Coaching & feedback
Chapter 3

Coaching & feedback

Hold teammates accountable, give and receive real feedback, and run effective one-on-ones.

Zone of Genius

Matching people to what needs to get done is an age-old problem in company building. And on a micro level, aligning yourself with the right role is also challenging. What should you delegate? Where should you focus your efforts?

Finding the right role must be an optimization between what you want, what you are good at, and what the organization needs now in order to achieve its goals, which in turn puts it into a path to achieve its mission.

We've found the Zone of Genius framework from The Big Leap by Gay Hendricks to be a useful way of ensuring there’s harmony between jobs and people. It’s pretty straightforward, here’s how it works.

The zones

There are four zones: Zone of Incompetence, Zone of Competence, Zone of Excellence, and Zone of Genius.

People’s performance consists of a mixture of skills, strengths, and talents. Here’s how we define them:

  • A strength is anything that gives you energy.
  • A talent is an innate ability that can’t be taught (for example, being incredible with numbers).
  • A skill is a competency that can be taught (for example, knowing Excel back to front).
Zone of Genius

Zone of Incompetence

The most obvious misalignment between people and tasks is where there is a lack of talent or skills. In this case, the person should either be retrained, redistributed in the organization, or asked to find a better match outside the company.

Zone of Competence

These are tasks that people are good at, but that other people can do better. Work that falls under this category should be delegated or redistributed to people more suited for it.

Zone of Excellence

It’s less clear when someone is talented and skilled in a particular area but the work doesn’t give them energy. They may be successful in the short term, but over time they will burn out. We call this the Zone of Excellence. It’s important to recognize when people are in this (or even better if they can recognize it) so you can do something about it.

Zone of Genius

When all talents, skills, and strengths are all aligned, we are in our Zone of Genius.

The things in your Zone of Genius are the things that you are uniquely good at in the world, and that you love to do (so much so, that time and space likely disappear when you do them). This is where you can add most value to the world and yourself. This is where you should be driving toward spending most, if not all, of your time. The same goes for your team; they're at their best when they're operating out of this place.

“Some people worry that if each of us operates solely in our Zone of Genius, no one will be available to do the un-fun stuff. This is a false fear. There are many personality types. For every activity that feels un-fun to you, there is someone out there who not only excels at it, but loves it. The key in any organization is for people to be transparent about what their Zone of Genius is, and then map all activities to the right people through Areas of Responsibility (AORs).”

- Matt Mochary, The Great CEO Within

Feedback and the Zone of Genius

Every person is unique. You can’t turn weaknesses into strengths, or create talent where there is none. These things are innate. All you can teach is skills and self-awareness, so direct your feedback there. Focus on doubling down on someone’s existing Zone of Genius, or shift them into a role better aligned with their Zone of Genius.

fear# Feedback

A good feedback system is an absolutely critical aspect of a functioning organization. At a macro level, when companies don’t do feedback well, pockets of disagreements within organizations grow, causing resentment, distrust, and ultimately organizational failure. At a micro level, feedback is the only way to achieve true personal growth. You are not objective enough about yourself to grow effectively without external feedback.

"If you avoid conflict to keep peace, you start a war inside yourself."

If feedback is so critical to a company's success, why do so many companies fail at it? In our experience, they fall short in three main areas: training to give feedback, training to receive feedback, and making it part of the culture. Ultimately, giving and receiving feedback is just hard; it triggers a negative emotional response. The alternative, though, is failure. There's no such thing as a workplace without feedback. If you're not hearing "bad news," people are too afraid to give feedback to you and each other.

Giving feedback

Giving and receiving effective feedback is a skill like any other, and it needs to be part of your on-boarding training if your team is going to be any good at it.

Fortunately, there are some excellent resources like Nonviolent Communication and Conscious Leadership that provide a good structure to do it.

  • Feedback should be given in private and regularly (i.e., weekly) at a time when someone is expecting it.
  • Use Radical Candor: care personally, and challenge directly. Beware of ruinous empathy.
  • Feedback should come from a place of love and good intentions.
  • Feedback should be specific and avoid sweeping statements, judgements, or labeling (e.g., avoid saying "I think you're lazy").
  • Feedback should be in a nonviolent communication format (provided below).

The key to giving feedback is to prevent activating people's “lizard brain” and provoking a feeling of anger or fear. These are powerful emotions and, once invoked, cloud higher-level thought.

The good news is there's a simple way of communicating feedback that avoids provoking anger and defensiveness. Simply communicate in the following format:

"When you do specific action, I feel emotion because the story in my head is fear. My request is specific request. Can you do that for me?"

