for guidance, had career conversations, and improved your 1:1 conversations, you’ll notice that you are earning your team’s trust and building a better culture.


Step 5. Give Guidance — Praise & Criticism — but make sure to focus on the good stuff.

Now you’re ready to start improving the way you give impromptu praise and criticism. Remember, impromptu guidance happens best in one- to two-minute conversations. (Review “Giving impromptu guidance” in Chapter Six.) Make sure you gauge your guidance. (Review “Gauge your impromptu guidance. Get a baseline, track your improvements” in Chapter Six.)

You may think you’re being radically candid, but one person may not have heard any criticism at all, another may have heard it as ruinously empathetic, and yet another as obnoxious aggression. You have to adjust for each individual. You have to be not just self-aware but relationally- and culturally-aware.

Step 6. Take a deep breath. Assess.

How’s it going? What’s working? What’s not working? Who can you talk to? Can your boss help? Your team? A mentor outside of work? A coach? Others from the Radical Candor community? Would you like to ask me a question?

Don’t try to do more new things until you feel 1) you’ve made good progress on the fundamental building block of management: getting and giving guidance, 2) you’ve gotten to know your direct reports better through your Career Conversations, and 3) you’re happy with your 1:1s.

Stay tuned for Part II…and keep us posted on what’s working, what’s not, and how we can help!

Podcast Episode 5: Career Conversations

As a manager, your job is to help your people grow. But have you ever asked yourself, “Grow into what?” This week, Russ and Kim talk about a technique for getting to know the people on your team, understanding the things that motivate them, learning about their dreams, and helping them make tangible progress towards those dreams.

Listen to this week’s episode:

Resolve to Be a Better Leader in 2017

It’s that time of year. A time for new beginnings. A time for renewal and resolution. Like many, you may be feeling inspired and committed to a set of New Year’s Resolutions. But have you committed to any that will help you be a better leader in 2017?

Maybe you’re not sure where to start, what leadership resolutions to choose. John Farmer, one of our engineers, and I developed a list of “Leadership New Year Resolutions” to help you start thinking about this. We recommend picking one, at most two, and truly resolving to do it better.

We’ve organized these resolutions around the 3 core responsibilities of a manager:

  1. Giving and receiving feedback
  2. Building a high-performing team

Which are both in service of:

  1. Driving better results

Feedback Resolutions

1. Listen more and be comfortable with silence

Have you ever counted how many ears you have and compared that to the number of mouths you have? For most people that is a 2:1 ratio – twice as many ears as mouths.

When you talk, you only repeat what you already know, but if you listen you may learn something new.

(Dalai Lama, big hitter.)

Resolve to listen more so that you can truly hear and learn more from the people on your team. Here’s an Andy Grove inspired process for soliciting their feedback. You must adjust your mindset and truly believe that the people on your team have a lot to teach you, and then you must listen!

2. Embark on a listening tour

It’s not just the people on your team that can teach you a lot. You probably work closely with peers as well, those who share your boss or cross-functional collaborators. Have you heard from them recently?
Resolve to ask ten peers how you can improve. Buckle up. I recommend specifically steering clear of “what am I doing well?” and just ask the question, “what can my team or I do better?” Remember to truly listen.

And here’s the trick – Don’t get mad, get curious. Understand going in that you might hear some difficult-to-hear things. That’s GREAT! Would you rather have those things whispered behind your back or show up suddenly on a peer review? Or would you rather go out there and hear them face to face and get a chance to improve?


3. Give more praise

Too many managers do praise poorly, if they do it at all. Praise is not about making someone feel good. Praise’s purpose is to show people what success looks like, what to do more of. Roanne Daniels at Bain Capital says beautifully, “Every time you praise someone you tell them what you value.”

Every time you praise someone you tell them what you value.

Resolve to give (approximately) 3 instances of praise for every instance of criticism. This will be easy once you form the habit. Think about this: you’re not walking around firing everyone on your team, which means they’re doing an awful lot more well than not. Take the time to see and immediately communicate those good things in 1-3 minute, informal conversations.

4. Ask your employees how happy and productive they feel at the end of each week

One of the great services you can provide to your employees is being a blocker eliminator. Sometimes your folks experience real blockers and sometimes they perceive blockers. In both cases, it will be hard for you to be helpful if you don’t know how the person is currently feeling.

Resolve to ask, “how productive were you this week?” to uncover and discuss blockers. Also ask, “how happy are you?” to understand the things either frustrating or enriching your team members. This will give you a chance to go all Darth-Vader-in-Rogue-One on those frustrating items and the opportunity to double down on those sources of happiness.


