In today’s episode of The Startup Chat, Steli and Hiten talk about 1-1 meetings. They highlight how to set them up, the importance of these meetings, their benefits and how to do them efficiently so that your startup and your team get the maximum benefit.

Your team is the lifeblood of the company so making sure that they are happy, supported and motivated only helps your startup in the long run. The purpose of a 1-1 is to give dedicated time to a member of your team. This meeting is an opportunity to motivate and support your employee, and to find out what they are experiencing while working at the company.

1-1 meetings must frequently be held and should focus on having open communication. These meetings are not performance reviews, project updates or status meetings. But meetings purely focused on active listening to the challenges, the successes or ideas that your employee has.

Tune into this week’s episode of The Startup Chat to hear clear advice about how to get started with 1-1 meetings. Steli and Hiten highlight issues that can come up, and they also share their top tips on things to keep in mind when holding meetings with your team members.

Time Stamped Show Notes:

00:39 1-1 team meetings defined.

01:32 How often to hold these meetings.

03:35 Ideas for the best approach.

04:55 Questions to ask at your meeting.

06:10 Mistakes for 1-1 meetings.

09:52 Etiquette for 1-1 meetings.

10:05 The power of listening.

10:25 The drawback of responding.

12:02  Avoid problem-solving.

13:30 Treat the 1-1 like an important relationship.

3 Key Points:

  • The 1-1 is their opportunity to speak, and it’s your opportunity to listen.
  • The skill of listening is very important and not responding to everything you hear.
  • How can you be as thoughtful as possible?



Steli Efti: Hey everybody. This is Steli Efti.



Hiten Shah: This is Hiten Shah, and it turns out in over 300 episodes we haven’t really talked about one-on-ones.



Steli Efti: It’s crazy.



Hiten Shah: And how to do them. Yeah, I think that this is going to be very interesting. Yeah, we’re going to talk about one-on-ones in The Startup Chat today.



Steli Efti: First of all …



Hiten Shah: Yeah?



Steli Efti: First of all, what is a one-on-one? Maybe very quick definition.



Hiten Shah: Okay. What is it, Steli? I mean, we’re doing a one-on-one right now, right?



Steli Efti: We’re doing a one-on-one right now.



Hiten Shah: I’m just kidding. What is a one-on-one?



Steli Efti: A one-on-one is when you take somebody that works with you, usually it’s people that you are managing or you’re responsible for, and you have a one-on-one conversation with them, usually to talk about their performance, how they’re doing, or to hear them out. Challenges they have, problems they have, things they need from you. It’s a conversation that’s a lot about the relationship between the company and the person, versus a talk about a project or work. A one-on-one is not having a conversation with somebody you’re managing about a project you both are working on. It’s about the relationship, about people’s performance, happiness, fulfillment at work, that kind of stuff.



Hiten Shah: Yep. Great definition. Okay, let’s start with an easy one. How often should it be done?



Steli Efti: Such a good question. I don’t fucking know.



Hiten Shah: Not an easy one, trust me.



Steli Efti: Yeah. I don’t fucking know.



Hiten Shah: Oh no!



Steli Efti: When my team was both smaller and at the same physical place, when we had an office, I tended to do a one-on-one walk with people once a month. That was kind of my cadence, but I would have these casual conversations about people’s performance more randomly throughout the week, but I would have a more formal walk with people I think once a month. In the early days, maybe even more often because thinking about it, I do think that more of a high level of frequency at the beginning when you have a small team is probably not a bad idea. I don’t know. I do think that it has to be at least once a month because once a quarter or once a year’s definitely not enough, but you could make a real good argument to doing this more frequently. It really depends I think on how senior the people are that you’re managing, and so how much feedback and guidance they need and how much air time they need from you to air out their issues and their challenges. The more senior the people on the team are that you’re managing, in my experience, the less maybe productive it is to have a one-on-one every week or every two weeks. There’s just not enough to talk about. But it’s a good question. I don’t know. What do you say?



Hiten Shah: Yeah, I think every two weeks.



Steli Efti: Every two weeks?



