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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.

Roll Out Radical Candor on Your Team

A number of you have asked how to roll out Radical Candor on your team. How can you get started with some of the ideas from the book and the podcast as a group? Last year, I wrote an Advice Column post answering a CEO’s question about introducing the concepts and starting to build a Radically Candid culture. But let’s get more specific. Here are a few simple things you can do:

1) Start a book discussion group.

Have your team read a chapter of the book each week and use our questions to get the conversation started.

2) Print the Radical Candor framework.

Put up the printouts in conference rooms, 1:1 rooms, or wherever your team will see it regularly. Having the ideas top of mind can help when a feedback situation arises.

3) Share your own stories.

Think of your own stories in each quadrant and share them with your team. When did somebody give you some Radically Candid feedback that maybe stung a little bit in the moment but stood you in good stead for the rest of your career?


For more ideas, read about this company who created a Radical Candor award. What other things have you and your team done to get started with Radical Candor?

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:

How to Have Effective 1:1s

There are a lot of ways to think about holding one-on-one meetings (1:1s) with the people on your teams. Heck, here at Candor, Inc. we don’t even fully agree on one exact prescription. We have a few tips below for thinking about how to have effective 1:1s.

Have them

Have regular 1:1s.

I have to start at the beginning here, because it’s simply not the case that all managers are holding regular 1:1s. This is a cardinal sin. 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. As a senior or junior manager, you must create the space for this.

I’ve historically held my 1:1s for 1 hour every week, and had a high bar for canceling or rescheduling. Currently, Elisse – our outstanding Marketing Director – and I have our 1:1 every other week for an hour. The reason for bi-weekly versus weekly is that we work very closely together – literally a couple feet from each other – all day every day, and we just don’t need to carve out that formal time every single week. But, if Elisse wanted the 1:1 to be an hour every week, I would respect that request, and adjust my schedule to accommodate her needs, no questions asked.

Be on time.

The 1:1 is really not your time, Ms. Manager… it’s their time. Being late is disrespectful. Constantly prioritizing “something else” – email, other meetings, etc. suggests that this particular 1:1 meeting is not as important to you as these other things. Remember, as a manager, in many ways, you represent the company to the employee. Think about the message that you and the company are sending to someone that their time is not that important to you. How do you think this will affect their engagement? (hint: not well)

Change the setting here and there.

Occasionally, go for a walk and have your 1:1. Occasionally, go get coffee. Go sit in the courtyard. Get lunch or breakfast or dinner. Most often, it’s probably easiest and most efficient to grab or schedule a room and get right into it. Every once in awhile, though, offer to change the setting. Think of it as a chance to interact with your team member more as a human being than as just the stodgy old boss.

It’s OK to cancel.

“If there’s nothing to discuss, it’s ok to cancel. People, too often, view 1:1s as mandatory, but it’s refreshing when you both acknowledge that things are ok for now, or the time may be better spent other ways… and you can do this as long as you both agree not to take a request to cancel personally.” – Ben Saitz, Chief Customer Officer at RocketFuel. Cancel occasionally, when you both agree, but beware not to do this regularly. See Have Them above.

Two Ears, One Mouth

They own the agenda… mostly

There is a reason you were given two ears to hear and one mouth to speak. You learn a heck of a lot more listening than talking. Use this as your guide to having an effective 1:1.

I think it’s pretty important that your employee owns the agenda. You might set some guidelines for things that you request to be in the agenda. Then again, you might not. An example of something that you might request is a regular update on their OKRs, KPIs, etc., and maybe you’ll ask that they communicate any blockers that you might be able to help with. Not crazy.

But I think 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. You’re saying, “You tell me what’s important,” and of course you can coach and guide them to help refine over time what’s important. Remember that Steve Jobs said “we hire people to tell us what to do, not the other way around.”

Have a Doc

I like the idea of using a Google Doc, or other shared doc, for a few reasons:

  1. A shared doc is easily accessible pretty much everywhere – across devices, even without a network connection if you choose the “Available offline” option.
  2. A shared doc is a great way to capture action items, what’s said, what’s decided, what’s due, etc. to help us remember these important things amid our busy-as-hell lives.
  3. A shared doc enables manager preparation – just because your employee is driving the agenda, doesn’t mean you need to be surprised! You could agree that the agenda is developed an hour or two in advance and take time to see what’s coming and prep.
  4. It allows you to keep a running archive of 1:1 content that could come in handy down the line for any number of reasons.

Three high leverage agenda items for your 1:1s

While the specific agenda items for a 1:1 should be set by your employee, it’s still ok to help structure the agenda to make the time as productive as possible. Many junior employees may be unsure as to what they should cover in the 1:1. Here are some topics to consider working into your 1:1s:


While I don’t recommend using a 1:1 for simple work status updates (those can easily be accomplished via email), it is entirely appropriate to include “Progress toward goals” as a standing agenda item in a 1:1. Your team member has quarterly goals – ie KPIs or OKRs – that are closely tied to the goals of the team and the company, and it’s very productive to understand the results that your team member is achieving. In the spirit, though, of allowing the employee to own the agenda, give him or her the autonomy to tee up the discussion and prioritize the specific items to cover. That week might be all good news, or maybe that week there’s a blocker that he she needs help with. Perhaps the employee just wants some advice on a problem they are working through. Be there to support them in the achievement of their goals and enable them to determine how you do that.