Resolutions for Building a Stronger Team

1. Let your directs fully own the agenda for your 1:1s

Not long ago, we posted an article about holding effective 1:1s. The idea that your employee owns the agenda is a simple, symbolic practice that helps them feel ownership and autonomy for their work and their time.

Resolve to give your employees this responsibility, as a way of saying, “You tell me what’s important.” Of course, you can coach and guide them over time to help refine their thinking about what’s important. Remember that Steve Jobs said “we hire people to tell us what to do, not the other way around.”

2. Understand your employees’ long term career aspirations

Part of your job as a manager is to help your employees grow. Have you ever asked yourself the question, though, “grow into what?” How can you hope to offer a shred of relevant career advice to your people if you don’t understand their dreams?

Resolve to ask your employees, “What do you see yourself doing at the pinnacle of your career – when you are happy, challenged and not longing for anything else?” And then listen. And listen. Ask clarifying questions. Push for a few dreams, not just one. Do not accept incremental steps that don’t sound like dreams. ONLY AFTER you understand their dreams – blurry, foggy versions of the dream – use three questions to bring them into focus. What’s the role? What’s the industry? What’s the size of company? Write these vision statements down. They’re gold.


Check out this video for a bit more on helping your employees grow.

Resolutions for Achieving Results

1. Delegate decision making

Your team will execute better and faster if you devolve decision-making responsibility deeper into your organization. You’re probably less likely to do as good a job as the people closest to the facts. Also, every time you make decisions for your team, realize you are robbing your employees of a chance for both growth and visibility. Finally, you can never scale as a manager if you continue to act like an individual contributor. Let it go. They will deliver.

Resolve to delegate more important stuff to your team. Focus more on what, not how, by making sure that your team has clear, measurable goals each quarter. Push decisions “into the facts”– explicitly identify who the decider is for key decisions, and make sure that person has what they need to decide.

2. Tighten up your meetings

The more time you and your team spend in ineffective meetings, the less time you spend on achieving important results. Ever felt like a meeting had way too many people in it, or that it was taking much longer than it needed to? Ever been a part of a meeting where half the room is trying to make a decision and half the room is just debating? These situations are a huge waste of time and a source of frustration for everyone.

Resolve to publish an agenda for your meetings. (Google Spreadsheets is great for this) Make it clear exactly what the objective is for each agenda item. You might use these objectives:

  • Relate = pass on information, ie “there will be fire drill today at 1:30PM”
  • Solve = brainstorming and problem solving. Debate lives here.
  • Decide = make a decision.

Clarifying the objective of an agenda item helps all attendees know what you’re trying to get done and can help identify who needs to attend. You can also set a time limit for each agenda item. Meetings should only take the time that they need – if a meeting is scheduled for 60 minutes and you are done in 45, CELEBRATE the fact that everyone gets back 15 minutes.


The Gimme/Candor-plug Resolution

Of course, we all know that resolutions often only last about six weeks into the year. It’s hard to change your behavior. And we want to help you continue your commitment to being a better leader throughout the year.

Resolve to listen to the Radical Candor podcast for weekly leadership lessons, inspiration and tips. Subscribe in iTunes or wherever you get your podcasts, or sign up here to get email notifications.

Also resolve to read Candor’s monthly newsletter for more stories and advice. Subscribe here.


Which of these resolutions will you commit to in 2017? Do you have other leadership resolutions? Tell us about them in the comments below, or reach out on Twitter or Facebook. We’d love to hear from you!

4 Ways to Help New Managers Succeed

I’ve had a 22 year operational management career, and naturally, I’ve had a lot of new managers in my organizations over the years. ‘New managers,’ in this case, means ‘new-to-management’ not so much ‘new-to-me’ or ‘new-to-the-org.’ I’m talking specifically about people new to the practice of management. Oh yeah, I was also a new manager once, many moons ago as a young Lieutenant in the US Marines.

So I really understand the struggles and challenges of being a new manager.

“Ask any new manager about the early days of being a boss—indeed, ask any senior executive to recall how he or she felt as a new manager. If you get an honest answer, you’ll hear a tale of disorientation and, for some, overwhelming confusion.”

From Becoming the Boss by Linda Hill, Harvard Business Review, 2007

One day, you’re an individual contributor, and likely, you’re a successful one because that is what typically earns you the opportunity to become a manager. Suddenly you’re promoted or get a new job as a manager. That’s great! The thing is, though, that what got you here with success, won’t get you continued success as a manager. I mean this quite literally.