Ensure that specific action is a fact, something that a camera would record. Emotion should be a core emotion, like anger, sadness, or fear. Don't avoid being vulnerable when describing your fear, make it as real and raw as possible. But also bear in mind that this is just a story in your head—other people may see situations differently and have different stories.

An example might be:

“When you didn't write any tests for that pull request you submitted last week, I feel fear because the story in my head is that you don’t place enough value on testing, and that without tests we will introduce bugs that will upset customers, affect revenue, and ultimately destroy our chances of creating a successful company. My request is that you write tests for every pull request you submit. Can you do that for me?”

Positive feedback

It is just as important to give positive feedback as it is to give critical feedback. You will find that some people need more positive feedback than others, and some people love public praise, whereas others don’t.

As with critical feedback, keep your praise specific. Otherwise you run the risk of operating in the quadrant of manipulative insincerity (see Radical Candor), which your report is going to see through.

For example:

“When you did specific action, I felt joy because the knock-on effect for the company meant …”

Receiving feedback

The reason why you feel that knot in your stomach whenever you are about to receive feedback is that your ego views it as an attack, provoking a fight, flight, or freeze response. Your ego thinks you're about to be killed—it's no wonder you feel nervous!

The key is to learn to evaluate ideas objectively and view feedback as a gift. Now this is easier said than done, and will require constant effort and practice. We definitely recommend reading the two books mentioned above, but here's a little shortcut.

When people are giving you critical feedback, as soon as they're finished, repeat back to them what you heard. Say “What I'm hearing is XYZ. Is that right?” It is important that the person giving feedback knows that you're hearing and listening to them. Not only will this mechanism do that, but it will also ensure that you have some breathing time to think. Keep asking, “Is that all?” and repeating back until you're sure you've squeezed every last ounce of feedback out of them.

Now, take that piece of feedback and take a second to think about it objectively. Be curious, run through the possibilities. Even if you don't agree with all of it, or with the format in which it was delivered, are there aspects of it that you can take to improve yourself? If you accept the feedback, suggest an action to resolve it. Thank them—giving feedback isn't easy, and by doing so, they've shown they care about you. You don’t have to accept all the feedback you’re given, but at least give a good explanation why not (and be curious to how the opposite might be true).

Making it part of our culture

As a manager, it is your responsibility to set a good example and ensure that giving and receiving regular feedback is part of our culture. We do not leave it to an annual performance review. People should not be in the dark all year as to their performance. Furthermore, tying feedback to compensation is the best way to politicize it.

There is a simple way to achieve this: make it part of your team’s weekly one-on-ones. Have a structured section at the end of a one-on-one for mutual feedback giving. Make sure that it's a requirement of all your managers, and ensure that it's recorded somewhere (we use Asana).

Lastly, publicly seek feedback from your team and discuss it. It sets a good example and demonstrates you're willing to be vulnerable and committed to growing.

"The leadership team gives me written feedback at our meetings, which I take and publish to the entire company. I address the feedback and discuss ways I'm trying to improve. Not only does this demonstrate a degree of vulnerability, but if people see that you view feedback as a gift, they will start doing likewise."

- Alex MacCaw, Clearbit CEO

Feedback and power dynamics

While we have tried to instill a culture of mutual feedback-giving at Clearbit, we have struggled to elicit critical feedback given upwards from a report to their manager. This is far from ideal; feedback is critical for the growth of both parties.

We are tackling this in a number of ways through training, anonymous feedback, and surveys, but it is an ongoing effort.

As a manager, you need to ensure that your reports feel safe giving you feedback, and that it’s worth their time. Trust builds over time. If your report sees you react positively to critical feedback by taking action, they’re more likely to give you more in the future. And they’re more likely to be candid.

It’s important to close the loop on critical feedback you’re given. If you decide to act on it, do so quickly and update your report at the next opportunity. If you don’t decide to act on it, explain why. But whatever you do, don’t treat feedback with silence.

Anonymous Feedback

At Clearbit, we have a culture of giving and receiving feedback, because it's one of the best ways of promoting self-growth. Ideally we can always put our name to feedback, but it's also important that we have an outlet for anonymous feedback. This is useful because:

  • It allows us to collect feedback in aggregate and survey employees
  • It lets people be candid when they perhaps otherwise wouldn't
  • It encourages us to focus on the message, not the messenger

We use TinyPulse to survey everyone by email weekly. We encourage everyone to fill out the survey, we look at it every week, and the results go directly into practice. We also periodically publish the aggregate results.

Every response submitted to TinyPulse is anonymous, and messages are viewable only by the Leadership team. The only breakdown we see is which department the respondent is in.

