3 Keys to Starting to do 1 on 1s with Your Team

“…if Tim doesn’t meet with each one of his employees in the next 24 hours, I will have no choice but to fire him and to fire you. Are we clear?”

- Ben Horowitz, The Hard Things About Hard Things, pg. 102

Ben Horowitz, VC and founder of Opsware (sold to HP for $1.6 Billion), said this to one of his reports when he discovered that a manager had not held 1 on 1s with his team members in over 6 months. Horowitz cared so much about a great work environment for his employees that he considered a lack of 1 on 1s a fireable offense for the manager and the manager’s manager.

Crazy? Over the top? Maybe not. Former Intel CEO and legendary author on leadership and management Andy Grove is an advocate for 1 on 1s as well. Many well known companies today including HubSpot, Moz, and Atlassian, use them, too.

And why do they all make 1 on 1s a key part of their management?

1 on 1s are an open line of communication to understand what is on the mind of each of your team members. It helps you get in front of problems before they blow up and it gives your team a recurring way to have their voices heard. It can also save you from having an employee leave the company without warning.

Even if you’ve bought into the importance of 1 on 1s, there’s still the question of how to get started from scratch. It can be intimidating and a little awkward at first, but with the right plan, you will learn invaluable things in the meeting and have much happier employees.

Ready to start your 1 on 1s? Here are some tips I’ve learned along the way from my own mistakes and the advice of more experienced leaders.

3 Keys to Starting 1 on 1s on Your Team

1) Scheduling 1 on 1s

At least 30 minutes, no more than 60 minutes.

- Context switching can be hard for you and your report. Meetings are usually about work issues, so switching to talking about themselves often doesn’t click right away. For this reason 15 minute 1 on 1s are ill-advised, because you’ll just be getting warmed up when it’s over. Shorter 1 on 1s also run the risk of a late start leaving no time for actual discussion. You can always end a meeting early if everything is good, but you want the flexibility to run a little longer if you’re digging into something important.

Always the same time and day.

- You want to get into a rhythm with these meetings. This ensures you have a regular discussion that your team member can count on. It also helps you avoid having to cancel and move them around constantly. Ideally, you’ll pick a time you know you’re more likely to be around and available on a regular basis.

Choose a frequency you can handle.

- Weekly is best, but if you have too many reports for that or know your team very well, every 2 weeks is fine. If you push to a full month between 1 on 1s you may be going too long between discussions. You will know you need to have 1 on 1s more frequently if every 1 on 1 seems to run long or you struggle to dig into issues that are really important to them.

2) Having a Good 1 on 1

This is their time.

- This meeting is not a status report on projects they’re working on. The other 39 hours (or likely really 59 or more for many of you) are all about what you and the company need. 1 on 1s are a time to listen to them and hear them out. The goal is to help them be more happy and productive at work. Set that standard from the very first meeting and you’ll have much more productive 1 on 1s.

Try to get out of the office.

- You want to hear about issues they’re having and talk about their goals and interests. This context switch from getting work done to talking about them can be hard. It can also be uncomfortable to talk about a problem you’re having with a coworker in a conference room near that person. Getting into a different environment, like going for a hike, to a coffee shop, or to grab a beer at a pub, can all help aide that context switch. Bonus points if you can pick a location they particularly like to further reinforce that this is their time.

Have a few questions ready.

- When you first start 1 on 1s, people can be a bit nervous and reserved.  Some more introverted employees will always be that way, so start from the first meeting having a few questions ready to ask them to spark conversation.  Some good examples of questions include:

  • How do you feel [current project they're on] is going? Is anything frustrating you? What are you enjoying about it?
  • Is anything exciting you at work right now?
  • What are your long term goals? Do you feel you’re making progress on them? (This is a question that often changes and needs revisited as you build trust.)
  • How could we make the team you’re on better?
  • You’ll find 101 questions for your one-on-ones here.

Be open and listen. It’s a friendly conversation, not an interrogation. The more they feel heard, the more they’re likely to open up. You won’t get everything in the very first meeting, but over time, you’ll see them trust you more and more as long as you avoid the pitfalls that can ruin 1 on 1s.

3) Avoiding Major Pitfalls

Never Cancel a 1 on 1.