The activities that led to success as an individual contributor LOOK NOTHING LIKE the activities that will lead to success as a manager.

They do not resemble one another at all. No hyperbole.

But despite this, new managers receive very little coaching on how to be successful in their new role.

“And as I neared the end of my corporate days, I realized I’d received much more management training in the last five years than I did in the first 20 years — when I really needed it — combined.”

From Why Do We Spend So Much Developing Senior Leaders and So Little Training New Managers? by Victor Lipman, Harvard Business Review, 2016

As I’ve talked to 100s of customers and prospects at Candor, Inc., the single most common concerns raised by senior leaders and HR pros alike has been “We have a ‘new manager’ problem that we badly need help with.” These companies are often communicating huge front line employee engagement issues related to the performance of their middle and entry level of management. This isn’t a huge surprise. Companies often invest extraordinary sums of money to have famous authors come in to distribute brain candy and consultants to build cohesive senior executive teams. But in so many of the companies I’ve seen, the investment level in training new and middle level managers is not remotely close.

The theory of senior level investment, according to Lipman, has to do with the leverage exerted upon the organization by a relatively small number of leaders. One C-Level person has massive impact on an org. Gotta fix that guy! That gal needs to improve! It is also often the case, though, that the front line and middle layer managers, in aggregate, have at least as much leverage on the organization and directly results in costly turnover and ineffective performance.

I think this problem is enormous and and not close to resolved. To get our own conversation going, here are some of the key areas I’ve seen new managers routinely struggle with:

  • Giving feedback
  • Helping their team grow
  • Driving team results
  • Formal performance management

Here are some ideas for how manager-focused L&D (Learning and Development) and senior executives can better mentor new managers in these areas.

1. Teach New Managers to Be More Than Cheerleaders

When it comes to giving feedback to their teams, new managers spend so much time in Ruinous Empathy that they should have to pay rent to Ruinous Empathy. They become cheerleaders, with refrains of “Go Team!” and “We are mighty”, almost complete with pom-poms. Like cheerleaders, new managers aren’t yelling, “R-U-N play-action more because that is the best way to exploit their over-aggressive linebackers!”


New managers perhaps don’t feel like they have the cachet or capital to challenge their teams too directly. Perhaps the new manager is trying logically to avoid micromanagement. It could also be that the new manager is flat-out conflict averse and struggles to issue a direct challenge no matter how justified. Indeed, it is human nature that the more difficult the conversation, the less clear we become. In either case, the manager is doing the individual and the remainder of the team a disservice by not clearly articulating performance problems.

New managers also become cheerleaders with their praise. They offer non-specific praise such as “Great job!” intended to make friends and to make people feel good. Often, the new manager is far too concerned with being liked versus being respected or competent. It’s normal to want to be liked. The manager’s job, of course, is to help the team be more successful and being liked may very well not fit into that plan.

We can help new managers avoid these natural tendencies by teaching them what good feedback looks like. An easy first step is to have them watch our Radical Candor video, listen to Kim’s First Round talk, and read some of the feedback articles on our site.

They’ll learn that when things aren’t going as well as hoped, they should “Just say it!” They’ll learn that giving criticism that is kind and clear is far more helpful than not saying it at all.

It’s also important for new managers to learn that showing you Care Personally does not simply mean to give more praise — praise is not the way to turn all direct challenges into Radical Candor. Managers should avoid the feedback sandwich – putting a piece of praise around a tough message – for two reasons. First, the praise is usually meaningless – very general, not particularly sincere. Second, and much more importantly, leading with praise in delivering a tough message confuses and dilutes the tough message.

When it comes to giving praise, new managers need to learn how to be more impactful. For example, when they give specific praise – praise that includes a clear articulation of what was achieved and why that achievement matters – they can help people to see and feel what success looks like in the organization. The Positive Coaching Alliance teaches us that “positive is powerful,” but are careful to say that generic, non-specific praise is just as useless for little kids as it is for adults. I’ve found similar results in the organizations I’ve run and in the little league teams I’ve coached.

We can also help new managers learn that more often than not, their team will actually prefer getting direct challenges. By providing a way for team members to gauge new managers’ feedback, they’ll get a strong message as to whether people think they’re pulling their punches.

2. Help New Managers Enable Their People’s Futures

New Managers tend to really struggle with helping their team grow because they are generally not taught how to have Career Conversations.

Great managers help bring some intentionality, structure, and accountability to the process of career planning for their people, by understanding the employee’s past and future, which then enables the employee to take relevant action right now.