Every month we ask the question “How happy are you at work?” You can think of this as an internal NPS score, and we use this to track team happiness over time. This gives us an early warning indication to issues (like scaling too rapidly).

Generally, when there is a significant issue, we do an all-hands results evaluation with the results and proposed solutions. For example, a survey showed that one of the most draining aspects of Clearbit was ineffective meetings. In response to this, we created a new meeting structure and stricter policies as to when meetings can be created.

Questions we’ve asked in the past include:

  • What is the most challenging aspect of giving/receiving feedback at Clearbit, and how can we help the company get better at it?
  • Do you feel like you have the opportunity to reach your full potential at our organization?
  • How can we improve our remote work culture?
  • How can the leadership team improve?
  • What are Clearbit’s blind spots?
  • Do you know what is expected of you at work?
  • How do you feel about Alex's performance as CEO? What are some areas he could improve on?
  • What did you like best at your previous employment that you'd like to see implemented here?
  • How likely are you to refer a friend to work here?

If you find that answers given in anonymous feedback surprise you and don’t reflect one-on-one feedback, it may indicate a lack of receptivity to feedback from your leadership, or a deeper issue.

Radical Candor

In Radical Candor, Kim Scott outlines the different types of feedback that managers give, and the traps you can fall into when doing so. She has developed a system for giving effective feedback outlined below.

The TLDR is:

  • Ideally, first build a relationship with anyone before giving them feedback. Make sure they know you care personally about them and their career.
  • Then be extremely candid and clear with your critical feedback. Leave no room for interpretation.
  • Do not sugarcoat feedback to make people feel better.
  • Do not get personal or make sweeping statements. Be specific.
  • Be humble. If you are wrong, you want to know.
  • For positive feedback, be just as specific. Otherwise you’re just being insincere.

The following are excerpts taken from Kim's book, Radical Candor.

The four quadrants

The four quadrants of feedback are Ruinous Empathy (the most common mistake), Manipulative Insincerity, Obnoxious Aggression, and Radical Candor.

Radical Candor

Manipulative Insincerity

“People give praise and criticism that is manipulatively insincere when they are too focused on being liked or think they can gain some sort of political advantage by being fake—or when they are just too tired to care or argue any more.When you are overly worried about how people will perceive you, you’re less willing to say what needs to be said.”

- Kim Scott, Radical Candor

Feedback that is manipulatively insincere rarely reflects what the speaker actually thinks; rather, it’s an attempt to push the other person’s emotional buttons in return for some personal gain. Manipulatively insincere feedback happens when you don’t care enough about a person to challenge directly.

Obnoxious Aggression

When you criticize someone without taking time to show you care about them personally, your feedback feels obnoxiously aggressive to the recipient.

When managers belittle employees, embarrass them publicly, or freeze them out, their behavior falls into this quadrant.

“Obnoxious Aggression sometimes gets great results short-term but leaves a trail of dead bodies in its wake in the long run.”

- Kim Scott, Radical Candor

Often Obnoxious Aggression stems from fear. Fear of rejection. Fear of anyone questioning your authority. If you find yourself shutting people down, look inside and figure out what fear is driving that response.

An example of obnoxious aggression would be:

“You didn’t prepare an update for our one-on-one, Alex; quite frankly, I think you’re incompetent!”

Ruinous Empathy

Ruinous empathy is the most common mistake people make when giving feedback. Managers sugarcoat feedback in an attempt to make it land better, but in reality they dilute the message and undermine the feedback. What’s worse is that sometimes managers use ruinous empathy to justify not giving feedback at all!

“There’s a Russian anecdote about a guy who has to amputate his dog’s tail but loves him so much that he cuts it off an inch each day, rather than all at once. His desire to spare the dog pain and suffering only leads to more pain and suffering. Don’t allow yourself to become that kind of manager!”

- Kim Scott, Radical Candor

We sometimes hear people say, “I didn’t say exactly that, but they definitely knew what I meant.” Well, no one can read your mind. It’s much easier to say exactly what you mean to say and remove all room for interpretation.

“Managers rarely intend to ruin an employee’s chance of success or to handicap the entire team by letting poor performance slide. And yet, that is often the net result of Ruinous Empathy. Similarly, praise that’s ruinously empathetic is not effective because its primary goal is to make the person feel better rather than to point out really great work and push for more of it.

Ruinous Empathy can also prevent a manager from asking for criticism. Typically, when a manager asks an employee for criticism, the employee feels awkward at best, afraid at worst. Instead of pushing through the discomfort to get an employee to challenge them, managers who are being ruinously empathetic may be so eager to ease the awkwardness that they simply let the matter drop.

