“Be brave enough to start a conversation that matters.” Dau Voire

Conversations at work are fuel for decisions and alignment. They are a vehicle for new information, for questions, for feedback. Conversations are how change happens.

I’m not talking about endless debate in 1-hr meetings of 10+ people — I’m talking about 1:1 conversations between managers and employees. 

While I’ve spent my career building technology at places like LinkedIn and Degreed, I am disheartened by the new trend in HR software to attempt to replace conversations. Feedback and recognition apps seem helpful on the outside but can make managers feel like they are connecting with employees when they are not.

This is one of the reasons 75% of professionals think new technology is contributing to job satisfaction (Economic Times, 2018). We are a long, long way from software being able to deliver value to our talent processes sans conversations. Even in a remote-first world, you need to be regularly having real conversations with those you work with. 

Here are four key conversations you need to be having regularly with your employees: 

  1. Career
  2. Performance
  3. Skills
  4. Purpose

Let’s talk about why each of these is important and an introduction to how you might have them. (I’ll be writing a deeper walk through on each of these in the coming weeks, subscribe to TechBuzz or Manager.School to be notified when they are published).


Career is the first conversation because lack of career development is the #1 reason employees leave companies (2015 study from LinkedIn).

The most important part of this conversation is to have it. It’s an easy one to miss since this is fully focused on the employee. Often managers combine this with performance conversations, which is a mistake. It’s easy to spend very little time actually listening to what an employee wants. It can feel disconnected from the current work, but this is the most important conversation when it comes to engagement. 


There are two sides to performance conversations. One we’re familiar with—the traditional once a year performance review. The other we aren’t as aware of—informal conversations about expectations and role. 

To put it bluntly, most performance conversations suck. Employees walk out demotivated, even if they have been doing fine, managers dread them, and talent groups spend exorbitant amounts of time planning and following up on them.

I’ve had the performance expectations conversation (poorly) a few times in my career. Usually when there was a screw-up. A deadline gets missed or the team botches a release. My boss came to me and said “We need to make sure that doesn’t happen again. Let’s have you write your job description so we’re all on the same page.” 

And so, I open the blank page and stare at it. What do I actually do here? What is my job? After writing a couple of mediocre sentences, I google for job descriptions. Add a few more things I see. Then close it. Life gets busy, my boss forgot to ask about it again, and it’s all water under the bridge. 

This is a terrible way to align on role expectations that does not work. 

The hilarity of it all is that nobody (neither employee nor manager) knows how to define expectations.

So, how do you figure this out? 

For performance, the key is to start early and talk often. Don’t save feedback for once a year. And find a positive mindset/mechanic for yourself to have hard conversations (i.e. Crucial Conversations, Radical Candor, etc.)

For expectations, the question you need to ask is not “What’s my job description?” (that would be like trying to start a company asking “what product should we build?”). 

You need to ask “How do I add value to my team?” and “What do my customers/stakeholders expect from me?” You define your role in the context of value to others. 


The most important skill someone can have today is the ability to learn. A 2018 IBM study confirms this with executives listing the most critical behavior for their teams as a “willingness to be flexible, agile, and adaptable to change”. With an ever decreasing half-life of skills (IBM says it’s now at 5-years), the ability to understand what skills you have, what skills you need, and how to develop those skills is more important than ever.

Many tech products try to measure skills, but each solution has issues. It takes too long (test/certifications), doesn’t actually measure skills (content assessments or skills inference from communication), or is just another to-do item (asking employees to list skills in an HRIS system). Each of these also takes years to yield results (after the sales process, implementation, and onboarding … and that assumes you can actually get your employees to use the software).

Something you can start doing today is having more frank conversations about the current and future skills of your employees. This is both personal and increases transparency.

Like the other conversations, deliberate conversations about skills often don’t happen. Spending time together to think and talk about what skills an employee has, what skills they want to have, what skills they need for the future, and how to bridge the gap can be very fruitful, both for actual job performance as well as engagement.


This conversation goes poorly because (like others) it either doesn’t happen or is simple a top-down edict. Misalignment between executives and employees is the most common issue I’ve encountered in my consulting work with enterprise companies. Here are of the comments I’ve heard:

  • “We never know when executives will change their minds. Sometimes they let us know they’ve changed their minds. Rarely do they tell us why.”
  • “Every day is firefighting. And just when you think you are making progress, you get ripped away to the next fire.”
  • “I spend 90% of my time just reacting to pressing issues.”

I’ve talked with people at companies from 10-person startups to construction companies to Facebook … and people everywhere agree that firefighting is the game of the day.

And this takes a toll. Lack of alignment on clear outcomes means that either you change so often that nothing ever really gets done or the work that is done is poor because those on the front-lines don’t understand the actual reasons for the work. 

It takes time to get aligned on purpose, but it’s time well spent. How do you do this? It starts with conversations. Pausing for a moment to talk about the actual purpose and goal of your company, your product, or your project can save a lot of time in the future and help everyone make better decisions along the way. 

Have the Conversation

I’ll go into more details about each of these conversations and tips for preparing and having them, but if there’s one thing to realize it’s this: 

Failing to carve out time for these conversations causes systemic issues.

You’ll see the result of not having these conversations with your employees when top talent leave, when projects take on a life of their own and go over time and over budget, and when you feel the need to motivate by pushing with top-down edicts.

When you create a small amount of space for these types of conversations with individuals and teams, you extend trust. You show you’re willing to share information and listen. You invest in longer-term outcomes and real relationships.

The future belongs to those who are brave enough to start the conversation.

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