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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!

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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