You can help new managers, and their teams, simply by providing basic training on Career Conversations. We’ll be bringing a bunch more content soon about the details of how to have good Career Conversations, so watch this space for additional resources.

3. Guide New Managers in Setting Expectations for and Driving Performance

Many new managers find themselves in difficult performance management situations because they haven’t clearly articulated standards for performance and they don’t always follow a sound process for delivering results. It’s difficult for the team to succeed if they don’t know what the expectations are.

Help new managers set expectations by coaching them on how to set goals – or OKRs – in collaboration with team members. OKR means Objectives and Key Results. In case you’re not totally familiar, Betterworks does a nice job defining OKR basics here. Even our tiny company, Candor, Inc. has a set of objectives for end of year 2017 and 2016, and supporting key results under each! These objectives are aligned to the company’s envisioned outcomes, in our case, profitability or a successful Series A. Managers should set OKRs collaboratively with the team, not dictate them to the team. Teach new managers to check that their team’s OKRs support the goals of both the company and the higher organization.

Driving results is hard. We’ve developed a process for helping drive better results more consistently. This process is a loop and operates conceptually like Boyd’s Cycle.



Your team should know what the company is trying to achieve, and they likely have some of the best ideas for what your team should be achieving. First, listen to their ideas in trying to figure out what results your team should be pursuing.


Remember that new ideas are fragile and therefore easily squished. A critical role a manager can play is to augment the voice of their team by helping the team clarify their ideas and by clarifying the manager’s own understanding of the ideas.


Allowing the team time and space to publicly debate the ideas is a critical step. Guidelines for good debate include making the discussion about the ideas and not about egos. It’s about finding the best answer together, not about who won the debate.


The manager doesn’t always need to decide, but the manager needs to make certain that the decider is clearly identified and that a decision gets made. If there are any follow up items or other process points, such as specific stakeholder checkins, for making a decision, the manager needs to make sure those are articulated.


Not everyone required to achieve results will have been involved in each step of this process. That’s ok, but those people need to be brought along after the decision is made.


Now it’s go time. Time to stop talking and start working. One of the great benefits of carefully abiding by the preceding process is that now the team can execute with great autonomy and purpose with buy-in and understanding.


Your team’s execution changes the context and uncovers new variables. The new context needs to be observed and understood and then used to feed the process again. Your team will have the best information; time to listen and go around the wheel again.

This is hard work, and in leading a team, managers should try to execute this cycle quickly but thoroughly to improve their ability to drive results. L&D can help new managers learn and understand this process by providing training resources and ongoing support. Watch this space for resources you can use to teach our “Get Stuff Done” results wheel!

4. Encourage New Managers to Utilize Formal Performance Management

I’ve seen this scenario far too often: The new manager sticks their neck out for an obvious under performer. They think they can coach everyone out of the problem. They think, because they were successful as an individual contributor, they can coach anyone out of a performance funk.

Of course, coaching is the right first step. It’s a great start. Good performance-related coaching includes a clear expectation for improvement and a clear timeline for improvement. I recommend that a manager start here and then re-assess the performance gap.

The problem arises as the coaching doesn’t take. After one or two cycles of accountable performance coaching, it’s time to move to a more formal process. The recommendation might sound aggressive, but I don’t think so, for a couple reasons:

  1. The new manager often struggles to identify that breaking point (when to move to a formal process) on their own. Even if they are able to identify when it’s time for more aggressive action, a concern about being wrong about their coaching often prevents them from acting. Beyond that, many organizations starve young managers of critical support from Human Resources Business Partners (HRBPs), who could help the manager find their footing and get control of the performance management problem. Without this support, a formal management process is the best way for new managers to navigate these difficult situations.
  2. I believe deeply that the formal Performance Improvement Plan (PIP) is a gift of clarity for the under-performer. It serves to clarify in writing the specific performance issues in a way that all critical stakeholders can understand – most importantly, the person struggling with performance. This answer is obvious when written at a distance and in theory in a blog post. But new managers often resist PIPs because of an excessive focus on the last line, which is often something like “failure to comply within 60 days will result in termination.” This line is more of a “cover-your-butt” tool to fire someone; using PIPs solely for this purpose is a huge miss. The rest of the document should be viewed as a great clarifying exercise. If you believe the harder the conversation, the less clear you are, then clarifying performance gaps and success criteria via a PIP is the greatest gift any manager – and especially a new one – can give a struggling team member.

L&D and senior executives can and should ensure that new managers know when and how to make use of formal performance management processes in their organization.


Does your company have any great training programs for new managers? What other areas have you seen present challenges for new managers?

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