Career Development

We have developed a very robust Career Conversation methodology here (more on it in later posts). Once a Career Action Plan is developed, allow space in the 1:1 to talk about and follow up on action items. Making this a habit like brushing and flossing will mean that you are investing in your folks in a differentiated way. Kevin Sheridan says in his LinkedIn post about the Top 3 Reasons Employees Quit, “[Managers] do not regularly meet with their direct reports to discuss Career Development, Learning, and Promotion Opportunities.” Regular investment in growth and development helps everyone – helps your employee grow towards their dreams, helps the team and company improve, and it helps your relationship with your employee.

Feedback: Get It, Don’t Give it

The 1:1 is not the place for the manager to give feedback to the employee. That’s not a typo. Recall that we favor short bursts – a few minutes – of feedback given immediately after the specific situation or event.

Instead think about the 1:1 as a chance to get feedback from your employees. If you want to build a culture of feedback, the best place to start is here. Follow our steps to get people to open up and prove you can take and that you value tough feedback: ask your go-to question, stay silent until your employee has the chance to answer, listen with the intent to understand not to cross-examine, and then reward the candor.

My co-founder, Kim, uses another approach, which can substitute or complement the above. She asks her direct reports to structure their 1:1 agendas by answering these questions:

  1. What’s on your mind this week?
  2. How happy were you this past week?
  3. How productive were you this past week?
  4. What feedback do you have for me?

For the record, Ben, quoted above, also favors an open-ended question style for his 1:1s. Questions are a great way to help guide your employee’s thinking about the 1:1 agenda. But, I’ve found that when working with more senior employees, it also works well to leave it entirely up to them and trust that they’ll prioritize the appropriate agenda items.

So remember, supercharge your 1:1s with your employees by making sure you have them, using the time to listen and learn what is important to your employee, and giving your employee ownership of the agenda (with some guidance on key topics to cover).

The Problem with Career Conversations Today

There are a long list of things that every manager needs to do every day, every week, every quarter, to be successful. One of these, which we’ve been heavily focused on to start, is feedback. We believe that feedback is at the center of what managers need to do to build good relationships and drive performance on their teams. But a manager’s responsibilities do not end there! And with our vision to help people enjoy their work and do the best work of their lives, neither does our area of focus. So let’s talk about an equally important responsibility of every manager: Career Conversations.

Career Conversations are exactly what they sound like – discussions about someone’s career with an emphasis on their long-term career aspirations. When done well, these 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. Only with a detailed understanding of both the path behind them and the dream in the distance is it possible to plan a path forward right now.

Why should managers have Career Conversations?

A common question to start is “Why should managers do this? Why should they have these conversations with their team?”

Average Manager vs. Great Manager



Image source: Julie Zhuo on Medium

The number one reason that managers should have Career Conversations with their team is that people need help with this. After having hundreds, possibly thousands of Career Conversations, I’ve seen a lot of self-defeating tendencies among people thinking about their careers. Flawed thinking, deprioritization, trying to live their parents’ dreams for them… it’s all bad, and people need help. We all do.

Reason number two: people on your team and in your organization are thinking about things like next step, career, growth, and development. They are actively considering all of their options within and beyond your company and your team. This report from LinkedIn found that people’s #1 motive for changing jobs is career opportunity.

So you can either not engage and then get surprised when someone hands in their resignation, or…

You can be a part of that conversation from the beginning and contribute to this decision-making as a trusted advisor. In this case, it might still be the right thing for someone to leave, but at least you’ve had some time to prepare for that departure. Maybe you can reduce the time that there’s a gap. You’ll save the company cycles in trying to figure out what to do to retain this person.

In short, your choice is to participate, be helpful, and be prepared or to bury your head in the sand and get surprised.

Finally, and extremely importantly, isn’t your job as a leader to help people grow? I hope this is an obvious ‘yes’ to you, but then a very reasonable question is “help them grow into what?”

Career Conversations are all about growth, and growth toward a dream. They will enable you to really help the people on your team, to be a leader who invests in the team and makes work more rewarding and more fun.

The Problem with Career Conversations Today

So what’s the problem? Aren’t managers already doing growth and career plans? Unfortunately, no. There are four main problems with Career Conversations today.

Problem 1: Career Conversations Club

Tyler Durden taught us that the first rule about Fight Club is that you do not talk about Fight Club. This is also the second rule about Fight Club… and there are only 4 rules!