- It may not seem like a big deal to you, but it really hurts your team member when you cancel a 1 on 1 with them. In their view, you’re saying, “this meeting isn’t important to me,” which then says to them they aren’t important to you. This is why scheduling the meetings at a recurring time you can stick to is so important. If you absolutely can’t make a 1 on 1, realize that rescheduling is much better than flat out canceling.

Always follow through.

- If you talk about problems they have, but never do anything about them, you’ll only further frustrate your team members. They’ll then shut you out and won’t give you feedback any more. The benefits of 1 on 1s will be lost. Instead, make sure you follow through and follow up with them on the issues they raise. That feeling of progress is what will build trust to discuss more things openly with you. It will also act as a pressure release valve on issues that may otherwise lead to major problems or them getting upset enough to look for other jobs.

Stick with it.

- The first 1 on 1 is often kind of awkward, like a first date. You may have never had a candid conversation about their needs, frustrations, and desires before, which means there is often some guardedness.  Stick with it, because over time, that awkwardness will fade. You’ll build a much stronger relationship with your team, which will have major impacts in the quality of all their work, their happiness on the job, and likelihood of staying with the company long term.


Get LighthouseWant to have better one on ones? Need help staying on top of what matters most to your team?

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How to Become a Better Leader Instantly

Whether building a career at a large company or starting your own, if you want to advance and grow, soft skills like leadership are just as important to develop as hard skills like programming languages and sales tactics. Despite being a species evolved to live and work in groups, most of us struggle to effectively communicate with and motivate others. This is unfortunate, given how important and helpful a skill it is to master.

I’ve been studying leadership for a while and there are many techniques for motivating and effectively working with others. Many take some practice and skill. Fortunately, there are a few things you can do to very quickly develop your skills, which I was reminded of as I was recently reading the excellent book, “Fierce Conversations: Achieving Success in Work and Life One Conversation at a Time.”

One tip in particular stood out as something I’d heard many times before and I realized it’s the single easiest, yet important tactic to learn:

Give specific praise regularly

Animal trainers around the world know the best way to train animals is through rewarding good behavior. Just think about the last time you were at Sea World and the seals and dolphins got fish and other treats after each trick they did.

While humans are much more complex creatures, we still like rewards, just often in a different form: praise. Because this praise is written or verbal, the key is to be specific.  Don’t just say, “Good Job.” Instead, you’ll want to pull out exactly what was good so they know to do it again. Some simple examples could be:

  • “Great work on the folder feature, Susan. I really like how you made your code clean and easy to follow with comments explaining each section of the code.”
  • “Your report on quarterly earnings was great, Tom. Your graphics were perfect for explaining to the board how we recovered from the rough month.”

After praise like that, I guarantee you that Susan will continue to comment her code and keep it clean and Tom is much more likely to keep investing time to make great graphics for his reports.

This type of praise is powerful for a few reasons:

1) People want to feel appreciated.

Assuming you like your job even a little bit, you want to do good work. There are parts where you’ll put in extra effort. People just want to be recognized for that hard work and that will motivate them to do more of it. Think back to a time someone thanked you for a great job on a project you slaved over for weeks. Give others that feeling.

2) The absence of praise will be felt.

When someone does subpar work and you give no praise, they will notice and want to work harder to seek your praise they previously enjoyed. On the other hand, if you don’t praise people regularly, they are less likely to continue to put in the extra effort on projects. We have all had those moments where we went the extra mile on something and were disappointed when no one noticed. Chances are, you didn’t do it again for that boss or coworker. Don’t be that kind of manager.

3) People want to be noticed.

Especially in the startup world, it’s easy to take great work from your team for granted. Everyone just ships feature after feature, marketing content over more content and keeps grinding. This is also why celebrating wins as a team matters; it’s an opportunity to recognize both the collective efforts of the team and specifically who made major efforts to help the team get there. This is the key to making people feel like they’re “part of something bigger” that draws so many to the lower pay and longer hours of startup life.

Can you remember the last time you praised each member of your team? Were you specific with them or just a vague, “Good job”?

This is just one of the awesome tactics you’ll learn in the book, Fierce Conversations. It covers many excellent topics and will help you understand how to have productive and often difficult conversations effectively with others in both your personal and professional life. I scored it a 9 out of 10 on my ratings scale and highly recommend it.