Hiten Shah: Is probably a good cadence. Then you get about 20 of these a year. I think it’s better than once a month. I feel like you don’t want that much time to go by. That’s just my sort of opinion and my experience. Also, it depends on your size of your team as a company as a whole, and size of your direct team and how much conversation is going on. I think that when it comes to one-on-ones, there’s so many different … There’s a lot of advice. This is one of those categories where the It Depends philosophy does really fall in, but there are a ton of best practices. I’m not sure if you and I should go through the best practices, but instead I think we should go through maybe what they are for and what they’re not for.



Steli Efti: Mm-hmm (affirmative).



Hiten Shah: I think people get that confused, and you already hinted at one thing, or really put it out there, which is they’re not about reviewing projects or what’s going on in terms of the tactical operations of the business or what a certain person’s working on and not working on. I’ll put it out there and say they’re not about that. What they are about is about the relationship that whoever you’re responsible for as a manager, the manager perspective, is the relationship the person has with you, since you’re responsible for them. Are you doing anything that they don’t like? As a manager, I think it’s really important to understand that because you might not understand that and the best managers that I know are actually tuning their approach depending on who they’re dealing with. Knowing how that other person feels about you and your approach and how you’re dealing with them is really important, so trying to get some good, bad, ugly out of them can be really useful. I think the second piece I’ll say before I pass it on to you about this is I think the way that I think about these one-on-ones, and I keep saying that on the I think because this is just a topic that I think you end up tailoring over time, and there are a lot of approaches. I’ve seen people do surveying and things like that, but really it’s about the person’s relationship with the company. That’s another big piece of it. It’s not just you. It’s how are they dealing with the people they work with? How are they dealing with the people in other departments? How are they dealing with random coworkers that they might not work with but have to deal with? How are they dealing with your boss, if you have a boss? Or even your counterparts in other areas. There’s so much to it, and I think that person’s relationship with the company’s really important and what I’ve seen people do is actually ask a net promoter style question, “From 0 to 10, how likely are you to recommend somebody else to the company?” Then you ask them, “Why? What’s up? Why would you rate it anything less than a 10, and what’s the reasoning?” That can really get out of you, or out of the person, some really good, crisp feedback that you might not be able to get any other way. I’ve seen companies be successful with that one specific tactic, which I just found interesting not because I’m suggesting anybody do it, but more so you’re looking to figure out what is this person’s relationship with the company, and how can you as their manager, or whoever’s responsible for them if your company doesn’t like the word manager, what can you do about it?



Steli Efti: Yeah. You know, I’ve made a lot of mistakes when it comes to one-on-ones, but I think one of the biggest ones was not being thoughtful enough in what I wanted to accomplish, and then often times what would happen is that the person that I would go on a one-on-one walk with, I would just ask, “What’s on your mind? What’s going on?” And instead of them talking about their relationship with the company and with me and about the things that were going well or not so well, having a really meaningful conversation about those topics, often times it would slip into them starting to talk about some problem with a current project they’re working on, and then it would just turn into a whole discussion about work and specific things in work, versus having a real one-on-one. I think that I’ve wasted a lot of one-on-ones just thinking that all I have to do is ask the question, “What’s on your mind? How are things going?” And then I let the person lead the discussion. I’m not against that, because I don’t think that you should be talking the entire time as the manager, if you are the manager, but I do think that it’s important to guide the person on what you want to talk about, and especially to stop them from potentially just going the easy route, which is just talk about something that’s like, “Oh, I’m trying to close this deal and this prospect told me this. What should I do?” I mean, that’s an important conversation to have potentially, but not the best one to have on a one-on-one, and I’ve done that mistake many times where I just let the conversation go in some kind of a direction, then afterwards I would feel like, “Shit, I still don’t know anything about how happy they are, what their relationship is with the company or with me.” We talked about all these things, but we didn’t really talk about stuff that’s important. I think that’s because we all think in kind of the day to day hustle and we’re all so task-oriented and project-oriented, so when somebody is asked to just go on a walk with you, they might not be prepared and spent time really thinking about it, so they might just be impulsively going to the first thing that comes to their mind, which is the project they’re working on right now. That’s a mistake that I’ve made. The other thing that I’ve struggled with sometimes, and that’s an interesting one, and I’m curious to hear your opinion on this, I think I’d read somewhere a long time ago that one-on-ones should be just about the employee talking to you. Just have them speak the entire time. It shouldn’t be about you at all. You should just ask and learn. I’ve always applied that, but then there were moments or times where I also had things on my mind that I really wanted to talk about with a person. Some problem, something in the way that we’re working that wasn’t working out, something that I wanted to bring to their attention, and because I started with asking them questions, it would be the entire conversation would be occupied with their problems, their challenges, the thing that they wanted to talk about, and then at the end of the walk I’d be like, “Shit, I wanted to talk about these really critical things and I didn’t get to it.” I didn’t get a good balance between them getting things out of their system that they needed to talk about, but then I still had some feedback or critique or things I wanted to talk about that I didn’t get to. I’m curious to hear your thoughts on that, on the … Like we talked about the purpose of the one-on-one is figuring out how the relationship between you and the person is going and the person and the company, but would you say the one-on-one is about their perspective on that relationship purely, or on both’s perspective? Or when you want to do that feedback, is that more of a performance review setup and not really good for a one-on-one? What are your thoughts on that?



