How To Make Your 1-On-1s Suck Less

How To Make Your 1-On-1s Suck Less


The world remains eventful, from terrible wars to face slapping on national TV.

So before we dive into my experience in running 1-on-1 meetings, here are 3 random and fun things I hope would bring you a bit of awe and joy:

1. Eliud Kipchoge, the world record holder of men's marathon, ran at a pace that most of us wouldn't even be able to run for a minute. It's so hard to wrap my head around how he could run so ridiculously fast for so unbelievably long!

2. A review of the book about Stewart Brand, the visionary who said "Stay Hungry. Stay Foolish."

3. It is mesmerizing to watch an octopus to turn into a huge balloon at a depth of around 1,600 meters. They are aliens.

On Leading:

3 Ways To Improve Your 1-On-1 Meetings

I've run teams of 5 people to teams of 500 people. What I've learned was that people leadership was all about discipline. While the content and methods of how we connect with people were important, it was discipline that brought sustained and high team performance.

Rookie Manager, circa 2001
The first team I led had only 3 people. It was at Accenture, 3 years into my professional career. I did not receive any leadership training. I was thrown into the role. The same was true for the 3 poor souls. They were thrown into the den with me.

Back then, I wasn't structured in how I led them. I didn't need to. The team was small and I could power through most things. When they were confused about something, I would just sit them down and talk things through. When there was animosity or disagreement among us, I would get everyone into a room and iron things out. I could afford hours to deal with them one on one. I was able to get by sufficiently with determination, hard work, and mere brute force.

Then my teams got bigger. My team members were more diverse. I began to have remote teams. My people leadership skills could not keep up. The situation was particularly bad when I got to Apple, where I had to lead a team of almost 500. I wasn't able to keep the team together. I confused them more than I clarified things for them. They felt misunderstood. They were constantly fighting, and the only thing that united them was me- how much they hated me. I could no longer brute force my way out of the mess.

The Tipping Point
I tried many things. I read books. I tried with different communication styles. I created open office hours and hosted many round tables. I hired a coach. Nothing worked. I continued to piss my team off. Worse, our results began to deteriorate, my boss began to go after my rear end, and it became a pain.

Then one day, during a visit to my old music teacher, who's now the headmaster of a school of 1,400 students and 150 teachers and staff, I complained to him about my workplace struggles. He listened, asked a few questions, and then said, "It's all discipline."

It's All Discipline
He explained that given the size of our teams, we would never be able to connect with everyone, hence it was a mistake to try to peanut-butter our time across everyone. Instead, he argued, we should be disciplined in whom we met, how often we met with them, and how we met with them.

For him, he chose to focus on becoming great at connecting with his direct reports. He worked on making his direct reports feel aligned, cared for, and heard. He also said he was very disciplined in ensuring his 1-on-1s were understandable and predictable. People would come more prepared when they understood the purpose and the agenda of the meetings. People would be less fearful, less self-concerned, more candid, and more open minded, when they felt the meetings were predictable.

More critically, he challenged me to be disciplined in attending to my direct reports' lives and growth in rapt attention. We should not show care only "occasionally" and "sporadically." We should not only care about their lives or empowering their growth when the agenda had spare time for it.

3 Disciplines to Great 1-on-1s

Since then, I began to work on how I had 1-on-1s with my direct reports, tweaking and iterating ways to improve them. I have also been sharing what I have experimented with my coaching clients, and continued to evolve them. Here are 3 tested methods that most leaders have found useful in running great 1-on-1 meetings:

1. Ruthlessly prioritize time for your direct reports
Always plan your 1-on-1s with your direct reports first. Be very disciplined in filling up your calendar with 1-on-1s with your direct reports first, before you add any other meetings. Take the word "ruthlessly" seriously and be as ruthless as you could be. If that means declining a meeting from your boss, do it. Be ruthless.

2. Dramatically increase the number of 1-on-1s with your direct reports
You should meet with you direct reports a lot more frequently. There are two reasons why. First, it is business critical that they are fully aligned with you and feel fully motivated, because they are the extension of you. They are the most important group of people that you need to connect with. Second, more 1-on-1s means more repetition in practicing 1-on-1s with your team. That's a great way to improve. I would suggest you to meet with them at least twice a month, or however you exemplify "dramatically."

Now, I understand that you might feel if we were to talk to our teams so often we would run out of things to talk about. It's okay. Here comes point 3 to the rescue ...

3. Have an agenda that focuses on work, life, and growth
Be regimented and stay genuinely curious in their lives outside of work. When your 1-on-1s are more than just work, there will be enough meaningful topics to talk about.

Always dedicate time to helping them grow. Understand their definition of growth. Remove obstacles for them. Be their muses, harbinger of hope, accountability buddy, whatever. Help them find their dreams; Help them chase their dreams. Put on your most hopeful self and hop in with them on their secret life explorations. Help them invent fake meat, put a dent in the universe, and extend human consciousness.

Here is an example of an agenda of my one on one meetings with my direct reports:

  1. How are you? How am I?
  2. What was fun last week? What was fun for me last week?
  3. What would you like to talk about? What would I like to talk about.
  4. What do you want to accomplish this week? What would I like to accomplish this week.
  5. What are your biggest concerns this week? What are my biggest concerns this week.
  6. What do you need the most this week? What do I need the most this week?
  7. What do you expect from me this week? What do I expect from you this week?
  8. What can I do to help you grow this week? How can you help me grow this week?
  9. What will I follow up on after this meeting? What will you follow up on after this meeting.
  10. What are you doing for fun this week? What am I doing for fun this week?

I have also put these methods to the test by working with my coaching clients to come up with their own version of leading more disciplined 1-on-1s. The benefits of this were clear: My clients felt more productive, and their teammates felt more cared for. All parties saw substantial and actionable outcomes from their 1-on-1s. Most importantly, both sides found the 1-on-1s something they actually looked forward to having more.

Give these a try, and let me know what you think.

You can support me:

Reply to this and chat with me! Tell me what you think of this. Or whatever is on your mind. I will always reply, I guarantee it.

And if I fail to keep my promise? Email me and let me know at 🙃

Share this with someone whom you think wants to sound smarter, and or anyone who deserves something light and fun.  (Plus, they trust your recommendations more than my LinkedIn ads.)

Thank you for reading this. I think about leadership & psychology in the showers. I know it's odd, but these topics are important and fun. I hope you find them useful too.

Work diligently. You are bound to be successful.