Managers often make the mistake of thinking that if they hang out in the Ruinous Empathy quadrant, they can build a relationship with their direct reports and then move over to Radical Candor. They’re pleasant to work with, but as time goes by, their employees start to realize that the only feedback they’ve received is “good job” and other vaguely positive comments. They know they’ve done some things wrong, but they’re not sure what, exactly. Their direct reports never know where they stand, and they aren’t being given an opportunity to learn or grow; they often stall or get fired. Not such a great way to build a relationship.”

- Kim Scott, Radical Candor

An example of ruinous empathy might be:

“When we put typos in emails to customers, it doesn’t look quite as professional as we should. I know you’re super busy, I totally get why this happens, but I’m hoping we can all make more of an effort.”

Radical Candor

“Radical Candor” is what happens when you put “Care Personally” and “Challenge Directly” together.

People will believe that you care personally when they trust you and believe you have their best interests at heart. This will only happen if you forge a deep personal connection with them. Take the time to really get to know everyone on your team, their strengths, their weaknesses, their desires out of life. Realize we are all human beings, with human feelings, and even at work, we need to be seen as such.

Then communicate feedback clearly and candidly. Do not beat around the bush or sugarcoat feedback. You will only water down the message, serving no one. You need to give feedback that, in a way, does not call into question your confidence in their abilities but leaves no room for interpretation.

“Candid feedback is offered humbly. Implicit with candor is that you’re simply offering your view of what’s going on and that you expect people to offer theirs. If it turns out that in fact you’re the one who got it wrong, you want to know. You are giving the other person insight into your internal story about them and offering them a chance to change it.

It turns out that when people trust you and believe you care about them, they are much more likely to:

  1. Accept and act on your praise and criticism
  2. Tell you what they really think about what you are doing well and, more importantly, not doing so well
  3. Engage in this same behavior with one another
  4. Embrace their role on the team
  5. Focus on getting results

The most surprising thing about Radical Candor may be that its results are often the opposite of what you fear. You fear people will become angry or vindictive; instead they are usually grateful for the chance to talk it through. And even when you do get that initial anger, resentment, or sullenness, those emotions prove to be fleeting when the person knows you really care.”

- Kim Scott, Radical Candor

An example of radical candor might be:

“The widget feature is now 30 days delayed after the mutually agreed-upon deadline. This makes me feel fear because the story in my head is that you don’t appreciate deadlines. The rest of the marketing and sales team are geared around this deadline, and missing it causes a lot of disruption. Further still, if we don’t have a culture of keeping to our commitments, then ultimately we will be slow to ship products, fail to raise a round, the company will go bankrupt, and everyone will lose their jobs. In the future, can you keep your commitments and deadlines?”

What happens in cases where you don’t have a personal connection with someone but still have candid feedback to give them? Give it to them anyway, with the same candor. It may upset them in the short term, but in the long term you will build that relationship and they will understand you are giving them feedback to try and help them.

An example of asking to give feedback to someone who you don't yet have a relationship with:

"You are extremely valuable to Clearbit (other group), and even though we don’t know each other very well yet, I wanted to give you some feedback. Are you open to that?"

Feedback rewrites

Providing ineffective feedback is one of the most common mistakes we see managers make. Time and time again, we see managers operating with ruinous empathy rather than being radically candid.

This is why we spend so much time during our manager training focused on good feedback. It’s also why we regularly audit the feedback our managers are giving. Below are some examples of real feedback, and how we would rewrite it.

Before (ruinous empathy):

"I wish we had taken more time to test the widget feature better. It seems that a lot of the issues we had could have been prevented by better testing in dev; if we had a better environment in there, it would help as well. I'll talk to sysops about it and start to thinking on it. Would be great for us to build a culture of testing things better early on locally and in dev before moving to staging and production."

Notice the ruinous empathist uses the word “we,” rather than being direct. They also beat around the bush, not directly addressing the issue, and start making excuses for the report.

Let’s rewrite that with some radical candor:

"The widget feature had a number of significant bugs in it, and you didn’t write any tests for it. When you don’t take the time to test, I feel fear, because the story in my head is that you don’t care about testing which is going to cause more bugs, decrease our shipping speed, and ultimately could make this new product fail. Can you ensure that the work you’re doing in the future is well tested?"

Notice how direct that is. The manager speaks in inarguable truths and demonstrates some vulnerability.

Let’s take a look at another example. First, the ruinous empathy:

"I wish we had communicated better around the Facebook fix. It feels like you never got to prioritize it after our conversation. If we had discussed it earlier, maybe I could have that assigned to someone else. Nothing huge, but probably something we can learn from."

