What to Expect When You Start Having 1 on 1s

Ben Horowitz advocates for 1 on 1s. So does Marc Benioff, the team at Bufferapp, and many, many others. Yet, in many ways they’re still shrouded in mystery.

Some people see them as a waste of time. Others are unsure how to make the most of them. Ask 10 managers and you very well could get 10 different answers.

If you’re convinced to get started with 1 on 1s, and never done them before, you’re in for a few surprises. Here’s a few tips for what your should expect:

1) They are different than any other meeting

As a manager and leader, you’re in a lot of meetings. Probably more than you should. And in most of them you’re being asked to give your opinion, make decisions, and answer questions that all focus on driving the business forward. One on ones are nothing like that.

As Ben Horowitz suggests after he took some heat for his firm stance on the importance of having 1 on 1s,

“The key to a good one-on-one meeting is the understanding that it is the employee’s meeting rather than the manager’s meeting. This is the free-form meeting for all the pressing issues, brilliant ideas and chronic frustrations that do not fit neatly into status reports, email and other less personal and intimate mechanisms.”

It bears repeating: One on ones are all about the team member, not you nor the company. You need to flip your mindset to thinking about what’s important to them and how you can help. This context switch can be difficult, but the payoff is huge. Set the standard that you recognize that these meetings are different from other meetings and you’ll be on your way.

2) You will learn important things you won’t hear any other way

You may think you know your team really well. You may think you know everything they’re thinking about for work and have addressed all their concerns they’ve aired publicly. If you’ve put in some effort to listen to your team in a group setting, that’s a great start, but there is always more they’ll bring up privately in 1 on 1s.

As URX CEO John Milinovich recently said in his interview with First Round Capital,

“There will always be things that people won’t bring up in a community forum that are still so important to address, especially before they become bigger issues.”

Build a trusting environment in your one on ones and follow through on what you hear and you’ll be amazed at what you’ll learn people are thinking about or have concerns with. The more you act on what they confide in you, the more they’ll share that will improve the company, your team, your management, and them as an employee. For the introverts on your team, who are less likely to bring up any issues publicly, this will be especially important.

3) They should bring things to talk about, and so should you.

It’s easy to put the obligation on your team member to drive the 1 on 1. It’s definitely important to let them talk about things that are important to them. However, especially early on, you need to bring some questions as well.  There’s a ton of different 1 on 1 questions you can rotate through and you can also use 1 on 1s as great coaching opportunities.

As Jason Lemkin (CEO EchoSign, VC @ Storm Ventures) writes,

“You may think you know if you have drinks together, or go see movies together, or whatever…But you don’t.  Even if people complain in that context, it will be general complaints.  You won’t learn what your top people need to find their growth path at your company.  Where they feel stalled out and frustrated.  You have to ask.

By mixing up the questions you ask, you will ensure you’re not missing anything they may be afraid to bring up.  You’ll also avoid 1 on 1s getting into a rut where certain topics become safe and easy, at the expense of never discussing any elephants in the room. You get out what you put into your 1 on 1s, so prepare, listen carefully, and follow through.

4) They may be a little awkward at first

Your first one on one won’t be easy. It can be especially awkward if you recently got promoted and now you’re having a one on one with a former peer. Fight through the ‘fight or flight’ urge to not ask the questions a manager should ask in a one on one. Those early questions will break the ice and give you your first opportunities to build deeper trust and rapport with them. Over time, you’ll get in a rhythm and build trust. Then you’ll probably even look forward to them.

Stick with them. The benefits are huge as Michael Wolfe (PipeDrive, Vontu, Kana) wrote,

“Over time you can build up a very good relationship with most people simply through this time investment. Even though you may need to discuss tough issues, try to build up enough trust and openness between you that you can enjoy solving problems and working to make the company better.”

It’s a relief when a problem at work is solved. If you form a real partnership with your team member to address the issues they bring up, they’ll trust and respect you more even if you don’t always give them the answer they want to hear.

5) You will quickly learn why this is a manager’s best tool.

The conversations in one on ones are the keys to understanding your people and motivating them.  Everyone has different drivers and idiosyncrasies; the better you understand them, the more effective you’ll be able to work with them.

As Ben Horowitz notoriously recalls when he almost fired two people over a manager not having one on ones,

“Being a good company doesn’t matter when things go well, but it can be the difference between life and death when things go wrong…and things always go wrong.”

Unfortunately, if you don’t do one on ones, Ben continued,

“…there is no possible way for him to even be informed as to whether or not his organization is good or bad.”

You can fix so many problems and improve the morale of everyone on your team with these meetings. You’ll find out about issues before they blow up. You’ll be able to help people when they’re struggling, and give them good and bad feedback regularly.  You can talk about career goals and growth opportunities regularly. Bit by bit you’ll see improvements across your company and you’ll wonder why you didn’t do them sooner.

black_alphaWant help getting started with one on ones? Want to build a better relationship with your team members?

Lighthouse keeps you organized and prepared for everything that matters to your team members including goals and 1 on 1s. Learn more at GetLighthouse.com

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.


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