Hacking 1-on-1s

I’m often asked for advice on conducting effective one-on-ones. I was recently speaking to Monisha Perkash, CEO of LUMOback, and she told me about a simple technique she uses for conducting one-on-one conversations with team members that I felt compelled to share. It’s called:

Happy / Worried / Frustrated

The majority of experienced leaders and employees I’ve come across, including the wise Ben Horowitz, believe that the one-on-one is primarily the employee’s meeting. It’s their chance to share how things are going, what’s blocking them or getting in their way of being effective and/or fulfilled in their role, and what they want or need from you as their manager. It’s easier to keep this meeting focused on the employee if you’re doing a good job of providing regular, real-time feedback and letting the employee know where they stand on a consistent basis.  There are great lists of questions out there, and I’ll share some that I recommend below. But if in your busy day you don’t quite get around to reviewing those longer lists or haven’t had time to prepare for your one-on-one (which you should and means you’re probably not prioritizing well :), then at least remember these three:

  • What are you happy about?
  • What are you worried about?
  • What are you frustrated about?

By explicitly asking your team members what they’re worried about and frustrated about, they’re more likely to feel comfortable sharing what’s not working with you.  When you simply ask ‘How are things going?’ they’re much less likely to bring up issues out of fear of being seen as complaining. Of course, there’s no substitute for creating a deep level of trust and rapport with your team, and making sure you know that you actually care about they’re well-being.  But, assuming you’ve done a halfway decent job of that, these questions will likely yield a treasure of information about your team member’s perspective on your team, your leadership and your company.

The Four Possible Contexts

There are (at least) four distinct contexts you could be discussing in your one-on-ones:

  1. the employee himself/herself
  2. you as their manager
  3. the team
  4. the company

You could apply Happy / Worry / Frustrated in each of these contexts. For example:

  • What are you happy about in terms of the way our team is working? (team)
  • What are you frustrated about in terms of how I’m managing you? (manager)
  • What about the company  most worries you? (company)

More Potential One-on-One Questions

Here are some more questions that teams I’ve worked with have found helpful to guide managers’ regular one-on-ones with team members:


  • Are you happy working here? What most frustrates you about your job?
  • What are the biggest obstacles to  you getting your job done?
  • Do you like what you’re working on? What else would you like to work on?
  • Do you like the people you’re working with?
  • Who makes your job harder than it needs to be?
  • What are your career goals?
  • What are your personal development goals?


  • How am I doing as your manager? What could I be doing better as your manager?
  • What do I do that makes your life harder than it needs to be?
  • How could I make your life easier?
  • Are you getting as much mentorship and training as you want?
  • Do you feel like you have the right level of autonomy?
  • To what degree am I honoring the company’s values? What else should I be doing, or not doing?


  • If we could improve in any way as a team, how would we do it? What’s the No. 1 problem with our team? Why?
  • If you were me, what changes would you make to our team?
  • What’s the biggest opportunity that our team is missing out on?
  • What are we not doing that we should be doing?
  • To what degree are we honoring the company’s values as a team? What else should we be doing, or not doing?


  • If you were CEO, what changes would you make? If we could improve in any way as a company, how would we do it?
  • What’s the No. 1 problem with our organization? Why?
  • What’s not fun about working here?
  • What don’t you like about the product?
  • What’s the biggest opportunity that we’re missing out on?
  • What are we not doing that we should be doing?
  • To what degree are we honoring the company’s values as a company? What else should we be doing, or not doing?

Now, go schedule those one-on-ones…

One Comment on “Hacking 1-on-1s”

  1. I can’t take credit for the Happy, Frustrated, Worried technique- I learned it from someone else. I will say that it has been very effective in helping us to be a transparent organization that embraces feedback. Dave, very nice article!

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