Notice the use of “we” again, and “feels like” to refer to something that isn’t a feeling. Also notice the weasel get-out excuse baked right in (presumably to make them feel better). Let’s try a rewrite:

"When you said you would prioritize fixing that bug with Facebook, and never created a prioritization card in Asana, I felt scared. The story in my head is that you don’t understand how important it is to the company we get this fixed, and you do not think it is important to keep to your commitments. Going forward, when you agree to something, can you do it?"

Running one-on-ones

The one-on-one is your most important meeting as a manager. They are the focal point of your team's relationship with you, and they are your best point of leverage to enact any changes you want to make.

When we talk to managers outside of Clearbit, one of the first questions we ask is how they run one-on-ones. Surprisingly, most have no system; instead, they run ad hoc, unstructured one-on-one meetings (often with hand-wavy justifications).

In our experience, this is a mistake. A one-on-one should be prepared for and highly structured to make the most use of the time available. This might seem onerous at first, but over time you will realize that the opposite is true; the structure is freeing. It lets you get the mundane topics quickly out of the way, and then focus on more blue-sky thinking.

The purpose of a one-on-one

A one-on-one serves a few purposes:

  1. Relationship building, creating an atmosphere of trust between you and your team, where it’s clear that you care personally about them
  2. Feedback giving and receiving, so people understand how they're performing and their areas of growth (This goes for you as well!)
  3. Information sharing, especially highlighting the status of immediate goals
  4. Top tasks accountability, ensuring that people do what they have committed to doing
  5. Career growth, talking through people's aspirations and helping them get there

Effective one-on-ones are like immune systems for companies. They’re critical for bubbling up and resolving issues that could otherwise spiral out of control. They’re also crucial in giving feedback to people so everyone is clear on how they’re performing.

Asking questions

Remember, one-on-ones aren't there for you to micromanage your team. Instead, you should be a sounding board that your team can use to bounce ideas off and come up with their own solutions. Ask questions rather than make statements. Help people come to their own conclusions; it's the only way they'll truly become independent.

“When the supervisor thinks the subordinate has said all he wants to about a subject, he should ask another question. He should try to keep the flow of thoughts coming by prompting the subordinate with queries until both feel satisfied they have gotten to the bottom of the problem.”

- Andy Grove, High Output Management

The Coaching Habit suggest six questions you can ask to help stimulate the conversation:

  1. The kick-start question: "What's on your mind?"
  2. The AWE question: "And what else?"
  3. The focus question: "What's the real challenge here for you?"
  4. The foundation question: "And what do YOU want?"
  5. The lazy question: "How can I help?"
  6. The strategic question: "If you're saying YES to this, what are you saying NO to?"
  7. The learning question: "What was most useful for you?"


When people commit to doing something, it's very important that you hold them accountable to that. Ensure that any commitment is written down in Asana with an owner and a due date to remove all disambiguation. We call these Impeccable Agreements.

You are your team's accountability partner. Make it clear that broken commitments are not acceptable.

Since they are now committed to keeping all of their agreements, it's very important for them to be careful about the things they say “yes” to. If they agree to too many things, they will stretch themselves in a way that will result in broken agreements.

Organizing one-on-ones

The first one-on-one meeting should occur soon after the onboarding process is complete. We recommend starting with a recurring 30-minute meeting every week; you can always make it longer down the road, if required.

We recommend doing all of your one-on-ones back to back on a single day. This is efficient, requires less context switching, and allows you to spot patterns you might otherwise miss.

The maximum amount of direct reports is seven. More than that, and you’re going to spend all your time in one-on-ones.


We are using Asana to track one-on-ones. Use our Asana template to create a new project and give access to both the manager and the team member. We recommend using the naming convention Manager <> Employee. It looks like this:

Asana template


The key to running an effective one-on-one is preparation. This lets you run your one-on-ones in 30 minutes, whizz through procedural work, and get to the more meaty topics (where the fun happens).

The four parts of preparing a one-on-one are:

  1. Update
  2. Issues & proposed solutions
  3. Topic
  4. Feedback


Your report will pre-write an update detailing what has happened since the last one-on-one. Updates should be added as comments to the Update task. Create a commitment with your report to do this every week prior to the one-on-one. Ideally, the update should include “what went well” and “what could improve,” grouped around your report's OKRs.

  1. Track progress toward KPIs. Any KPI that’s lagging should be turned into an issue below.
  2. Bubble up any pertinent information about how your goals have gone (e.g., What new information did you gather about the customer? The product?).