Hiten Shah: I like just to hear their perspective. I think it’s one of the hardest things to do as humans not to respond to criticism or feedback, and really it’s I think the person who’s managing’s responsibility to listen. That’s their opportunity to speak pretty much without you judging them, if you’re doing it well. The way to be a great manager is to listen. The key, in my mind, is to listen and listen really well. Sure, if you feel like responding, be very discerning about what you respond to because that’s also very critical. If you respond to everything you hear, then what ends up happening is the person’s not going to feel very heard.



Steli Efti: Mm-hmm (affirmative).



Hiten Shah: That’s the last thing you want. You want this person that you’re having a one-on-one with to not just feel heard, but be heard. I think the skill of listening is super important and not turning it into one of these things where you’re sitting there and you’re looking to respond to everything you hear. It’s easy to respond and make the person feel potentially in your mind good or make yourself feel good by the response, but really that doesn’t help either of you. This is their opportunity to speak. It’s your opportunity to listen and figure out what’s going on. Usually it’s not like you have one one-on-one. You probably have three or four one-on-ones with different people in sort of the same week or whatever, the same month. You can triangulate where the company’s sentiment is that way if you listen.



Steli Efti: Mm-hmm (affirmative).



Hiten Shah: If you’re just responding and reacting, you actually can’t do that as well. I’d be taking notes. I’d be thinking through this and I think you’re right, to me the reviews, when you review somebody and you’re doing quarterly reviews or monthly reviews or whatever it is your company does, bi-annual reviews, that’s your opportunity to get feedback and really get very prescriptive about what you’re seeing, but I would actually keep the feedback and all that to a minimum unless the person is asking for help specifically on something, because then obviously it’s your job to help them.



Steli Efti: I love that. Alright, so let’s wrap this episode up maybe with a tip from both of us. I’ll hijack your last point to give my tip to the listeners, which is even when people … Make sure that the one-on-one is not about you solving all their problems or suggesting solutions to everything that they bring up. Not to say that you should never offer a solution if there’s a problem where there’s a solution, but to double click on what you said with listening, really often times if somebody maybe describes a problem they have with another person in the company, instead of you stepping in and solving and mitigating and mediating or telling them, like maybe you should just ask more questions to understand how their conflict has developed, what this person has tried, what this person would do next to solve this issue, and ask the right questions to help them potentially come up with solutions, or at least come up with a different perspective on a situation, versus you being the person that takes over. It creates that relationship where they come with their bag of problems because they know you’re going to take it away from them and just solve all those problems. A, it’s really hard to feel truly understood when you constantly are trigger happy with offering solutions to everything that they propose, but also it creates this relationship where they’re dependent on you solving their problems, versus you empowering them to come up with a different point of view, a different way of thinking, which helps them then go and solve a problem on their own.



Hiten Shah: Yep. My tip would just be treat it like one of your, just treat it like a really important relationship to you. If you treat the people that you’re working with like that, and in the one-on-ones especially approach it like that, you’ll be a lot more thoughtful and I think that’s really the key, is how can you be as thoughtful as possible and actually hear the person and listen to them and process what they’re saying and take it as feedback for you?



Steli Efti: Beautiful. Alright, that’s it from us for this episode. We’ll hear you soon.



Hiten Shah: See ya.