Similarly, the single biggest problem with Career Conversations is that there are no Career Conversations. Often leaders think they’re having Career Conversations, but they’re really just having imposter conversations. For example, some leaders believe they are having Career Conversations because they’re having performance reviews. But performance reviews tend to be mostly backward looking, and we’re talking about mostly the future. Performance reviews are not Career Conversations.

Other times, leaders just don’t know that they’re supposed to be having these types of conversations, and even if it crosses their minds, they don’t know exactly what to do or they’re just too darn busy trying to deliver the quarter, ship product, or audit the accounts to free up the time to do it.

New first rule about Career Conversations: Do talk about Career Conversations. We need to educate managers on the importance and proper process for Career Conversations.

Problem 2: Short-term focus

If Career Conversations are happening at all, they are rather frequently carried out with an excessively short-term focus. There is a time to be sure to deal with the short-run in Career Conversations, but that’s just not the place to start. Steven Covey argued that “Some habits of ineffectiveness are rooted in our social conditioning toward quick-fix, short-term thinking.”

One example of excessive short-term focus I’ve seen is the idea that promotion = career development. This is just not true at all. Promotions, at their absolute best, represent incremental personal growth – a scope increase that brings new challenges, responsibilities, and requires new thinking. That’s good!

Promotions, at their worst, are nothing. A nominal title change with virtually no change to anything else. At their most normal, promotions represent a rare, formal recognition of a job well done that includes pay and title increase. They feel good for about a week, but those feelings are ephemeral. Generally, it’s back to business as usual, the promotion offering no clarity on what the future holds, what it should hold, and how to get there.

Career Conversations require us to deal explicitly with future, and nothing about promotions is rooted in a compelling, shared-understanding of the future.

Problem 3: Check-in-the-box mentality

I want to tell you a story, maybe you’ve heard it before. It’s called, The Ridiculousness of the IDP. Ah, the IDP, or the Individual Development Plan. Once upon a time, the Chief-Whatchamahoozit at Company XYZ, Inc. gathered his VPs together to look at employee engagement survey scores. They had some good analysts there at XYZ, so it was plain to see on the slides that people didn’t plan to be with the company in the next 3-5 years. They could further plainly see that “development” and “career” were reasons why. The HR person, passionate about growth and development and looking to be action-oriented, said, “maybe we should have everyone do an IDP.”

The VPs, desperate themselves for an action-plan, said, “Great idea! IDPs! Let’s gather our directors and give them the good news!”

They then said, “Hey directors, I need everyone in your organization to do an IDP.”
Director-gal said, “OK, boss, by when?”

VP responded, “Next Friday.”

Then Director-gal gathered her managers and stated, “We need everyone to have done their IDPs done by next Wednesday.”

Manager-guy then turned to his team and said, “Gang, I need your IDPs done by next Monday.”

Everyone said ‘ok’, and they hammered out their IDPs over the weekend. David started working on his IDP on Saturday, finished it up Sunday evening, and made sure he filled in all the spaces on the sheet. Monday came and everyone said, “we’re 100% compliant on IDPs” and on it went, right on up the chain.

Meanwhile no one had any idea what was in any of the IDPs, and worse, no one – and I mean no one – ever looked at a single one of those IDPs again.

This is a sad story, and I think we can all agree, that this sucks. A lot. Boxes checked, impact absent.

Problem 4: Haphazard and random

We plan our families, as we should. We sometimes plan our meals, but probably not as often as we should. We plan our weekends and our vacations. Those are fun. With all of this planning, though, somehow for the thing we spend most of our waking hours on, our careers, we’re surprisingly unstructured and haphazard. If we focus on our careers at all we will often do so with no real intentionality, with no grounding in anything logical, and without a shred of analytical thinking. These plans are almost never grounded in a compelling future, are almost never grounded in a shared sense of one’s past, and therefore it’s nearly impossible to arrive at any sort of relevant conclusion about what someone should do right now in service to their career aspirations.

How Can We Do Career Conversations Better?

We’ve got to start doing Career Conversations with a more structured, intentional approach. We have to understand the past and the future in order to know what to do in the present, what to do right now.

Start with the Past – Life Story

The first step is to understand people’s motivations and values, the things that drive them. It’s amazing what you can learn from a person’s life story if you pay close attention to and ask about their major pivots and transitions. Why did they make them? What did those transitions teach them about what they love and hate about their work?

Talk about the Future – Dreams

Step two is understanding where people want to be at the pinnacle of their careers. Some are skeptical that our younger workers know what they want to be when they grow up. Everyone has dreams, though, and we just have to help people make them a little more tangible. Others worry about honing in on a single vision too early in their career. Don’t use those worries as excuses; there are ways to deal with them.

Plan for the Present – Career Action Plan

With an understanding of the past and the future, we’re only now able to build a relevant and thoughtful action plan with clear owners and clear timelines. We can see the path behind us, we can see the lighthouse in the distance, and now we just need to start laying some flagstones on the ground to connect the two.

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

We want to help managers get better at Career Conversations — awareness of the issues is just the first step! We’d love to know how we can best help you with these. Tell us what’s most challenging for you!

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