Here's an sample update from our Growth team:

O1: Sprint toward Q4 revenue goal


  • HubSpot integration launch went well. Achieved 95% of target leads.
  • Dynamic Forms Webinar pushed 100 leads
  • Homepage A/B test going live today


  • We have 2-3 more weeks to drive Q4 demand. Feels like we're not on track to hit our goals.
  • Moving blog to primary domain is proving to be a PITA
  • Shipped some sloppy copy / assets in the sprint*

This update will be read in silence at the beginning of the one-on-one (or even better, pre-read) so that everyone is synchronized on the state of the company.

Issues and proposed solutions

Issues are typically things that are blocking your reports’ work and need your assistance or insight.

Any issues that crop up should be written up in the issue style and created as Asana tasks under the Issues section. Ideally, they also have a proposed solution that you can quickly approve. For example:

Issue Leadership team is not putting expenses in the right category from their corporate credit cards. This is causing lots of extra admin overhead for our accounting team. Proposed solution Leadership team moves entirely onto Airbase (should have already received physical cards).


Topics are open-ended points of discussion that your report wants to cover. This is usually where the magic happens, where blue-sky thinking flows, and where creativity is unleashed.

Prompt your report to create topics prior to the meeting. This will encourage some prep work and time to think from both parties.

Topics should have a good description that you can quickly read to gain context, but not necessarily contain a conclusion.


Ideally, feedback should be prepared beforehand by both parties. This allows for more thought-out and considered feedback rather than off-the-cuff ideas. If you haven't prepared feedback, then do it at the end of the one-on-one.

Feedback should be in the Like that / Wish that format.

  1. Like that… Say what you liked about the team member’s actions since the previous meeting? Be specific. During the week, actively look for actions to compliment.
  2. Wish that… What do you wish would change? Be as specific and vulnerable as possible.
  3. It's required that... behavior that needs to change/improve, otherwise the next step is performance improvement plans (PIPS).

It is important to also elicit negative feedback about your or the company’s actions. Do this any way you can, be very thankful for it, and then act to resolve the stated issues quickly. This is the key to making a team member feel heard and valued.

While we have a culture of feedback, we have found it difficult to elicit feedback from reports back to their managers. When asking for feedback, be sure to leave several seconds so the other person has time to think and respond, versus feeling the urge to close the awkward silence too soon.


Run one-on-one meetings according to the following template.

  1. Kick off the meeting by asking your team member about the highlight of their week. This doesn't need to be restricted to work; anything will do. This gets everyone in a great headspace and builds on your relationship.
  2. Then read your team member's prepared update in silence. Read the entire thing before asking any questions. This update should be grouped around their OKRs for the quarter, and be split into “what went well” and “what could improve” sections around each objective.
  3. Next, go through your team member's issues (and proposed solutions). Try to keep to a few minutes for each issue and not get bogged down in minutiae. For clear asks, give an immediate response or create a follow-up task. Otherwise, we recommend helping people come to their own conclusions, which will foster a sense of healthy independence.
  4. Next, talk about topics. These are more open-ended discussions and time for blue-sky thinking.
  5. Now ask, "What are the three most important things you want to get done by this time next week?" Remember, ideally you are not telling people what to do; they should get used to figuring this out for themselves. Preferably whatever they come up with should be related to their OKRs. Jot down the three tasks in Asana, and set the owner and due date for the next one-on-one. Hold people accountable. If tasks are not completed, ask why, and then ask for a “habit” so that this never happens again. This ensures that your team is working to a regular accountability cadence, and it encourages their minds to be focused on their top priorities.
  6. Lastly comes feedback. We have written a whole section on this above, but the key aspect is that if there is any critical feedback, there is mutual trust that it will be shared.
  7. Then high-five. This seals any commitments and leaves the meeting on a good note.

One-on-one schedule

  • Highlight of the week - 2 minutes
  • Read prepared update (in silence) - 5 minutes
  • Questions regarding update - 3 minutes
  • Issues & proposed solutions - 5 minutes
  • Topics - 5 minutes
  • Top tasks - 5 minutes
  • Prepared feedback - 5 minutes
  • High five

Professional development

The goal of professional development is to help your people accomplish their growth goals and, in doing so, improve your team's performance. Each member of your team should become clear around their own values, talents, skills, knowledge, and goals. Once they have that level of self-awareness, they should understand in detail what the next steps are for developing those traits and achieving their goals.

Your job is to guide them to the answer themselves. Then, once you understand where employees are trying to go, you can make adjustments in their current role to move them in the right direction. This knowledge will also shape the feedback you're giving them.

You should have a distinct understanding of the future plans of everyone on your team. Do they want to become a senior engineer, transition from SDR or AE, or start their own business? To grow is human. If we don't provide an environment where people feel like they can grow, they will simply leave.

A great place to discuss this is in your team's one-on-ones. We recommend having a professional development conversation at least once every quarter.

“It's important to remember that Clearbit is just a phase in people's lives. At some point everyone currently working at Clearbit will leave. Indeed, at some point, Clearbit won't exist! Our goal is to try and make it one of the best phases of people's lives, and set them up for whatever they want to do next.”

- Alex MacCaw, Clearbit CEO

Talking about Clearbit as a phase is an important idea to convey to your report before they share their career goals because most folks are used to keeping their true goals hidden lest they are looked upon as disloyal or having conflicting goals with the company. The manager-employee relationship is really a symbiotic one: the employee creates value for the company in exchange for growth opportunities that may or may not continue at the company.

Growth doesn't have to be at work

You may find that your report is quite happy in their current role and career. Perhaps they are focused on areas outside of work. That's totally fine. Don't force your definition of growth down their throats. If someone is doing great work for the company, and they're happy doing just that, let them do their thing.

Growth doesn’t have to be an up-level progression

Growth is really learning new skills. You can grow by learning peripheral skills that interest you; e.g., as a back-end engineer, you can grow by learning distributed systems design (go deeper) or by learning front-end development or marketing (go broader).

These skills don't necessarily advance you to the next level if the skills are not highly valued in your role. But you may still highly value the skills yourself because you want to found your own startup later. (This is also why being explicit about supporting the employee’s career goal up front is critical.)

The up-level progression is simply a recognition of your achievement of mastery in a set of skills highly valued in your current role and the impact that the new role will have.

Growth is not management

For whatever reason, our society drills into us that to have career growth, we need to go into management. This is absolutely not the case. If your report wants to go into management, great—but that’s not a promotion, that's a career change.

Management requires a totally different skill set. If you have a report adamant on going into management, start discussing how to grow that skill set with them first. For a start, they should know this book back to front.

Leveling system

Career discussions are not promotion discussions. The trouble with bringing conversations back to compensation is that it promotes short-term thinking. A career is a decades-long endeavor that surpasses any one company's corporate ladder.

That said, for better or for worse, we do have a leveling system. If someone wants to get paid more at Clearbit, they will need to move up in the leveling system (not necessarily directly up, but possibly also up via a lateral move).

Why do we have a leveling system? It's the best answer we've come up with to make compensation objective and fair. It is far from perfect, though. Don't confuse the levels that we've made up with steps in your career. It's a rigid system that doesn't pretend to encompass the richness of someone's life.

Every department maintains their leveling system (which you can find in our wiki). Here's an example of the various levels in Engineering that we are currently hiring for:

  • Software Engineer (IC2)

    • Write readable, tested, idiomatic code (e.g., good structure, following code style)
    • Apply relevant knowledge, tools, and techniques (e.g., using background queues to buffer writes)
    • and so on...
  • Sr. Software Engineer (IC3)

    • Lead substantial technical projects ​(e.g., scope, track, deliver on requirements)
    • Identify and resolve ambiguous technical issues (e.g., use tracing to debug request lifecycle)
    • and so on...
  • Principal Software Engineer (IC4)

    • Strong individual contributor and technical leader (including everything for Sr. Software Engineer)
    • Support other team members on technical issues
    • Establish team technical policies (in harmony with the rest of Clearbit Engineering)
    • and so on...
  • Engineering Manager (M3)

    • Run standups, retrospectives, and other team meetings where needed
    • Provide continuous feedback and regular performance assessment
    • and so on...

Notice that we have an IC4 level that's higher than the manager level. It's important that we have IC levels that are equal to or higher than manager levels, otherwise you're signaling that the only way to get promoted is to go into management.

Having a discussion

Your professional development discussion should revolve around an 18-month plan and a longer vision. Ask your report to come to your one-on-one prepared with answers to the following questions:

  • How would you describe your success in your current role?
  • What do you actually do that makes you as good as you are?
  • Which part of your current role do you enjoy most?
  • How does professional success intersect with personal happiness in the context of your current role? Do you think it's achievable? Why/why not?
  • What would be the perfect role for you?
  • What goals (inside and outside of work) do you have over the next 18 months?
  • What would you like to be doing five years from now?
  • Write down five to ten skills or competencies you think are required to get to this place, and then rate yourself on each of these on a scale of 1–10.

Since this is all prepared, you can do some thinking of your own prior to the meeting. The first thing to consider is self-awareness. Has your report listed all the skills and competencies required to get to where they want to be, and how does their competency rating compare to yours?

If there's a lack of self-awareness, ask your report if they'd be interested in seeing your scores for them for each skill and competency. While this can be a tricky conversation, the alternative is doing them a disservice by not opening their eyes to any blind spots.

Lastly, ask your report for ideas on how to work on developing these areas. It's much better if the ideas come from them! Try to morph their role and incorporate growth in the areas they're interested in.


Mentors can be a powerful way of catalyzing personal growth. You should be a mentor to your team, but it's also helpful to look for additional mentors outside of the company.

In chapter one, we talked about setting up an advisory board of three to five people who have experience in your domain and have committed to helping you. The difference between an advisor and a mentor is that an advisor directs and a mentor guides. Advisors have such deep domain knowledge that you can ask specific technical questions. Mentors should have a deeper understanding of what in particular motivates you, and they should serve more as a sounding board. Both roles have their place.

We suggest working with your reports to set up similar support structures for them. Prompt your team to look in their network for people who can serve as mentors, and if you have anyone relevant in your network, offer an introduction.

Personal coaching

An alternative to being mentored is using a personal coach. The leadership team at Clearbit all have coaches via a service called Torch. We also extend life coaching services to the entire team through Modern Health.

Taking responsibility for your own growth

Ultimately the ownership for career growth lies with the employee (not the manager). This is counterintuitive.

Managers and the company are there to provide opportunities and shortcuts to growth. They have opportunities to apply in the real world some skill, or experts that have done it before to ask questions of. But they don't own growth. The employee owns it.

This just means that an employee, not their manager, should be in the driver’s seat about their own career. An employee should seek clarity around what they want to learn next and jointly work with their manager to seek out those things.

Unfortunately, it’s all too common for folks to expect their manager to tell them what they should go grow next. While it’s important to explain our ladder and what the company needs, it’s just as important to bounce the question back to your report: What do they want out of their life?

Common management mistakes

As a manager, it's only inevitable that you're going to make mistakes. The important thing is to learn from them, improve, and move on. However, there are mistakes that we see people make time and time again.


The most common mistake we see in managers is “heroing.” That is doing the work of your subordinates on their behalf.

You may think you are being “nice” by lending a hand, but you are actually perpetuating the problem by not setting your team up for long-term success.

More often than not, this stems from an issue of trust. You don’t trust that the work will be done up to your level of quality. Sometimes this is true; after all, you have probably been at the company for years and built up institutional knowledge. However, as long as you continue to badly delegate, then this will continue to be true and your team won’t have a chance to learn.

There are a few ways to think about this. Is your lack of trust in their ability due to an issue with effective training, or did you make the wrong hire?

If it is due to a lack of training, then consider whether this might be a great opportunity for your team member to gain experience. If the work isn’t mission critical, delegate it and monitor what happens. Provide feedback and iterate. The extra effort is worth it in the long term.

If the team member is a wrong fit, then consider making a change. The longer you wait, the longer this problem will persist because you will spend all your time doing IC work rather than recruiting.

Is it ok to “hero”?

In a perfect system, we should never have to “hero.” Everyone has their designated work and they delegate effectively. However, there will be extenuating circumstances that require someone to step in once in a while (especially in a startup). In these cases, it is okay to “hero”—the key thing to remember is to make it obvious to everyone that you are “heroing.” Tell your team member that you will “hero” them once in this circumstance, but that they should come up with a habit to prevent this from happening again.

Not prioritizing hiring

Not hiring effectively is the other big mistake I see in management. Being excellent at hiring is a skill we require from all managers at Clearbit. Slow hiring leads to a vicious cycle of managers doing too much IC work, not having enough time to work on hiring, and then having to do more IC work.

The only way to break yourself out of this cycle is to pause your IC work and focus on hiring. It’s clearly much better to preempt this and hire ahead of time.

Not acting fast enough when someone isn't working out

Time and time again, we see managers that drag their feet in firing people who clearly are not working out. It's important to remember that your team reflects on you. If you are not making a change that clearly needs to be made, it'll be noticed.

Not only that, you're also creating an unfair environment for the rest of the team because they are shouldering additional burden, not just because of the underperforming teammate, but also due to your indecisiveness.

Ruinous Empathy

As mentioned in the section on Radical Candor above, we have found ruinous empathy to be the most common mistake managers make when giving feedback.

Ruinous empathy makes managers sugarcoat feedback in an attempt to make people feel better. Managers will often justify this to themselves because they think it'll make the feedback land better. In reality by doing this, they are diluting the message and undermining the feedback, helping no one.

What's worse is that sometimes managers use ruinous empathy to justify not giving feedback at all.

Get access to the entire book for free

New chapters published every month